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Taxifolin

CAS No.:
480-18-2
Catalog Number:
AG003945
Molecular Formula:
C15H12O7
Molecular Weight:
304.2516
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
250mg
95%
In Stock USA
United States
$61
- +
1g
95%
In Stock USA
United States
$123
- +
5g
95%
In Stock USA
United States
$391
- +
Product Description
Catalog Number:
AG003945
Chemical Name:
Taxifolin
CAS Number:
480-18-2
Molecular Formula:
C15H12O7
Molecular Weight:
304.2516
MDL Number:
MFCD00006845
IUPAC Name:
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
InChI:
InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1
InChI Key:
CXQWRCVTCMQVQX-LSDHHAIUSA-N
SMILES:
Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
EC Number:
207-543-4
UNII:
9SOB9E3987
Properties
Complexity:
428  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
304.058g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
304.254g/mol
Monoisotopic Mass:
304.058g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
127A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.5  
Literature
Title Journal
Structure-Dependent Modulation of Aryl Hydrocarbon Receptor-Mediated Activities by Flavonoids. Toxicological sciences : an official journal of the Society of Toxicology 20180701
Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties. Molecules (Basel, Switzerland) 20161121
Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. Toxicological sciences : an official journal of the Society of Toxicology 20150201
Dietary flavonoids fisetin and myricetin: dual inhibitors of Plasmodium falciparum falcipain-2 and plasmepsin II. Fitoterapia 20140401
Taxifolin prevents diabetic cardiomyopathy in vivo and in vitro by inhibition of oxidative stress and cell apoptosis. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20140101
Silibinin inhibits hepatitis C virus entry into hepatocytes by hindering clathrin-dependent trafficking. Cellular microbiology 20131101
Production, composition and toxicology studies of Enzogenol® Pinus radiata bark extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20121201
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. Chemical research in toxicology 20121119
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells. Phytotherapy research : PTR 20121101
Inhibition of melanin production by a combination of Siberian larch and pomegranate fruit extracts. Fitoterapia 20120901
Taxifolin suppresses UV-induced skin carcinogenesis by targeting EGFR and PI3K. Cancer prevention research (Philadelphia, Pa.) 20120901
A theoretical study on cellular antioxidant activity of selected flavonoids. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120701
Dual inhibition of chaperoning process by taxifolin: molecular dynamics simulation study. Journal of molecular graphics & modelling 20120701
Biotransformation of flavonols and taxifolin in hepatocyte in vitro systems as determined by liquid chromatography with various stationary phases and electrospray ionization-quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120615
Dihydroquercetin: More than just an impurity? European journal of pharmacology 20120605
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones. Parasitology research 20120601
[Effects of different processing on active components in fructus polygoni orientalis by HPLC analysis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120401
Molecular characterization and expression analysis of dihydroflavonol 4-reductase (DFR) gene in Saussurea medusa. Molecular biology reports 20120301
The influence of Cd²⁺, Hg²⁺ and Pb²⁺ on taxifolin binding to bovine serum albumin by spectroscopic methods: with the viewpoint of toxic ions/drug interference. Environmental toxicology and pharmacology 20120301
Contribution of flavonoids and catechol to the reduction of ICAM-1 expression in endothelial cells by a standardised Willow bark extract. Phytomedicine : international journal of phytotherapy and phytopharmacology 20120215
Efficacy of glucosamine alendronate alone & in combination with dihydroquercetin for treatment of osteoporosis in animal model. The Indian journal of medical research 20120201
[Effect of the liposomal form of taxifolin complexes with metals of variable valence on skin regeneration after chemical burn]. Tsitologiia 20120101
Extraction of dihydroquercetin from Larix gmelinii with ultrasound-assisted and microwave-assisted alternant digestion. International journal of molecular sciences 20120101
Micronization of taxifolin by supercritical antisolvent process and evaluation of radical scavenging activity. International journal of molecular sciences 20120101
Study of skin anti-ageing and anti-inflammatory effects of dihydroquercetin, natural triterpenoids, and their synthetic derivatives. Bioorganicheskaia khimiia 20120101
Antioxidant composition causes antiexsudorific effect in the model of chronic venous insufficiency. Bulletin of experimental biology and medicine 20111101
The thermal and enzymatic taxifolin-alphitonin rearrangement. Journal of natural products 20111028
Investigation of flavonoids bearing different substituents on ring C and their cu2+ complex binding with bovine serum albumin: structure-affinity relationship aspects. Journal of agricultural and food chemistry 20111012
