| Identification | More | [Name]
BETA-CARYOPHYLLENE | [CAS]
87-44-5 | [Synonyms]
(1R,9S)-8-METHYLEN-4,11,11-TRIMETHYL-BICYCLO[7.2.0]UNDEC-4-ENE
8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE
B-CARYOPHYLLENE
BETA-CARYOPHYLLEN
BETA-CARYOPHYLLENE
CARYOPHYLLENE
CARYOPHYLLENE NATURAL
CARYOPHYLLENE, (-)-TRANS-
FEMA 2252
TRANS-(1R,9S)-8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE
(-) TRANS CARYOPHYLLEN
(-)-TRANS-CARYOPHYLLENE
TRANS-CARYOPHYLLENE
(-)-E-caryophyllene
(E)-beta-Caryophylene
(E)-Caryophyllene
[1R-(1R*,4E,9S*)]-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]-4-undecene
[1R-(1R*,4E,9S*)]-8-methylene-4,11,11-trimethylbicyclo[7.2.0]-4-undecane
4,11,11-trimethyl-8-methylene-,(1r-(1r*,4e,9s*))-bicyclo(7.2.0)undec-4-en
4,11,11-trimethyl-8-methylene-,[1R-(1R*,4E,9S*)]-Bicyclo[7.2.0]undec-4-ene | [EINECS(EC#)]
201-746-1 | [Molecular Formula]
C15H24 | [MDL Number]
MFCD00075925 | [Molecular Weight]
204.35 | [MOL File]
87-44-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
<25℃ | [alpha ]
D -8 to -9° (chloroform) | [Boiling point ]
129-130 °C/14 mmHg (lit.) | [density ]
0.902 g/mL at 20 °C(lit.)
| [vapor pressure ]
6Pa at 20℃ | [FEMA ]
2252 | [refractive index ]
n20/D 1.5(lit.)
| [Fp ]
205 °F
| [storage temp. ]
-20°C | [solubility ]
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
Colourless | [Specific Gravity]
0.90 | [Odor]
at 100.00 %. sweet woody spice clove dry | [biological source]
synthetic | [Odor Type]
spicy | [Optical Rotation]
[α]23/D 7.5°, neat | [Water Solubility ]
88μg/L at 20℃ | [JECFA Number]
1324 | [Merck ]
1875 | [BRN ]
2044564 | [Henry's Law Constant]
3.7×10-4 mol/(m3Pa) at 25℃, Copolovici and Niinemets (2015) | [Stability:]
Light Sensitive | [Major Application]
cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care | [Cosmetics Ingredients Functions]
PERFUMING
SKIN CONDITIONING
FRAGRANCE | [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 | [InChIKey]
NPNUFJAVOOONJE-GFUGXAQUSA-N | [SMILES]
[H][C@@]12CC\C(C)=C\CCC(=C)[C@H]1CC2(C)C | [LogP]
6.23 at 25℃ | [CAS DataBase Reference]
87-44-5(CAS DataBase Reference) | [EPA Substance Registry System]
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (87-44-5) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS08 | [Signal word ]
Danger | [Hazard statements ]
H304-H317 | [Precautionary statements ]
P261-P272-P280-P301+P310-P302+P352-P331 | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
1
| [RTECS ]
DT8400000
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HS Code ]
29021990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Asp. Tox. 1
Skin Sens. 1B | [Safety Profile]
A skin irritant.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. |
| Hazard Information | Back Directory | [General Description]
Pale yellow oily liquid with an odor midway between odor of cloves and turpentine. | [Reactivity Profile]
The unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE(87-44-5), 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. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
This chemical is combustible. | [Description]
β-Caryophyllene (Item No. 21572) 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.1,2,3,4,5,6 It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM).7 β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 μM in a reporter assay).2 β-Caryophyllene (1 and 2.5 μM) reduces the production of reactive oxygen species (ROS) in and protects against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+).3 It also decreases the β-amyloid burden in the hippocampus and cerebral cortex and improves memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day.4 β-Caryophyllene (50 mg/kg) increases the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 (Item No. 10006974).5 | [Chemical Properties]
Clear colorless liquid | [Chemical Properties]
β-Caryophyllene has a woody-spicy, dry, clove-like aroma. | [Occurrence]
Three 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. | [Uses]
β-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. | [Definition]
ChEBI: 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. | [Preparation]
Isolated 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 values]
Detection at 64 to 90 ppb | [Taste threshold values]
Taste 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 | [Health effects]
β-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. | [Carcinogenicity]
Caryophyllene 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). | [storage]
Store at -20°C | [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 |
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