Zingerone

Title: Zingerone
CAS Registry Number: 122-48-5
CAS Name: 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone
Additional Names: (4-hydroxy-3-methoxyphenyl)ethyl methyl ketone; vanillylacetone; zingherone; zingiberone
Molecular Formula: C11H14O3
Molecular Weight: 194.23
Percent Composition: C 68.02%, H 7.27%, O 24.71%
Literature 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).
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.
Melting point: mp 40-41°
Boiling point: bp14 187-188°
Flash point: Flash point: 208°F (98°C)
Use: In fragrances, flavors and cosmetics; in artificial spice oils.
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Zingerone
Zingerone
Identifiers
CAS number 122-48-5 N
PubChem 31211
ChemSpider 28952 YesY
UNII 4MMW850892 YesY
ChEBI CHEBI:68657 N
ChEMBL CHEMBL25894 YesY
Jmol-3D images Image 1
Properties
Molecular formula C11H14O3
Molar mass 194.22 g/mol
Melting point 40–41 °C
Boiling point 187–188 °C at 14 mmHg
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Zingerone, also called vanillylacetone, is a key component of the pungency of ginger.[1] Zingerone is a crystalline solid that is sparingly soluble in water, but soluble in ether.[2]

Zingerone is similar in chemical structure to other flavor chemicals such as vanillin and eugenol. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.

Fresh ginger does not contain zingerone; cooking the ginger transforms gingerol, which is present, into zingerone through a retro-aldol reaction (reversal of aldol addition).

Ginger compounds have been shown to be active against enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea. This type of diarrhea is the leading cause of infant death in developing countries. Zingerone is likely the active constituent responsible for the antidiarrheal efficacy of ginger.[3]