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Isoquercitrin

CAS No.:
482-35-9
Catalog Number:
AG0035K3
Molecular Formula:
C21H20O12
Molecular Weight:
464.3763
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
≥98%
1 week
United States
$100
- +
250mg
90%
1 week
United States
$191
- +
1g
90%
1 week
United States
$344
- +
5g
90%
1 week
United States
$1260
- +
Product Description
Catalog Number:
AG0035K3
Chemical Name:
Isoquercitrin
CAS Number:
482-35-9
Molecular Formula:
C21H20O12
Molecular Weight:
464.3763
MDL Number:
MFCD00017746
IUPAC Name:
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
InChI:
InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
InChI Key:
OVSQVDMCBVZWGM-QSOFNFLRSA-N
SMILES:
OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
UNII:
6HN2PC637T
Properties
Complexity:
758  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
464.095g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0
Molecular Weight:
464.379g/mol
Monoisotopic Mass:
464.095g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
207A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.4  
Literature
Title Journal
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Quercetin glycosides induced neuroprotection by changes in the gene expression in a cellular model of Parkinson's disease. Journal of molecular neuroscience : MN 20150301
Induction of hepatic apolipoprotein A-I gene expression by the isoflavones quercetin and isoquercetrin. Life sciences 20140806
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK. Bioorganic & medicinal chemistry 20140701
Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats. Toxicology 20130308
A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway. Journal of medicinal chemistry 20130214
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Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells. Phytotherapy research : PTR 20121101
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Bioactivity-guided fractionation of the triglyceride-lowering component and in vivo and in vitro evaluation of hypolipidemic effects of Calyx seu Fructus Physalis. Lipids in health and disease 20120101
Diuretic activity of Lophophytum leandri. Natural product communications 20120101
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Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. Journal of pharmaceutical and biomedical analysis 20111215
Anticonvulsant, antidepressant-like activity of Abelmoschus manihot ethanol extract and its potential active components in vivo. Phytomedicine : international journal of phytotherapy and phytopharmacology 20111115
Persicaria hydropiper (L.) spach and its flavonoid components, isoquercitrin and isorhamnetin, activate the Wnt/β-catenin pathway and inhibit adipocyte differentiation of 3T3-L1 cells. Phytotherapy research : PTR 20111101
Suppressive effect of enzymatically modified isoquercitrin on phenobarbital-induced liver tumor promotion in rats. Archives of toxicology 20111101
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In vivo antioxidative effect of isoquercitrin on cadmium-induced oxidative damage to mouse liver and kidney. Naunyn-Schmiedeberg's archives of pharmacology 20110501
Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells. Bioorganic & medicinal chemistry 20110501
[Studies on the chemical constituents from Conyza canadensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110501
Concomitant apoptosis and regeneration of liver cells as a mechanism of liver-tumor promotion by β-naphthoflavone involving TNFα-signaling due to oxidative cellular stress in rats. Toxicology 20110428
Regioselective deglycosylation of onion quercetin glucosides by Saccharomyces cerevisiae. Biotechnology letters 20110401
[Absorption of flavonoids from Abelmoschus manihot extract by in situ intestinal perfusion]. Yao xue xue bao = Acta pharmaceutica Sinica 20110401
Flavonoid composition of Juniperus oblonga Bieb. Bulletin of experimental biology and medicine 20110401
Diuretic and potassium-sparing effect of isoquercitrin-an active flavonoid of Tropaeolum majus L. Journal of ethnopharmacology 20110324
Antihypertensive effects of isoquercitrin and extracts from Tropaeolum majus L.: evidence for the inhibition of angiotensin converting enzyme. Journal of ethnopharmacology 20110324
A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells. Bioorganic & medicinal chemistry letters 20110315
Bioactive compounds from the fern Lepisorus contortus. Journal of natural products 20110225
Aglycone specificity of Thermotoga neapolitana β-glucosidase 1A modified by mutagenesis, leading to increased catalytic efficiency in quercetin-3-glucoside hydrolysis. BMC biochemistry 20110101
Isoquercitrin is the most effective antioxidant in the plant Thuja orientalis and able to counteract oxidative-induced damage to a transformed cell line (RGC-5 cells). Neurochemistry international 20101201
Inhibition of influenza virus replication by plant-derived isoquercetin. Antiviral research 20101101
The selected flavonol glycoside derived from Sophorae Flos improves glucose uptake and inhibits adipocyte differentiation via activation AMPK in 3T3-L1 cells. Bioorganic & medicinal chemistry letters 20101015
[Simultaneous determination of rutin, isoquercitrin and chlorogenic acid in Farfarae Flos by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001
alpha-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans. Archives of biochemistry and biophysics 20100901
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity. Natural product communications 20100801