Effects of flavonoids on prostaglandin E2 production and on COX-2 and mPGES-1 expressions in activated macrophages. Planta medica 20110901
Stereospecific pharmacokinetics of racemic homoeriodictyol, isosakuranetin, and taxifolin in rats and their disposition in fruit. Chirality 20110401
Stability of Pycnogenol® as an ingredient in fruit juices subjected to in vitro gastrointestinal digestion. Journal of the science of food and agriculture 20110130
Plasma protein binding of polyphenols from maritime pine bark extract (USP). Journal of pharmaceutical and biomedical analysis 20110105
[Biological activity of water-soluble nanostructures of dihydroquercetin with cyclodextrins]. Biofizika 20110101
[Antiproliferative and antioxidant activity of new dihydroquercetin derivatives]. Eksperimental'naia i klinicheskaia farmakologiia 20100901
A new chromone derivative from Berchemia lineata. Yao xue xue bao = Acta pharmaceutica Sinica 20100901
Effect of taxifolin glycoside on atopic dermatitis-like skin lesions in NC/Nga mice. Phytotherapy research : PTR 20100701
Effects of a nanocomplex containing antioxidant, lipid, and amino acid on thermal burn wound surface. Bulletin of experimental biology and medicine 20100701
[Anticoagulant activity of extracts from cedar bark, anthocyanidins of spruce and birch bark, and cellulose of aspen, fir, and wheat straw]. Eksperimental'naia i klinicheskaia farmakologiia 20100601
[Study on the chemical constituents of Cudrania tricuspidata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601
Cytotoxic activities of several geranyl-substituted flavanones. Journal of natural products 20100423
[Study on the chemical constituents from Sarcopyramis nepalensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100401
Identification of hepatoprotective flavonolignans from silymarin. Proceedings of the National Academy of Sciences of the United States of America 20100330
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic & medicinal chemistry 20100315
[Study on HPLC-FPS of raw and processed fructus polygoni orientalis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100301
[Dihydroflavones in Rhododendron concinnum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100301
Substituted pyrazinecarboxamides as abiotic elicitors of flavolignan production in Silybum marianum (L.) gaertn cultures in vitro. Molecules (Basel, Switzerland) 20100114
[Peroxidation of lecithin in the presence of dihydroquercetin and its complex with ferrous iron ions]. Biofizika 20100101
[Comparative pharmacokinetics of dihydroquercetin in rats upon peroral administration of a parent compound and liposomal flamen D]. Eksperimental'naia i klinicheskaia farmakologiia 20100101
[Beneficial action of the liposomal form of dihydroquercetin on the process of skin regeneration after thermal burn]. Tsitologiia 20100101
Effects of Pinus brutia bark extract and Pycnogenol in a rat model of carrageenan induced inflammation. Phytomedicine : international journal of phytotherapy and phytopharmacology 20091201
Comparison of quercetin and dihydroquercetin: antioxidant-independent actions on erythrocyte and platelet membrane. Chemico-biological interactions 20091110
Constitutive and aluminium-induced patterns of phenolic compounds in two maize varieties differing in aluminium tolerance. Journal of inorganic biochemistry 20091101
Structure and antioxidant activity of brominated flavonols and flavanones. Journal of mass spectrometry : JMS 20091001
Influence of exogenous salicylic acid on flavonolignans and lipoxygenase activity in the hairy root cultures of Silybum marianum. Cell biology international 20090901
A fragmentation study of dihydroquercetin using triple quadrupole mass spectrometry and its application for identification of dihydroflavonols in Citrus juices. Rapid communications in mass spectrometry : RCM 20090901
[Studies on the chemical constituents in ethyl acetate extraction from the fruit of Polygonum orientale]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090901
Permeation of astilbin and taxifolin in Caco-2 cell and their effects on the P-gp. International journal of pharmaceutics 20090813
Nanodispersions of taxifolin: impact of solid-state properties on dissolution behavior. International journal of pharmaceutics 20090730
Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP-2 uvrA. Environmental and molecular mutagenesis 20090701
A highly sensitive and robust UPLC-MS with electrospray ionization method for quantitation of taxifolin in rat plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090615
Stereospecific high-performance liquid chromatography of taxifolin, applications in pharmacokinetics, and determination in tu fu ling (Rhizoma smilacis glabrae) and apple (Malus x domestica). Biomedical chromatography : BMC 20090601
Peroxidation processes in rats during the delayed period after chronic administration of dihydroquercetin. Bulletin of experimental biology and medicine 20090501
Screening of flavonoids as candidate antibiotics against Enterococcus faecalis. Journal of natural products 20090401
