tetrahydrodiferuloylmethane
tetrahydrocurcumin
 
Notes:
Tetrahydrocurcumin (THC), one of the major metabolites of curcumin, exhibits many of the same physiologic and pharmacological activities as curcumin and in some systems may exert greater antioxidant activity than curcumin (PMID: 16061427).
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1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (Click)
CAS Number: 36062-04-1Picture of molecule
FDA UNII: 00U0645U03
Nikkaji Web: J478.221F
Beilstein Number: 3485469
MDL: MFCD04152347
XlogP3-AA: 2.80 (est)
Molecular Weight: 372.41748000
Formula: C21 H24 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Food Chemicals Codex Listed: No
Boiling Point: 564.07 °C. @ 760.00 mm Hg (est)
Flash Point: 385.00 °F. TCC ( 196.20 °C. ) (est)
logP (o/w): 2.728 (est)
Soluble in:
 water, 9.434 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
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Suppliers:
Charkit Chemical
TETRAHYDROCURCUMINOIDS (THC) WHITE CURCUMIN
Sabinsa Corporation
SabiWhite®
Santa Cruz Biotechnology
For experimental / research use only.
Tetrahydro Curcumin
Sigma-Aldrich
For experimental / research use only.
Tetrahydrocurcumin
analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants
Recommendation for tetrahydrodiferuloylmethane usage levels up to:
 not for fragrance use.
 
Recommendation for tetrahydrodiferuloylmethane flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 124072
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Chemidplus: 0036062041
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References:
 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 124072
Pubchem (sid): 135078032
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB05789
FooDB: FDB005352
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 turmeric plant
Search Trop  Picture
 zedoary
Search Trop  Picture
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Synonyms:
3,5-heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-
1,7-bis-(4-hydroxy-3-methoxy-phenyl)-heptane-3,5-dione
1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptane dione
1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione
1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
 tetrahydrocurcumin
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Articles:
PubMed: Differential cellular uptake and metabolism of curcuminoids in monocytes/macrophages: regulatory effects on lipid accumulation.
PubMed: Tetrahydrocurcumin induces G2/M cell cycle arrest and apoptosis involving p38 MAPK activation in human breast cancer cells.
PubMed: A high-throughput quantification method of curcuminoids and curcumin metabolites in human plasma via high-performance liquid chromatography/tandem mass spectrometry.
PubMed: Comparative absorption of curcumin formulations.
PubMed: Curcuma longa extract associated with white pepper lessens high fat diet-induced inflammation in subcutaneous adipose tissue.
PubMed: Chemopreventative effects of tetrahydrocurcumin on human diseases.
PubMed: Development of a liquid chromatographic method for the simultaneous quantification of curcumin, β-arteether, tetrahydrocurcumin and dihydroartemisinin. Application to lipid-based formulations.
PubMed: Structure-activity relationship analysis of curcumin analogues on anti-influenza virus activity.
PubMed: Turmeric curcumin inhibits entry of all hepatitis C virus genotypes into human liver cells.
PubMed: Microbial transformation of curcumin to its derivatives with a novel Pichia kudriavzevii ZJPH0802 strain.
PubMed: Novel racemic tetrahydrocurcuminoid dihydropyrimidinone analogues as potent acetylcholinesterase inhibitors.
PubMed: Synthesis of amino acid conjugates of tetrahydrocurcumin and evaluation of their antibacterial and anti-mutagenic properties.
PubMed: Curcumin and aging.
PubMed: Development, characterization and permeability assessment based on caco-2 monolayers of self-microemulsifying floating tablets of tetrahydrocurcumin.
PubMed: Highly stabilized curcumin nanoparticles tested in an in vitro blood-brain barrier model and in Alzheimer's disease Tg2576 mice.
PubMed: Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes.
PubMed: Infusion pharmacokinetics of Lipocurc™ (liposomal curcumin) and its metabolite tetrahydrocurcumin in Beagle dogs.
PubMed: Tissue distribution of (Lipocurc™) liposomal curcumin and tetrahydrocurcumin following two- and eight-hour infusions in Beagle dogs.
PubMed: Inhibition of Ca(2+) release-activated Ca(2+) channel (CRAC) by curcumin and caffeic acid phenethyl ester (CAPE) via electrophilic addition to a cysteine residue of Orai1.
PubMed: Antioxidant combinations protect oral fibroblasts against metal-induced toxicity.
PubMed: Formation of tetrahydrocurcumin by reduction of curcumin with cultured plant cells of Marchantia polymorpha.
PubMed: Tetrahydrocurcumin ameliorates homocysteinylated cytochrome-c mediated autophagy in hyperhomocysteinemia mice after cerebral ischemia.
PubMed: Tetrahydrocurcumin extends life span and inhibits the oxidative stress response by regulating the FOXO forkhead transcription factor.
PubMed: Tetrahydrocurcumin alleviates hypertension, aortic stiffening and oxidative stress in rats with nitric oxide deficiency.
