Caryophyllene

{{#if:204.36 g/molC₁₅H₂₄0.9052 g/cm³262-264 °C; 129-130 °C (14 mm Hg)|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties

Caryophyllene
File:Beta-Caryophyllen.svg
IUPAC name 4,11,11-trimethyl-8-methylene- bicyclo[7.2.0]undec-4-ene
Other names β-Caryophyllene; trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
Identifiers
CAS number	87-44-5 7pxY
PubChem	5281515
ChemSpider	4444848 7pxY
UNII	BHW853AU9H 7pxY
ChEBI	CHEBI:10357 7pxY
ChEMBL	CHEMBL445740 7pxY
Jmol-3D images	Image 1
SMILES C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C <p><p style="word-wrap: break-word;">
InChI InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 7pxY Key: NPNUFJAVOOONJE-GFUGXAQUSA-N 7pxY InChI=1/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 Key: NPNUFJAVOOONJE-GFUGXAQUBC
Molecular formula	C15H24
Molar mass	204.36 g/mol
Density	0.9052 g/cm3
Boiling point	262-264 °C; 129-130 °C (14 mm Hg)
14pxY (verify) (what is: 10pxY/10pxN?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Caryophyllene (11px /ˌkæri.ɵfɪˈliːn/), or (−)-β-caryophyllene, 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 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.

Natural sources

The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ([ ]):

• Cannabis, hemp, marijuana (Cannabis sativa) [3.8–37.5% of cannabis flower essential oil]
• Black Caraway (Carum nigrum) [7.8%]
• Cloves (Syzygium aromaticum) [3.56% of clove bud essential oil]
• Hops (Humulus lupulus) [5.1–14.5%]
• Basil (Ocimum spp.) [5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum]
• Oregano (Origanum vulgare) [4.9%]
• Black pepper (Piper nigrum) [7.29%]
• West African Pepper (Piper guineense) [57.59% (black); 51.75% (white)]
• Rosemary (Rosmarinus officinalis) [0.1–8.3%]
• True cinnamon (Cinnamomum zeylanicum) [6.9–11.1%]
• Malabathrum (Cinnamomum tamala) [25.3%]

Compendial status

• Food Chemical Codex ^,

External links

• "Some Proof that Marijuana is a Powerful Medicine", Aaron Rowe, Wired Magazine, June 29, 2008de:Caryophyllene