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SMB01366

Sigma-Aldrich

Hexahydrocurcumin

≥95% (HPLC)

Synonym(s):

5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one, (RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone

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About This Item

Empirical Formula (Hill Notation):
C21H26O6
CAS Number:
36062-05-2
Molecular Weight:
374.43
Beilstein:
2486876
MDL number:
MFCD18783096
UNSPSC Code:
12352205
NACRES:
NA.21

Assay

≥95% (HPLC)

form

solid

mp

87—88 °C

storage temp.

2-8°C

SMILES string

O=C(CC(O)CCC1=CC(OC)=C(O)C=C1)CCC2=CC(OC)=C(O)C=C2

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

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General description

Hexahydrocurcumin (HHC), classified as a linear diarylheptanoid, serves as a potent and selective COX-2 inhibitor. It is a natural glucuronide metabolite derived from curcumin, a well-known natural compound found in both the rhizome of Curcuma longa, commonly known as turmeric, and Zingiber officinale, or ginger. This compound distinguishes itself with exceptional stability and enhanced bioavailability in comparison to curcumin, offering an array of therapeutic attributes, including anti-inflammatory, anticancer, antioxidant, and neuroprotective properties. HHC has also demonstrated its therapeutic potential by reducing prostaglandin E2 (PGE2) production and inhibiting nitric oxide overproduction, paving the way for its use in combating a range of health concerns, from colon cancer to inflammatory responses. Additionally, HHC is also recognized for its role in preventing the formation of aberrant crypt foci in a dimethylhydrazine rat model of colon cancer and enhancing the efficacy of 5-fluorouracil

Application

Hexahydrocurcumin finds application in metabolomic research for investigating a wide range of health benefits, primarily encompassing its roles in managing oxidative stress, cancer, inflammation, and various other health conditions.

Biochem/physiol Actions

In vitro, hexahydrocurcumin (HHC) exhibited a marked decrease in the viability of HT-29 human colon cancer cells compared to the control. HHC also significantly down-regulated COX-2 mRNA expression (control: 100.05% ± 0.03% vs HHC: 61.01% ± 0.35%, P < 0.05) without affecting COX-1 mRNA. Notably, when HHC was added to a low dose of 5-Fluorouracil in combined treatment, it exerted a synergistic effect against the growth of HT-29 cells, leading to a more substantial reduction in cell viability compared to monotherapy

Features and Benefits

  • High quality compound suitable for multiple research applications
  • Compatible with a wide variety of chromatographic and spectrometry techniques

Other Notes

For additional information on our range of Biochemicals, please complete this form.
This product is intended for research purposes only, and it is not meant for human consumption.

WGK

WGK 3

Flash Point(F)

424.4 °F

Flash Point(C)

218 °C

Regulatory Information

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Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: translocation of nuclear factor-?B as potential target
Zhao et al.
Molecular Medicine Reports, 11, 3087-3093 (2015)
Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on HT-29 human colon cancer cells
Srimuangwong et al.
World Journal of Gastroenterology, 18, 2383-2389 (2012)
Feng Li et al.
Food chemistry, 135(2), 332-337 (2012-08-08)
Hexahydrocurcumin, 1-dehydro-[6]-gingerdione, 6-dehydroshogaol and 6-shogaol were evaluated for their antioxidant and anti-inflammatory activities in the present study. The relative antioxidant potencies of ginger compounds decreased in similar order of 1-dehydro-[6]-gingerdione, hexahydrocurcumin>6-shogaol>6-dehydroshogaol in both 1,1-diphenyl-2-picyrlhydrazyl (DPPH) radical-scavenging and trolox equivalent antioxidant

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