10166. Zingerone

Nomenclature

CAS number: 122-48-5
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone; (4-hydroxy-3-methoxyphenyl)ethyl methyl ketone; vanillylacetone; zingherone; zingiberone.
C11H14O3; mol wt 194.23.
C 68.02%, H 7.27%, O 24.71%.

Description and references

Isolated from ginger root or prepd from vanillin and acetone followed by catalytic hydrogenation: Nomura, J. Chem. Soc. 111, 769 (1917); idem, US 1263796 (1918); US 1306710 (1919); Cotton, US 2381210 (1945 to Penn. Coal Prod.); K. Banno, T. Mukaiyama, Bull. Chem. Soc. Jpn. 49, 1453 (1976).

Chemical structure

Properties

Crystals from acetone, petr ether, ether + petr ether, mp 40-41°. bp14 187-188°. Spicy, pungent odor, characteristic of ginger. Flash point: 208°F (98°C). Sparingly sol in water, petr ether; sol in ether, dil alkalies.

Use

In fragrances, flavors and cosmetics; in artificial spice oils.