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(OC)=C(O)C=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
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 |
|||
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Inactive ingredient | Prosoria Psoriasis Treatment Approved UseRelieves and helps prevent recurrence of psoriasis symptoms including scaling, flaking, itching, redness, irritation. |
PubMed
Title | Date | PubMed |
---|---|---|
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. | 1997 Sep 12 |
|
Hydrogen-bonding and C-H...pi interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (tetrahydrocurcumin). | 2004 Aug |
|
Protective role of tetrahydrocurcumin against erythromycin estolate-induced hepatotoxicity. | 2004 May |
|
Tetrahydrocurcumin: effect on chloroquine-mediated oxidative damage in rat kidney. | 2006 Nov |
|
Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor. | 2008 Mar-Apr |
|
Optimized turmeric extracts have potent anti-amyloidogenic effects. | 2009 Dec |
|
Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. | 2010 Dec 5 |
|
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. | 2010 Oct |
|
Tetrahydrocurcumin protects against cadmium-induced hypertension, raised arterial stiffness and vascular remodeling in mice. | 2014 |
|
Tetrahydrocurcumin exerts protective effect on vincristine induced neuropathy: Behavioral, biochemical, neurophysiological and histological evidence. | 2015 Aug 5 |
|
Ameliorative efficacy of tetrahydrocurcumin against arsenic induced oxidative damage, dyslipidemia and hepatic mitochondrial toxicity in rats. | 2015 Jun 25 |
|
Effect of tetrahydrocurcumin on the profiles of drug-metabolizing enzymes induced by a high fat and high fructose diet in mice. | 2015 Sep 5 |
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%.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Brand Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
00U0645U03
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
124072
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
00U0645U03
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
1362136
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | RxNorm | ||
|
DTXSID30865801
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
36062-04-1
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
687845
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
C096277
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
609-201-3
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY | |||
|
67263
Created by
admin on Fri Dec 15 19:00:22 GMT 2023 , Edited by admin on Fri Dec 15 19:00:22 GMT 2023
|
PRIMARY |
PARENT (METABOLITE)
SUBSTANCE RECORD