Hexahydrocurcumin

• CAT Number: I003319
• CAS Number: 36062-05-2
• Molecular Formula: C21H26O6
• Molecular Weight: 374.43
• Purity: ≥95%
• Synonyms: 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one
• InChI: 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
• InChIKey: RSAHICAPUYTWHW-UHFFFAOYSA-N
• SMILES: COC1=C(C=CC(=C1)CCC(CC(=O)CCC2=CC(=C(C=C2)O)OC)O)O

Hexahydrocurcumin is one of the major metabolites of curcumin and a selective, orally active COX-2 inhibitor. Hexahydrocurcumin is inactive against COX-1. Hexahydrocurcumin has antioxidant, anticancer and anti-inflammatory activities[1][2].
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) treatment significantly decreased the viability of HT-29 colon cancer cells in a time- and concentration-dependent. The respective IC50 values for 24 and 48 h of Hexahydrocurcumin exposureare 77.05 and 56.95, respectively[1].
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) combined with 5-fluorouracil (5-FU; 5 µM) markedly reduces the COX-2 expression. The level of COX-1 is not altered[1].
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) combined with 5-fluorouracil (5-FU; 5 µM) markedly reduces the COX-2 protein. The level of COX-1 protein is not altered[1].
Hexahydrocurcumin (7-14 μM; 24 hours) attenuates lipopolysaccharide (LPS)-elicited increase of prostaglandin E2 (PGE2) in murine macrophages (RAW 264.7) in a concentration-dependent manner[2].
Hexahydrocurcumin (50 mg/kg; oral administration; daily; for 16 weeks; male Wistar rats) treatment significantly reduces the numbers of aberrant crypt foci (ACF) in colon cancer rats. Hexahydrocurcumin also markedly decreases COX-2 protein expression. The levels of COX-1 protein is not different from normal rats[3].

Reference

[1]. Srimuangwong K, et al. Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on HT-29 human colon cancer cells. World J Gastroenterol. 2012 May 21;18(19):2383-9.
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[2]. Li F, et al. In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin. Food Chem. 2012 Nov 15;135(2):332-7.
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[3]. Srimuangwong K, et al. Effects of hexahydrocurcumin in combination with 5-fluorouracil on dimethylhydrazine-induced colon cancer in rats. World J Gastroenterol. 2012 Dec 21;18(47):6951-9.
 [Content Brief]