β-Caryophyllene

β-Caryophyllene is among the most common sesquiterpenes in essential oils, particularly in copaiba, black pepper and clove. The compound is a weak skin allergen and oxidation does not increase its allergenicity.

Skin. β-Caryophyllene oxidizes readily in air, with only 50 percent of the original compound remaining after 6 weeks; caryophyllene oxide is the major product. After 10 weeks of air exposure, β-caryophyllene shows only weak sensitizing capacity in a local lymph node assay.

Among 1,511 consecutive dermatitis patients, two (0.14 percent) reacted to 3.9 percent oxidized β-caryophyllene (containing 25 percent β-caryophyllene and 75 percent caryophyllene oxide).

Oral. Acute oral LD50 in rats exceeds 5 g/kg; rabbit dermal LD50 exceeds 5 g/kg.

Mutagenicity. Non-mutagenic in Salmonella TA98 and TA100, antimutagenic in several assays. Non-genotoxic in the mouse bone marrow micronucleus test.

Anticancer. Significant glutathione S-transferase induction in mouse liver and small intestine; moderate cytotoxicity against multiple cancer cell lines. Increased survival in ascites tumor mice after four intraperitoneal doses of 20 mg/kg.

β-Caryophyllene is a CB2 agonist, studied for anti-inflammatory activity.

β-Caryophyllene is the key carrier of the woody-spicy notes of black pepper and clove. Its CB2 activity is under study for anti-inflammatory and pain applications.

Sealed and cool storage matters because of rapid oxidation to caryophyllene oxide.