643. Anethole

Nomenclature

CAS number: 4180-23-8; 104-46-1 (unspecified stereo)
1-Methoxy-4-(1E)-1-propen-1-ylbenzene; trans-p-propenylanisole; trans-1-p-anisylpropene; anise camphor; isoestragole; Monasirup (RPR).
C10H12O; mol wt 148.20.
C 81.04%, H 8.16%, O 10.80%.

Description and references

Chief constituent of anise, star anise and fennel oils; responsible for the characteristic odor and flavor of aniseed. Isoln: A. Cahours, Ann. 41, 56 (1842). Description of prepns and properties: A. Wagner, Manuf. Chem. 23, 56 (1952). Prepn from estragole, q.v., and separation of isomers: Y.-R. Naves, Compt. Rend. 246, 1734 (1958). Improved synthesis: R. J. DePasquale, Synth. Commun. 10, 225 (1980). Characterization of isomers: Y.-R. Naves et al., Bull. Soc. Chim. Fr. 1958, 566; and comparative pharmacology: J.-R. Boissier et al., Therapie 22, 309 (1967). HPLC determn in alcoholic beverages: P. Curro et al., J. Chromatogr. 404, 273 (1987). Isoln by supercritical fluid extraction: L. K. Liu, Anal. Commun. 33, 175 (1996). Metabolism in humans: J. Caldwell, J. D. Sutton, Food Chem. Toxicol. 26, 87 (1988). Review of use as aroma chemical: G. S. Clark, Perfum. Flavor. 18, 11-18 (1993); of safety evaluation as flavoring substance: P. Newberne et al., Food Chem. Toxicol. 37, 789-811 (1999).

Chemical structure

Properties

Colorless, slightly oily liquid; sweet, characteristic odor and taste. mp 21.4°. d420 0.9883. bp 231-237°; bp2.3 81-81.5°. nD20 1.56145. uv max (ethanol): 259 nm (ε 22300). Freely sol in alcohol; 1 ml dissolves in 2 ml alc. Sol in benzene, ethyl acetate, acetone, carbon disulfide, petr ether. Very slightly sol in water. Misc with ether, chloroform. LD50 i.p. in rats: 900 mg/kg (Boissier).

Derivative

cis-Anethole.

Nomenclature

CAS number: 25679-28-1

Description and references

Naturally occurs in trace amounts in oils of anise, star anise and fennel; by-product in prepn of synthetic anethole. Stereospecific prepn: Y.-R. Naves, Helv. Chim. Acta 43, 230 (1960).

Properties

Camphoraceous, unpleasant, fennel-like odor. mp 22.5°. d420 0.9878. bp2.3 79-79.5°. nD20 1.55455. uv max (ethanol): 253.5 nm (ε 18500). LD50 i.p. in rats: 93 mg/kg (Boissier).

Use

Flavoring agent in foods and beverages; in perfumery, particularly for soap and dentifrices; pharmaceutic aid (flavor).

Therapeutic Category

Antitussive.