8.1 Sweet Mary's Charms

 Sweet Mary's Charms

by JD Ellis and Rob Brown 

Wowza!  Because of the rapidly growing popularity for vaporizing cannabis concentrates, as well adding additional terpenes to concentrates and carts, I started out to write an article on the properties of the volatile compounds in our beloved sweet Mary, highlighting any that we should be concerned about, as we start isolating the individual terpenes and concentrating them. 

For reference, I picked up a copy of Essential Oil Safety, Second Edition, by Robert Tisserant and Rodney Young, planning to look up sweet Mary's individual terpenes and terpenoids and present any concerns that were highlighted. 

Hee, hee, hee, as a really old program manager, I prefer to let the experts do the heavy lifting, with Moi simply organizing and presenting the data in a format that supports the  theory I'm propounding.  

As step two, I downloaded a number of articles listing the terpenes, terpenoids, and flavonoids so as to identify which ones I needed to research, followed by picking several my friend Rob's keen minds, because his family has been in the essential business for generations and it was conversations with him that led me to dig deeper. 

Alas the rabbit hole not only got deeper, but proved to be a circuitous labyrinth, cause not only did the various on line experts not agree on which volatile compounds were present, but Essential Oil Safety doesn't list them all and most don't have MSDS or SDS sheets available.   

The whole thang compounded of course by my having taken organic chemistry just after the middle of the previous century, and it has since advanced at the very same time that mah memory of those hoary days of yore more than half a century ago, declined. 

Fortunately mah friend Rob was there for me to help me through the morass of conflicting information from sage sources, and as karma and fate meant it to be all along, instead of researching a simple article, I was launched into a new exciting adventure calling for multiple articles.  

Leave us not forget my previous comment regarding rabbit holes, and the dearth of agreement on exactly what sweet Mary's charms are present, so for this first article I importuned Rob to give me a base to work with, by providing a list of the 10 most common terpenes, terpenoids, and flavonoids that his companies scientists have found in sweet Mary, as well as the next 20 less common. 

The balance of this article addresses that list, but I will be following with a second article based on a study detailed in one of the Oxford Academic Botanical Journals, based on  Northern Lights and Hawaiian Indica male and female plants, where they've identified 68 volatile compounds using a gas chromatograph.   

Their complete report is at: 

https://academic.oup.com/botlinnean/article-lookup/doi/10.1111/j.1095-8339.2005.00417.x 

I decided to do so after noting that all the volatile compounds detailed in their study aren't terpenes, terpenoids, or flavonoids, nor are they on our first list of 30 most common.   

Different strains of course have varying amounts of these compounds, and some studies suggest over 200 volatile compounds in sweet Mary, but this study stopped at the most prevalent 68 for those two strains.    

That article will be presented separately under the title, The Oxford Academic Botanical Journal Follow-up and here we will focus on Rob's list of 10/20. 

Establishing a standard for even one strain is complicated by the rules of Mother Nature's Kitchen, so not only are no two plants exactly the same with regard to constituents, but different areas on the same plant are different.   

Furthermore, the plant produces the terpenes in reaction to its environment, ranging from attracting pollinators to repelling predators or even attracting the predators of those predators.  They provide anti-bacterial, mold, and UV protection, as well as serve other functions, so as its environmental conditions change, so does its terpene balance.  We therefore won't being trying to quantify exactly how much of each is present, only that it is and its properties. 

I would like to also note that other studies show tri-terpenes in Mary's fibers and roots, which we don't address here, but will follow up on separately as well. 

Sooo, starting at the beginning, one question that we might ask ourselves up front, is how has it come about that our beloved sweet Mary has become the lady with 1000 different faces, by displaying an astounding number of different volatile compounds. 

Besides the major terpenes, sweet Mary is blessed with minor fractions, some too small to show up at the cut off point of a GC, but having tremendous impact.  For instance  (Z)-3-hexenyl-a-methyl butyrate is am ester of butyric acid and has a fruity odor resembling fresh green apple sweet fruity pear. 

Anyone familiar with butyric acid know it smells like an open sewer, but its esters can be delightful, and Rob pointed out that in perfumery it is the subtleties of minute fractions that make huge differences.  With esters minute quantities are required and with Thiols/mercaptans, another potent source of odor and flavor, fractions in the low parts per billionth range. 

Check out human odor and taste threshold for various substances at:  http://www.leffingwell.com/odorthre.htm 

If you look at the odor profile of the individual terpenes, it also changes with concentration.  At 100% it produces a different odor than it does at .01%, not just stronger and of course they are not stand alone in the plant, but an admix of many at varying ratios. 

Mary shares all those terpenes/terpenoids/flavonoids with the rest of the plant world, it is only the total number present and her versatility in varying their production in the different strains, that is astounding.  That opens the question as to what guidance the hand of man has provided since we began to cultivate plants in the fertile crescent, after the end of the last ice age when the mega fauna died off???? 

Certainly our ancestors in our hoary past, were as a matter of record smart enough to selectively breed the cereal grains from wild grasses, as well as the fruits and vegetables from their wild ancestors, so clearly had the skills had they chosen to do so. 

Given the evidence that some cultures actually even worshiped cannabis as a god, it is hard to believe that they were unaware of or ignored it. 

Consider just its utility as a strong twine, rope, cloth fiber source and the nutrition of the oil rich seeds to hunter gatherers.......... 

Let's also not lose sight of the Lord's instruction to Moses in Exodus, to have a perfumer make Holy Anointing Oil using cannabis, so it was certainly known to the Jewish priesthood, which has Sumerian ties back before recorded history.  Not to forget the priesthood were the scientists and doctors of the era. 

Due to marijuana proscription in the 1930's, little legal research has been possible in the US and many other locations, so until fairly recently the generally accepted explanation was that it was the medicinal effects of the THC that we were experiencing when consuming cannabis products. 

However, with closer examination, it became apparent that each individual terpene, terpenoid, and flavonoid in the mixture contributes its medicinal effect, so that the overall effect is an entourage of the constituent effects.  The whole become at least the sum of it's parts, if not greater. 

The really good news is that to date there is no record of a lethal overdose from cannabis and its entourage that resulted in death, at the mixes and levels encountered in the plant. 

The individual constituents do have medicinal effects however, and as things have progressed, some suppliers are adding terpenes to their products, derived both from cannabis, as well as synthetics and other plant sources.  It is easy to see where terpene mixes more potent than sweet Mary offers, might result in different results, leading us to the subject of essential oil safety. 

Cannabis essential oils are an admix of aromatic hydrocarbon alkene molecules ranging from about C-10 to about C-55.  C of course stands for carbon, and the number tells how many carbon atoms there are, but since these are Alkenes, vis a vis simple Alkanes, some of these carbon atoms are double bonded, and other atoms like oxygen may be included. 

We are loosely calling these essential oil constituents terpenes, and flavonoids, but the range also includes plant waxes, chlorophyll, pheophytin, and carotene, not to mention that some are terpenoids, versus terpenes.  For instance, the C-21/22 cannabinoids are phenolic di-terpenoids, based on a C-20 diterpene.  

An alkene differs from a simple alkane, in that some of the carbon atoms are double bonded to each other and can form aromatic rings, while the alkanes carbons are all single bonded to each other, with the remaining carbon bonds with hydrogen. 

A C-5 isoprene is half of an aromatic ring, shaped like a hobby horse, and when you turn one upside down and stick two isoprenes together, they form a ring.  Two isoprenes together are called a monoterpene. 

If you put three of these isoprenes together, you have a sesquiterpene.  Sesqui means one and one half.  The anthocyanin plant pigments, which are also glycosides, flavonoids, and triglycerides are C-15 and water soluble plant sugars. 

They not only add color to an essential oil, but are also glycosides, or plant sugars and flavonoids.  Some of the color in cannabis essential oil comes from the plant pigments, and plant sugars caramelize when heated, turning darker.  Both add to harshness when vaporized. 

Four isoprenes are a diterpene, with di of course means two.  Variations based on that C-20 diterpene, such as the C-21 phenolic diterpenoid cannabinoids, and C-22 phenolic diterpenoid carboxylic acid, are called terpenoids.   

A C-22 carboxylic acid can be changed into its base C-21 phenolic form through heat and aging, via a process called decarboxylation.  In this case it loses one carbon atom, two oxygen atoms, and one hydrogen, as the COOH carboxyl group disassociates and is given off in the form of CO2 and H2O. 

The C-30 group is where the plant waxes fall, most of which coat the leaves and stem, but some of which coats the trichome caps.  They are not terpenes or terpenoids. 

Plant waxes protect the plant from losing moisture, UV, and the environment in general.   It is essentially inert when eaten, but when vaporized, coats the lungs and requires that the lungs expectorate it, thus adding to harshness. 

We would really rather not extract the plant waxes, as there is nothing in them that we want, and leaving them in place, helps seal the interior of the plant cells from the solvent. 

There is also a wax membrane over the trichome, which typically comes along for the ride anyway, but is a small percent of the whole and typically not an issue. 

At tetra-terpene C-40 we have beta Carotene, which is also non polar, so extracted by non polar solvents, but not so much with polar solvents like alcohol.  It is yellow to red in color and adds much of the color seen in non polar extracted essentials oils. 

A vivid green, Chlorophyll falls at C-55, and is polar due to the magnesium ion in its head. It's molecule is similar to human hemoglobin and some in food is a salubrious thing, but alas it can be overdone enough in concentrates to give some patients severe gastric distress, and any in a vaporization concentrate adds off-flavors and harshness. 

It's polar, so it has a love affair with polar solvents like alcohol, but not so much with non polar solvents. 

So here is where it gets interesting, the exact same C-55 molecule that forms chlorophyll when the magnesium ion is present in its head, becomes Pheophytin when deprotonated by removing the magnesium ion.    

Lacking the magnesium ion, Pheophytin is non polar, readily extracted with non polar solvent, and is olive brown in color.  It gives some insight into why non polar extractions from older dry material produces a dark brown concentrate, while the same fresh cut or minimally dried material produced a light yellow extraction. 

Raw cannabis essential oil contains some of all of the above, the levels of each determined through genetics, as well as by the extraction process and subsequent processing.   

Some whole plant extraction processes seek to extract them all, in the belief that all constituents add to our beloved Mary's entourage medicinal properties, while others seek to exclude everything heaver than C-22 to smooth out the vaporization properties, and lighten its color. 

Those seeking to reduce the rate that the molecules heavier than C-22 are extracted, often do so by dropping the extraction temperatures to below -30C for non polar extractions and below  -50C for polar extractions.   