PubMed: Regulatory effects of curcumin on lipid accumulation in monocytes/macrophages.
PubMed: Enhancement of curcumin oral absorption and pharmacokinetics of curcuminoids and curcumin metabolites in mice.
PubMed: Molecular docking studies of curcumin analogs with phospholipase A2.
PubMed: Tetrahydrocurcumin, a major metabolite of curcumin, induced autophagic cell death through coordinative modulation of PI3K/Akt-mTOR and MAPK signaling pathways in human leukemia HL-60 cells.
PubMed: Tetrahydrocurcumin is more effective than curcumin in preventing azoxymethane-induced colon carcinogenesis.
PubMed: Optimized turmeric extract reduces β-Amyloid and phosphorylated Tau protein burden in Alzheimer's transgenic mice.
PubMed: Microbial conversion of curcumin into colorless hydroderivatives by the endophytic fungus Diaporthe sp. associated with Curcuma longa.
PubMed: Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism.
PubMed: Bioactive antioxidant mixtures promote proliferation and migration on human oral fibroblasts.
PubMed: Antioxidant and vascular protective effects of curcumin and tetrahydrocurcumin in rats with L-NAME-induced hypertension.
PubMed: In vitro inhibitory effect of tetrahydrocurcuminoids on Fusarium proliferatum growth and fumonisin B₁ biosynthesis.
PubMed: Controlled release of oral tetrahydrocurcumin from a novel self-emulsifying floating drug delivery system (SEFDDS).
PubMed: Revisiting dietary antioxidants, neurodegeneration and dementia.
PubMed: Tetrahydrocurcumin confers protection against amyloid β-induced toxicity.
PubMed: Tetrahydrocurcuminoid cream plus targeted narrowband UVB phototherapy for vitiligo: a preliminary randomized controlled study.
PubMed: A liquid chromatography-tandem mass spectrometric method for quantification of curcuminoids in cell medium and mouse plasma.
PubMed: Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents.
PubMed: Antioxidants counteract nicotine and promote migration via RacGTP in oral fibroblast cells.
PubMed: Curcuminoids activate p38 MAP kinases and promote UVB-dependent signalling in keratinocytes.
PubMed: Monoacetylcurcumin strongly regulates inflammatory responses through inhibition of NF-kappaB activation.
PubMed: Combined treatment of tetrahydrocurcumin and chlorogenic acid exerts potential antihyperglycemic effect on streptozotocin-nicotinamide-induced diabetic rats.
PubMed: Comparative and combined effect of chlorogenic acid and tetrahydrocurcumin on antioxidant disparities in chemical induced experimental diabetes.
PubMed: Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts.
PubMed: Optimized turmeric extracts have potent anti-amyloidogenic effects.
PubMed: Cardioprotective effect of tetrahydrocurcumin and rutin on lipid peroxides and antioxidants in experimentally induced myocardial infarction in rats.
PubMed: Dimethoxycurcumin, a Synthetic Curcumin Analogue, Induces Heme Oxygenase-1 Expression through Nrf2 Activation in RAW264.7 Macrophages.
PubMed: Curcumin is a potent DNA hypomethylation agent.
PubMed: Modulation of macrophage functions by compounds isolated from Zingiber officinale.
PubMed: Natural derivatives of curcumin attenuate the Wnt/beta-catenin pathway through down-regulation of the transcriptional coactivator p300.
PubMed: Tetrahydrocurcumin inhibits HT1080 cell migration and invasion via downregulation of MMPs and uPA.
PubMed: Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor.
PubMed: Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS.
PubMed: Curcumin structure-function, bioavailability, and efficacy in models of neuroinflammation and Alzheimer's disease.
PubMed: Inhibition of monoamine oxidase-B by the polyphenolic compound, curcumin and its metabolite tetrahydrocurcumin, in a model of Parkinson's disease induced by MPTP neurodegeneration in mice.
PubMed: Anti-cancer and anti-angiogenic effects of curcumin and tetrahydrocurcumin on implanted hepatocellular carcinoma in nude mice.
PubMed: Effect of tetrahydrocurcumin on insulin receptor status in type 2 diabetic rats: studies on insulin binding to erythrocytes.
PubMed: Comparative radical-scavenging activity of curcumin and tetrahydrocurcumin with thiols as measured by the induction period method.
PubMed: Influence of tetrahydrocurcumin on tail tendon collagen contents and its properties in rats with streptozotocin-nicotinamide-induced type 2 diabetes.
PubMed: Curcumin attenuates dimethylnitrosamine-induced liver injury in rats through Nrf2-mediated induction of heme oxygenase-1.
PubMed: Antihyperlipidemic effect of curcumin and tetrahydrocurcumin in experimental type 2 diabetic rats.
PubMed: Influence of tetrahydrocurcumin on hepatic and renal functional markers and protein levels in experimental type 2 diabetic rats.
PubMed: Influence of tetrahydrocurcumin on erythrocyte membrane bound enzymes and antioxidant status in experimental type 2 diabetic rats.
