Zingerone
| Zingerone | |
|---|---|
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4-(4-hydroxy-3-methoxyphenyl)-2-butanone |
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| Identifiers | |
| CAS number | 122-48-5  |
| PubChem | 31211 |
| ChemSpider | 28952  |
| UNII | 4MMW850892 |
| ChEMBL | CHEMBL25894 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C11H14O3 |
| Molar mass | 194.22 g/mol |
| Melting point |
40–41 °C |
| Boiling point |
187–188 °C at 14 mmHg |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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]
[edit] References
- ^ 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.
- ^ Steffen Arctander, Perfume and Flavor Materials of Natural Origin, pg. 280
- ^ 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.
