Zingerone

Zingerone
Zingerone
IUPAC name 4-(4-hydroxy-3-methoxyphenyl)-2-butanone
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	122-48-5
SMILES
style="background: #F8EABA; text-align: center;" colspan="2" | 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 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. (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.

Its synthesis from vanillin can be found in one of the experiments of the Home Chemistry Society: Preparation of Zingerone from vanillin

References

cs:Zingeron