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β-Caryophyllene

CAS No.
87-44-5
Chemical Name:
β-Caryophyllene
Synonyms
CARYOPHYLLENE;β-Caryophyllene;TRANS-CARYOPHYLLENE;B-CARYOPHYLLENE;β-caryophyllen;β-caryophyllen;(E)-Caryophyllene;1-caryophyllene;Bicyclo7.2.0undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-;L-Caryophyllene
CBNumber:
CB3414149
Molecular Formula:
C15H24
Molecular Weight:
204.35
MDL Number:
MFCD00075925
MOL File:
87-44-5.mol
Last updated:2024-04-24 17:21:45

β-Caryophyllene 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℃
FEMA 2252 | BETA-CARYOPHYLLENE
refractive index n20/D 1.5(lit.)
Flash point 205 °F
storage temp. -20°C
solubility Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
color Colourless
Specific Gravity 0.90
Odor at 100.00 %. sweet woody spice clove dry
Odor Type spicy
optical activity [α]23/D 7.5°, neat
Water Solubility 88μg/L at 20℃
Merck 14,1875
JECFA Number 1324
BRN 2044564
Stability Light Sensitive
LogP 6.23 at 25℃
Substances Added to Food (formerly EAFUS) BETA-CARYOPHYLLENE
FDA 21 CFR 172.515
CAS DataBase Reference 87-44-5(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII BHW853AU9H
EPA Substance Registry System Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (87-44-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H304-H317
Precautionary statements  P261-P272-P280-P301+P310-P302+P352-P331
Risk Statements  36/37/38
Safety Statements  26-36-24/25
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  1
RTECS  DT8400000
HS Code  29021990
NFPA 704
1
0 0

β-Caryophyllene price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W225299 β-Caryophyllene natural, ≥80%, FG 87-44-5 SAMPLE-K $56 2024-03-01 Buy
Sigma-Aldrich W225299 β-Caryophyllene natural, ≥80%, FG 87-44-5 1KG $117 2024-03-01 Buy
Sigma-Aldrich W225299 β-Caryophyllene natural, ≥80%, FG 87-44-5 9KG $526 2024-03-01 Buy
Sigma-Aldrich W225299 β-Caryophyllene natural, ≥80%, FG 87-44-5 20KG $656 2024-03-01 Buy
Sigma-Aldrich W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 1kg $79.8 2024-03-01 Buy
Product number Packaging Price Buy
W225299 SAMPLE-K $56 Buy
W225299 1KG $117 Buy
W225299 9KG $526 Buy
W225299 20KG $656 Buy
W225207 1kg $79.8 Buy

β-Caryophyllene Chemical Properties,Uses,Production

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. 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). β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 μM in a reporter assay). 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+). 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. 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 .

Chemical Properties

β-Caryophyllene has a woody-spicy, dry, clove-like aroma.

Chemical Properties

Clear colorless liquid

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.

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.

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.

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

General Description

Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

The 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.

Fire Hazard

BETA-CARYOPHYLLENE is combustible.

Safety Profile

A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

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).

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View Lastest Price from β-Caryophyllene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Beta-Caryophyllene pictures 2024-04-24 Beta-Caryophyllene
87-44-5
US $10.00 / kg 1kg 99.6% 100000 Ouhuang Engineering Materials (Hubei) Co., Ltd
β-Caryophyllene  pictures 2024-03-28 β-Caryophyllene
87-44-5
US $0.00 / kg 25kg 98% Inquiry PNP Biotech Co. Ltd
β-Caryophyllene pictures 2023-10-11 β-Caryophyllene
87-44-5
US $0.00-0.00 / kg 1kg 0.99 50000kg Hebei Yibangte Import and Export Co. , Ltd.
  • Beta-Caryophyllene pictures
  • Beta-Caryophyllene
    87-44-5
  • US $10.00 / kg
  • 99.6%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
  • β-Caryophyllene pictures
  • β-Caryophyllene
    87-44-5
  • US $0.00-0.00 / kg
  • 0.99
  • Hebei Yibangte Import and Export Co. , Ltd.
CARYOPHYLLENE, (-)-trans-(SG) HUMULENE, alpha-(SG) 8-METHYLENE-4,11,11-TRIMETHYLBICYCLO-UNDEC-4-ENE CAROPHYLENE BETA-CARYPOPHYLLENE CARYOPHYLLEN BETA NATUERLICH NATURAL β-CARYOPHYLLENE B-CARYOPHYLLENE, NATURAL 8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE FCC (-)-TRANS-CARYOPHYLLENE WITH GC BETA-CARYOPHYLLENE 80+% FCC (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 BETA-CARYOPHYLLEN BETA-CARYOPHYLLENE CARYOPHYLLENE, (-)-TRANS- FEMA 2252 TRANS-(1R,9S)-8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE (-) TRANS CARYOPHYLLEN (-)-TRANS-CARYOPHYLLENE (-)-E-caryophyllene (E)-beta-Caryophylene [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 8-methylene-4,11,11-trimethyl-,(e)-(1r,9s)-(-)-bicyclo(7.2.0)undec-4-en beta-(E)-Caryophyllene beta-cariofillene beta-trans-caryophyllene Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)- Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]- Caryophyllene (E) CARYOPHYLLENE ,alpha + beta MIXT. E-beta-caryophyllene t-.beta.-caryophyllene (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene (E,1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene 1R-(1R*,4E,9S*)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0] B-Caryophyllene Fcc ()-trans-Caryophyllene,β-Caryophyllene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene β-Caryophyllene,()-trans-Caryophyllene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene β-Caryophyllene, froM CinnaMoMuM caMphora (-)-trans-Caryophyllene >=98.5% (suM of enantioMers, GC) β-Caryophyllene Beta-87-44-5 factory Direct Salebest in Quality NATURAL B-CARYOPHYLLENE TIANFU CHEM-- BETA-CARYOPHYLLENE (1R,9S,E)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene beta-Caryophyllene solution Eugenol EP Impurity A β-Caryophyllene, 90%, from Cinnamomum camphora (L.) J. Presl β-Caryophyllene ( (-)-trans-Caryophyllene) (-)-trans-Caryophyllene Solution (-)-trans-Caryophyllene@100 μg/mL in Methanol (-)-β-caryophyllene BETA-CARYOPHYLLENE USP/EP/BP