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β-Caryophyllene

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CAS:87-44-5
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β-Caryophyllene Basic information
Product Name:β-Caryophyllene
Synonyms:β-caryophyllen;1-caryophyllene;2-Methylene-6,10,10-trimethyl bicyclo[7.2.0]undec-5-ene;BetaCarryophellene;β-caryophyllene,[1R-(1R,4E,9S)]-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene,(E)-caryophyllene;Bicyclo7.2.0undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-;CARYOPHYLLENE, (-)-trans-(SG);HUMULENE, alpha-(SG)
CAS:87-44-5
MF:C15H24
MW:204.35
EINECS:201-746-1
Product Categories:Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sesqui-Terpenoids;Biochemistry;Terpenes;Terpenes (Others)
Mol File:87-44-5.mol
β-Caryophyllene Structure
β-Caryophyllene Chemical Properties
Melting point <25℃
alpha D -8 to -9° (chloroform)
Boiling point 129-130 °C/14 mmHg (lit.)
density 0.901 g/mL at 25 °C (lit.)
vapor pressure 6Pa at 20℃
refractive index n20/D 1.5(lit.)
FEMA 2252 | BETA-CARYOPHYLLENE
Fp 205 °F
storage temp. -20°C
solubility Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
form Liquid
color Colourless
Specific Gravity0.90
Odorat 100.00 %. sweet woody spice clove dry
Odor Typespicy
Optical Rotation[α]23/D 7.5°, neat
biological sourcesynthetic
Water Solubility 88μg/L at 20℃
Merck 14,1875
JECFA Number1324
BRN 2044564
Stability:Light Sensitive
Major Applicationcleaning products
cosmetics
flavors and fragrances
food and beverages
personal care
Cosmetics Ingredients FunctionsPERFUMING
SKIN CONDITIONING
FRAGRANCE
InChI1S/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
InChIKeyNPNUFJAVOOONJE-GFUGXAQUSA-N
SMILES[H][C@@]12CC\C(C)=C\CCC(=C)[C@H]1CC2(C)C
LogP6.23 at 25℃
CAS DataBase Reference87-44-5(CAS DataBase Reference)
EPA Substance Registry SystemBicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (87-44-5)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36-24/25
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 1
RTECS DT8400000
TSCA TSCA listed
HS Code 29021990
Storage Class10 - Combustible liquids
Hazard ClassificationsAsp. Tox. 1
Skin Sens. 1B
MSDS Information
ProviderLanguage
SigmaAldrich English
β-Caryophyllene Usage And Synthesis
Descriptionβ-Caryophyllene is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties.
Chemical Propertiesβ-Caryophyllene has a woody-spicy, dry, clove-like aroma.
OccurrenceThree isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry, black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and caraway herb.
Usesβ-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.
DefinitionChEBI: A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of <greek beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.
PreparationIsolated from oil of clove stems and separated from eugenol by treating the oil with 7% sodium carbonate solution, extracting with ether, repeating the carbonate treatment on the concentrated extracts, and finally steam distilling.
Aroma threshold valuesDetection at 64 to 90 ppb
Taste threshold valuesTaste characteristics at 50 ppm: spicy, pepper-like, woody, camphoraceous with a citrus background.
Synthesis Reference(s)Journal of the American Chemical Society, 86, p. 485, 1964 DOI: 10.1021/ja01057a040
Air & Water ReactionsInsoluble in water.
Reactivity ProfileThe unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.
Health effectsβ-caryophyllene has shown anti-inflammatory activity via decreasing TLR-4, IL-1?, and  TNF-α levels. It attenuated oxidative stress by restoring antioxidant enzymes and repressing lipid peroxidation as well as GSH  depletion.
Fire HazardBETA-CARYOPHYLLENE is combustible.
Safety ProfileA skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
CarcinogenicityCaryophyllene showed significant activity as an inducer of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis (253a).
References[1] HAZEKAMP A, TEJKALOVá K, PAPADIMITRIOU S A. Cannabis: From Cultivar to Chemovar II—A Metabolomics Approach to Cannabis Classification[C]. 2016: 0. DOI: 10.1089/can.2016.0017
[2] CHUNYAN WU . trans-Caryophyllene is a natural agonistic ligand for peroxisome proliferator-activated receptor-α[J]. Bioorganic & Medicinal Chemistry Letters, 2014, 24 14: Pages 3168-3174. DOI: 10.1016/j.bmcl.2014.04.112
[3] GUIFANG WANG  Jingwei D  Weibin Ma. β-Caryophyllene (BCP) ameliorates MPP+ induced cytotoxicity.[J]. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2018: 1086-1091. DOI: 10.1016/j.biopha.2018.03.168
[4] YUJIE CHENG  Sha L  Zhi Dong. β-Caryophyllene ameliorates the Alzheimer-like phenotype in APP/PS1 Mice through CB2 receptor activation and the PPARγ pathway.[J]. Pharmacology, 2014, 94 1-2: 1-12. DOI: 10.1159/000362689
[5] AMINE BAHI . β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice[J]. Physiology & Behavior, 2014, 135: Pages 119-124. DOI: 10.1016/j.physbeh.2014.06.003
[6] L.I.G. PAULA-FREIRE . The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice[J]. Phytomedicine, 2014, 21 3: Pages 356-362. DOI: 10.1016/j.phymed.2013.08.006
[7] JüRG GERTSCH. Beta-caryophyllene is a dietary cannabinoid.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2008, 105 26: 9099-9104. DOI: 10.1073/pnas.0803601105
[8] HANNAH C. HUFF. Differential Interactions of Selected Phytocannabinoids with Human CYP2D6 Polymorphisms[J]. Biochemistry Biochemistry, 2021, 60 37: 2749-2760. DOI: 10.1021/acs.biochem.1c00158
Tag:β-Caryophyllene(87-44-5) Related Product Information
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