A phenolic ketone with diverse biological activities
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Isomer(s)
36797Butyl 4-hydroxybenzoate
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Zingerone

Item No. 24909

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(4-hydroxy-3-methoxyphenyl)-2-butanone
CAS Number
122-48-5
Synonyms
  • NSC 15335
  • Vanillylacetone
Molecular Formula
C11H14O3
Formula Weight
194.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/m
SMILES
COC1=C(O)C=CC(CCC(C)=O)=C1
InChi Code
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
InChi Key
OJYLAHXKWMRDGS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    25 g

    $75

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    50 g

    $105

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    100 g

    $149

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    250 g

    $333

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    Cayman Chemical
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    Product Description

    Zingerone is a phenolic ketone originally isolated from ginger that has antioxidant, anti-inflammatory, anticarcinogenic, and antidiarrheal activities.1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay with an EC50 value of 41.6 μmol.3 Zingerone (6 mg/kg per day) prevents myocardial expression of TNF-α, IL-1β, and IL-6 in rats following myocardial infarction induced by isoproterenol (Item No. 15592).4 It decreases 1,2-dimethylhydrazine-induced tumor incidence by 67% and aberrant crypt foci formation by 68.85% in rats when administered at a dose of 20 mg/kg per day.5 Zingerone (10 mM) decreases E. coli heat-labile enterotoxin-induced fluid accumulation in the ileal loop of mice.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nomura, H. LXIV.—The pungent principles of ginger. Part I. A new ketone, zingerone (4-hydroxy-3-methoxyphenylethyl methyl ketone) occurring in ginger. J. Chem. Soc. 111, 769-776 (1917).

    2. Ahmad, B., Rehman, M.U., Amin, I., et al. A review on pharmacological properties of zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone). ScientificWorldJournal 2015:816364, (2015).

    3. Manjunatha, J.R., Bettadaiah, B.K., Negi, P.S., et al. Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes. Food Chem. 136(2), 650-658 (2013).

    4. Hemalatha, K.L., and Prince, P.S.M. Anti-inflammatory and anti-thrombotic effects of zingerone in a rat model of myocardial infarction. Eur. J. Pharmacol. 791, 595-602 (2016).

    5. Vinothkumar, R., Vinothkumar, R., Sudha, M., et al. Chemopreventive effect of zingerone against colon carcinogenesis induced by 1,2-dimethylhydrazine in rats. Eur. J. Cancer Prev. 23(5), 361-371 (2014).

    6. Chen, J.-C., Huang, L.-J., Wu, S.-L., et al. Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice. J. Agric. Food Chem. 55(21), 8390-8397 (2007).

    Product Citations

    Moaddel, R., Rossi, M., Rodriguez, S., et al. Identification of gingerenone A as a novel senolytic compound. PLoS One 17(3), e0266135 (2022).