3705. Estragole

Nomenclature

CAS number: 140-67-0
1-Methoxy-4-(2-propenyl)benzene; p-allylanisole; chavicol methyl ether; esdragol.
C10H12O; mol wt 148.20.
C 81.04%, H 8.16%, O 10.80%.

Description and references

Main constituent of tarragon oil (estragon oil), the oil from Artemisia dracunculus L., Compositae (esdragon) where it occurs to an extent of 60-75%: Grimaux, Bull. Soc. Chim. [3] 11, 34 (1894); Daufresne, ibid. [4] 3, 333 (1908). Occurs also in pine oil and in American turpentine oil. Prepn: Tiffeneau, Compt. Rend. 139, 482 (1904); Verley, DE 154654; D. Wigfield, K. Taymaz, Tetrahedron Lett. 1973, 4841; P. Gramatica et al., Gazz. Chim. Ital. 104, 629 (1974). Toxicity study: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (l964).

Chemical structure

Properties

Liquid. d421 0.9645. bp764 216°; bp25 108-114°; bp12 95-96°. nD17.5 1.5230. Sol in alcohol, chloroform. Forms azeotropic mixtures with water. LD50 in rats, mice (mg/kg): 1820, 1250 orally (Jenner).

Use

In perfumes and as flavor in foods and liqueurs.