A diarylheptanoid and polyphenol with diverse biological activities
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Gingerenone A

Item No. 36841

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,7-bis(4E-hydroxy-3-methoxyphenyl)-4-hepten-3-one
CAS Number
128700-97-0
Molecular Formula
C21H24O5
Formula Weight
356.4
Purity
≥95%
Formulation (Request formulation change)
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble
λmax
224 nm
SMILES
COC(C=C1CC/C=C/C(CCC2=CC(OC)=C(C=C2)O)=O)=C(C=C1)O
InChi Code
InChI=1S/C21H24O5/c1-25-20-13-15(8-11-18(20)23)5-3-4-6-17(22)10-7-16-9-12-19(24)21(14-16)26-2/h4,6,8-9,11-14,23-24H,3,5,7,10H2,1-2H3/b6-4+
InChi Key
FWDXZNKYDTXGOT-GQCTYLIASA-N
Origin
Plant/Zingiber officinale Roscoe
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $28

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    10 mg

    $50

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    25 mg

    $104

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Gingerenone A is a diarylheptanoid and polyphenol that has been found in Z. officinale and has diverse biological activities.1,2,3,4,5 It inhibits tyrosinase (IC50 = 9.4 µM for the mushroom enzyme) and scavenges DPPH (Item No. 14805) radicals in a cell-free assay (IC50 = 12.6 µM).1,2 Gingerenone A (5 and 10 µM) also inhibits JAK2 and p70 ribosomal S6 kinase 1 (p70S6K1).3 It selectively decreases the viability of ionizing radiation-induced senescent WI38 fibroblasts over proliferating fibroblasts when used at a concentration of 20 µM.4 Gingerenone A (50 mg/kg) prevents increases in body weight but does not affect caloric intake in a mouse model of high-fat diet-induced obesity.5 It decreases tumor weight in an HCT116 colon cancer mouse xenograft model when administered at doses of 5 and 20 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Athipornchai, A., Niyomtham, N., Pabuprapap, W., et al. Potent tyrosinase inhibitory activity of curcuminoid analogues and inhibition kinetics studies. Cosmetics 8(2), 35 (2021).

    2. Li, N., Wang, L., Zu, L., et al. Antioxidant and cytotoxic diarylheptanoids isolated from Zingiber officinale rhizomes. Chin. J. Chem. 30, 1351-1355 (2012).

    3. Byun, S., Lim, S., Mun, J.Y., et al. Identification of a dual inhibitor of Janus kinase 2 (JAK2) and p70 ribosomal S6 kinase1 (S6K1) pathways. The Journal of Biological Chemisty 290(39), 23553-23562 (2015).

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

    5. Suk, S., Kwon, G.T., Lee, E., et al. Gingerenone A, a polyphenol present in ginger, suppresses obesity and adipose tissue inflammation in high-fat diet-fed mice. Mol. Nutr. Food Res. 61(10), (2017).