β-Caryophyllene Property

Melting point:

<25℃

Boiling point:

129-130 °C/14 mmHg (lit.)

alpha 

D -8 to -9° (chloroform)

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

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℃

JECFA Number

1324

Merck 

14,1875

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 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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H304May be fatal if swallowed and enters airways

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P331Do NOT induce vomiting.

β-Caryophyllene Chemical Properties,Usage,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 (K_i = 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

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.

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).