8317. Safrole

Nomenclature

CAS number: 94-59-7
5-(2-Propenyl)-1,3-benzodioxole; 4-allyl-1,2-methylenedioxybenzene; allylcatechol methylene ether; allyldioxybenzene methylene ether; m-allylpyrocatechin methylene ether.
C10H10O2; mol wt 162.19.
C 74.05%, H 6.21%, O 19.73%.

Description and references

Constituent of several essential oils, notably of sassafras in which it is present to the extent of about 75%. Has been used as topical antiseptic; pediculicide. Metabolism studies: Oswald et al., Biochim. Biophys. Acta 230, 237 (1971). Toxicity data: Hagan et al., Toxicol. Appl. Pharmacol. 7, 18 (1965). Review of carcinogenic risk: IARC Monographs 10, 231-241 (1976).

Chemical structure

Properties

Colorless or slightly yellow liq; sassafras odor. d20 1.096. mp ≈11°. bp 232-234°. nD20 1.5383. Insol in water. Very sol in alcohol. Miscible with chloroform, ether. LD50 in rats, mice (mg/kg): 1950, 2350 orally (Hagan).

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-229.

Use

In perfumery; denaturing fats in soap manuf; also in manuf of heliotropin. Formerly as flavoring agent in foods, drugs and beverages.