Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H24O6 |
| Molecular Weight | 372.4117 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CCC(=O)CC(=O)CCC2=CC=C(O)C(OC)=C2)=CC=C1O
InChI
InChIKey=LBTVHXHERHESKG-UHFFFAOYSA-N
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
| Molecular Formula | C21H24O6 |
| Molecular Weight | 372.4117 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tetrahydrodiferuloylmethane (aka Tetrahydrocurcumin) is a bioactive metabolite of curcumin. It has been shown to have anti-inflammatory, anti-oxidant, anti-cancer, and neuroprotective effects in several in vitro and in vivo models. However, there have been no advances in human trials for these conditions. It should be noted that tetrahydrocurcumin is used in non-medicinal skin care formulations intended for skin whitening, skin soothing, and anti-oxidant effects.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26899573 |
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Target ID: P55211|||Q9UEQ3 Gene ID: 842.0 Gene Symbol: CASP9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26899573 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Inactive ingredient | Prosoria Psoriasis Treatment Approved UseRelieves and helps prevent recurrence of psoriasis symptoms including scaling, flaking, itching, redness, irritation. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of tetrahydrocurcumin on the profiles of drug-metabolizing enzymes induced by a high fat and high fructose diet in mice. | 2015-09-05 |
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| Tetrahydrocurcumin exerts protective effect on vincristine induced neuropathy: Behavioral, biochemical, neurophysiological and histological evidence. | 2015-08-05 |
|
| Ameliorative efficacy of tetrahydrocurcumin against arsenic induced oxidative damage, dyslipidemia and hepatic mitochondrial toxicity in rats. | 2015-06-25 |
|
| Tetrahydrocurcumin protects against cadmium-induced hypertension, raised arterial stiffness and vascular remodeling in mice. | 2014 |
|
| Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. | 2010-12-05 |
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| Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. | 2010-10 |
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| Optimized turmeric extracts have potent anti-amyloidogenic effects. | 2009-12 |
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| Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor. | 2008-05-30 |
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| Tetrahydrocurcumin: effect on chloroquine-mediated oxidative damage in rat kidney. | 2006-11 |
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| Hydrogen-bonding and C-H...pi interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (tetrahydrocurcumin). | 2004-08 |
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| Protective role of tetrahydrocurcumin against erythromycin estolate-induced hepatotoxicity. | 2004-05 |
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| Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. | 1997-09-12 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28386319
Adult male Sprague-Dawley rats were given traumatic brain injury using a modified weight drop method. The treatment group received 25 mg/kg of Tetrohydrocurcumin dissolved in saline and delivered by intraperitoneal injection. Relative to control animals, rats which were treated with tetrahydrocurcumin showed signs of increased autophagy in the injured cortex, reduced oxidative stress, reduced apoptosis and altered expression of apoptotic factors, and improved neurological function.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26899573
Human breast cancer MCF-7 cells were grown in RPMI 1640 medium with 10% fetal bovine serum and 1% immune body and incubated at 37 deg-C under a 5% CO2 atmosphere. Cells were grown for 24 hours before incubation with various concentrations of Tetrahydrocurcumin for 12, 24 and 48 hours. After treatment cell viability was determined using the MTT method. Induction of apoptosis was tested by treating MCF-7 cells with 0, 70, and 100 micro-M of tetrahydrocurcumin. Tetrahydrocurcumin showed an antiproliferative effect with a 24 hour IC50 of 107.8 micro-M. This was linked to cell cycle arrest in the G0/G1 phase. Treatment of MCF-7 cells with 100 micro-M tetrahydrocurcumin increased apoptotic cell death by 37.8%.
| Substance Class |
Chemical
Created
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Edited
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