U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TETRAHYDRODIFERULOYLMETHANE

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P42574
Gene ID: 836.0
Gene Symbol: CASP3
Target Organism: Homo sapiens (Human)
Target ID: P55211|||Q9UEQ3
Gene ID: 842.0
Gene Symbol: CASP9
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Inactive ingredient
Prosoria Psoriasis Treatment

Approved Use

Relieves and helps prevent recurrence of psoriasis symptoms including scaling, flaking, itching, redness, irritation.
PubMed

PubMed

TitleDatePubMed
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
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
Patents

Sample Use Guides

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
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
TETRAHYDRODIFERULOYLMETHANE
INCI  
INCI  
Official Name English
TETRAHYDROCURCUMIN [INCI]
Common Name English
TETRAHYDROCURCUMIN
Systematic Name English
1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)HEPTANE-3,5-DIONE
Systematic Name English
TETRAHYDRODIFERULOYLMETHANE [INCI]
Common Name English
NSC-687845
Code English
3,5-HEPTANEDIONE, 1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)-
Systematic Name English
SABIWHITE
Brand Name English
Code System Code Type Description
FDA UNII
00U0645U03
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
PUBCHEM
124072
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
DAILYMED
00U0645U03
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
RXCUI
1362136
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID30865801
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
CAS
36062-04-1
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
NSC
687845
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
MESH
C096277
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
609-201-3
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY
CHEBI
67263
Created by admin on Fri Dec 15 19:00:22 UTC 2023 , Edited by admin on Fri Dec 15 19:00:22 UTC 2023
PRIMARY