Home Other Building Blocks 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione

1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione

CAS No.:
36062-04-1
Catalog Number:
AG003DRJ
Molecular Formula:
C21H24O6
Molecular Weight:
372.4117
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$19
- +
5g
98%
In Stock USA
United States
$44
- +
25g
98%
In Stock USA
United States
$100
- +
100g
98%
In Stock USA
United States
$288
- +
Product Description
Catalog Number:
AG003DRJ
Chemical Name:
1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
CAS Number:
36062-04-1
Molecular Formula:
C21H24O6
Molecular Weight:
372.4117
MDL Number:
MFCD04152347
IUPAC Name:
1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
InChI:
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
SMILES:
COc1cc(CCC(=O)CC(=O)CCc2ccc(c(c2)OC)O)ccc1O
EC Number:
609-201-3
UNII:
00U0645U03
NSC Number:
687845
Properties
Complexity:
437  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
372.157g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
372.417g/mol
Monoisotopic Mass:
372.157g/mol
Rotatable Bond Count:
10  
Topological Polar Surface Area:
93.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.8  
Literature
Title Journal
Effect of tetrahydrocurcumin on the profiles of drug-metabolizing enzymes induced by a high fat and high fructose diet in mice. Chemico-biological interactions 20150905
Tetrahydrocurcumin exerts protective effect on vincristine induced neuropathy: Behavioral, biochemical, neurophysiological and histological evidence. Chemico-biological interactions 20150805
Ameliorative efficacy of tetrahydrocurcumin against arsenic induced oxidative damage, dyslipidemia and hepatic mitochondrial toxicity in rats. Chemico-biological interactions 20150625
Tetrahydrocurcumin protects against cadmium-induced hypertension, raised arterial stiffness and vascular remodeling in mice. PloS one 20140101
Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes. Food chemistry 20130115
Tissue distribution of (Lipocurc™) liposomal curcumin and tetrahydrocurcumin following two- and eight-hour infusions in Beagle dogs. Anticancer research 20121001
Infusion pharmacokinetics of Lipocurc™ (liposomal curcumin) and its metabolite tetrahydrocurcumin in Beagle dogs. Anticancer research 20121001
Tetrahydrocurcumin ameliorates homocysteinylated cytochrome-c mediated autophagy in hyperhomocysteinemia mice after cerebral ischemia. Journal of molecular neuroscience : MN 20120501
Tetrahydrocurcumin alleviates hypertension, aortic stiffening and oxidative stress in rats with nitric oxide deficiency. Hypertension research : official journal of the Japanese Society of Hypertension 20120401
Formation of tetrahydrocurcumin by reduction of curcumin with cultured plant cells of Marchantia polymorpha. Natural product communications 20120401
Tetrahydrocurcumin is more effective than curcumin in preventing azoxymethane-induced colon carcinogenesis. Molecular nutrition & food research 20111201
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. Molecular nutrition & food research 20111101
Tetrahydrocurcumin extends life span and inhibits the oxidative stress response by regulating the FOXO forkhead transcription factor. Aging 20111101
Bioactive antioxidant mixtures promote proliferation and migration on human oral fibroblasts. Archives of oral biology 20110801
Antioxidant and vascular protective effects of curcumin and tetrahydrocurcumin in rats with L-NAME-induced hypertension. Naunyn-Schmiedeberg's archives of pharmacology 20110501
Controlled release of oral tetrahydrocurcumin from a novel self-emulsifying floating drug delivery system (SEFDDS). AAPS PharmSciTech 20110301
In vitro inhibitory effect of tetrahydrocurcuminoids on Fusarium proliferatum growth and fumonisin B₁ biosynthesis. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20110201
Tetrahydrocurcumin confers protection against amyloid β-induced toxicity. Neuroreport 20110105
Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. Chemico-biological interactions 20101205
Antioxidants counteract nicotine and promote migration via RacGTP in oral fibroblast cells. Journal of periodontology 20101101
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. European journal of medicinal chemistry 20101001
Tetrahydrocurcuminoid cream plus targeted narrowband UVB phototherapy for vitiligo: a preliminary randomized controlled study. Photomedicine and laser surgery 20101001
Comparative and combined effect of chlorogenic acid and tetrahydrocurcumin on antioxidant disparities in chemical induced experimental diabetes. Molecular and cellular biochemistry 20100801
Curcuminoids activate p38 MAP kinases and promote UVB-dependent signalling in keratinocytes. Experimental dermatology 20100601
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species. European journal of medicinal chemistry 20100301
Combined treatment of tetrahydrocurcumin and chlorogenic acid exerts potential antihyperglycemic effect on streptozotocin-nicotinamide-induced diabetic rats. General physiology and biophysics 20100301
Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts. Methods in molecular biology (Clifton, N.J.) 20100101
Optimized turmeric extracts have potent anti-amyloidogenic effects. Current Alzheimer research 20091201
Curcumin is a potent DNA hypomethylation agent. Bioorganic & medicinal chemistry letters 20090201
Cardioprotective effect of tetrahydrocurcumin and rutin on lipid peroxides and antioxidants in experimentally induced myocardial infarction in rats. Die Pharmazie 20090201
Natural derivatives of curcumin attenuate the Wnt/beta-catenin pathway through down-regulation of the transcriptional coactivator p300. Biochemical and biophysical research communications 20081226