That actually slows down the extraction rate for all of the molecules, but locks the water solubles up in ice and slows down dissolution of the longer heavier molecules more than the lighter ones.  That allows us to extract predominantly C-10 through C-22 non water soluble molecules.  

Interestingly, the dielectric index of polar solvents like ethanol as we lower the temperature, with it becoming less polar as the temperature falls, making it more selective. 

Anyone experimenting with vaporizing the individual mono and sesquiterpenes, will note they do indeed have their own medicinal properties all by themselves, and you may even notice some of those properties were ones most of us originally ASSumed were cannabinoid medicinal properties. 

A dab of linalool for instance produces that calm, serene catholic eye in my own system, and b Myrcene leaves no doubt where a large portion of couch lock comes from, while d- Limonene and a-Pinene sharpens my alertness. 

Along with an increase in vaporizing cannabis concentrates, has come an intense interest in the mono and sesqui-terpenes, not only for their medicinal effects, but for their aroma and flavor.  While most of the longer heavier terpene based molecules have pungent flavors, all of its pungent aroma is the mono and sesqui-terpenes. 

Since the various terpenes are shared across the plant kingdom, there is a growing interest in adding mono and sesqui-terpenes to a concentrate to enhance its flavor, or make it flow better in a e-pen cart.  Those range from natural flavors to custom flavors like bubble gum and Girl Scout cookies, depending on the audience. 

While the plant world shares terpenes, minor fractions in those terpenes alter the aroma and flavor some, so it is difficult to mimic the original plant terpene balance, but at that level it gets mostly down to a matter of taste. 

I say mostly, because there is also the issue of essential oil safety.  The beloved terpenes that we seek and covet do indeed have their own medicinal and chemical properties, some of which are used to sanitize toilet bowls, strip paint, and remove metal oxides, and can come from a variety of sources, some insalubrious, sooooo as we enter this realm, it pays to pay attention. 

All terpenes off the shelf are also not necessarily extracted as is from plants due to ecconomics, and many are produced by pyrolysis of  more readily available terpenes like b-pinene.  Most b-Myrcene comes from industrial processing b-pinene, and serves as the base starting material for a range other terpenes  such as geraniol, nerol, linalool, and isophytol. 

Poison is always in the dosage.  Some have a wide range and tolerance, and a small amount of some like digitalis can even have desirable medicinal effects, yet kill at only slightly higher dosage. 

Possibly of more concern are the carcinogens, mutagens, teratogens, and reproductive toxins amongst them, that are pernicious at sub lethal doses. 

There is also the issue of chronic exposure, by which we continue to ingest sub lethal doses and the effects accumulate, rearing their ugly heads after much of the damage has been done. 

As a final note, may I add that when combusted or vaporized at high temperature, the volatile molecules break down into shorter chains, forming different substances, some of which are free radicals and some of which are carcinogens, mutagens, teratogens, or reproductive toxins, and some have lower LD-50 doses than the original. 

Cutting to the chase, here's Rob's of the most common terpenes found in cannabis:

 

List of Most Common Terpenes Found in Cannabis

NO

Compound

Formula

Odor/Flavor

1

D-Limonene 

C10H16

Citrus, orange

2

Beta Myrcene

C10 H16

peppery  terpenic  spicy  balsamic  plastic  

3

Beta Caryophellene

C15H24

Clove terpentine

4

Linalool

C10H18O

Citrus, orange, floral, terpy, waxy and rose

5

Alpha pinene

C10H16

Pine Sol

6

Beta Pinene

C10H16

Cooling, woody, piney, turpentine, mint

7

Humulene

C15H24

Woody

8

Phytol

C20H40-O

mild light floral balsam green jasmin

9

Nerolidol

C15H26-O

floral green waxy citrus woody

10

Alpha Bisabolol

C15H26-O

Mild floral peppery clean

11

Terpinolene

C10H16

fresh woody sweet pine citrus

12

alpha Terpineol

C10H18-O

Pine terpene lilac citrus woody floral

13

Citral 

C10H16-O

Sharp lemon sweet

14

Eucalyptol 

C10H18-O

Eucalyptus herbal camphor

15

Ocimene 

C10H16

Citrus tropical green terpene woody green

16

L-Limonene

C10H16

Terpene pine herbal peppery

17

Camphor 

C10H16-O

Camphoreous

18

Camphene

C10H16

Camphoraceous, piney citrus green minty and spicy

19

Eugenol 

C10H12-O2

Sweet spicy clove woody

20

Citronellol 

C10H20-O

floral leather waxy rose bud citrus

21

Menthol

C10H20-O

peppermint cooling mentholic minty

22

Borneol 

C10H18-O

Piney, camphor-like odor

23

Alpha fenchone 

C10H16-O

Camphoric

24

Fenchol 

C10H18-O

Camphor borneol pine woody dry sweet lemon

25

Alpha phellandrene

C10H16

Citrus herbal terpene green woody peppery

26

Delta - 3 - Carene

C10H16

Sweet citrus terpenic fir needle

27

Farnesene 

C10H24

Sweet herbal

28

Geraniol 

C10H18-O

citrus herbal lavender bergamot myrrh neroli green

29

Nerol

C10H18-O

Sweet floral fruity rose waxy citrus

30

Gamma terpinene

C10H16

Sweet natural neroli citrus magnolia

31

Valencene 

C15H24

Oily woody terpene lemon/lime tropical herbal

 

Let's take a look at their properties: 

Odor profiles taken from:  http://www.thegoodscentscompany.com 

Compound molecular weight: http://www.net-comber.com/chem-mass-3.html   

1.0       d limonene aka optical isomer of Dipentene; D-(+)-Limonene; Carvene; (+)-4-            Isopropenyl-1-methylcyclohexene; (+)- R-Limonene; (R)-1-Methyl-4-(1-            methylethyenyl)cyclohexene  Cyclohexene, 1-methyl-4-(1-methylethenyl)- 

Limonene is a naturally occurring chemical found in most aromatic plants. If the plant is green, you can be certain that limonene is present.  

There are two primary forms of limonene, D for dextro, and L for laveo. D-Limonene offers more of a fresh citrus note and comes from the pith or peel of many citrus fruits. L-Limonene, D-Limonene’s opposite chiral sibling, is more associated with Mints and herbs.  

Limonene is used either knowingly or unknowingly in many commercial goods products as an ingredient with in an ingredient. Most beverages and confections incorporate flavors that contain D’ or L’ Limonene.

Limonene is isolated from many natural sources, typically separated and purified via vacuum distillation. It can also be produced synthetically.  

Depending on what source it is derived from, Limonene can and will smell vastly different. For example, D Limonene usually smells like oranges; however, in the case where it has been extracted and enriched from Lime it will smell more like Lime.   

Analytically, it will look exactly the same no matter the source it comes from. Kind of crazy! Smells different, looks the same!           

1.1  Physical Properties

Chemical formula

C10H16

CAS

5989-27-5

Molar mass

136.23 g/mole

Appearance

Colorless to pale yellow

Density

0.84

Melting Point

-40°C (-40°F)

Boiling point

168°C (334.4°F)

Flash point

CLOSED CUP: 45°C (113°F).

Vapor pressure

0.198 mm/hg @ 25C

Solubility in water

Insoluble in cold water, hot water. Soluble in alcohol and diethyl ether.

Odor

Citrus, orange, fresh and sweet

 

 

1.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9924496

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+4186

PEL

20 ppm, 110 mg/m3; sensitization of skin (Sh); Peak limitation category: II(2); Pregnancy risk group: C; (DFG 2005).

TLV

None established

LD-50 Oral

Acute oral toxicity (LD50): 4400 mg/kg [Rat].

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known developmental toxin

May cause adverse reproductive effects and birth defects (teratogenic)

It may affect behavior/central nervous and peripheral nervous system. Central nervous system effects may include excitement, somnolence, delirium, ataxia, convulsions, and stupor while peripheral system effects may include spastic paralysis.

 

It may affect respiration (respiratory depression, choking, coughing, dyspnea, cyanosis). Other symptoms may include cyanosis, fever, and tachycardia.

 

Systemic absorption of large doses may produce pulmonary edema and chemical pneumonitis. The urine may smell like violets.

 

Chronic Potential Health Effects:

 

Ingestion: Prolonged or repeated ingestion may produce nausea,

lowered blood sugar and cholesterol, and kidney damage (hematuria, albuminuria, tubular necrosis), and may also affect the liver. Skin: It may be a weak sensitizer and responsible for some rare allergic responses (dermatitis

 

Non-Human Toxicology Values

Acute oral toxicity (LD50): 4400 mg/kg [Rat]. Acute dermal toxicity (LD50): >5000 mg/kg [Rabbit].

 

 

 

 

2.0       beta Myrcene aka 7-Methyl-3-methyleneocta-1,6-diene; 7-Methyl-3-methylene-1,6-octadiene; 1,6-Octadiene, 7-methyl-3-methylene,  

Beta-Mycrene is present in many natural plants, but it is more selective than most terpenes as it is the smallest of all terpenes, chemically speaking.  It is not easily soluble in most normal solvents, fats, or other essential oils and terpenes. As it is more difficult to extract natural beta-mycrene, Extract Consultants offers the synthetic form.  

It is found naturally and extracted from citrus plants, and synthesized from other aroma chemicals.   It is most commonly found in hops, sweet basil, lemongrass, bay leaves, mangoes, and verbena. 

Beta-Mycrene has a highly unique flavor and aroma that differs depending upon the amount present, but generally it is peppery, spicy vegetable-like, with woody floral and slight balsamic notes.  

Beta-Mycrene has been studied for it’s powerful sedative properties, and other medicinal benefits. Traditionally plants that contain beta Myrcene have been used as analgesic (pain reliever), antibacterial, anti-inflammatory, antispasmodic. 

However, too much consumption of beta-myrcene has been known to cause and/or increase anxiety and create physical discomfort.           

2.1  Physical Properties

Chemical formula

C10 H16

CAS

123-35-3

Molar mass

136.25

Appearance

Yellow oily liquid

Density

0.794 g

Melting Point

-10C/14F/263K

Boiling point

166-168C331-334F/430-441K

Flash point

39C/103F/312K

Vapor pressure

2.29 mm/hg @ 25C

Solubility in water

5.6g/L @ 25C. 

