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Merck
CN

SMB00370

Tetrahydrocurcumin

≥96% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C21H24O6
CAS Number:
36062-04-1
Molecular Weight:
372.41
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
329824974
MDL number:
MFCD04152347
Beilstein/REAXYS Number:
3485469

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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

SMILES string

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

InChI key

LBTVHXHERHESKG-UHFFFAOYSA-N

assay

≥96% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

200

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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

WGK 3

flash_point_f

385.2 °F

flash_point_c

196.2 °C

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Certificates of Analysis (COA)

Lot/Batch Number
0000424202
0000424202
0000415771
0000415771
0000404497

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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
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
Jia-Ching Wu et al.
Food & function, 5(1), 12-17 (2013-11-14)
Chemoprevention is a relatively new and promising strategy to prevent human degenerative diseases, including cancer, and is defined as the use of natural dietary compounds and/or synthetic substances to block, inhibit, reverse, or retard the progress of human diseases. Tetrahydrocurcumin
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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