Zingerone

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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 to 41 °C (104 to 106 °F; 313 to 314 K)
Boiling point 187 to 188 °C (369 to 370 °F; 460 to 461 K) at 14 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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]

References[edit]

  1. ^ Monge, P; Scheline, R; Solheim, E (1976). "The metabolism of zingerone, a pungent principle of ginger". Xenobiotica; the fate of foreign compounds in biological systems 6 (7): 411–23. doi:10.3109/00498257609151654. PMID 997589. 
  2. ^ Steffen Arctander, Perfume and Flavor Materials of Natural Origin, pg. 280
  3. ^ Chen, Jaw-Chyun; Li-Jiau Huang, Shih-Lu Wu, Sheng-Chu Kuo, Tin-Yun Ho, Chien-Yun Hsiang (2007). "Ginger and Its Bioactive Component Inhibit Enterotoxigenic Escherichia coli Heat-Labile Enterotoxin-Induced Diarrhea in Mice". Journal of Agricultural and Food Chemistry 55 (21): 8390–7. doi:10.1021/jf071460f. PMID 17880155.