Odor

peppery  terpenic  spicy  balsamic  plastic  

2.2 Toxicology

MSDS

https://www.spectrumchemical.com/MSDS/M0070.PDF

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/myrcene#section=Isolation-and-Evacuation

https://www.ncbi.nlm.nih.gov/pubmed/21415873

Fema GRAS

http://www.ift.org/~/media/Food%20Technology/pdf/2005/08/0805feat_gras22complete.pdf

PEL

Not available

TLV

Not available

LD-50

ORAL (LD50): Acute: >5000 mg/kg [Rat].

DERMAL (LD50): Acute: >5000 mg/kg [Rabbit]

Human Toxicology Values

https://oehha.ca.gov/proposition-65/crnr/notice-intent-list-beta-myrcene

 

It may affect behavior/central nervous and peripheral nervous system. Central nervous system effects may include excitement, somnolence, delirium, ataxia, convulsions, and stupor while peripheral system effects may include spastic paralysis.

 

It may affect respiration (respiratory depression, choking, coughing, dyspnea, cyanosis). Other symptoms may include cyanosis, fever, and tachycardia.

Listed as both an antimutagenic and a carcinogen???????

 

 

 

 3.0       b-caryophyllene aka (1R-(1R*,4E,9S))-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene  

Beta-Caryophyllene is present in many aromatic plants that produce essential oils, namely cloves and bay leaves.  

The commercial source of natural beta-caryophyllene is usually oil from clove leaves, however it is further processed, usually through vacuum fractional distillation, to separate, purify and enrich other materials used for flavorings, fragrances, and pharmaceuticals. The aroma is noticeably clove like, and with an astringent, spicy taste.  

Beta-caryophyllene is a sesquiterpene, containing three isoprene units, making it chemically larger than other terpenes like pinene, limonene and mycrene. Unique to beta-caryophyllene is a cyclobutane ring, which is very rare to find in a nature.  

Since it has the cyclobutane ring, it is very popular in biotech research. Beyond that, we regularly find it in many products humans consume.  

It is often used in spice blends, alcohol, fragrance blends for candles, cookies and Christmas candies.  

Some studies suggest that Beta-caryophyllene is thought to be highly sedative, and may support other medicinal benefits, including antidepressant, anxiolytic (anxiety reliever), anti-inflammatory, analgesic (pain reliever), antioxidant, and as a neuroprotective as it can slow damage being done to the brain and nervous system.  

3.1  Physical Properties

Chemical formula

C15H24

CAS

87-44-5

Molar mass

204.188 g/mol

Appearance

Pale yellow oily liquid

Density

0.9075 at 68° F (NTP, 1992)

Melting Point

 

Boiling point

264 to 266° F at 14 mm Hg (NTP, 1992)

Flash point

214° F (NTP, 1992)

Vapor pressure

0.013 mm/hg @ 25C

Solubility in water

<1 mg/mL at 70° F (NTP, 1992)

Odor

sweet woody spice clove dry

 

 

3.2 Toxicology

MSDS

http://www.thegoodscentscompany.com/data/rw1060851.html

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/beta-caryophyllene

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen.

Not a known teratogen

Not a know reproductive toxin

Non-Human Toxicology Values

NA

 

 

 4.0       Linalool aka 3,7-dimethyl-1,6-octadien-3-ol 

Linalool is a natural occurring aroma chemical that can also be produced synthetically. It occurs in many aromatic plants that produce essential oils including lavender and lavandin, orange, sweet basil, and bois de rose (rosewood.) Linalool is a floral alcohol that is often associated with lavender.  

Linalool is often found in food, beverages, confections, sauces, personal care products, aromatherapy, and many other consumer goods that contain essential oils and flavorings.  

Some studies have suggested that Linalool may offer many medicinal benefits, including traditional use as an analgesic, anti-inflammatory, antidepressant, antipsychotic, anti-epileptic, and a sedative. Further studies are being done to test its potential for being an anti-anxiety booster.            

4.1  Physical Properties

Chemical formula

C10H18O

CAS

78-70-6

Molar mass

154.25

Appearance

Colorless to light yellow liquid

Density

0.861

Melting Point

-74 deg C

Boiling point

199 deg C @ 760 mmHg

Flash point

78C

Vapor pressure

0.016 mm/hg @ 25C

Solubility in water

Soluble

Odor

citrus floral sweet bois de rose woody green blueberry

 

 

4.2 Toxicology

MSDS

https://fscimage.fishersci.com/msds/21702.htm

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/Linalool

PEL

NA

TLV

NA

LD-50 Oral

Oral, mouse: LD50 = 3 gm/kg;  Oral, rat: LD50 = 2790 mg/kg;    

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Draize test, rabbit, eye: 100 uL Moderate;Draize test, rabbit, skin: 500 mg/24H Mild; Draize test, rabbit, skin: 100 mg/24H Severe

Skin, rabbit: LD50 = 5610 mg/kg;Skin, rat: LD50 = 5610 mg/kg;

Oral, mouse: LD50 = 3 gm/kg;

Oral, rat: LD50 = 2790 mg/kg;

 

 

 

 

5.0 alpha Pinene aka 2-Pinene, ±)-pin-2-ene;,6,6-Trimethyl-bicyclo[3.1.1]hept-2-ene;2,6,6-trimethylbicyclo-(3,1,1)-2-heptene;2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene;2,6,6-Trimethylbicyclo(3.1.1)-2-heptene;2,6,6-trimethyl-     bicyclo(3.1.1)hept-2-en;2,6,6-trimethylbicyclo[3,1,1]-2-heptene (alpha-pinene);2,6,6-trimethylbicyclo[3,1,1]-heptene (alpha-pinene).  

Alpha-pinene and beta-pinene are aroma chemicals found in virtually every aromatic plant and/or fruit. Some botanicals have very high amounts, while others contain only trace amounts.  

They are regularly ingested in daily life, due to their presence in our environment, where they are found in vast amounts of natural growing botanicals, especially conifers (pine trees), but also in rosemary, and many, many others.  

They can be found in any number of consumers products, including chewing gum, beverages, over-the-counter (OTC) medicines, household cleaners, perfumes and cosmetics; the list goes on and on.  

Alpha- and beta-pinene are known to have many medicinal benefits. They are known to be a bronchodilator, helping to increase airflow in the lungs, which is highly beneficial to people with respiratory conditions like asthma.  

Beyond that, they have been shown to be a good analgesic (relieves pain), an anti-inflammatory, antibacterial, and an antioxidant. They are also believed to aid in memory retention, and an anti-proliferative, which means that it has the potential to inhibit the growth of cancer cells. 

            5.1  Physical Properties

Chemical formula

C-10 H-16

CAS

80-56-8

Molar mass

136.24 g/mol-1

Appearance

Clear colorless liquid

Density

0.858 gm/ml @ 20C

Melting Point

-64C/-83F/209K

Boiling point

155C/311F/428K

Flash point

33C

Vapor pressure

4.75 mm/hg @ 25C

Solubility in water

Very low

Odor

Fresh camphor sweet pine earthy woody

 

 

 

5.3 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9926571

https://www.extractconsultants.com/wp-content/uploads/2016/10/TP1000_MSDS.pdf

http://www.thegoodscentscompany.com/data/rw1006351.html#tosafty

.gov

https://tools.niehs.nih.gov/cebs3/ntpviews/index.cfm?action=testarticle.properties&cas_number=80-56-8

PEL

None listed

TLV

NA

LD-50 Oral

ORAL (LD50): Acute: 3700 mg/kg [Rat].

Human Toxicology Values

As little as 15 mL (1/2 oz.) has proved fatal to a child, but a few children have survived 2 and even 3 oz. /ingestions/. Mean lethal dose in adult probably lies between 4 and 6 oz. /Turpentine/[Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-393]

FATAL DOSE ABOUT 180 G ORALLY AS TURPENTINE /WHICH CONTAINS 58-65% ALPHA-PINENE/.[The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 969]

Porphyritenic and hazardous to those with defects in hepatic heme synthesis.

Non-Human Toxicology Values

LD50 Rabbit (New Zealand white) dermal (24 hr application) >5000 mg/kg[The Flavor and Fragrance High Production Volume Consortia; Revised Robust Summaries for Bicyclic Terpene Hydrocarbons Submitted to the EPA under the HPV Challenge Program..p. 145 (November 9, 2006). Available from, as of October 8, 2008: http://www.epa.gov/chemrtk/pubs/summaries/bictrphy/c13610tc.htm]

LCt50 Rat for inhalation of saturated vapors 625 mg/L/min.

LD50 Rat oral 3.7g/kg[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2972]

No apparent reproductive toxicity

Not a known Carcinogen

Not a known Teratogen

Not a know Mutagen

 6.0       beta-Pinene aka 2,2,6-trimethyl bicyclo(3.1.1)hept-2-ene 

Alpha-pinene and beta-pinene are aroma chemicals found in virtually every aromatic plant and/or fruit. Some botanicals have very high amounts, while others contain only trace amounts.  

They are regularly ingested in daily life, due to their presence in our environment, where they are found in vast amounts of natural growing botanicals, especially conifers (pine trees), but also in rosemary, and many, many others.  

They can be found in any number of consumers products, including chewing gum, beverages, over-the-counter (OTC) medicines, household cleaners, perfumes and cosmetics; the list goes on and on.  

Alpha- and beta-pinene are known to have many medicinal benefits. They are known to be a bronchodilator, helping to increase airflow in the lungs, which is highly beneficial to people with respiratory conditions like asthma.  

Beyond that, they have been shown to be a good analgesic (relieves pain), an anti-inflammatory, antibacterial, and an antioxidant. They are also believed to aid in memory retention, and an anti-proliferative, which means that it has the potential to inhibit the growth of cancer cells. 

6.1  Physical Properties

Chemical formula

C-10 H-16

CAS

127-91-3

Molar mass

136.23 g/mol-1

Appearance

Clear colorless liquid

Density

0.872 gm/ml @ 20C

Melting Point

-61C/-83F/209K

Boiling point

167C/333F

Flash point

43C

Vapor pressure

2.93 mm/hg @ 25C

Solubility in water

Very low

Chiral rotation

-50.7 degree (1S, 5S-Pinene)

Odor

Cooling, woody, piney and turpentine-like with a fresh minty, eucalyptus and camphoraceous note with a spicy peppery and nutmeg nuance

 

6.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9926571

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5615

PEL

NA

TLV

NA

LD-50 Oral

ORAL (LD50): Acute: 3700 mg/kg [Rat].

Human Toxicology Values

Reported Fatal Dose: 
3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). /PINENE/
[Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-170] **PEER REVIEWED** 

About 150 mL may constitute a human oral fatal dose. /Pinene/
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 3242] **PEER REVIEWED** 

Classified as moderately alergenic.

