A metabolite of curcumin with diverse biological activities
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Tetrahydrocurcumin

Item No. 11757

Technical Information
Formal Name
1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione
CAS Number
36062-04-1
Synonyms
  • NSC 687845
Molecular Formula
C21H24O6
Formula Weight
Purity
≥95% (mixture of tautomers)
A crystalline solid
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 5 mg/mlEthanol: 0.25 mg/ml
λmax
281 nm
SMILES
OC1=C(OC)C=C(CCC(CC(CCC2=CC=C(O)C(OC)=C2)=O)=O)C=C1
InChi Code
InChI=1S/C21H24O6/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/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3
InChi Key
LBTVHXHERHESKG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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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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    Product Description

    Tetrahydrocurcumin is a metabolite of curcumin (Item Nos. 81025 | 81025.1) that has diverse biological activities, including antioxidant, anti-inflammatory, anti-angiogenic, and anticancer properties.1,2,3,4 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay with an EC50 value of 16.8 μM.1 Tetrahydrocurcumin (50 µM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 expression in RAW 264.7 cells.2 It also inhibits LPS-induced increases in TNF-α release when used at a concentration of 100 µM and increases in nitric oxide (NO) production and IL-6 levels in a concentration-dependent manner. Tetrahydrocurcumin reduces carrageenan-induced paw edema in rats (ED50 = 20 mg/kg).3 It also reduces the formation of neocapillaries and decreases microvascular density as well as VEGF, VEGF receptor 2 (VEGFR2), and hypoxia-inducible factor-1α (HIF-1α) expression in a CaSki cervical cancer nude mouse xenograft model when administered at doses of 100, 300, and 500 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Zhao, F., Gong, Y., Hu, Y., et alCurcumin 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. Mukhopadhyay, A., Basu, N., Ghatak, N., et alAnti-inflammatory and irritant activities of curcumin analogues in rats. Agents Actions 12, 508-515 (1982).

    4. Yoysungnoen, B., Bhattarakosol, P., Patumraj, S., et alEffects of tetrahydrocurcumin on hypoxia-inducible factor-1α and vascular endothelial growth factor expression in cervical cancer cell-induced angiogenesis in nude mice. Biomed. Res. Int. 391748 (2015).