Caryophyllene
Encyclopedia
Caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene
that is a constituent of many essential oil
s, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of hemp Cannabis sativa
, rosemary Rosmarinus oficinalis
, and hops
. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene
(obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane
ring, a rarity in nature.
Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper
. In a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich
), beta-caryophyllene was shown to selectively bind to the cannabinoid receptor
type-2 (CB2
) and to exert significant cannabimimetic antiinflammatory effects in mice. Since the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system
is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychomimetic effects.
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.
of each source is given in square brackets ([ ]):
Sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations...
that is a constituent of many essential oil
Essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
s, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of hemp Cannabis sativa
Cannabis sativa
Cannabis sativa is an annual herbaceous plant in the Cannabaceae family. Humans have cultivated this herb throughout recorded history as a source of industrial fibre, seed oil, food, recreation, spiritual enlightenment and medicine...
, rosemary Rosmarinus oficinalis
Rosemary
Rosemary, , is a woody, perennial herb with fragrant, evergreen, needle-like leaves and white, pink, purple or blue flowers, native to the Mediterranean region. It is a member of the mint family Lamiaceae, which includes many other herbs, and is one of two species in the genus Rosmarinus...
, and hops
Hops
Hops are the female flower clusters , of a hop species, Humulus lupulus. They are used primarily as a flavoring and stability agent in beer, to which they impart a bitter, tangy flavor, though hops are also used for various purposes in other beverages and herbal medicine...
. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene
Humulene
Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene, which is a terpenoid consisting of 3 isoprene units. It is found in the essential oils of Humulus lupulus from which it derives its name. It is an isomer of β-caryophyllene, and the two are...
(obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane
Cyclobutane
Cyclobutane is an organic compound with the formula 4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes...
ring, a rarity in nature.
Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper
Black pepper
Black pepper is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit, known as a peppercorn when dried, is approximately in diameter, dark red when fully mature, and, like all drupes, contains a single seed...
. In a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich
ETH Zurich
The Swiss Federal Institute of Technology Zurich or ETH Zürich is an engineering, science, technology, mathematics and management university in the City of Zurich, Switzerland....
), beta-caryophyllene was shown to selectively bind to the cannabinoid receptor
Cannabinoid receptor
The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...
type-2 (CB2
Cannabinoid receptor 2 (macrophage)
Cannabinoid receptor 2 , also known as CB2 or CNR2, is a G protein-coupled receptor from the cannabinoid receptor family, which in humans is encoded by the CNR2 gene...
) and to exert significant cannabimimetic antiinflammatory effects in mice. Since the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system
Endocannabinoid system
The endocannabinoid system refers to a group of neuromodulatory lipids and their receptors that are involved in a variety of physiological processes including appetite, pain-sensation, mood, and memory; it mediates the psychoactive effects of cannabis and, broadly speaking, includes:* The...
is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychomimetic effects.
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.
Natural sources
The approximate quantity of caryophyllene in the essential oilEssential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
of each source is given in square brackets ([ ]):
- CannabisCannabisCannabis is a genus of flowering plants that includes three putative species, Cannabis sativa, Cannabis indica, and Cannabis ruderalis. These three taxa are indigenous to Central Asia, and South Asia. Cannabis has long been used for fibre , for seed and seed oils, for medicinal purposes, and as a...
, hempHempHemp is mostly used as a name for low tetrahydrocannabinol strains of the plant Cannabis sativa, of fiber and/or oilseed varieties. In modern times, hemp has been used for industrial purposes including paper, textiles, biodegradable plastics, construction, health food and fuel with modest...
, marijuana (Cannabis sativaCannabis sativaCannabis sativa is an annual herbaceous plant in the Cannabaceae family. Humans have cultivated this herb throughout recorded history as a source of industrial fibre, seed oil, food, recreation, spiritual enlightenment and medicine...
) [3.8–37.5% of cannabis flower essential oilCannabis flower essential oilCannabis flower essential oil, also known as hemp essential oil, is obtained by steam distillation from the flowers and upper leaves of the Cannabis plant...