Non-Human Toxicology Values

LD50 Rabbit (New Zealand white) dermal (24 hr application) >5000 mg/kg[The Flavor and Fragrance High Production Volume Consortia; Revised Robust Summaries for Bicyclic Terpene Hydrocarbons Submitted to the EPA under the HPV Challenge Program..p. 145 (November 9, 2006). Available from, as of October 8, 2008: http://www.epa.gov/chemrtk/pubs/summaries/bictrphy/c13610tc.htm]

LCt50 Rat for inhalation of saturated vapors 625 mg/L/min.

LD50 Rat oral 3.7g/kg[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2972]

No apparent reproductive toxicity

Not mutagenic

 

 

 

7.0       a-humulene (a-caryophyllene) aka 3,7,10-humulatriene  

Alpha Humulene is an interesting material not often found in large quantities in nature.  The largest concentrations of Alpha Humulene, other than Cannabis, come from Hops where concentrations definitely vary dependent on the “strain” of Hop cone extracted. 

It is however present in many aromatic and plants and most Alpha Humulene is extracted from cloves where it tends to sit right beside it brother Beta Caryophyllene along with a number of other terpenes found in the low boiling portion of clove oil.   

Organoleptically, Humulene smells and taste very different than Beta Caryophyllene.  It is a warm woody and floral material that marries very well with spicy and herbal flavors and aromas and is the component that softens certain cannabis and hop flavors. 

7.1  Physical Properties

Chemical formula

C15H24

CAS

6753-98-6

Molar mass

204.35 g/mol

Appearance

Clear light yellow liquid

Density

0.889 g/mLat20 °C (68 °F)

Melting Point

< 25 °C (77 °F; 298 K)

Boiling point

66 -168 °C (331 -334 °F)

Flash point

90 °C (194 °F)-closed cup

Vapor pressure

0.008 mm/hg @ 25C

Solubility in water

0.01396 mg/L @ 25 °C

Odor

Woody

 

 

 

7.2 Toxicology

MSDS

http://datasheets.scbt.com/sds/aghs/en/sc-233773.pdf

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/Humulene

PEL

NA

TLV

NA

LD-50 Oral

>48 mg/kg

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

>48 mg/kg

 

 

 

 

 

8.0       Nerolidol aka 3,7,11-trimethyl-1,6,10-dodecatrien-3-ol  

Nerolidol is also referred to as peruviol, and is naturally occurring, found in the essential oils of many, many plants. It is present in many flowers, herbs and spices including neroli, ginger, jasmine, lavender, tea, and lemongrass.  It is used extensively  in food flavorings, industrial and fine fragrance. 

Organoleptically, Nerolidol is a soft aromatic alcohol with a huge diversity of use in flavors and fragrances.  Concentrated Nerolidol is a green and waxy floral and woody character but upon dilution and in presence of other synergistic aroma molecules, Nerolidol often is perceived to be melon like with a touch of citrus.  Flavor and Fragrances experts use this material for its tenacity and breath of application. 

Nerolidol has been studied for its antifungal, antimicrobial, and anti-parasitic properties. It is also currently being tested and studied for its purposes as a skin-penetration enhancer for transdermal delivery medicines.  

8.1  Physical Properties

Chemical formula

C15 H26 O

CAS

7212-44-4

Molar mass

222.372 g/mol

Appearance

Colorless to pale yellow clear oily liquid

Density

0.87000 to 0.87600 @  25.00 °C.

Melting Point

-75 °C

Boiling point

114.00 °C. @ 1.00 mm Hg

Flash point

205.00 °F. TCC ( 96.11 °C. )

Vapor pressure

0.001 mm/hg @ 25C

Solubility in water

1.532 mg/L @ 25 °C (est)

Odor

floral green waxy citrus woody

 

 

 

8.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=H59605&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fh59605%3Flang%3Den

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/nerolidol

PEL

NA

TLV

NA

LD-50 Oral

Rat-> 5,000 mg/kg LD50 Oral-Mouse-15,000 mg/kg

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Rat-> 5,000 mg/kg LD50 Oral-Mouse-15,000 mg/kg

 

 

 

 

 

 

 

 

9.0       Alpha Bisabolol aka 3-Cyclohexene-1-methanol,.alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (R*,R*)  

Alpha Bisabolol also known as Levomenol is produced both naturally and synthetically. It is present in many natural materials including Lemon, bergamot, carrot seeds and cedarwood but it is usually obtain naturally using vacuum distillation from it most abundant source, German Chamomile, and sometimes Candida Albicans. 

Organoleptically, is a sweet, mild light floral and woody sesquiterpene alcohol. It is used extensively in perfumery used in perfumery as a companion material adding synergy to complex mixtures of materials and for its long lasting fixative power. 

Alpha Bisabolol is used extensively in cosmetics and nutraceuticals for Anti inflammatory , bactericidal and antimycotic properties which has made it a key ingredient in many skin care products. 

9.1  Physical Properties

Chemical formula

C15-H26-O

CAS

515-69-5

Molar mass

222.36 g/mole

Appearance

Colorless viscous oil

Density

0.929

Melting Point

51.5C

Boiling point

314.00 to  315.00 °C. @ 760.00 mm Hg

Flash point

275.00 °F. TCC ( 135.00 °C. )

Vapor pressure

0.00004 mm/hg @ 25C

Solubility in water

1.688 mg/L @ 25 °C

Odor

Mild floral peppery clean

 

 

9.2 Toxicology

MSDS

https://www.spectrumchemical.com/MSDS/B0709.pdf

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/1201551

PEL

NA

TLV

NA

LD-50 Oral

Acute oral toxicity (LD50): >5000 mg/kg [Rat].

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Acute oral toxicity (LD50): >5000 mg/kg [Rat].

 

 

 

 

 

 

10.0     terpinolene aka p-Mentha-1,4(8)-diene cyclohexene, 1-methyl-4-(1-methylethylidene)-1-Methyl-4-propan-2-ylidene cyclohexene p- menth-1,4,8-diene P-meth-1-EN-8-YL-formate- 4-iso propylidene-1-methyl cyclohexene  

Terpinolene is a naturally occurring terpene that is found in traces in many botanicals including apples, cumin, and lilacs.  It is found in larger concentrations in Marjoram and Lime oils and certain conifers. 

Organoleptically Terpineolene is a fresh citrus pine aroma chemical with a diverse range of application.  It is used in many fragrances for the household and cleaning industry and blends nicely into Lemon and Orange flavors and fragrances.  In cannabis it is often perceived as a that citus pine note often found in many sativa strains including Lambs Bread Mango ( my personal favorite) 

Terpinolene is often used for products sold as antifungal or  antibacterial, some studies have suggested that Terpinolene may acts as a powerful sleep aid.            

10.1  Physical Properties

Chemical formula

C10H16

CAS

586-62-9

Molar mass

136.23

Appearance

Colorless oil

Density

0.861 g/mL at 25 °C (77 °F)

Melting Point

 

Boiling point

184 - 185 °C (363 - 365 °F)

Flash point

64 °C (147 °F) - closed cup

Vapor pressure

1.126 mm/hg @ 25C

Solubility in water

Insoluble in water

Odor

fresh woody sweet pine citrus

 

 

 

10.2 Toxicology

MSDS

http://www.chemblink.com/MSDS/586-62-9_MSDS.htm

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5702

PEL

Not available

TLV

Not available

LD-50 Oral

LD50 Oral - rat - 4,390 mg/kg

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

LD50-Oral - rat - 4,390 mg/kg

 

 

 

11.0     alpha Terpineol aka 2-(4-methyl-3-cyclohexen-1-yl)-2-propanol  

Alpha-terpineol occurs naturally as a monoterpene alcohol. It is commonly found in natural plant oils such as cajuput oil, pine oil, and petit grain oil. There are four different isomers, but alpha-terpineol is the major constituent.  

Alpha-terpineol has a pleasant, lilac-like aroma to it, thus making it a common ingredient in many perfumes, cosmetics and flavorings. It is one of the two most abundant aroma constituents of lapsang souchong tea, coming from the drying of the tea via pine smoke. It is also a major chemical constituent of skullcap, a flowering member of the mint family.  

Alpha-terpineol occurs naturally, however it is more commonly manufactured from alpha-pinene, which is found in abundance in nature and readily available, making it synthetic. D-limonene has also been used to create the synthetic form of alpha-terpineol.  

Alpha Terpineol has been studied for its potential to treat cancers as an antitumor, some studies have shown that alpha-terpineol inhibits the growth of tumor cells.  

11.1  Physical Properties

Chemical formula

C10 H18 O

CAS

98-55-5

Molar mass

154.25266000

Appearance

Colorless viscous liquid to solid

Density

0.93000 to 0.93600 @  25.00 °C.

Melting Point

40.00 to  41.00 °C. @ 760.00 mm Hg

Boiling point

214.00 to  218.00 °C. @ 760.00 mm Hg

Flash point

191.00 °F. TCC ( 88.33 °C. )

Vapor pressure

0.028 mm/hg @ 25C

Solubility in water

710 mg/L @ 25 °C

Odor

Pine terpene lilac citrus woody floral

 

 

11.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9927291

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/alpha-TERPINEOL

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

 12.0     Citral aka GERANIAL; 5392-40-5; Trans-Citral; 3,7-dimethylocta-2,6-dienal; Geranialdehyde  

Citral is a naturally occurring aldehyde that contains two enantiomers, geranial and neral whose ratio’s vary dependent on the origin of the oil extracted containing citral.   

Citral is present in large quantities in Lemongrass and Litsea Cubeba where it is extracted and purified to be used in flavors and fragrances but Citral is unique in that it is often used as precursor to produce other very important high implacta and stable aroma chemicals for flavors and fragrances. 

Organoleptically Citral is a rich and powerful lemony material.  It is often described as fresh candy like citrus and is used extensively in the flavor world for is citrus power in natural and artificial lemons grapefruits and limes.  It is also used to impart sweet in apple cherry and berry flavorings. 

Citral does have its share of challenges in many products.  It is quite unstable and converts quickly and oxidizes often resulting in color changes or issues in finished products. 

12.1  Physical Properties

Chemical formula

C10 H16 O

CAS

5392-40-5

Molar mass

152.23672000

Appearance

Colorless to pale yellow clear liquid

Density

0.88500 to 0.89100 @  25.00 °C.

Melting Point

<-10°C.

