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SMB00370

Sigma-Aldrich

Tetrahydrocurcumin

≥96% (HPLC)

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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
Empirical Formula (Hill Notation):
C21H24O6
CAS Number:
Molecular Weight:
372.41
Beilstein/REAXYS Number:
3485469
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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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This Item
C7727C1386PHR2209
Tetrahydrocurcumin ≥96% (HPLC)

SMB00370

Tetrahydrocurcumin

Curcumin ≥94% (curcuminoid content), ≥80% (Curcumin)

C7727

Curcumin

Curcumin from Curcuma longa (Turmeric), powder

C1386

Curcumin

Curcumin Pharmaceutical Secondary Standard; Certified Reference Material

PHR2209

Curcumin

form

powder

form

powder

form

powder

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-10 to -25°C

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


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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

Ammonium formate ≥99.995% trace metals basis

Sigma-Aldrich

516961

Ammonium formate

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

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
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
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
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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