Anethole

Title: Anethole
CAS Registry Number: 4180-23-8; 104-46-1 (unspecified)
CAS Name: 1-Methoxy-4-(1E)-1-propenylbenzene
Additional Names: trans-p-propenylanisole; trans-1-p-anisylpropene; anise camphor; isoestragole
Trademarks: Monasirup (RPR)
Molecular Formula: C10H12O
Molecular Weight: 148.20
Percent Composition: C 81.04%, H 8.16%, O 10.80%
Literature 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).
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 (e 22300). Practically insol in water. Misc with ether, chloroform; sol in benzene, ethyl acetate, acetone, carbon disulfide, petr ether; 1 ml dissolves in 2 ml alc. LD50 i.p. in rats: 900 mg/kg (Boissier).
Melting point: mp 21.4°
Boiling point: bp 231-237°; bp2.3 81-81.5°
Index of refraction: nD20 1.56145
Absorption maximum: uv max (ethanol): 259 nm (e 22300)
Density: d420 0.9883
Toxicity data: LD50 i.p. in rats: 900 mg/kg (Boissier)
Derivative Type: cis-Anethole
CAS Registry Number: 25679-28-1
Literature 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 (e 18500). LD50 i.p. in rats: 93 mg/kg (Boissier).
Melting point: mp -22.5°
Boiling point: bp2.3 79-79.5°
Index of refraction: nD20 1.55455
Absorption maximum: uv max (ethanol): 253.5 nm (e 18500)
Density: d420 0.9878
Toxicity data: 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).
Therap-Cat: Antitussive.
Anethole Trithione Angelic Acid Angelica Angelica Lactone Angiogenin

Anethole
Anethole acsv.svg
Identifiers
CAS number 104-46-1 YesY
PubChem 637563
ChemSpider 553166 YesY
UNII 21C2F5E8RE YesY
KEGG D02377 YesY
ChEBI CHEBI:35616 YesY
ChEMBL CHEMBL452630 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H12O
Molar mass 148.20 g mol−1
Density 0.998 g/cm3
Melting point 20 to 21 °C; 68 to 70 °F; 293 to 294 K
Boiling point 234 °C; 81 °C at 2 mmHg
Hazards
MSDS External MSDS
Related compounds
Related compounds Anisole; Estragole
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It contributes a large component of the distinctive flavors of anise and fennel (both in the botanical family Apiaceae), anise myrtle (Myrtaceae), liquorice (Fabaceae), and star anise (Illiciaceae). Closely related to anethole is its isomer estragole, abundant in tarragon (Asteraceae) and basil (Lamiaceae), that has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid.[1] Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This difference causes certain anise-flavored liqueurs to become opaque when diluted with water, the Ouzo effect.