Boiling point

228.00 to  229.00 °C. @ 760.00 mm Hg

Flash point

195.00 °F. TCC ( 90.00 °C. )

Vapor pressure

0.2 mm/hg @ 25C

Solubility in water

1340 mg/L @ 25 °C

Odor

Sharp lemon sweet

 

 

12.3 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9923493

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/Citral

PEL

NA

TLV

NA

LD-50 Oral

(LD50): 4960 mg/kg [Rat].

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

(LD50): 4960 mg/kg [Rat]. Acute dermal toxicity (LD50): 2550 mg/kg [Rabbit]

 

 

 

 

 

13.0     Eucalyptol aka Cineol, 1,8-Cineol; 1,8-Epoxy-p-menthane; 1,3,3-Trimethyl-2-               oxabicyclo[2.2.2]octane

Eucalyptol or Cineol is a naturally occurring terpene alcohol usually identified for its medicinal character.  It is present in many herbs spices and camphoraceous plants including most conifers, mint oils and herbs.   

It is most often extracted and purified from Eucalyptus varieties with most of the production coming from Chinese Eucalyptus globulous.  Like many aromatic plants eucalyptol often takes on a slight aroma from its origin; that is cineol from Peppermint smells a little like mint.  Cineol from marjoram imparts an herbal note into the Eucalyptol. 

Eucalyptus and Eucalyptol have been used traditionally for centuries and most of us have been introduced to its traditional healing properties through cough and cold remedies that are used around the world.  Cineol if often added to mouthwash, tooth paste and pain relief compounds because of its sensory effect and medicinal qualities.           

13.1  Physical Properties

Chemical formula

C10-H-18-O

CAS

470-82-6

Molar mass

154.25 g/mole

Appearance

Colorless

Density

0.921

Melting Point

1.5°C (34.7°F)

Boiling point

176.5°C (349.7°F)

Flash point

CLOSED CUP: 49°C (120.2°F).

Vapor pressure

1.9 mm/hg @ 25C

Solubility in water

Very slightly soluble in cold water

Odor

Eucalyptus herbal camphor

 

 

13.2 Toxicology

MSDS

https://www.sciencelab.com/msds.php?msdsId=9924005

http://www.ugsmedical.com/MSDS/SDS_New/sds_Elyptol.pdf

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/Eucalyptol

PEL

TWA1000ppm ( 1,880 mg/m3)

TLV

Not available

LD-50 Oral

Acute oral toxicity (LD50): 2480 mg/kg [Rat]

Human Toxicology Values

Classified Reproductive system/toxin/female, Reproductive system/toxin/male [SUSPECTED].

Acute Potential Health Effects: May affect behavior, respiratory tract, and nervous system

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Non-Human Toxicology Values

Acute oral toxicity (LD50): 2480 mg/kg [Rat]

H411 (65.85%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

 

 

 

14.0     Ocimene  aka 3,7-dimethyl-1,3,6-octatriene  

Ocimene is a terpene that is found in nature in many aromatic plants including lavender, basil, spearmint tarragon oils, mango fruits and even cashew. 

Organoleptically Ocimene is a herbal floral lavender like aroma chemical with hints of mango and citrus.  It is often used in light floral fragrances like lilies and lavender and in green fresh household fragrances to add value to top notes.  

It is important to note that there are many different isomers and qualities of Ocimene that are available both from nature and sometimes from synthesis.   

14.1  Physical Properties

Chemical formula

C10 H16

CAS

13877-91-3

Molar mass

136.23752000

Appearance

Colorless clear liquid

Density

0.79700 to 0.80500 @  25.00 °C.

Melting Point

50 °C (122 °F; 323 K)

Boiling point

176.00 to  178.00 °C. @ 760.00 mm Hg

Flash point

143.00 °F. TCC ( 61.67 °C. )

Vapor pressure

1.559 mm/hg @ 25C

Solubility in water

2.012 mg/L @ 25 °C

Odor

Citrus tropical green terpene woody green

 

 

14.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/PleaseWaitMSDSPage.do?language=&country=US&brand=ALDRICH&productNumber=74730&PageToGoToURL=http://www.sigmaaldrich.com/catalog/product/aldrich/74730?lang=en&region=US

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/_E_-beta-ocimene

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

 

Non-Human Toxicology Values

NA

 

 

 

   

 

 

 

 15.0     L-Limonene aka (4S)-1-methyl-4-prop-1-en-2-ylcyclohexene  

Limonene is a naturally occurring chemical found in most aromatic plants. If the plant is green, you can be certain that limonene is present. There are two primary forms of limonene, D for dextro, and L for laveo.  

D-Limonene offers more of a fresh citrus note and comes from the pith or peel of many citrus fruits. L-Limonene, D-Limonene’s opposite chiral sibling, is more associated with Mints and herbs.  

Limonene is used either knowingly or unknowingly in many commercial goods products as an ingredient with in an ingredient. Most beverages and confections incorporate flavors that contain D’ or L’ Limonene.

Limonene is isolated from many natural sources, typically separated and purified via vacuum distillation. It can also be produced synthetically.  

Depending on what source it is derived from, Limonene can and will smell vastly different. For example, D Limonene usually smells like oranges; however, in the case where it has been extracted and enriched from Lime it will smell more like Lime.   

Analytically, it will look exactly the same no matter the source it comes from. Kind of crazy! Smells different, looks the same! 

15.1  Physical Properties

Chemical formula

C10 H16

CAS

5989-54-8

Molar mass

136.23752000

Appearance

Colorless clear liquid

Density

0.83900 @  25.00 °C.

Melting Point

 

Boiling point

176.00 to  177.00 °C. @ 760.00 mm Hg

Flash point

127.00 °F. TCC ( 52.78 °C. )

Vapor pressure

1.54 mm/hg @ 25C

Solubility in water

4.581 mg/L @ 25 °C

Odor

Terpene pine herbal peppery

 

 

15.2 Toxicology

MSDS

https://www.sciencelab.com/msds.php?msdsId=9924495

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/_-_-Limonene

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

 16.0     Camphor aka 1.7.7-trimethylbiclo(2.2.1)heptan-2-one

 

Camphor is a natural occurring terpene found in a many aromatic plants including Camphor Laurel wood  oil an origin of natural camphor gum or natural camphor crystals. Natural camphor it used in fragrances, flavors and OTC pharmaceutical preparations.  Camphor is available in a natural and a synthetic material.

Camphor is a very impactful aromatic chemical compound. It is classified as a corrosive compound and is difficult to import and ship and must be labeled accordingly.  This material should be used cautiously.   

Even though it is found in many aromatic plants including Lavandin oils and other lavender Vera essential oils as well as being a main constituent in certain varieties of food grade essential oils like Rosemary and Marjoram it should be used cautiously and sparingly in flavors and fragrances. RIFM and FEMA guidelines should be consulted on acceptable levels for finished goods 

Camphor has been used for centuries, with various uses. It’s used for fireworks and other explosives and munitions, as a deterrent for pests, is often used as a disinfectant, insecticide and germicide. In the culinary world, is used as a flavor component for savory and camphoraceous applications.  

Traditional use of camphor suggests that it has both stimulant and a sedative property.  Most consumers can recognize camphor in a variety of products including mouth wash and over the counter anti-inflammatory, anti-arthritic, and anti-spasmodic sports and pain topical preparations.  

16.1  Physical Properties

Chemical formula

C10 H16 O

CAS

76-22-2

Molar mass

152.23672000

Appearance

White to pale yellow crystalline solid

Density

0.992 g·cm−3

Melting Point

176.00 to  177.00 °C. @ 760.00 mm Hg

Boiling point

204.00 to  205.00 °C. @ 760.00 mm Hg

Flash point

148.00 °F. TCC ( 64.44 °C. )

Vapor pressure

0.65 mm/hg @ 25C

Solubility in water

1600 mg/L @ 25 °C

Odor

Camphoraceous

 

 

16.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9923284

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/camphor

PEL

NA

TLV

NA

LD-50 Oral

(LD50): 1310 mg/kg [Mouse]

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a know teratogen.

Special Remarks on Chronic Effects on Humans:

May affect genetic material based on animal data. Passes through the placental barrier in human.

 

Special Remarks on other Toxic Effects on Humans:

 

Acute Potential Health Effects: Skin: Causes skin irritation. May cause epileptic seizures. Eye: Causes eye irritation.

 

May cause epileptic seizures. Inhalation: Causes irritation of the respiratory tract (mucous membranes)and may cause

emphysema.

 

May affect behavior - the brain and Central Nervous system (muscle contraction and spasticity).

 

May affect the heart. Ingestion: Cause irritation of the gastrointestional tract (nausea, vomiting.

 

May affect behavior - the brain and Central Nervous system (dizziness, convulsions, seizures, change of motor activity, rigidity). May be harmful if swallowed.

 

Certain medical conditions may be aggravated by exposure: kidney disorders, liver disorders, heart disorders, epilepsy. Chronic Potential Health Effects: none identified.

Non-Human Toxicology Values

(LD50): 1310 mg/kg [Mouse]

 

 

 

 

 

 

 17.0     Camphene aka 2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane  

Camphene is a natural occurring monoterpene found in a just a few aromatic plants including Oranges, Pine needles, Tarragon. Lemon and Marjoram not unlike most terpenes Camphene is not soluble in water but is soluble in most organic solvents and vaporizes at room temperature. 

Organoleptically Camphene is a powerful fresh conifer aroma and is often used in pine, evergreen and cedar fragrance formulations.  It is often added to citrus to fresh lemon and lime flavors and frrances helping to add a “pop” and effervescent intensity to a flavor or a fragrance compound. Synthetic camphene is available but be wary because the cas number and chemical arrangement of Synthetic Camphene is different than the natural material. 

Some studied suggest that Natural Camphene has antifungal, anti-biotic and anti-cytotoxic and has been studied for the effects of hyperlipidemia (a condition that effects the cardiovascular system). 

17.1  Physical Properties

Chemical formula

C10 H16

CAS

79-92-5

Molar mass

136.23752000

Appearance

Colorless to light yellow crystalline solid (est)

Density

0.85 g/mL at 25 °C(lit.)

Melting Point

36 - 38 deg C

Boiling point

159.00 to  160.00 °C. @ 760.00 mm Hg

Flash point

95.00 °F. TCC ( 35.00 °C. )

Vapor pressure

3.0 mm/hg @ 25C

Solubility in water

4.6 mg/L @ 25 °C (exp)

Odor

Camphoraceous, cooling, piney woody with terpy nuances. It has citrus and green minty and green spicy notes

 

 

17.2 Toxicology

MSDS

https://fscimage.fishersci.com/msds/83984.htm

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/camphene

PEL

NA

TLV

NA

LD-50 Oral

Oral, rat: LD50 = >5 gm/kg;

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Inhalation, rat: LC50 = 17100 mg/m3/4H;

Inhalation, rat: LC50 = 17100 mg/m3/5M;
Inhalation, rat: LC50 = 17100 mg/m3/1H; 

Oral, rat: LD50 = >5 gm/kg;

Skin, rabbit: LD50 = >2500 mg/kg;

 

 

 

18.0     Eugenol aka 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid;             Allylguaiacol   

Eugenol is a naturally occurring aromatic alcohol found in trace quantities in many aromatic

Plants.  

