Cannabis flower essential oil
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Cannabis flower essential oil, also known as hemp essential oil, is an
essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
obtained by
steam distillation Steam distillation is a separation process that consists in distilling water together with other volatile and non-volatile components. The steam from the boiling water carries the vapor of the volatiles to a condenser; both are cooled and re ...
from the flowers,
panicles A panicle is a much-branched inflorescence. (softcover ). Some authors distinguish it from a compound spike inflorescence, by requiring that the flowers (and fruit) be pedicellate (having a single stem per flower). The branches of a panicle ar ...
(flower cluster), stem, and upper leaves of the
hemp Hemp, or industrial hemp, is a botanical class of '' Cannabis sativa'' cultivars grown specifically for industrial or medicinal use. It can be used to make a wide range of products. Along with bamboo, hemp is among the fastest growing plants ...
plant (''Cannabis sativa L''.). Hemp essential oil is distinct from
hemp seed oil Hemp oil (hemp seed oil) is oil obtained by pressing hemp seeds. Cold pressed, unrefined hemp oil is dark to clear light green in color, with a nutty flavor. The darker the color, the grassier the flavour. It should not be confused with hash oi ...
(hemp oil) and
hash oil Hash oil or cannabis oil, is an oleoresin obtained by the extraction of cannabis or hashish. It is a cannabis concentrate containing many of its resins and terpenes – in particular, tetrahydrocannabinol (THC), cannabidiol (CBD), and other ...
: the former is a
vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or f ...
that is cold-pressed from the seeds of low-
THC Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...
varieties of hemp, the latter is a
THC Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...
-rich
extract An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts ...
of dried female hemp flowers (
marijuana Cannabis, also known as marijuana among other names, is a psychoactive drug from the cannabis plant. Native to Central or South Asia, the cannabis plant has been used as a drug for both recreational and entheogenic purposes and in various t ...
) or resin (
hashish Hashish ( ar, حشيش, ()), also known as hash, "dry herb, hay" is a drug made by compressing and processing parts of the cannabis plant, typically focusing on flowering buds (female flowers) containing the most trichomes. European Monitoring ...
). A pale yellow liquid, cannabis flower essential oil is a volatile oil that is a mixture of
monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...
s,
sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modific ...
s, and other
terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...
compounds. The typical scent of hemp results from about 140 different terpenoids. The essential oil is manufactured from both low-THC ("fibre-type") and high-THC ("drug-type") varieties of hemp. As most of the phytocannabinoids are nearly insoluble in water, hemp essential oil contains only traces of
cannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
. Even in "drug-type" hemp, the
THC Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...
content of the essential oil does not exceed 0.08%. Most of the material is produced in Canada, as well as small scale cultivations in Switzerland and Germany. Hemp essential oil is used as a scent in perfumes, cosmetics, soaps, and candles. It is also used as a flavoring in foods, primarily candy and beverages.


Yield

The yield depends on the hemp type (drug, fiber) and pollination; sex, age, and part of the plant; cultivation (indoor, outdoor etc.); harvest time and conditions; drying; and storage. For example, fresh buds from an Afghani variety yielded 0.29% essential oil. Drying and storage reduced the content from 0.29% to 0.20% after 1 week, and to 0.13% after 3 months. Monoterpenes showed a significantly greater loss than sesquiterpenes, but none of the major components completely disappeared in the drying process. About 1.3 L of essential oil per ton resulted from freshly harvested outdoor-grown hemp, corresponding to about 10 L/ha. The yield of nonpollinated ("
sinsemilla Cannabis sinsemilla () also known as sensimilla, sinse or sensi (can be translated into English as seedless cannabis) is the female ''Cannabis'' plant that has not been fertilized and therefore does not develop seeds, increasing the density of can ...
") hemp at 18 L/ha was more than twofold compared with pollinated hemp (8 L/ha).


