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IUPAC name
122-48-5 N
ChemSpider 28952 YesY
Jmol 3D model Interactive image
PubChem 31211
UNII 4MMW850892 YesY
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 YesYN ?)
Infobox references

Zingerone, also called vanillylacetone, is a key component of the pungency of ginger, but imparts the "sweet" flavor of cooked ginger.[1] Zingerone is a crystalline solid that is sparingly soluble in water, but soluble in ether.[2]

Zingerone is similar in chemical structure[which?] 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 via reverse aldol reaction, which is present, into zingerone through a retro-aldol reaction (reversal of aldol addition).

Biological effects[edit]

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]

Zingerone also stimulates the release of catecholamines, which aids in breakdown of fat cells and zingerone was shown to inhibit obesity-induced inflammation.[4]


  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. 
  4. ^ Pulbutr P. et al. Lipolytic Effects of zingerone in adipocytes isolated from normal diet-fed rats and high fat diet-fed rats. International Journal of Pharmacology. Jul 2011; 7(5):29-34