Organoleptically it is a warm, sweet and spicy aroma reminiscent of cloves. Infact it is the main chemical component of the buds leaves and stem oils extracted from Cloves which are produced mainly in Indonesia and Madagascar but also in in most tropical climates around the world. Cloves are one of the largest spices traded in the world and because of this many tones of Clove leaf and bud oils are produced from the siftings and seconds of this plant.  It is from theseOils that Eugenol, Iso Eugenol and even a fermented natural vanillin are now derived. 

Eugenol is has its own set of in certain applications especially when it comes to the skin.  This chemical

And all essential oils that contain Eugenol are pretty muched banned from “leave on” personal care like lotions or creams due to the sensitization of the skin when in contact with even very low levels of Eugenol. 

Interesting enough, internally, we can use Eugenol, Cloves and Allspice in food, beverages and confections.  It can an is used extensively in Fragrances designed for Candles and potpourri and plug ins

But on the skin, no sir.  Take care in using Eugenol and clove understanding that this molecule will numb the skin.  Most of us have fond memories of Eugenol because it is the aroma we all know when visiting the dentist.  Eugenol is not only used in spicy warm flavors and fragrances but also in dental preparations to numb the mouth. 

18.1  Physical Properties

Chemical formula

C10 H12 O2

CAS

97-53-0

Molar mass

164.20404000

Appearance

Pale to dark yellow clear liquid.

Density

1.06400 to 1.07000 @  25.00 °C.

Melting Point

-12.00 to  -10.00 °C. @ 760.00 mm Hg

Boiling point

252.00 to  253.00 °C. @ 760.00 mm Hg

Flash point

> 200.00 °F. TCC ( > 93.33 °C. )

Vapor pressure

0.01 mm/hg @ 25C

Solubility in water

754 mg/L @ 25 °C (est)

Odor

Sweet spicy clove woody

 

 

18.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9924007

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/eugenol

PEL

NA

TLV

NA

LD-50 Oral

LD50: Acute: 1930 mg/kg [Rat]. 3000 mg/kg [Mouse]. 2130 mg/kg

[Guinea pig].

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

ORAL (LD50): Acute: 1930 mg/kg [Rat]. 3000 mg/kg [Mouse]. 2130 mg/kg [Guinea pig].

 

 

 

 

 

 19.0     Citronellol aka 3,7-Dimethyl-6-octenal; 2,3-Dihydrocitral; beta-Citronellal; Rhodinal 

Citronellol is a naturally occurring aroma chemical present in trace quantities in many aromatic plants.

It is a key chemical constituent of Rose, Geranium and Citronella oils.  It is available in natural and

Synthetic qualities. Natural Citronellol is usually fractionated and futher purified from Citronella oil which is produced commercially in Indonesia, Sri Lanka, China and Vietnam.  Some other countries plant

Citronella oil and in some in South and Central America new commercial plantations are popping up in order to meet a high and growing demand for not only Citronella oil but also the natural terpenes/aroma chemicals that are fractionated from this important oil.  Synthetic Citronellol can be and is produced through several reactions starting with Turpentine. 

Organoleptically, Citronellol is a rosy waxy and green floral fragrance and flavor material that is used extensively in Detergents, Fabric softeners, household cleaners, beverages and confections.  It is a very important material one that would be difficult for creative formulators to live with out.   Citronellol is usually the base of most rose and floral fragrances and can be used at fairly high percentages with out problems.   

Citronellol has been studied extensively through its parent Citronella oil for use as insect repellent and currently it is present in almost every natural mosquito repellent in the world including the imfamous TIKI TORCH we enjoy on hot summer nights.  

19.1  Physical Properties

Chemical formula

C10 H20 O

CAS

106-22-9

Molar mass

156.26860000

Appearance

Colorless to pale yellow clear liquid (est)

Density

0.85000 to 0.86000 @  25.00 °C.

Melting Point

77-83 °C(lit.)

Boiling point

225.00 °C. @ 760.00 mm Hg

Flash point

> 200.00 °F. TCC ( > 93.33 °C. )

Vapor pressure

0.02 mm/hg @ 25C

Solubility in water

105.5 mg/L @ 25 °C (est)

Odor

floral leather waxy rose bud citrus

 

 

19.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9923496

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6805

PEL

NA

TLV

NA

LD-50 Oral

ORAL (LD50): Acute: 2420 mg/kg [Rat].

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

ORAL (LD50): Acute: 2420 mg/kg [Rat].

DERMAL (LD50): Acute: &gt;2500

mg/kg [Rabbit].

 

 

 

 

20.0     Menthol aka Hexahydrothymol; (1alpha,2beta,5alpha)-5-Methyl-2-(1-            methylethyl)cyclohexanol 

Menthol is an a naturally occurring terpene alchohol that is available in synthetically.  the synthetic material is primarly dominated by BASF and Symrise.  It is one of the top five flavor material/commodities traded in our world.  Humans consume thousands of metric tonnes of both natural and synthetic menthol each year mainly n tooth paste, chewing gum, confections and pain relief topical like Ben Gay and Icy Hot…Natural menthol is extracted from a crude mint oil produced in India China and the United States called mentha arvensis ( a cheaper replacer for peppermint oils) also known by its common name Cornmint oil.   Menthol is detected inmany essential oils and aromatic plants but primarily in the mint family. 

Organoleptically Menthol is a fresh, cool and intense mint aroma and good pharma grade menthol is always in a bold crystal that resembles what some of us might wear around our neck as jewelery At room temperature it is a solid, but melts in to a liquid around 42 C.   

Menthol is found in many consumer products, from cold medicines to cigarettes. It triggers cold-sensitive receptors in human skin, which creates the familiar icy sensation when it is applied to the skin, eaten, or inhaled.  This gives menthol many anesthetic properties, as well as being a counterirritant, and is why it is used in many cough suppressants to relieve throat irritation.  

Menthol also acts as a decongestant hence it is found in many vapor rubs used for the treatment of colds and other respiratory illnesses. It is also great for oral hygiene, and many toothpastes and mouthwashes contain menthol. 

20.1  Physical Properties

Chemical formula

C10 H20 O

CAS

2216-51-5

Molar mass

156.26860000

Appearance

Colorless crystals

Density

0.89

Melting Point

41.00 to  44.00 °C. @ 760.00 mm Hg

Boiling point

212.00 to  216.00 °C. @ 760.00 mm Hg

Flash point

190.00 °F. TCC ( 87.78 °C. )

Vapor pressure

0.032 mm/hg @ 25C

Solubility in water

434.5 mg/L @ 25 °C

Odor

peppermint cooling mentholic minty

 

 

20.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9924607

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+593

PEL

NA

TLV

NA

LD-50 Oral

(LD50): 800 mg/kg Cat

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Acute dermal toxicity (LD50): 5001 mg/kg [Rabbit].

Oral LD-50 Cat 800 mg/kg

 

 

 

 

 

 21.0     Borneol aka Borneol; Isoborneol; 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol; 507-            70-0; (+)-Borneol; (-)-Borneol   

Borneol is an easily oxidized organic compound and terpene. It is found naturally in high-concentrations in plants such as camphor, rosemary, and some mint varieties. 

Organoleptically it is herbal and camphoraceous.  Borneol has a minty pine like taste but is cooling and

Fresh in the right proportions.  

Essential oils containing Borneol have been used for centuries in traditional Chinese medicine as a moxa for acupuncture.  

Traditionally borneol  has been used as an analgesic (pain reliever), anti-fungal, antioxidant, antibacterial, and has been used traditionally for anti-fibrosis suggesting that it may help to regulate the body’s response to injuries. Additionally, it has been an ingredient selected to be formulated into certain natural insect repellants including flea and mosquito remedies.  

21.1  Physical Properties

Chemical formula

C10H18 O

CAS

507-70-0

Molar mass

154.253 g/mol

Appearance

White to off white crystals

Density

1.011 g/cm3 (20 °C)

Melting Point

202 deg C

Boiling point

212 deg C

Flash point

150 deg F (60 deg C) /closed cup/

Vapor pressure

0.035 mm/hg @ 25C

Solubility in water

738 mg/L at 25 deg C

Odor

Piney, camphor-like odor

 

 

21.2 Toxicology

MSDS

https://www.fishersci.ca/store/msds?partNumber=AC160650025&productDescription=l-borneol-98-acros-organics-4&language=en&countryCode=CA

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/Borneol

PEL

NA

TLV

NA

LD-50 Oral

LD50 = 5800 mg/kg ( Rat

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

LD50 = 5800 mg/kg ( Rat

 

 

 

 

 

 22.0     Alpha fenchone  aka 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one 

Alpha Fenchone  is a aroma chemical which little information exists for use as a flavor or fragrance chemical. D fenchone on the other hand are present in many essential oils with high levels reported in both fennel and cedarleaf.  Natural fenchone is currently extracted from Cedarleaf oil.   

It is currently used in both flavor and fragrances and is approved for use by FEMA and RIFM.

Little data is available for alpha fenchone a camphoraceous terpene ketone. We do know it is being manufactured in limited quantities for experimental use and is regulated by the EPA and has been assigned its own TASCA number and status. 

22.1  Physical Properties

Chemical formula

C10 H16 O

CAS

1195-79-5

Molar mass

1861492

Appearance

Colorless oily liquid

Density

0.945 g/cm³

Melting Point

5.00 to  6.00 °C. @ 760.00 mm Hg

Boiling point

193.00 to  194.00 °C. @ 760.00 mm Hg

Flash point

140.00 °F. TCC ( 60.00 °C. )

Vapor pressure

0.463 mm/hg @ 25C

Solubility in water

73.14 mg/L @ 25 °C

Odor

Camphoric

 

 

22.2 Toxicology

MSDS

https://www.alfa.com/en/content/msds/English/L15151.pdf

.gov

https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/fenchone_508.pdf

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

 23.0     Fenchol aka 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 

Fenchol is an isomer of terpineol and is used in flavor and fragrances extensively.  Most Fenchol is derived synthetically and purified to 95% of greater but it occurs naturally in Limes, Pine, Rosemary and hops.   