Constituents

Sixty-eight components were detected by GC and GC/mass spectrometry (MS) in fresh bud oil distilled from high-potency, indoor-grown hemp. The 57 identified constituents were 92% monoterpenes, 7% sesquiterpenes, and approx. 1% other compounds (
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double b ...
s,
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
s). The dominating monoterpenes were
myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from ''Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. Π...
(67%) and
limonene Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The -isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring a ...
(16%). In the essential oil from outdoor-grown hemp, the monoterpene concentration varied between 47.9 and 92.1% of the total terpenoid content. The sesquiterpenes ranged from 5.2 to 48.6%. The most abundant monoterpene was β-
myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from ''Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. Π...
, followed by trans-
caryophyllene Caryophyllene (), more formally (−)-β-caryophyllene, (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of ''Syzygium aromaticum'' (cloves), the ess ...
, α-
pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...
, trans-
ocimene Ocimenes are a group of isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. α-Ocimene and the two β-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. ...
, and α-
terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
. Another report said there were 140 terpenoids, dominated by α-
pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...
and
limonene Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The -isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring a ...
which together often comprise 75% of the live plant's volatiles. However, extracted essential oils can change in composition, and the live plant, dried plant and essential oil can smell rather different. Even in "drug-type" hemp, the
THC Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...
content of the essential oil was not more than 0.08%. In the essential oil of five different European hemp cultivars, the dominating terpenes were
myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from ''Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. Π...
(21.1–35.0 %), α-
pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...
(7.2–14.6 %), α-
terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
(7.0–16.6 %), trans-
caryophyllene Caryophyllene (), more formally (−)-β-caryophyllene, (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of ''Syzygium aromaticum'' (cloves), the ess ...
(12.2.–18.9 %), and α-
humulene Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them be ...
(6.1–8.7 %). The main differences between the cultivars were found in the contents of α-
terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
and α-
pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...
. Other terpenoids present only in traces are
sabinene Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (''Quercus ilex'') and Norway spruce (''Picea abies''). It has a strained ...
, α-
terpinene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
, 1,8-
cineole Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up ~70% - 90% of eucal ...
(
eucalyptol Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up ~70% - 90% of eucal ...
),
pulegone Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as ''Nepeta cataria'' (catnip), ''Mentha piperita'', and pennyroyal. It is classified as a monoterpene. Pulegone is a clear colorles ...
, γ-
terpinene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
,
terpineol Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil ...
-4-ol,
bornyl acetate Bornyl acetate is a chemical compound. Its molecular formula is C12H20O2 and its molecular weight is 196.29 g/mol. It is the acetate ester of borneol. It is used as a food additive, flavouring agent, and odour agent. It is a component of the esse ...
, α-
copaene Copaene, or more precisely, α-copaene, is the common (or trivial) chemical name of an oily liquid hydrocarbon that is found in a number of essential oil-producing plants. The name is derived from that of the resin-producing tropical copaiba tree, ...
, alloaromadendrene, viridiflorene, β-
bisabolene Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) and are present in the essential oils of bisabol, and of a wide variety of o ...
, γ-
cadinene Cadinenes are a group of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. The name is derived from that of the Cade juniper (''Juniperus oxycedrus'' L.), the wood of which yields an oil from which cadinene is ...
, trans-β- farnesene, trans-
nerolidol Nerolidol, also known as peruviol and penetrol , is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers. There are four isomers of nerolidol', which differ in th ...
, and β-
bisabolol Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (''Matricaria recut ...
. The major
alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in wh ...
present in an essential oil obtained by extraction and steam distillation was the n-C29 alkane
nonacosane Nonacosane is a straight-chain hydrocarbon with a molecular formula of C29H60, and the structural formula CH3(CH2)27CH3. It has 1,590,507,121 constitutional isomers. Nonacosane occurs naturally and has been reported to be a component of a pheromon ...
(55.8 and 10.7%, respectively).


Uses

The various terpenes in cannabis have antifungal, antimicrobial, antiviral and insect repellent functions that could be commercially valuable when used externally. Cannabis essential oils that are cannabinoid-free have been tested for central nervous effects. Natural
monoterpenes Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...
and
sesquiterpenes Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificatio ...
from cannabis flowers have relaxing, sedative and anti-depressant effects when inhaled. Their application in
aromatherapy Aromatherapy is based on the usage of aromatic materials including essential oils and other aroma compounds, with claims for improving psychological and physical well-being. It is offered as a complementary therapy or as a form of alternative ...
is increasing, but the high price of the natural oil (50$ per milliliter) is a limiting factor. In Switzerland and Austria, specific landraces with high essential oil content but no discernible amounts of cannabinoids have been developed for the purpose of flavoring beverage products. For those applications, oils with high monoterpene percentages (but a low
alpha-humulene Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them be ...
or caryophyllene oxide concentration) are desirable. Terpenes used in THC vaping products, legal in some jurisdictions in the
United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...
, are not true cannabis terpenes, but synthetic and
racemic In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
with potential health hazards. Due to health promoting effects, natural THC-free cannabis flower oil is the preferred ingredient in the legal European market. Unregulated additives in US vaping products have led to serious health consequences, including fatal outcomes.


See also

*
Cannabis concentrate Cannabis concentrate (also called marijuana concentrate, marijuana extract, or cannabis extract) is a tetrahydrocannabinol (THC) and/or cannabidiol (CBD) concentrated mass. Cannabis concentrates contain high THC levels that range from 40% to ...
*
Cannabidiol Cannabidiol (CBD) is a phytocannabinoid discovered in 1940. It is one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. , clinical research on CBD in ...


References


Sources

* *


Further reading

* – discusses similar terpenes in hops and cannabis


External links


Hemp Essential Oil: Sweet Smell of Success
{{cannabis Essential oils Preparations of cannabis