Zingerone

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Zingerone

IUPAC name	4-(4-hydroxy-3- methoxyphenyl)-2-butanone
Identifiers
CAS number	[122-48-5]
SMILES	OC1=C(OC)C=C(CCC(C)=O)C=C1
Properties
Molecular formula	C₁₁H₁₄O₃
Molar mass	194.22 g/mol
Melting point	40-41 °C
Boiling point	187-188 °C at 14 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Zingerone, also called vanillylacetone, is the principal organic compound responsible for giving ginger its pungent taste. It is a crystalline solid that is sparingly soluble in water, but soluble in ether.

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.

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. ^[1]

[edit] References

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^ 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): 8390–8397. doi:10.1021/jf071460f.