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(S)-Verbenone

(1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one

(1S,5S)-(-)-Verbenone · l-Verbenone

Bicyclic monoterpenoid alkene ketone · C₁₀H₁₄O

Chemical structure of (S)-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, balsamic, lightly camphoraceous, the signature of rosemary verbenone CT.

Safety

Antiplatelet · Caution with antibiotics

(S)-Verbenone is the form usually found in plant essential oils, especially rosemary verbenone CT.

Cardiovascular. 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.

Oral. Intraperitoneal LD50 in mice for mixed isomer verbenone was 250 mg/kg.

Usage guidelines

Concern level
Moderate · antiplatelet
Anticoagulant therapy and surgery
Caution for oral use
Oils with high content
Rosemary verbenone CT 7.6 to 12.3 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

(S)-Verbenone, the levogyric or l-verbenone, is the dominant isomer in rosemary verbenone CT and is responsible for the commercial value of this chemotype.