Organoleptically, Fenchol is has a sweet lemon Pine medicinal aroma and tastes and tastes somewhat cool and earthy.  It is not super strong but adds synergy and body to citrus and earthy herbal perfumes and flavors.   

23.1  Physical Properties

Chemical formula

C10 H18 O

CAS

1632-73-1

Molar mass

154.25266000

Appearance

Pale yellow solid

Density

0.94300 @ 25.00 °C

Melting Point

35.00 to  40.00 °C. @ 760.00 mm Hg

Boiling point

201.00 to  202.00 °C. @ 760.00 mm Hg

Flash point

165.00 °F. TCC ( 73.89 °C. )

Vapor pressure

0.069 mm/hg @ 25C

Solubility in water

461.4 mg/L @ 25 °C

Odor

Camphor borneol pine woody dry sweet lemon

 

 

23.2 Toxicology

MSDS

https://www.nwmissouri.edu/naturalsciences/sds/e/Endo-Fenchol.pdf

.gov

http://webbook.nist.gov/cgi/cbook.cgi?ID=1632-73-1

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

24.0     Alpha phellandrene aka Menthadiene; P-Mentha-1,5-diene; Alpha-Fellandrene; Dihydro-p-cymene; 99-83-2   

Alpha Phellandrene and Beta Phellandrene are cyclic mono terpenes and double bond isomers that are found both in nature and produced synthetically.  these molecules are present sometimes together and often by themselves in trace quantities in 100’s of essential oils and aromatic plants including citrus oils, marjoram, parsley, sage and Ginger.  

Large amounts of this aromatic material in Dillweed  Oil which is produced in the United States and East Europe; however, unlike dillweed oil which is used extensively in pickling and culinary applications, alpha phellandrene rarely finds its way into these applications. 

Organoleptically, Alpha phellandrene has a green, fresh peppery smell that is used extensively in fragrances. Its blends well into woody, spicy and heavy floral compounds and help to add lift and complexity to white blossom floral concepts. 

Alpha Phellandrene has been studied for its potential benefits in tumor reduction, anti-inflammatory, insect repellency and DNA damage and repair. 

24.1  Physical Properties

Chemical formula

 

CAS

4221-98-1

Molar mass

136.23

Appearance

Light yellow liquid

Density

0.844 g/mL at 20 °C(lit.)

Melting Point

-40.6C

Boiling point

171-174 °C(lit.)

Flash point

42.0 °C (107.6 °F)-closed cup

Vapor pressure

1.856 mm/hg @ 25C

Solubility in water

2.862 mg/L @ 25 °C (est)

Odor

Citrus herbal terpene green woody peppery

 

 

24.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=77429&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F77429%3Flang%3Den

.gov

 

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

25.0     Delta - 3 - Carene aka 13466-78-9; 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene;             Delta-3-Carene; Monoterpenes; Bicyclo[4.1.0]hept-3-ene, 3,7,7-trimethyl-

 

Delta-3-Carene is a bicyclic monoterpene.  It occurs naturally in 100’s of aromatic plants and certain foods.  Its main source is from turpentine which contains greater than 25%i Delta 3 Carene in most cases.  It is also present in other conifer oils like fir needle and pine oils, large concentrations have been identified and  isolated from  cypress and juniper berry wood. 

Organoleptically, Delta-3-carene is a bland light citrusy and pine like material.  It is often described by

Formulators as “limonene like” as it resembles a limonene note; however, if smelled and tasted in close

Time proximity they are vastly different. 

Delta-3-Carene can be used at pretty high levels in flavors and are often seen at an average of 100-150 ppm in many flavor formulas being used for consumer products ranging from Jams and Jellies, confections, and seasonings.  Because of its inclusion in a multitude of essential oils, absolutes and oleo resins this molecule is often identified in the QC process for finished goods, but and the originating natural source cannot be 100 % clearly identified.           

25.1  Physical Properties

Chemical formula

C10H16

CAS

13466-78-9 

Molar mass

136.24

Appearance

Colorless

Density

0.865 g/mL at 25 °C

Melting Point

19.2C

Boiling point

168-169°C

Flash point

55 °C (131 °F) closed cup

Vapor pressure

3.72 mm/hg @ 25C

Solubility in water

Non soluble in water

Odor

Sweet citrus terpenic fir needle

 

 

25.2 Toxicology

MSDS

https://www.nwmissouri.edu/naturalsciences/sds/0-9/3-Carene.pdf

.gov

https://www.osha.gov/chemicaldata/chemResult.html?RecNo=247

PEL

None available

TLV

TWA 20 ppm

LD-50 Oral

LD50 rat 4,800 mg/kg

Human Toxicology Values

TLV-A4 Not classifiable as a human carcinogen

Not a known mutagen

Not a known teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

LD50 Oral-rat-4,800 mg/kg

 

 

 

 

 

 

 26.0     Farnesene aka 1,6,10-Dodecatriene, 7,11-dimethyl-3-methylene, (6E); ,6,10-Dodecatriene, 7,11-dimethyl-3-methylene, (E); (E)-7,11-Dimethyl-3-            methylenedodeca-1,6,10-triene; (E)-7,11-Dimethyl-3-methylene-1,6,10-    dodecatriene  

Farnesene is a general term referring to a set of six sesquiterpenes that are all very similar. Farnecene occurs usually in nature as one isomer E farnesene which is detectable in the chromatography of certain essential oils.  Synthetic farnescene is usually a mixture of more than one isomer. 

Organoleptically, Farnescene has been described as a dry citrus herbal aroma characteristic of bergamot and neroli oils.  It is used in perfumery as a fruity middle note to add value to Berries, Melons and certain floral compounds like Gardenia, where it is naturally present in fairly high levels. 

A-farnesene has been found in the skin of apples, and some flavor experts believe that it is one of the responsible materials that is characteristic of green apples often it is used in fruit flavors like apples adding a dry woody character to the formula. 

Certain studies have suggested that farnesene and the sesquiterpenes contained within have been shown to have many medicinal benefits for humans, such as anti-inflammatory, antispasmodic, and calming or sedative benefits and like many terpenes have been studied for antibacterial, antifungal, many antitumor health benefit. 

26.1  Physical Properties

Chemical formula

C15 H24

CAS

502-61-4

Molar mass

204.35628000

Appearance

Pale yellow to yellow clear liquid

Density

0.84400 to 0.87900 @  25.00 °C.

Melting Point

< 25 °C

Boiling point

260.00 to  262.00 °C. @ 760.00 mm Hg

Flash point

> 212.00 °F. TCC ( > 100.00 °C. )

Vapor pressure

0.01 mm/hg @ 25C

Solubility in water

0.01053 mg/L @ 25 °C (est)

Odor

citrus herbal lavender bergamot myrrh neroli green

 

 

26.2 Toxicology

MSDS

https://farnesene.net/wp-content/uploads/2014/03/amyris-safety-data-sheet.pdf

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Farnesene

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutgen

Not a know teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

 27.0     Geraniol aka trans-3,7-dimethyl-2,7-octadien-1-ol  

Geraniol is a naturally occurring terpene alcohol that is present in many essential oils and Aromatic plants with the largest concentration occurring in Palamarosa, Geranium and Citronella oils. It can also be produced synthetically and there have been many synthetic qualities created and currently manufactured around the world for different reasons. 

Geraniol is also present in many flowers and fruit oils and it is one of the key aroma molecules for the base of the majority of floral fragrances in the world.  At the same time its use levels have been narrowed once Geraniol was added to the European 26 registered Allergens listing published almost a decade ago.  This being said Geraniol now has to be labeled on all products containing Geraniol that are intended for use on the skin. 

Organaleptically geraniol is a mild aromatic alcohol that is a sweet and waxy rose aroma with wide versatility in fragrance and flavor formulas including not only a myriad of florals but also peach, apples and apricot making it an excellent choice for detergent, soaps and household fragrances. 

Geraniol is also on the 25 b 4 a list as a approved material for use in EPA approved pesticides and herbicides and is often seen in natural repellents on the market today, including “ Skin so Soft” a lotion made by Avon that was mistakenly found to be an excellent insect repellent.  

27.1  Physical Properties

Chemical formula

C10 H18 O

CAS

106-24-1

Molar mass

154.25266000

Appearance

Clear colorless liquid

Density

0.87000 to 0.88500 @  25.00 °C.

Melting Point

-16.00 to  -14.00 °C. @ 760.00 mm Hg

Boiling point

229.00 to  230.00 °C. @ 760.00 mm Hg

Flash point

226.00 °F. TCC ( 108.00 °C. )

Vapor pressure

0.021 mm/hg @ 25C

Solubility in water

100 mg/L @ 25 °C (exp)

Odor

Sweet floral fruity rose waxy citrus

 

 

27.2 Toxicology

MSDS

http://www.sciencelab.com/msds.php?msdsId=9924126

.gov

https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+484

PEL

NA

TLV

NA

LD-50 Oral

Acute oral toxicity (LD50): 3600 mg/kg [Rat]. Acute dermal toxicity (LD50): 5001 mg/kg [Rabbit].

Human Toxicology Values

Not a known carcinogen

Not a known mutgen

Not a know teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

Acute oral toxicity (LD50): 3600 mg/kg [Rat]. Acute dermal toxicity (LD50): 5001 mg/kg [Rabbit].

 

 

 

 

 

28.0     Nerol aka 2-cis-3,7-Dimethyl-2,6-octadien-ol *cis-Geraniol * Z)-Geraniol * erol * beta-Nero  

Nerol, is a naturally occurring aromatic terpene that is found in a number of flowers, fruits herbs and spices.  It occurs in Neroli oils and Petitgrain as well as other citrus fruits and flowers like lemongrass and hops.  

Organoleptically-Nerol is characterized as a green waxy floral citrus note and has a similar but more lemony bitter character.  It is used in a multitude of floral fragrances and citrus flavors and is often found in many expensive and fine fragrances sold in department stores. 

Nerol and essential oils containing Nerol have been used traditionally been used as an antibacterial for treating cuts and other small wounds. Some studies have suggested that Nerol and Eseetnial oils containin Nerol may help to regulate normal blood pressure and can be incorporated into a tonic to promote proper functioning of the cardiovascular system and circulation. 

28.1  Physical Properties

Chemical formula

C10 H18 O

CAS

106-25-2

Molar mass

154.25266000

Appearance

Colorless clear liquid

Density

0.87500 to 0.88300 @  25.00 °C.