Effect of liposomes containing antioxidant, phospholipid, and amino acid on skin regeneration after chemical burn. Bulletin of experimental biology and medicine 20090401
Determination and pharmacokinetic study of taxifolin in rabbit plasma by high-performance liquid chromatography. Phytomedicine : international journal of phytotherapy and phytopharmacology 20090301
Dihydroquercetin (taxifolin) and other flavonoids as inhibitors of free radical formation at key stages of apoptosis. Biochemistry. Biokhimiia 20090301
Effect of Pinus massoniana bark extract on IFN-gamma-induced ICAM-1 expression in HaCaT human keratinocytes. Journal of ethnopharmacology 20090225
[Effect of dihydroquercetin on active and passive ion transport systems in plant vacuolar membranes]. Izvestiia Akademii nauk. Seriia biologicheskaia 20090101
[Detection of polymeric forms of dihydroquercetin by optical absorption and light scattering]. Prikladnaia biokhimiia i mikrobiologiia 20090101
[Kinetic regulations of dihydroquercetin oxidation with horseradish peroxide]. Bioorganicheskaia khimiia 20090101
Taxifolin glycoside inhibits dendritic cell responses stimulated by lipopolysaccharide and lipoteichoic acid. The Journal of pharmacy and pharmacology 20081101
Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels. Phytotherapy research : PTR 20080901
Differential effects of dietary flavonoids on reactive oxygen and nitrogen species generation and changes in antioxidant enzyme expression induced by proinflammatory cytokines in Chang Liver cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080501
Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity. Biochemical pharmacology 20080301
Compounds from Kadsura heteroclita and related anti-HIV activity. Phytochemistry 20080301
In vive study of dihydroquercetin genotoxicity. Bulletin of experimental biology and medicine 20080301
Biotransformation of (+)-catechin into taxifolin by a two-step oxidation: primary stage of (+)-catechin metabolism by a novel (+)-catechin-degrading bacteria, Burkholderia sp. KTC-1, isolated from tropical peat. Biochemical and biophysical research communications 20080208
[Interaction of taxifolin (dihydroquercetin) with dimyristoylphosphatidylcholine multilamellar liposomes]. Biofizika 20080101
Taxifolin fibers as biomedical nanomaterial. Doklady. Biochemistry and biophysics 20080101
Acceleration of fibril formation and thermal stabilization of collagen fibrils in the presence of taxifolin (dihydroquercetin). Bulletin of experimental biology and medicine 20071201
Kinetic model for the antiradical activity of the isolated p-catechol group in flavanone type structures using the free stable radical 2,2-diphenyl-1-picrylhydrazyl as the antiradical probe. Journal of agricultural and food chemistry 20070711
Effects of carovertin on the reaction of retinal pigmented epithelium and radial glia to bright light. Bulletin of experimental biology and medicine 20070701
The chemopreventive effect of taxifolin is exerted through ARE-dependent gene regulation. Biological & pharmaceutical bulletin 20070601
Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening. Journal of medicinal chemistry 20070531
Synchronized and sustained release of multiple components in silymarin from erodible glyceryl monostearate matrix system. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20070501
Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade). Biological & pharmaceutical bulletin 20070301
Novel transgenic rice overexpressing anthocyanidin synthase accumulates a mixture of flavonoids leading to an increased antioxidant potential. Metabolic engineering 20070101
[High-performance liquid chromatographic method for the determination of dihydroquercetin in extracts of medicinal plants]. Biomeditsinskaia khimiia 20070101
Influence of silymarin and its flavonolignans on H(2)O(2)-induced oxidative stress in human keratinocytes and mouse fibroblasts. Burns : journal of the International Society for Burn Injuries 20061201
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. Journal of molecular graphics & modelling 20061101
[Studies on chemical constituents of Cercis chinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061101
Differential effects of flavonoids on bovine kidney low molecular mass protein tyrosine phosphatase. Journal of enzyme inhibition and medicinal chemistry 20060801
Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death. Investigative ophthalmology & visual science 20060701
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Inhibition of Mammalian thioredoxin reductase by some flavonoids: implications for myricetin and quercetin anticancer activity. Cancer research 20060415
Gene characterization, analysis of expression and in vitro synthesis of dihydroflavonol 4-reductase from [Citrus sinensis (L.) Osbeck]. Phytochemistry 20060401
Flavonoid 3'-O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry 20060201
Taxifolin ameliorates cerebral ischemia-reperfusion injury in rats through its anti-oxidative effect and modulation of NF-kappa B activation. Journal of biomedical science 20060101
The effect of dihydroquercetin on slow vacuolar channels. Doklady. Biochemistry and biophysics 20060101