PubMed: Tetrahydrocurcumin prevents brain lipid peroxidation in streptozotocin-induced diabetic rats.
PubMed: The study of human skin irritation of a novel herbal skin care product and ingredients by human single closed patch testing.
PubMed: Roles of heme oxygenase-1 in curcumin-induced growth inhibition in rat smooth muscle cells.
PubMed: Nephroprotective and hepatoprotective effects of curcuminoids.
PubMed: Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism.
PubMed: The effects of tetrahydrocurcumin and green tea polyphenol on the survival of male C57BL/6 mice.
PubMed: Comparative cytotoxicity and ROS generation by curcumin and tetrahydrocurcumin following visible-light irradiation or treatment with horseradish peroxidase.
PubMed: Effect of tetrahydrocurcumin on plasma antioxidants in streptozotocin-nicotinamide experimental diabetes.
PubMed: What really declines with age? The Hayflick Lecture for 2006 35th American Aging Association.
PubMed: Changes in glycoprotein components in streptozotocin--nicotinamide induced type 2 diabetes: influence of tetrahydrocurcumin from Curcuma longa.
PubMed: Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives.
PubMed: Curcumin induces pro-apoptotic endoplasmic reticulum stress in human leukemia HL-60 cells.
PubMed: Tetrahydrocurcumin: effect on chloroquine-mediated oxidative damage in rat kidney.
PubMed: Comparison of systemic availability of curcumin with that of curcumin formulated with phosphatidylcholine.
PubMed: Modulation of function of three ABC drug transporters, P-glycoprotein (ABCB1), mitoxantrone resistance protein (ABCG2) and multidrug resistance protein 1 (ABCC1) by tetrahydrocurcumin, a major metabolite of curcumin.
PubMed: Effect of tetrahydrocurcumin on lipid peroxidation and lipids in streptozotocin-nicotinamide-induced diabetic rats.
PubMed: Antioxidant effect of tetrahydrocurcumin in streptozotocin-nicotinamide induced diabetic rats.
PubMed: Curcumin is an inhibitor of p300 histone acetylatransferase.
PubMed: Effect of tetrahydrocurcumin on blood glucose, plasma insulin and hepatic key enzymes in streptozotocin induced diabetic rats.
PubMed: Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin.
PubMed: Effect of tetrahydrocurcumin on erythromycin estolate-induced lipid peroxidation in rats.
PubMed: Elucidation of anti-allergic activities of curcumin-related compounds with a special reference to their anti-oxidative activities.
PubMed: Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography.
PubMed: Protective role of antioxidative food factors in oxidative stress caused by hyperglycemia.
PubMed: Relationship between intracellular ROS production and membrane mobility in curcumin- and tetrahydrocurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells.
PubMed: Protective role of tetrahydrocurcumin (THC) an active principle of turmeric on chloroquine induced hepatotoxicity in rats.
PubMed: Suppression of protein kinase C and nuclear oncogene expression as possible action mechanisms of cancer chemoprevention by Curcumin.
PubMed: Hydrogen-bonding and C-H...pi interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (tetrahydrocurcumin).
PubMed: Interventions in aging and age-associated pathologies by means of nutritional approaches.
PubMed: Modulation of arachidonic acid metabolism by curcumin and related beta-diketone derivatives: effects on cytosolic phospholipase A(2), cyclooxygenases and 5-lipoxygenase.
PubMed: Protective role of tetrahydrocurcumin against erythromycin estolate-induced hepatotoxicity.
PubMed: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites.
PubMed: Contact allergy to tetrahydrocurcumin.
PubMed: Studies on the role of some synthetic curcuminoid derivatives in the inhibition of tumour specific angiogenesis.
PubMed: The protective effects of tetrahydrocurcumin on oxidative stress in cholesterol-fed rabbits.
PubMed: Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine.
PubMed: Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced renal injury in mice.
PubMed: Mechanisms of cancer chemoprevention by curcumin.
PubMed: Recent studies on the biofunctions and biotransformations of curcumin.
PubMed: Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production.
PubMed: Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down-regulation of IkappaB kinase and NFkappaB activation in macrophages.
PubMed: Inhibition of radiation-induced lipid peroxidation by tetrahydrocurcumin: possible mechanisms by pulse radiolysis.
PubMed: Chemoprevention by curcumin during the promotion stage of tumorigenesis of mammary gland in rats irradiated with gamma-rays.
PubMed: Biotransformation of curcumin through reduction and glucuronidation in mice.
PubMed: Inhibitory effects of curcumin and tetrahydrocurcuminoids on the tumor promoter-induced reactive oxygen species generation in leukocytes in vitro and in vivo.
PubMed: Chemopreventive effects of carotenoids and curcumins on mouse colon carcinogenesis after 1,2-dimethylhydrazine initiation.
PubMed: Involvement of the beta-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin.
PubMed: Effects of curcumin, demethoxycurcumin, bisdemethoxycurcumin and tetrahydrocurcumin on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion.
PubMed: The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat.
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