Zingerone

Zingerone

Names
IUPAC name 4-(4-hydroxy-3-methoxyphenyl)-2-butanone
Identifiers
CAS Number	122-48-5 N
ChEBI	CHEBI:68657 N
ChEMBL	ChEMBL25894 Y
ChemSpider	28952 Y
Jmol interactive 3D	Image
PubChem	31211
UNII	4MMW850892 Y
InChI InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3 Y Key: OJYLAHXKWMRDGS-UHFFFAOYSA-N Y InChI=1/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3 Key: OJYLAHXKWMRDGS-UHFFFAOYAN
SMILES O=C(C)CCc1cc(OC)c(O)cc1
Properties
Chemical formula	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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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]

References

1. ↑ Monge, P; Scheline, R; Solheim, E (1976). "The metabolism of zingerone, a pungent principle of ginger". Xenobiotica 6 (7): 411–23. doi:10.3109/00498257609151654. PMID 997589. 
2. ↑ Steffen Arctander, Perfume and Flavor Materials of Natural Origin, pg. 280
3. ↑ 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.