] - Black Caraway (Carum nigrum) [7.8%]
- CloveCloveCloves are the aromatic dried flower buds of a tree in the family Myrtaceae. Cloves are native to the Maluku islands in Indonesia and used as a spice in cuisines all over the world...
s (Syzygium aromaticum) [3.56% of clove bud essential oilOil of clovesOil of cloves, also known as clove oil, is an essential oil from the clove plant, Syzygium aromaticum.* CAS number: 8000-34-8It is a natural analgaesic and antiseptic used primarily in dentistry for its main ingredient eugenol...
] - HopsHopsHops are the female flower clusters , of a hop species, Humulus lupulus. They are used primarily as a flavoring and stability agent in beer, to which they impart a bitter, tangy flavor, though hops are also used for various purposes in other beverages and herbal medicine...
(Humulus lupulusHumulus lupulusHumulus lupulus is a species of Humulus in the Cannabaceae family.Common hop is a dioecious, perennial herbaceous climbing plant which sends up new shoots in early spring and dies back to the cold-hardy rhizome in autumn...
) [5.1–14.5%] - BasilBasilBasil, or Sweet Basil, is a common name for the culinary herb Ocimum basilicum , of the family Lamiaceae , sometimes known as Saint Joseph's Wort in some English-speaking countries....
(OcimumOcimumOcimum is a genus of about 35 species of aromatic annual and perennial herbs and shrubs in the family Lamiaceae, mostly native to the tropical and warm temperate regions of the Old World.Some species include:...
spp.) [5.3–10.5% O. gratissimumOcimum gratissimumOcimum gratissimum, also known as Clove Basil, African Basil, and in Hawaii as Wild Basil, is a species of Ocimum. It is naturalized in Hawaii.-Pharmacology of extracts and essential oils:...
; 4.0–19.8% O. micranthum] - OreganoOreganoOregano – scientifically named Origanum vulgare by Carolus Linnaeus – is a common species of Origanum, a genus of the mint family . It is native to warm-temperate western and southwestern Eurasia and the Mediterranean region.Oregano is a perennial herb, growing from 20–80 cm tall,...
(Origanum vulgare) [4.9%] - Black pepperBlack pepperBlack pepper is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit, known as a peppercorn when dried, is approximately in diameter, dark red when fully mature, and, like all drupes, contains a single seed...
(Piper nigrum) [7.29%] - West African PepperWest African PepperWest African Pepper, also known as Ashanti Pepper, Benin Pepper, False Cubeb, Guinea Cubeb, Uziza Pepper or "Guinea pepper", called locally kale, kukauabe, masoro, sasema and soro wisa, is a West African spice that corresponds to the dried fruit of Piper guineense...
(Piper guineense) [57.59% (black); 51.75% (white)] - RosemaryRosemaryRosemary, , is a woody, perennial herb with fragrant, evergreen, needle-like leaves and white, pink, purple or blue flowers, native to the Mediterranean region. It is a member of the mint family Lamiaceae, which includes many other herbs, and is one of two species in the genus Rosmarinus...
(Rosmarinus officinalisRosemaryRosemary, , is a woody, perennial herb with fragrant, evergreen, needle-like leaves and white, pink, purple or blue flowers, native to the Mediterranean region. It is a member of the mint family Lamiaceae, which includes many other herbs, and is one of two species in the genus Rosmarinus...
) [0.1–8.3%] - True cinnamon (Cinnamomum zeylanicum) [6.9–11.1%]
- MalabathrumMalabathrumMalabathrum, also known as Malobathrum or Malabar leaf, is the name used in classical and medieval texts for the leaf of the plant Cinnamomum tamala . In ancient Greece and Rome, the leaves were used to prepare a fragrant oil, called Oleum Malabathri, and were therefore valuable...
(Cinnamomum tamala) [25.3%]
External links
- "Some Proof that Marijuana is a Powerful Medicine", Aaron Rowe, Wired Magazine, June 29, 2008