Zingerone

Zingerone
Names
	IUPAC name 4-(4-hydroxy-3-methoxyphenyl)-2-butanone
Identifiers
CAS Number	122-48-5;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.004.136
CompTox Dashboard (EPA)	DTXSID8047420 ;
	SMILES OC1=C(OC)C=C(CCC(C)=O)C=C1;
Properties
Chemical formula	C11H14O3
Molar mass	194.22 g/mol
Melting point	40-41 °C
Boiling point	187-188 °C at 14 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.

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]

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

References

^ Chen, Jaw-Chyun (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. {{cite journal}}: Cite has empty unknown parameters: |1=, |2=, |3=, and |month= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

[1] Chen, Jaw-Chyun (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. {{cite journal}}: Cite has empty unknown parameters: |1=, |2=, |3=, and |month= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

[1]