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Verbenone

4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one

2-Pinen-4-one

Bicyclic monoterpenoid alkene ketone · C₁₀H₁₄O

Chemical structure of Verbenone
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
1196-01-6
Molecular formula
C₁₀H₁₄O
Molecular weight
150.22 g/mol
Aroma
Fresh wood, lightly camphoraceous, with a balsamic finish, the signature of rosemary verbenone CT.

Safety

Antiplatelet · Caution with antibiotics

Verbenone is a bicyclic monoterpene ketone, common in rosemary verbenone chemotype. Two isomers (R)- and (S)- exist with different biological activity. (S)-Verbenone is the form usually found in plant essential oils.

Oral. Intraperitoneal LD50 in mice was 250 mg/kg.

Cardiovascular. Verbenone shows strong in vitro antiplatelet activity.

Drug interactions. (-)-Verbenone alters the distribution of erythromycin and ampicillin in mice, increasing lung concentration while not altering hepatic concentration.

Usage guidelines

Concern level
Moderate · antiplatelet
Anticoagulant therapy and surgery
Caution for oral use
Antibiotic interaction
May interfere with erythromycin and ampicillin distribution
Oils with high content
Rosemary verbenone CT 8 to 12 percent

Found in essential oils

Principal sources
Rosemary0.5 – 12.3 %
Piri-piri1.1 – 3.9 %
Mastic0 – 2.9 %
Hinoki root2.4 %
Cistus0 – 2.0 %
Labdanum0 – 1.2 %

Pharmacokinetics

(-)-Verbenone is converted to (-)-10-hydroxyverbenone in both rats and humans. In humans this occurs mainly through CYP2A6, in male rats through CYP2C11.

Notes

Verbenone is the natural oxidation product of α-pinene. Its characteristic fresh wood note gives rosemary verbenone CT its premium commercial value.