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BETA-CARYOPHYLLENE

CAS No.
87-44-5
Chemical Name:
BETA-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
Modify Date:2022-08-15 17:40:08

BETA-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.)
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)
form neat
Specific Gravity 0.90
color Colourless
optical activity [α]23/D 7.5°, neat
JECFA Number 1324
Merck 14,1875
BRN 2044564
Stability Light Sensitive
CAS DataBase Reference 87-44-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) BETA-CARYOPHYLLENE
FDA 21 CFR 172.515
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) 
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

BETA-CARYOPHYLLENE price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 1kg $78.7 2022-05-15 Buy
Sigma-Aldrich W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 9kg $372 2022-05-15 Buy
Sigma-Aldrich W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 20kg $535 2022-05-15 Buy
Sigma-Aldrich PHL80717 (−)-trans-Caryophyllene phyproof? Reference Substance 87-44-5 100MG $231 2022-05-15 Buy
Sigma-Aldrich CRM40483 beta-Caryophyllene solution certified reference material, 2000?μg/mL in methanol, ampule of 1?mL 87-44-5 1mL $151 2022-05-15 Buy
Product number Packaging Price Buy
W225207 1kg $78.7 Buy
W225207 9kg $372 Buy
W225207 20kg $535 Buy
PHL80717 100MG $231 Buy
CRM40483 1mL $151 Buy

BETA-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).

Global( 319)Suppliers
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Henan DaKen Chemical CO.,LTD.
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Hebei Guanlang Biotechnology Co., Ltd.
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Xi'an Kono chem co., Ltd.,
029-86107037 13289246953 info@konochemical.com China 2996 58
Shaanxi Pioneer Biotech Co., Ltd .
+8613259417953 sales@pioneerbiotech.com China 3001 58
Hubei xin bonus chemical co. LTD
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View Lastest Price from BETA-CARYOPHYLLENE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-09-17 β-Caryophyllene
87-44-5
US $0.00 / kg 25kg 98% Inquiry PNP Biotech Co. Ltd
2021-07-23 BETA-CARYOPHYLLENE
87-44-5
US $1.00 / PCS 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2021-07-02 (-)-trans-Caryophyllene >=98.5% (sum of enantiomers, GC)
87-44-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi 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