Tetrahydrocurcumin inhibits HT1080 cell migration and invasion via downregulation of MMPs and uPA. Acta pharmacologica Sinica 20080701
Anti-cancer and anti-angiogenic effects of curcumin and tetrahydrocurcumin on implanted hepatocellular carcinoma in nude mice. World journal of gastroenterology 20080407
Curcumin attenuates dimethylnitrosamine-induced liver injury in rats through Nrf2-mediated induction of heme oxygenase-1. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080401
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. Inflammopharmacology 20080401
Effect of tetrahydrocurcumin on insulin receptor status in type 2 diabetic rats: studies on insulin binding to erythrocytes. Journal of biosciences 20080301
Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor. Anticancer research 20080101
Influence of tetrahydrocurcumin on tail tendon collagen contents and its properties in rats with streptozotocin-nicotinamide-induced type 2 diabetes. Fundamental & clinical pharmacology 20071201
The effects of tetrahydrocurcumin and green tea polyphenol on the survival of male C57BL/6 mice. Biogerontology 20071001
Influence of tetrahydrocurcumin on hepatic and renal functional markers and protein levels in experimental type 2 diabetic rats. Basic & clinical pharmacology & toxicology 20071001
Influence of tetrahydrocurcumin on erythrocyte membrane bound enzymes and antioxidant status in experimental type 2 diabetic rats. Journal of ethnopharmacology 20070925
Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. Carcinogenesis 20070801
Roles of heme oxygenase-1 in curcumin-induced growth inhibition in rat smooth muscle cells. Experimental & molecular medicine 20070630
The study of human skin irritation of a novel herbal skin care product and ingredients by human single closed patch testing. Journal of the Medical Association of Thailand = Chotmaihet thangphaet 20070601
Tetrahydrocurcumin prevents brain lipid peroxidation in streptozotocin-induced diabetic rats. Journal of medicinal food 20070601
Changes in glycoprotein components in streptozotocin--nicotinamide induced type 2 diabetes: influence of tetrahydrocurcumin from Curcuma longa. Plant foods for human nutrition (Dordrecht, Netherlands) 20070301
Curcumin induces pro-apoptotic endoplasmic reticulum stress in human leukemia HL-60 cells. Biochemical and biophysical research communications 20070223
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. Molecular and cellular biochemistry 20070201
Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biological & pharmaceutical bulletin 20070101
Comparative cytotoxicity and ROS generation by curcumin and tetrahydrocurcumin following visible-light irradiation or treatment with horseradish peroxidase. Anticancer research 20070101
Antihyperlipidemic effect of curcumin and tetrahydrocurcumin in experimental type 2 diabetic rats. Renal failure 20070101
Comparative radical-scavenging activity of curcumin and tetrahydrocurcumin with thiols as measured by the induction period method. In vivo (Athens, Greece) 20070101
Tetrahydrocurcumin: effect on chloroquine-mediated oxidative damage in rat kidney. Basic & clinical pharmacology & toxicology 20061101
Antioxidant effect of tetrahydrocurcumin in streptozotocin-nicotinamide induced diabetic rats. Life sciences 20060927
Effect of tetrahydrocurcumin on lipid peroxidation and lipids in streptozotocin-nicotinamide-induced diabetic rats. Basic & clinical pharmacology & toxicology 20060801
Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin. Journal of pharmaceutical and biomedical analysis 20060224
Effect of tetrahydrocurcumin on plasma antioxidants in streptozotocin-nicotinamide experimental diabetes. Journal of basic and clinical physiology and pharmacology 20060101
Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050925
Relationship between intracellular ROS production and membrane mobility in curcumin- and tetrahydrocurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells. Oral diseases 20050701
Protective role of tetrahydrocurcumin (THC) an active principle of turmeric on chloroquine induced hepatotoxicity in rats. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20050430
Effect of tetrahydrocurcumin on erythromycin estolate-induced lipid peroxidation in rats. Journal of basic and clinical physiology and pharmacology 20050101
Effect of tetrahydrocurcumin on blood glucose, plasma insulin and hepatic key enzymes in streptozotocin induced diabetic rats. Journal of basic and clinical physiology and pharmacology 20050101
Hydrogen-bonding and C-H...pi interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (tetrahydrocurcumin). Acta crystallographica. Section C, Crystal structure communications 20040801
Interventions in aging and age-associated pathologies by means of nutritional approaches. Annals of the New York Academy of Sciences 20040601
Protective role of tetrahydrocurcumin against erythromycin estolate-induced hepatotoxicity. Pharmacological research 20040501
Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochemical and biophysical research communications 20031010
Contact allergy to tetrahydrocurcumin. Contact dermatitis 20030401
Studies on the role of some synthetic curcuminoid derivatives in the inhibition of tumour specific angiogenesis. Journal of experimental & clinical cancer research : CR 20030301
The protective effects of tetrahydrocurcumin on oxidative stress in cholesterol-fed rabbits. Journal of atherosclerosis and thrombosis 20020101
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. Journal of medicinal chemistry 19970912
Properties