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SMB00370

Sigma-Aldrich

Tetrahydrocurcumin

≥96% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C21H24O6
Numéro CAS:
36062-04-1
Poids moléculaire :
372.41
Beilstein:
3485469
Numéro MDL:
MFCD04152347
Code UNSPSC :
12352205
ID de substance PubChem :
329824974
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Essai

≥96% (HPLC)

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

LBTVHXHERHESKG-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

385.2 °F

Point d'éclair (°C)

196.2 °C

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Certificats d'analyse (COA)

Lot/Batch Number
0000404497
0000376022
0000376022
0000343813
0000404497

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Bisdemethoxycurcumin analytical standard

Supelco

90594

Bisdemethoxycurcumin

Curcumin matrix substance for MALDI-MS, ≥99.5% (HPLC)

Supelco

78246

Curcumin

Desmethoxycurcumin United States Pharmacopeia (USP) Reference Standard

USP

1173100

Desmethoxycurcumin

Formate d’ammonium ≥99.995% trace metals basis

Sigma-Aldrich

516961

Formate d′ammonium

USP

USP

1151866

Curcuminoids

Demethoxycurcumin analytical standard

Supelco

90593

Demethoxycurcumin

(+)-α-Tocopherol Type VI, from vegetable oil, liquid (≥0.88M based on potency, density and molecular wt.), BioReagent, suitable for insect cell culture, ≥1000 IU/g

Sigma-Aldrich

T1539

(+)-α-Tocopherol

tert-Butylhydroquinone 97%

Sigma-Aldrich

112941

tert-Butylhydroquinone

Curcumin primary reference standard

00280590

Curcumin

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
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
Pidaran Murugan et al.
Life sciences, 79(18), 1720-1728 (2006-06-30)
Oxidative stress has been suggested to be a contributory factor in development and complication of diabetes. In the present study, we have investigated the effect of tetrahydrocurcumin (THC), one of the active metabolites of curcumin on antioxidants status in streptozotocin-nicotinamide
Upa Kukongviriyapan et al.
The Tohoku journal of experimental medicine, 239(1), 25-38 (2016-05-07)
Cadmium (Cd) is a non-essential heavy metal with high toxicity potential. Humans are exposed to Cd present in diet, polluted air, and cigarette smoke. Cd exposure has been associated with increased risk of chronic diseases, including hypertension, atherosclerosis, diabetes, and
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