Estragole or its metabolites administered to mice produce malignant liver
Estragole is a chemical compound with a molecular formula C10H12O which
belongs to alkenylbenzenes. It is also known as 1-allyl-4-methoxybenzene,
3-(p-methoxyphenyl)propane, 4-allyl-1- methoxybenzene, 4-allylanisole,
4-allylmethoxybenzene, 4-methoxyallylbenzene, p-allyl anisole,
1-methoxy-4-(2-propenyl)benzene, chavicol methyl ether, chavicyl methyl ether,
esdragol, esdragole, esdragon, estragol, isoanethole, methyl chavicol, o-methyl
chavicol, NCI-C60946, p-allylanisole, p-methoxyallylbenzene, and tarragon.
Estragole is metabolized by the liver to 1'-hydroxyestragole and several
epoxide compounds. 1'-Hydroxyestragole is further conjugated with sulfate to
form a sulfuric acid ester compound that readily binds to DNA and is responsible
to most, if not all, of estragole's hepatocellular carcinogenicity in mice.
Metabolism of estragole through this pathway appears to be quantitatively
consistent among humans and rodents.
Widespread human exposure to estragole occurs through the consumption of
basil, bay, marjoram, anise, and fennel herbs. Estragole is a constituent of
terpentine oil. Indoor air exposure may result from the use of terpentine oil in
furniture and other wood treatments.