Free radical scavenging activities and inhibition of inflammatory enzymes of phenolics isolated from Tripodanthus acutifolius. Journal of ethnopharmacology 20100720
Oral bioavailability of quercetin from different quercetin glycosides in dogs. The British journal of nutrition 20100701
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Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni. Journal of natural products 20100226
Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone. Toxicology 20100209
Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats. Archives of toxicology 20100201
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids. Bioorganic & medicinal chemistry 20100101
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Fifty-two week chronic toxicity of enzymatically decomposed rutin in Wistar rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101
Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase. Journal of agricultural and food chemistry 20091223
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Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis. Allergology international : official journal of the Japanese Society of Allergology 20090901
In vitro and in vivo determination of antioxidant activity and mode of action of isoquercitrin and Hyptis fasciculata. Phytomedicine : international journal of phytotherapy and phytopharmacology 20090801
Isoquercitrin isolated from Hyptis fasciculata reduces glioblastoma cell proliferation and changes beta-catenin cellular localization. Anti-cancer drugs 20090801
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Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods. Journal of agricultural and food chemistry 20080528
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Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20080501
HPLC analysis and pharmacokinetic study of quercitrin and isoquercitrin in rat plasma after administration of Hypericum japonicum thunb. extract. Biomedical chromatography : BMC 20080401
The opposing effects of the flavonoids isoquercitrin and sissotrin, isolated from Pterospartum tridentatum, on oral glucose tolerance in rats. Phytotherapy research : PTR 20080401
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The effect of flavonoid derivatives on doxorubicin transport and metabolism. Bioorganic & medicinal chemistry 20080215
Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb. Bioorganic & medicinal chemistry 20080201
Quercetin 3-glucoside protects neuroblastoma (SH-SY5Y) cells in vitro against oxidative damage by inducing sterol regulatory element-binding protein-2-mediated cholesterol biosynthesis. The Journal of biological chemistry 20080125
Chemical constituents from the leaves of Ilex pernyi. Yao xue xue bao = Acta pharmaceutica Sinica 20080101
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Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20071001
[Isolation and preparation of flavones from the leaves of Lindera aggregata using high speed counter-current chromatography]. Se pu = Chinese journal of chromatography 20070901
Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake. The Journal of pharmacology and experimental therapeutics 20070801
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An unusual C6-C6' linked flavonoid from Miconia cabucu (Melastomataceae). Phytochemistry 20070701
The anti-thrombotic active constituents from Centella asiatica. Biological & pharmaceutical bulletin 20070501
Flavonoids from Astragalus hamosus. Natural product research 20070501
Simultaneous determination of seven flavonoids in Potentilla multifida by HPLC. Journal of chromatographic science 20070401
Reactive oxygen species scavenging activity of flavone glycosides from Melilotus neapolitana. Molecules (Basel, Switzerland) 20070227
Identification and determination of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry. Journal of separation science 20070201
Effect of enzymatically modified isoquercitrin in spontaneously hypertensive rats. Journal of nutritional science and vitaminology 20070201
Enzyme-catalyzed change of antioxidants content and antioxidant activity of asparagus juice. Journal of agricultural and food chemistry 20070110
Distinct inhibitory mechanisms of isoquercitrin gallate and its aglycone on zymosan-induced peroxynitrite production in macrophages. Nitric oxide : biology and chemistry 20070101
Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside. BioFactors (Oxford, England) 20070101
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers. Journal of natural products 20061201
Intestinal absorption of hawthorn flavonoids--in vitro, in situ and in vivo correlations. Life sciences 20061125
Constituents from the leaves of Phellodendron amurense and their antioxidant activity. Chemical & pharmaceutical bulletin 20060901
A new alpha-methylanthraquinone glucoside from Emex spinosus. Natural product research 20060710
The flavonol quercetin-3-glucoside inhibits cyanidin-3-glucoside absorption in vitro. Journal of agricultural and food chemistry 20060628
Qualitative and quantitative analysis of flavonoids of the strawberry tree - Arbutus unedo L. (Ericaceae). Acta pharmaceutica (Zagreb, Croatia) 20060601
Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro. British journal of pharmacology 20060401
Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus. Journal of natural products 20060401
In vitro degradation of the flavonol quercetin and of quercetin glycosides in the porcine hindgut. Archives of animal nutrition 20060401
Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. Toxicology 20060116
Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM 20060101
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents. Phytochemical analysis : PCA 20060101
Antimicrobial activity of flavonoids from Pelargonium radula (Cav.) L'Hérit. Acta pharmaceutica (Zagreb, Croatia) 20051201
Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways. European journal of pharmacology 20051017
[Studies on chemical constituents from flowers of Apocynum venetum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050901
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Pressurized liquid extraction-capillary electrophoresis-mass spectrometry for the analysis of polar antioxidants in rosemary extracts. Journal of chromatography. A 20050819
Difference in absorption of the two structurally similar flavonoid glycosides, hyperoside and isoquercitrin, in rats. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20050401
[Studies on chemical constituents from Salvia roborowskii Maxim]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050201
Antifungal activity of camptothecin, trifolin, and hyperoside isolated from Camptotheca acuminata. Journal of agricultural and food chemistry 20050112
In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer. Nutrition journal 20050101
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts]. Se pu = Chinese journal of chromatography 20050101
Preliminary HPLC study on some polyphenols of Geranium robertianum L. (Geraniaceae). Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20050101
Lack of carcinogenicity of enzymatically modified isoquercitrin in F344/DuCrj rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20041201
Isolation of angiotensin converting enzyme (ACE) inhibitory flavonoids from Sedum sarmentosum. Biological & pharmaceutical bulletin 20041201
Glycosides from Grewia damine and Filicium decipiens. Natural product research 20041201
Cytotoxic activity of nepetin, a flavonoid from Eupatorium ballotaefolium HBK. Die Pharmazie 20041201
Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers. Journal of agricultural and food chemistry 20041117
Synthesis and biological evaluation of flavonoids as vasorelaxant agents. Bioorganic & medicinal chemistry letters 20040802
The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. The British journal of nutrition 20040601
Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum. The British journal of nutrition 20040601
[Studies on the chemical constituents of Knoxia corymbosa]. Yao xue xue bao = Acta pharmaceutica Sinica 20040601
Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation. Journal of agricultural and food chemistry 20040407
Depsides from the petals of Papaver rhoeas. Planta medica 20040401
Mycobacterium tuberculosis growth inhibition by constituents of Sapium haematospermum. Journal of natural products 20040401
Antiviral flavonoids from the seeds of Aesculus chinensis. Journal of natural products 20040401
Evaluation of the toxicity of enzymatically decomposed rutin with 13-weeks dietary administration to Wistar rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301
Characterization of flavonols in cranberry (Vaccinium macrocarpon) powder. Journal of agricultural and food chemistry 20040128
[HPLC investigation of antioxidant components in Solidago herba]. Acta pharmaceutica Hungarica 20040101
Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. Life sciences 20031226
Field survey of Glycyrrhiza plants in Central Asia (3). Chemical characterization of G. glabra collected in Uzbekistan. Chemical & pharmaceutical bulletin 20031101
Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity. Journal of natural products 20030901
Herbal remedies of Solidago--correlation of phytochemical characteristics and antioxidative properties. Journal of pharmaceutical and biomedical analysis 20030808
Inhibition of clastogenicity of benzo[a]pyrene and of its trans-7,8-dihydrodiol in mice in vivo by fruits, vegetables, and flavonoids. Mutation research 20030606
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity. Journal of natural products 20030501
Absorption of quercetin-3-glucoside and quercetin-4'-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. Biochemical pharmacology 20030401
Transformation of flavonoids by intestinal microorganisms. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20030301
Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical. Phytomedicine : international journal of phytotherapy and phytopharmacology 20030101
The inhibitory effects of 12 medicinal plants and their component compounds on lipid peroxidation. The American journal of Chinese medicine 20030101
Biorelevant dissolution testing of St John's wort products. The Journal of pharmacy and pharmacology 20021201
Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. Chemical & pharmaceutical bulletin 20021101
Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata. Journal of natural products 20021101
Iridoids from Phlomis aurea Decne growing in Egypt. Die Pharmazie 20020901
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). British journal of cancer 20020520
Antioxidant and photoprotective activity of a crude extract of Culcitium reflexum H.B.K. leaves and their major flavonoids. Journal of ethnopharmacology 20020201
Quercetin, but not its glycosides, is absorbed from the rat stomach. Journal of agricultural and food chemistry 20020130
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