Zingerone

Zingerone
Zingerone
Names
Preferred IUPAC name
4-(4-Hydroxy-3-methoxyphenyl)butan-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.136 Edit this at Wikidata
UNII
  • 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 checkY
    Key: OJYLAHXKWMRDGS-UHFFFAOYSA-N checkY
  • 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
  • O=C(C)CCc1cc(OC)c(O)cc1
Properties
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
Insoluble
Solubility Miscible in ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger.[1] Zingerone is a crystalline solid that is sparingly soluble in water and 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, but it is produced by cooking or drying of the ginger root, which causes a reverse aldol reaction on gingerol.

  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.