Zingerone

Chembox new
Name = Zingerone
ImageFile = Zingerone.png ImageName = Zingerone
IUPACName = 4-(4-hydroxy-3-
methoxyphenyl)-2-butanone
Section1 = Chembox Identifiers
CASNo = 122-48-5
SMILES = OC1=C(OC)C=C(CCC(C)=O)C=C1
Section2 = Chembox Properties
Formula = C₁₁H₁₄O₃
MolarMass = 194.22 g/mol
Density =
MeltingPt = 40-41 °C
BoilingPt = 187-188 °C at 14 mmHg

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. [cite journal
first = Jaw-Chyun
last = Chen
authorlink =
coauthors = Li-Jiau Huang, Shih-Lu Wu, Sheng-Chu Kuo, Tin-Yun Ho, Chien-Yun Hsiang
year = 2007
month =
title = Ginger and Its Bioactive Component Inhibit Enterotoxigenic Escherichia coli Heat-Labile Enterotoxin-Induced Diarrhea in Mice
journal = Journal of Agricultural and Food Chemistry
volume = 55
issue = 21
pages = 8390–8397
id =
doi =10.1021/jf071460f
]

It's synthesis from vanillin can be found in one of the experiments of the [http://www.homechemistry.org/index.php?title=Main_Page Home Chemistry Society] : [http://www.homechemistry.org/index.php?title=Preparation_of_Zingerone_%28Ginger_aroma%29_from_vanillin Preparation of Zingerone from vanillin]

References