[Studies on the flavonoids in stem of Rhododendron anthopogonoide II]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051201
Effect of ascovertin on morphological changes in rat retina exposed to high-intensity light. Bulletin of experimental biology and medicine 20051101
Structure-property studies on the antioxidant activity of flavonoids present in diet. Free radical biology & medicine 20051015
The interaction of flavonoids with mitochondria: effects on energetic processes. Chemico-biological interactions 20050415
[The influence of antioxidants on morphological structure of internal organs of rats in acute hypoxia]. Voprosy pitaniia 20050101
[Morphological changes of rat ovaries after their monopolar coagulation and ascovertin correction]. Morfologiia (Saint Petersburg, Russia) 20050101
Inhibitory activity of diacylglycerol acyltransferase (DGAT) and microsomal triglyceride transfer protein (MTP) by the flavonoid, taxifolin, in HepG2 cells: potential role in the regulation of apolipoprotein B secretion. Atherosclerosis 20041001
Experimental evidence that flavonoid metal complexes may act as mimics of superoxide dismutase. Archives of biochemistry and biophysics 20040815
Prevention of macrophage adhesion molecule-1 (Mac-1)-dependent neutrophil firm adhesion by taxifolin through impairment of protein kinase-dependent NADPH oxidase activation and antagonism of G protein-mediated calcium influx. Biochemical pharmacology 20040615
Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells. Biochemical pharmacology 20040415
A hydroxyl group of flavonoids affects oral anti-inflammatory activity and inhibition of systemic tumor necrosis factor-alpha production. Bioscience, biotechnology, and biochemistry 20040101
Silymarin extraction from milk thistle using hot water. Applied biochemistry and biotechnology 20040101
[Clinical efficacy of a novel hemorheological drug ascovertin in patients with vascular encephalopathy]. Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20040101
Methylation of dihydroquercetin acetates: synthesis of 5-O-methyldihydroquercetin. Journal of natural products 20031201
Effects of flavonoids on the resistance of microsomes to lipid peroxidation in vitro and ex vivo. Bulletin of experimental biology and medicine 20031201
Green tea catechins as a BACE1 (beta-secretase) inhibitor. Bioorganic & medicinal chemistry letters 20031117
Flavonoid dihydroquercetin, unlike quercetin, fails to inhibit expression of heat shock proteins under conditions of cellular stress. Biochemistry. Biokhimiia 20030901
Effect of ascovertin on morphofunctional changes in the ovaries in monopolar coagulation. Bulletin of experimental biology and medicine 20030401
Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica. Bioorganic & medicinal chemistry letters 20030324
Neuroprotective effects of antioxidative flavonoids, quercetin, (+)-dihydroquercetin and quercetin 3-methyl ether, isolated from Opuntia ficus-indica var. saboten. Brain research 20030307
Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots. Journal of agricultural and food chemistry 20030212
Extraction of nutraceuticals from milk thistle: part II. Extraction with organic solvents. Applied biochemistry and biotechnology 20030101
[Studies on chemical constituents of Choerospondias axillaris]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20030101
Structure-antioxidant activity relationships of flavonoids: a re-examination. Free radical research 20021101
Functional expression and mutational analysis of flavonol synthase from Citrus unshiu. European journal of biochemistry 20020801
Anti-human immunodeficiency virus-type 1 activity of constituents from Juglans mandshurica. Archives of pharmacal research 20020801
Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action. FEBS letters 20020605
Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. Journal of natural products 20020601
[Studies on the chemical constituents from Ampelopsis grossedentata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020401
The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. Chemical research in toxicology 20020301
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chemical research in toxicology 20010301
Influence of metal ions on flavonoid protection against asbestos-induced cell injury. Archives of biochemistry and biophysics 20010101
[The first one of phosphorylated flavonoids]. Bioorganicheskaia khimiia 20010101
Structure activity relationships for the chemical behaviour and toxicity of electrophilic quinones/quinone methides. Advances in experimental medicine and biology 20010101
Modulation of hepatic lipoprotein synthesis and secretion by taxifolin, a plant flavonoid. Journal of lipid research 20001201
Biological evaluation of proanthocyanidin dimers and related polyphenols. Journal of natural products 19990701
Monohydroxyethylrutoside, a dose-dependent cardioprotective agent, does not affect the antitumor activity of doxorubicin. Clinical cancer research : an official journal of the American Association for Cancer Research 19971001
Inhibition of reverse transcriptases by flavonoids. Antiviral research 19890901
Properties