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SMB00370

Sigma-Aldrich

Tetrahydrocurcumin

≥96% (HPLC)

Sinónimos:

Tetrahydrocurcumin, 1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione, HZIV 81-2, NSC687845, Tetrahydrodiferuloylmethane, 1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione

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About This Item

Fórmula empírica (notación de Hill):
C21H24O6
Número de CAS:
36062-04-1
Peso molecular:
372.41
Beilstein/REAXYS Number:
3485469
MDL number:
MFCD04152347
UNSPSC Code:
12352205
PubChem Substance ID:
329824974
NACRES:
NA.25

assay

≥96% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc(CCC(=O)CC(=O)CCc2ccc(O)c(OC)c2)ccc1O

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

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General description

Tetrahydrocurcumin (THC) is a colorless metabolite of curcumin. It has a similar structure to that of curcumin. THC lacks the α, β-unsaturated carbonyl moiety in its chemical structure. It is naturally sourced from the roots of Curcuma zedoaria, Zingiber mioga, and Zingiber officinale.

Application

Tetrahydrocurcumin (THC) has been used as a neuroprotective agent to study its therapeutic potential in improving mitochondrial dysfunction in the ischemic stroke mice model.

Biochem/physiol Actions

Tetrahydrocurcumin is well-studied in treating cancer for its excellent anti-cancer, anti-angiogenic, and chemopreventative activities. It also exerts anti-inflammatory properties. Tetrahydrocurcumin has been shown to have antioxidant and protective effects against diabetes, and vascular dysfunction via alleviation of oxidative stress.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

385.2 °F

flash_point_c

196.2 °C

Certificados de análisis (COA)

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Bharat B Aggarwal et al.
Molecules (Basel, Switzerland), 20(1), 185-205 (2014-12-31)
Curcumin (diferuloylmethane), a golden pigment from turmeric, has been linked with antioxidant, anti-inflammatory, anticancer, antiviral, antibacterial, and antidiabetic properties. Most of the these activities have been assigned to methoxy, hydroxyl, α,β-unsaturated carbonyl moiety or to diketone groups present in curcumin.
Sunmin Park et al.
Genes & nutrition, 11, 2-2 (2016-08-03)
Menopausal symptoms are associated with inflammation. Curcumin is a well-known anti-inflammatory bioactive compound from turmeric whereas tetrahydrocurcumin (THC) is a major metabolite of curcumin that may have different efficacies. However, they have not been studied for anti-menopausal symptoms and anti-osteoarthritis
Nandan K Mondal et al.
Neurochemistry international, 122, 120-138 (2018-11-26)
The objectives of this study are to identify the mechanism of mitochondrial dysfunction during cerebral ischemic/reperfusion (I/R) injury and the therapeutic potential of tetrahydrocurcumin (THC) to mitigate mitochondrial dysfunction in experimental stroke model. In our study, 8-10 weeks old male
Pornprom Yoysungnoen et al.
World journal of gastroenterology, 14(13), 2003-2009 (2008-04-09)
To determine the effect of tetrahydrocurcumin (THC) on tumor angiogenesis compared with curcumin (CUR) by using both in vitro and in vivo models of human hepatocellular carcinoma cell line (HepG2). The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) assay was used for testing the
Ching-Shu Lai et al.
Biomolecules, 10(6) (2020-06-04)
In recent decades, cancer has been one of the leading causes of death worldwide. Despite advances in understanding the molecular basis of tumorigenesis, diagnosis, and clinical therapies, the discovery and development of effective drugs is an active and vital field
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