7224. Phenethyl Alcohol

Nomenclature

CAS number: 60-12-8
Benzeneethanol; 2-phenylethanol; β-phenylethyl alcohol; benzyl carbinol; β-hydroxyethylbenzene.
C8H10O; mol wt 122.16.
C 78.66%, H 8.25%, O 13.10%.

Description and references

Found in a number of natural essential oils, such as rose, carnation, hyacinth, Aleppo pine, orange blossom, geranium Bourbon, neroli and in the essential oil of champaca. Prepd by reduction of ethyl phenylacetate with sodium in abs alcohol: Bouveault, Blanc, Bull. Soc. Chim. [3] 31, 672 (1904); Leonard, J. Am. Chem. Soc. 47, 1778 (1925); by hydrogenation of phenylacetaldehyde in the presence of nickel catalyst: Skita, Ritter, Ber. 43, 3398 (1910); v. Braun, Kochend"orfer, Ber. 56, 2176 (1923); Milligan, Reid, J. Am. Chem. Soc. 44, 204 (1922). Isoln from the fungus Gibberella fujikuroi: Cross et al., J. Chem. Soc. 1963, 2937. Antibacterial activity: R. M. E. Richards et al., J. Pharm. Pharmacol. 21, 681 (1969). Use as preservative in ophthalmic solutions: R. M. E. Richards, R. J. McBride, ibid. 24, 145 (1972). Toxicity: Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964).

Chemical structure

Properties

Liquid. Floral odor, rose character. mp -27°. d2525 1.017 to 1.019. bp750 219-221°; bp14 104°; bp12 98-100°. nD20 1.530 to 1.533. Two ml dissolve in 100 ml water after thorough shaking. One part is clearly sol in 1 part of 50% alc. Miscible with alcohol, ether. LD50 orally in rats: 1790 mg/kg (Jenner).

Use

Pharmaceutic aid (antimicrobial). In flavors and perfumery (esp rose perfumes).