| Identification | Back Directory | [Name]
HEXAHYDROCURCUMIN | [CAS]
36062-05-2 | [Synonyms]
HEXAHYDROCURCUMIN
Hexahydrocurcumin, BR
1,7-Bis(3-methoxy-4-hydroxyphenyl)-5-hydroxy-3-heptanone
1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-hydroxyheptan-3-one
5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
3-Heptanone, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-
(RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
5-Hydroxy-1-(4-hydroxy-3-Methoxycyclohexyl)-7-(4-hydroxy-3-Methoxyphenyl)heptan-3-one | [Molecular Formula]
C21H26O6 | [MDL Number]
MFCD18783096 | [MOL File]
36062-05-2.mol | [Molecular Weight]
374.43 |
| Chemical Properties | Back Directory | [Melting point ]
80-82℃ | [Boiling point ]
622.6±55.0 °C(Predicted) | [density ]
1.226 | [Fp ]
218℃ | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Sparingly), Ethyl Acetate (Slightly), DCM, DMSO | [form ]
neat | [pka]
10.02±0.20(Predicted) | [color ]
Pale Yellow | [BRN ]
2486876 | [Major Application]
food and beverages | [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]
O=C(CC(O)CCC1=CC(OC)=C(O)C=C1)CCC2=CC(OC)=C(O)C=C2 |
| Hazard Information | Back Directory | [Description]
Hexahydrocurcumin is a natural product and glucuronide metabolite of curcumin that has anti-inflammatory, antioxidant, and anticancer properties.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 | [Uses]
Hexahydrocurcumin is an intermediate in the synthesis of Gingerenone A (G387500) which is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders. | [Definition]
ChEBI: Hexahydrocurcumin is a diarylheptanoid. | [in vivo]
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]. | Animal Model: | Male Wistar rats (100-120 g) injected with dimethylhydrazine (DMH)[3] | | Dosage: | 50 mg/kg | | Administration: | Oral administration; daily; for 16 weeks | | Result: | Significantly reduced the numbers of ACF in colon cancer rats. Also markedly decreased COX-2 protein expression. |
| [target]
PGE | NOS | COX | [IC 50]
COX-2 | [References]
[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] FENG ZHAO. Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: translocation of nuclear factor-κB as potential target.[J]. Molecular medicine reports, 2015: 3087-3093. DOI: 10.3892/mmr.2014.3079
[3] KHANITTA SRIMUANGWONG. Effects of hexahydrocurcumin in combination with 5-fluorouracil on dimethylhydrazine-induced colon cancer in rats.[J]. World Journal of Gastroenterology, 2012, 18 47: 6951-6959. DOI: 10.3748/wjg.v18.i47.6951 |
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