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Caryophyllene (), or (−)-ß-caryophyllene, is a natural bicyclic sesquiterpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
 that is a constituent of many essential oil
Essential oil

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material 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 plant in the Cannabaceae family. It is a herb that has been used throughout recorded history by humans as a source of fiber, for its seed oil, as food , as a drug , as medicine , and for spiritual purposes ....
, and rosemary Rosmarinus oficinalis
Rosemary

Rosemary is a woody, perennial plant herb with fragrant evergreen needle-like leaf. It is native to the Mediterranean region. It is a member of the mint family Lamiaceae, which also includes many other herbs....
. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and a-humulene
Humulene

Humulene, or a-humulene or a-caryophyllene, is a naturally-occurring monocyclic terpene. It is found in the essential oils of Humulus lupulus from which it derives its name, Lindera strychnifolia and others....
 (obsolete name: a-caryophyllene), a ring-opened isomer.






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Caryophyllene (), or (−)-ß-caryophyllene, is a natural bicyclic sesquiterpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
 that is a constituent of many essential oil
Essential oil

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material 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 plant in the Cannabaceae family. It is a herb that has been used throughout recorded history by humans as a source of fiber, for its seed oil, as food , as a drug , as medicine , and for spiritual purposes ....
, and rosemary Rosmarinus oficinalis
Rosemary

Rosemary is a woody, perennial plant herb with fragrant evergreen needle-like leaf. It is native to the Mediterranean region. It is a member of the mint family Lamiaceae, which also includes many other herbs....
. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and a-humulene
Humulene

Humulene, or a-humulene or a-caryophyllene, is a naturally-occurring monocyclic terpene. It is found in the essential oils of Humulus lupulus from which it derives its name, Lindera strychnifolia and others....
 (obsolete name: a-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane
Cyclobutane

Cyclobutane, C4H8, with a molecular mass of 56.107g/mol, is a four carbon alkane in which all the carbon atoms are arranged cyclically, hence cyclobutane....
 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 plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
. Recently, in a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich
ETH Zurich

ETH Z?rich or Swiss Federal Institute of Technology Z?rich is a science and technology university in the Z?rich, Switzerland. Locals sometimes refer to it by the name Poly, derived from the original name Eidgen?ssisches Polytechnikum or Federal Polytechnic Institute....
), beta-caryophyllene was shown to selectively bind to the cannabinoid receptor
Cannabinoid receptor

The cannabinoid receptors are a class of Receptor s under the G-protein coupled receptor superfamily. Their ligand s are known as cannabinoids or endocannabinoids depending on whether they come from external or internal sources, respectively....
 type-2 (CB2
Cannabinoid receptor 2 (macrophage)

Cannabinoid receptor 2 , also known as CB2 or CNR2, is a human gene. The protein encoded by this gene is a G protein-coupled receptor from the cannabinoid receptor family....
) 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 Receptor s that are involved in a variety of physiological processes including appetite, nociception, Mood , and memory....
 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

  • Cannabis, hemp, marijuana (Cannabis sativa
    Cannabis sativa

    Cannabis sativa is an annual plant in the Cannabaceae family. It is a herb that has been used throughout recorded history by humans as a source of fiber, for its seed oil, as food , as a drug , as medicine , and for spiritual purposes ....
    )
  • Caraway (Carum carvi)
  • Cloves (Syzygium aromaticum)
  • Hops
    Hops

    Hops are the female flower cones, also known as strobiles, of the hop . They are used primarily as a flavoring and stability agent in beer, though hops are also used for various purposes in other beverages and Herbalism....
     (Humulus lupulus
    Humulus lupulus

    Humulus lupulus is a species of Humulus in the Cannabaceae family.Common hop is a dioecious, Perennial plant herbaceous climbing plant which sends up new shoots in early spring and dies back to the cold-hardy rhizome in autumn....
    )
  • Many Ocimum
    Ocimum

    Ocimum is a genus of about 35 species of aromatic annual and perennial herbs and shrubs in the family Lamiaceae, native to the tropical and warm temperate regions of the Old World....
     (Basil) species
  • Oregano (Origanum vulgare)
  • Pepper (Piper nigrum)
  • Rosemary (Rosmarinus oficinalis
    Rosemary

    Rosemary is a woody, perennial plant herb with fragrant evergreen needle-like leaf. It is native to the Mediterranean region. It is a member of the mint family Lamiaceae, which also includes many other herbs....
    )
  • True cinnamon (Cinnamomum zeylanicum)


trans-Caryophyllene constitutes about 3.8–37.5% of cannabis flower essential oil
Cannabis flower essential oil

Cannabis flower essential oil, also known as hemp essential oil, is obtained by steam distillation from the flowers and upper leaves of the Cannabis plant....
.

Essential oil of cinnamon (Cinnamomum zeylanicum) contains about 6.9–11.1% beta-caryophyllene.

External links

  • , Aaron Rowe, Wired Magazine, June 29, 2008