A natural product and an active metabolite of curcumin
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Parent Compound(s)
81025Curcumin 81025.1Curcumin (technical grade)
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Hexahydrocurcumin

Item No. 11714

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
CAS Number
36062-05-2
Molecular Formula
C21H26O6
Formula Weight
374.4
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 5 mg/mlEthanol: 0.25 mg/ml
λmax
279 nm
SMILES
OC1=C(OC)C=C(CCC(O)CC(CCC2=CC=C(O)C(OC)=C2)=O)C=C1
InChi Code
InChI=1S/C21H26O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,16,22,24-25H,3-4,7-8,13H2,1-2H3
InChi Key
RSAHICAPUYTWHW-UHFFFAOYSA-N
Origin
Plant/Curcuma longa
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $95

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    5 mg

    $417

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    10 mg

    $739

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    Product Description

    Hexahydrocurcumin is a natural product and an active metabolite of curcumin.1 It reduces prostaglandin E2 (PGE2) production stimulated by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) by 37% in human colonic epithelial cells when used at a concentration of 20 µM. Hexahydrocurcumin (3.125-25 µM) inhibits overproduction of nitric oxide induced by LPS in RAW 264.7 macrophage cells in a concentration-dependent manner.2 It does not affect LPS-induced cytokine release but inhibits LPS-induced iNOS and COX-2 upregulation and NF-κB activation when used at a concentration of 50 µM. Hexahydrocurcumin prevents the formation of aberrant crypt foci in a dimethylhydrazine rat model of colon cancer and potentiates the effect of 5-fluorouracil (Item No. 14416).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ireson, C., Orr, S., Jones, D.J., et al. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res. 61(3), 1058-1064 (2001).

    2. Zhao, F., Gong, Y., Hu, Y., et al. Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: Translocation of nuclear factor-κB as potential target. Mol. Med. Rep. 11(4), 3087-3093 (2015).

    3. Srimuangwong, K., Tocharus, C., Tocharus, J., et al. Effects of hexahydrocurcumin in combination with 5-fluorouracil on dimethylhydrazine-induced colon cancer in rats. World J. Gastroenterol. 18(47), 6951-6959 (2012).