Dehydrozingerone

Dehydrozingerone
Names
IUPAC name
(E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one
Other names
  • Vanillylidene acetone
  • Vanillidene acetone
  • Vanillylidenacetone
  • Vanillalacetone
  • Dehydrogingerone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 214-096-9
KEGG
UNII
  • InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
    Key: AFWKBSMFXWNGRE-ONEGZZNKSA-N
  • CC(=O)/C=C/C1=CC(=C(C=C1)O)OC
Properties
C11H12O3
Molar mass 192.214 g·mol−1
Appearance Yellow-orange solid
Density 1.15 g/cm3
Melting point 129-130 °C
Practically insoluble in water. Soluble in Dimethyl Sulfoxide and Ethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dehydrozingerone is a phenolic α,β-unsaturated ketone found in ginger (Zingiber officinale). It is studied for its antioxidant, antimicrobial and anti-inflammatory properties.

Production

Dehydrozingerone is typically prepared by a base-catalyzed Claisen–Schmidt condensation of vanillin with acetone:

C8H8O3 + C3H6O → C11H12O3 + H2O

Uses

The preparative transformation is selective reduction to produce the saturated ketone zingerone:

C11H12O3 + H2 → C11H14O3

References

  1. ↑ Kubra, I. R.; Bettadaiah, B. K.; Murthy, P. S.; Rao, L. J. (2011). "Structure–function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds". Journal of Food Science and Technology. 51 (2). PMC: 245–255. doi:10.1007/s13197-011-0488-8. PMC 3907648. PMID 24493881.
  2. ↑ "Dehydrozingerone". PubChem. Retrieved 31 December 2025.
  3. ↑ Hung-Cheng, Shih; Ching-Yuh, Chern; Ping-Chung, Kuo; You-Cheng, Wu; Yu-Yi, Chan; Yu-Ren, Liao; Che-Ming, Teng; Tian-Shung, Wu (4 March 2014). "Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects". International Journal of Molecular Sciences. 15 (3): 3926–3951. Bibcode:2014IJMSc..15.3926S. doi:10.3390/ijms15033926. ISSN 1422-0067. PMC 3975376.
  4. ↑ Usha, Esther (2011). "Studies on Hydrogenation of Dehydrozingerone". ir.cftri.res.in. Retrieved 2025-12-31.