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
CAS Number	1080-12-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81361;
ChEMBL	ChEMBL106509;
ChemSpider	4510464;
EC Number	214-096-9;
KEGG	C17840;
PubChem CID	5354238;
UNII	8CJX5I27B7;
	InChI 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;
	SMILES CC(=O)/C=C/C1=CC(=C(C=C1)O)OC;
Properties
Chemical formula	C11H12O3
Molar mass	192.214 g·mol−1
Appearance	Yellow-orange crystalline solid
Density	1.15 g/cm3
Melting point	129-130 °C
Solubility in water	Practically insoluble in water; soluble in DMSO, ethanol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dehydrozingerone is a phenolic α,β-unsaturated ketone found in ginger (Zingiber officinale). It is studied for its antioxidant, antimicrobial and anti-inflammatory properties.^[1]^[2]

Production

Dehydrozingerone is typically prepared by a base-catalyzed Claisen–Schmidt condensation of vanillin with acetone:^[3]

C₈H₈O₃ + C₃H₆O → C₁₁H₁₂O₃ + H₂O

Uses

The preparative transformation is selective reduction to produce the saturated ketone zingerone:^[4]

C₁₁H₁₂O₃ + H₂ → C₁₁H₁₄O₃

References

^ 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.
^ "Dehydrozingerone". PubChem. Retrieved 31 December 2025.
^ 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.
^ Usha, Esther (2011). "Studies on Hydrogenation of Dehydrozingerone". ir.cftri.res.in. Retrieved 2025-12-31.

[pmcreview-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.

[pubchem-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.

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