Melting Point

-15.00 °C. @ 760.00 mm Hg

Boiling point

225.00 to  227.00 °C. @ 760.00 mm Hg

Flash point

226.00 °F. TCC ( 107.78 °C. )

Vapor pressure

0.013 mm/hg @ 25C

Solubility in water

255.8 mg/L @ 25 °C

Odor

Sweet natural neroli citrus magnolia

 

 

28.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=N7761&brand=SIGMA&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Fsigma%2Fn7761%3Flang%3Den

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/nerol

PEL

NA

TLV

NA

LD-50 Oral

Oral Rat 4500 mg/kg

Human Toxicology Values

Not a known carcinogen

Not a known mutgen

Not a know teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

LD50 Intramuscular Mouse 3 GM/KG

LD50 Skin Rabbit> 5000 mg/kg

 

 

 

 

 

 29.0     Gamma terpinene aka P-Mentha-1,4-diene; Crithmene; 99-85-4; Moslene; Gamma- Terpinene  

Gamma Terpinene is a aromatic terpene found in and as a main chemical component of many

Aromatic plants including lime oil, mandarin and even in many camphoraceous essential oils like peppermint, rosemary and tea tree.and is present from trace amount to respectable quantities in many many more.  It is isolated and recovered during the fractionation and concentrations of citrus essential oils and other aromatic plant oil enrichment. 

Organoleptically, Gamma Terpinene is similar to other terpinenes and is a fresh citrus tropical lime

Aroma.  It is used extensively in flavors and fragrances in citrus, spice and herbs formulations. 

29.1  Physical Properties

Chemical formula

CAS

Molar mass

Appearance

Density

Melting Point

Boiling point

Flash point

Vapor pressure

Solubility in water

Odor

29.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=223190&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F223190%3Flang%3Den

.gov

https://pubchem.ncbi.nlm.nih.gov/compound/gamma-terpinene

PEL

NA

TLV

NA

LD-50 Oral

LD50 Oral-rat-3,650 mg/kg

Human Toxicology Values

Not a known carcinogen

Not a known mutgen

Not a know teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

LD50 Oral-rat-3,650 mg/kg

 

 

 

 

 

 30.0     Valencene aka 4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene  

Valencene is a naturally occurring terpene found in few essential oils.  It is found in its largest concentrations in Valencia oranges and grapefruits rarely exceeding .5 % in cold pressed citrus oils. Often it is found to be as high as 2 % in the essence ( or Evaporative juice oils).  Valencene is never found naturally at 90% or greater and is sold usually in concentration of 50% or 70%. 

Organoleptically, Valencene is a high impact molecule that should be used sparingly due to cost and impact.  Valencene has an intense orange and grapefruit aroma that is warm and very sweet smelling and tasting. 

It is used mainly in flavors to enrich oranges grapefruit an lemon-lime beverage flavorings, as well as being used in certain fragrances for its tenacity and longevity. 

30.1  Physical Properties

Chemical formula

C15 H24

CAS

4630-07-3

Molar mass

204.35628000

Appearance

Clear pale yellow to yellow liquid

Density

0.91000 to 0.92200 @  25.00 °C.

Melting Point

-0.583C

Boiling point

274.00 °C. @ 760.00 mm Hg

Flash point

212.00 °F. TCC ( 100.00 °C. )

Vapor pressure

0.011 mm/hg @ 25C

Solubility in water

0.05011 mg/L @ 25 °C (est)

Odor

sweet fresh citrus grapefruit woody orange asprin dry green oily

 

 

30.2 Toxicology

MSDS

http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=75056&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F75056%3Flang%3Den

.gov

https://comptox.epa.gov/dashboard/dsstoxdb/results?search=Valencene

https://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr557.pdf

PEL

NA

TLV

NA

LD-50 Oral

NA

Human Toxicology Values

Not a known carcinogen

Not a known mutgen

Not a know teratogen

Not a known reproductive toxin

Non-Human Toxicology Values

NA

 

 

 

 

 

 

 Summary of Toxicity and Health Concerns

 

NO

Compound

Concerns

1

d-Limonene 

LD-50 Rat 4400 Mg/Kg, May cause adverse reproductive effects and birth defects (teratogenic), It may affect behavior/central nervous and peripheral nervous system. Central nervous system effects may include excitement, somnolence, delirium, ataxia, convulsions, and stupor while peripheral system effects may include spastic paralysis.

 

It may affect respiration (respiratory depression, choking, coughing, dyspnea, cyanosis). Other symptoms may include cyanosis, fever, and tachycardia.

 

Systemic absorption of large doses may produce pulmonary edema and chemical pneumonitis. The urine may smell like violets.

 

Chronic Potential Health Effects:

 

Ingestion: Prolonged or repeated ingestion may produce nausea,

lowered blood sugar and cholesterol, and kidney damage (hematuria, albuminuria, tubular necrosis), and may also affect the liver. Skin: It may be a weak sensitizer and responsible for some rare allergic responses (dermatitis

 

2

Beta Myrcene

LD-50 Rat 5000 

 

It may affect behavior/central nervous and peripheral nervous system. Central nervous system effects may include excitement, somnolence, delirium, ataxia, convulsions, and stupor while peripheral system effects may include spastic paralysis.

 

It may affect respiration (respiratory depression, choking, coughing, dyspnea, cyanosis). Other symptoms may include cyanosis, fever, and tachycardia.

 

Systemic absorption of large doses may produce pulmonary edema and chemical pneumonitis. The urine may smell like violets.

 

Chronic Potential Health Effects:

 

Ingestion: Prolonged or repeated ingestion may produce nausea,

lowered blood sugar and cholesterol, and kidney damage (hematuria, albuminuria, tubular necrosis), and may also affect the liver. Skin: It may be a weak sensitizer and responsible for some rare allergic responses (dermatitis

 

Proposed as a CA Measure 65 carcinogen.  https://oehha.ca.gov/proposition-65/crnr/notice-intent-list-beta-myrcene

 

Fema GRAS substance status.  https://www.femaflavor.org/fema-gras-flavoring-substance-list

 

b-Myrcene toxicology studies.  https://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr557.pdf

 

GRAS flavoring substances:  http://www.ift.org/~/media/Food%20Technology/pdf/2005/08/0805feat_gras22complete.pdf

 

FDA GRAS list:

https://www.accessdata.fda.gov/scripts/fdcc/index.cfm?set=SCOGS&sort=Sortsubstance&order=ASC&startrow=201&type=basic&search=

 

3

Beta Caryophellene

LD-50 Rat NA

4

Linalool

LD-50 Rat 2790 mg/kg

5

Alpha pinene

LD-50 Rat 3700 mg/kg

6

Beta Pinene

LD-50 Rat 3700 mg/kg

7

Humulene

LD-50 Rat >48 mg/kg

8

Nerolidol

LD-50 Rat >5000 mg/kg

9

Alpha Bisabolol

LD-50 Rat >5000 mg/kg

10

Terpinolene

LD-50 Rat 4390 mg/kg

11

alpha Terpineol

LD-50 Rat NA

12

Citral 

LD-50 Rat 4960 mg/kg

13

Eucalyptol 

LD-50 Rat 2580 mg/kg

14

Ocimene 

LD-50 Rat NA

15

L-Limonene

LD-50 Rat NA

16

Camphor 

LD-50 Rat 1310  mg/kg      Special Remarks on Chronic Effects on Humans:

May affect genetic material based on animal data. Passes through the placental barrier in human.

 

Special Remarks on other Toxic Effects on Humans:

 

Acute Potential Health Effects: Skin: Causes skin irritation. May cause epileptic seizures. Eye: Causes eye irritation.

 

May cause epileptic seizures. Inhalation: Causes irritation of the respiratory tract (mucous membranes)and may cause

emphysema.

 

May affect behavior - the brain and Central Nervous system (muscle contraction and spasticity).

 

May affect the heart. Ingestion: Cause irritation of the gastrointestional tract (nausea, vomiting.

 

May affect behavior - the brain and Central Nervous system (dizziness, convulsions, seizures, change of motor activity, rigidity). May be harmful if swallowed.

 

Certain medical conditions may be aggravated by exposure: kidney disorders, liver disorders, heart disorders, epilepsy. Chronic Potential Health Effects: none identified.                                

17

Camphene

LD-50 Rat >5 gm/kg

18

Eugenol 

LD-50 Rat 1930

19

Citronellol 

LD-50 Rat 2420

20

Menthol

LD-50 Cat 800 mg/kg

21

Borneol 

LD-50 Rat 5800 mg/kg

22

Alpha fenchone 

LD-50 Rat NA

23

Fenchol 

LD-50 Rat NA

24

Alpha phellandrene

LD-50 Rat NA

25

Delta - 3 - Carene

LD-50 Rat 4800 mg/kg

26

Farnesene 

LD-50 Rat NA

27

Geraniol 

LD-50 Rat 3600 mg/kg

28

Nerol

LD-50 Rat 4500 mg/kg

29

Gamma terpinene

LD-50 Rat 3650 mg/kg

30

Valencene 

LD-50 Rat NA

 Sooo, to summarize the toxicity of the 31 terpenes and terpenoids above, the poison is always in the dosage, and none show toxicity at the levels encountered vaporizing, but there are concerns with d-Limonene being a teratogen, b-Myrcene being a carcinogen, and Camphor being a mutagenic and inducing epileptic seizures. 

b-Myrcene also has Fema GRAS status, confusing things somewhat, but is also a major component of beer and if it were a serious carcinogen, you would ostensibly expect to see increased levels of kidney and liver cancers amongst beer drinkers.   

It does however bring us to the observation that more than 200 volatile compounds are found in cannabis, and we just looked at 30 major ones, how about the other 169 or so? 

To answer that in part, check up the next article in our series, The Oxford Academic Botanical Journal Follow up, which addresses 68 of the volatile compounds found in the Northern Lights and Hawaiian Indica male and female plants that they tested, not just the most common ones. 

In closing, note the colors of the different terpenes and terpenoids above, and the only one that isn't clear, white, or pale yellow is C20H40-O Phytol, a diterpenoid, which can be yellow to red.  Some of the C15 flavonoids are also red, and we will be discussing them later. 

A big thanks to Extract Consultants who continues to furnish all of the terpenes and terpenoids that we’ve used in our experiments, as well as in support of these series of articles. 

While many terpenes available today are synthetic, Extract Consultants offer all-natural organic forms of the terpene concentrates and blends, which are available in sizes suitable for individual use, through commercial bulk quantities, as well as in Terpene Sampler Kits.


Print  

Comments powered by CComment