Zingerone
| Zingerone | |
| Names | |
|---|---|
| IUPAC name
4-(4-hydroxy-3-methoxyphenyl)-2-butanone
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| Identifiers | |
122-48-5  |
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| ChEBI | CHEBI:68657 |
| ChEMBL | ChEMBL25894  |
| ChemSpider | 28952 |
| Jmol 3D model | Interactive image |
| PubChem | 31211 |
| UNII | 4MMW850892 |
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| Properties | |
| 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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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]
