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β-Caryophyllene

β-Caryophyllene Structure
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
MOL File:
87-44-5.mol
Modify Date:
2024/10/16 17:52:58

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)
form Liquid
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℃
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

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
NFPA 704
1
0 0

β-Caryophyllene price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 1SAMPLE-K ₹4880.63 2022-06-14 Buy
Sigma-Aldrich(India) W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 1KG ₹6760.95 2022-06-14 Buy
Sigma-Aldrich(India) W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 9KG ₹37585.95 2022-06-14 Buy
Sigma-Aldrich(India) W225207 β-Caryophyllene ≥80%, FCC, FG 87-44-5 20KG ₹45343.58 2022-06-14 Buy
Sigma-Aldrich 22075 (−)-trans-Caryophyllene ≥98.0% (sum of enantiomers, GC) 87-44-5 1ML ₹5867.03 2022-06-14 Buy
Product number Packaging Price Buy
W225207 1SAMPLE-K ₹4880.63 Buy
W225207 1KG ₹6760.95 Buy
W225207 9KG ₹37585.95 Buy
W225207 20KG ₹45343.58 Buy
22075 1ML ₹5867.03 Buy

β-Caryophyllene Chemical Properties,Uses,Production

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.

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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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