HEXAHYDROCURCUMIN
HEXAHYDROCURCUMIN Basic information
- Product Name:
- HEXAHYDROCURCUMIN
- Synonyms:
-
- HEXAHYDROCURCUMIN
- 5-Hydroxy-1-(4-hydroxy-3-Methoxycyclohexyl)-7-(4-hydroxy-3-Methoxyphenyl)heptan-3-one
- (RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
- 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
- Hexahydrocurcumin, BR
- 3-Heptanone, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-
- CAS:
- 36062-05-2
- MF:
- C21H26O6
- MW:
- 374.43
- Mol File:
- 36062-05-2.mol
HEXAHYDROCURCUMIN Chemical Properties
- Melting point:
- 80-82℃
- Boiling point:
- 622.6±55.0 °C(Predicted)
- Density
- 1.226
- Flash point:
- 218℃
- storage temp.
- 2-8°C
- solubility
- Chloroform (Sparingly), Ethyl Acetate (Slightly), DCM, DMSO
- form
- Solid
- pka
- 10.02±0.20(Predicted)
- color
- Pale Yellow
- BRN
- 2486876
HEXAHYDROCURCUMIN Usage And Synthesis
Description
Hexahydrocurcumin is a natural product and glucuronide metabolite of curcumin that has anti-inflammatory, antioxidant, and anticancer properties. It reduces prostaglandin E2 (PGE2) production stimulated by phorbol 12-myristate 13-acetate (PMA; ) 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. 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 .
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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