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quercetagetin
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy- (9CI)

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Name:2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
CAS Number: 90-18-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-973-6
FDA UNII: SV68G507VO
Nikkaji Web:J10.601A
MDL:MFCD00017428
XlogP3:1.20 (est)
Molecular Weight:318.23830000
Formula:C15 H10 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 732.40 °C. @ 760.00 mm Hg (est)
Flash Point: 537.00 °F. TCC ( 280.40 °C. ) (est)
logP (o/w): 2.230 (est)
Soluble in:
 water, 2234 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
6-Hydroxyquercetin 98%
BOC Sciences
For experimental / research use only.
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy- 95%
Carbosynth
For experimental / research use only.
Quercetagetin
EMD Millipore
For experimental / research use only.
Quercetagetin
ExtraSynthese
For experimental / research use only.
Quercetagetin (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Quercetagetin
 
Safety Information:
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for quercetagetin usage levels up to:
 not for fragrance use.
 
Recommendation for quercetagetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281680
National Institute of Allergy and Infectious Diseases:Data
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
Chemidplus:0000090186
 
References:
 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281680
Pubchem (sid):135021668
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (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
KEGG (GenomeNet):C10122
HMDB (The Human Metabolome Database):Search
FooDB:FDB011897
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 orange fruit juice
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy- (9CI)
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyrone
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
 flavone, 3,3',4',5,6,7-hexahydroxy- (8CI)
3,3',4',5,6,7-hexahydroxyflavone
3,5,6,7,3',4'-hexahydroxyflavone
 

Articles:

PubMed:eNOS-JNK1-AR signaling pathway mediates deltamethrin-induced germ cells apoptosis in testes of adult rats.
PubMed:Plant-Derived Flavones as Inhibitors of Aurora B Kinase and Their Quantitative Structure-Activity Relationships.
PubMed:Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells--A SAR study.
PubMed:Inhibition of RNA binding to hepatitis C virus RNA-dependent RNA polymerase: a new mechanism for antiviral intervention.
PubMed:A novel copigment of quercetagetin for stabilization of grape skin anthocyanins.
PubMed:A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.
PubMed:Quercetagetin inhibits macrophage-derived chemokine in HaCaT human keratinocytes via the regulation of signal transducer and activator of transcription 1, suppressor of cytokine signalling 1 and transforming growth factor-β1.
PubMed:New thiophene and flavonoid from Tagetes minuta leaves growing in Saudi Arabia.
PubMed:Appraisal of biological activities and identification of phenolic compound of African marigold (Tagetes erecta) flower extract.
PubMed:Quantitative determination of phenolic compounds by UHPLC-UV-MS and use of partial least-square discriminant analysis to differentiate chemo-types of Chamomile/Chrysanthemum flower heads.
PubMed:Anti-Inflammatory Effect of Quercetagetin, an Active Component of Immature Citrus unshiu, in HaCaT Human Keratinocytes.
PubMed:Sourcing the affinity of flavonoids for the glycogen phosphorylase inhibitor site via crystallography, kinetics and QM/MM-PBSA binding studies: comparison of chrysin and flavopiridol.
PubMed:Structural and functional analysis of the natural JNK1 inhibitor quercetagetin.
PubMed:Eight flavonoids and their potential as inhibitors of human cytomegalovirus replication.
PubMed:Influences of four different light-emitting diode lights on flowering and polyphenol variations in the leaves of chrysanthemum (Chrysanthemum morifolium).
PubMed:Inhibition of Pim-1 attenuates the proliferation and migration in nasopharyngeal carcinoma cells.
PubMed:Isolation of a new phlorotannin, a potent inhibitor of carbohydrate-hydrolyzing enzymes, from the brown alga Sargassum patens.
PubMed:HPLC-ESIMS(n) profiling, isolation, structural elucidation, and evaluation of the antioxidant potential of phenolics from Paepalanthus geniculatus.
PubMed:Antioxidant and cytotoxic flavonols from Calotropis procera.
PubMed:ISOLATION OF FIVE BIOACTIVE COMPONENTS FROM EUPATORIUM ADENOPHORUM SPRENG USING STEPWISE ELUTION BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY.
PubMed:Investigation into the antioxidant activity and chemical composition of alcoholic extracts from defatted marigold (Tagetes erecta L.) residue.
PubMed:Isolation and identification of an antioxidant flavonoid compound from citrus-processing by-product.
PubMed:Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-β-glucoside, a major antioxidant of Athrixia phylicoides.
PubMed:Activation of a non-genomic Pim-1/Bad-Pser75 module is required for an efficient pro-survival effect of Bcl-xL induced by androgen in LNCaP cells.
PubMed:The membrane transport of flavonoids from Crossostephium chinense across the Caco-2 monolayer.
PubMed:Binding of protein kinase inhibitors to synapsin I inferred from pair-wise binding site similarity measurements.
PubMed:The flavonoids luteolin and quercetagetin inhibit lipoteichoic acid actions on H9c2 cardiomyocytes.
PubMed:Antioxidant effects of Glechoma hederacea as a food additive.
PubMed:[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].
PubMed:[Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro].
PubMed:Transcriptional regulation of Pim-1 kinase in vascular smooth muscle cells and its role for proliferation.
PubMed:Free radical scavengers and antioxidants from Tagetes mendocina.
PubMed:Structure-activity relationships of flavonoids as potential inhibitors of glycogen phosphorylase.
PubMed:Biochemical and structural analysis of substrate promiscuity in plant Mg2+-dependent O-methyltransferases.
PubMed:The effect of flavonoids on transduction mechanisms in lipopolysaccharide-treated human gingival fibroblasts.
PubMed:Effects of various methoxyflavones on vincristine uptake and multidrug resistance to vincristine in P-gp-overexpressing K562/ADM cells.
PubMed:Structure-activity relationship of flavonoids for inhibition of epidermal growth factor-induced transformation of JB6 Cl 41 cells.
PubMed:Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase.
PubMed:Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.
PubMed:[Studies on the flavonoids from whole herbs of Seriphidium terrae-albae].
PubMed:Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida).
PubMed:Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima.
PubMed:Identification of radical scavenging compounds in Rhaponticum carthamoides by means of LC-DAD-SPE-NMR.
PubMed:Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.
PubMed:Kinetic study of flavonoid reactions with stable radicals.
PubMed:G2-M arrest and antimitotic activity mediated by casticin, a flavonoid isolated from Viticis Fructus (Vitex rotundifolia Linne fil.).
PubMed:Variations in lipophilic and vacuolar flavonoids among European Pulicaria species.
PubMed:Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UV spectral analysis.
PubMed:The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae.
PubMed:Geographical variation in the surface flavonoids of Pulicaria dysenterica.
PubMed:The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties.
PubMed:Protective effect of flavonoids on endothelial cells against linoleic acid hydroperoxide-induced toxicity.
PubMed:Antioxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion.
PubMed:Inhibition of tomato bushy stunt virus infection using a quercetagetin flavonoid isolated from Centaurea rupestris L.
PubMed:Antimicrobial activity of flavonoids from leaves of Tagetes minuta.
PubMed:HIV-1 integrase pharmacophore: discovery of inhibitors through three-dimensional database searching.
PubMed:A biologically active lipophilic flavonol from Tanacetum parthenium.
PubMed:Influence of anti-inflammatory flavonoids on degranulation and arachidonic acid release in rat neutrophils.
PubMed:Cytotoxic terpenoids and flavonoids from Artemisia annua.
PubMed:Effects of flavonoids on Naja naja and human recombinant synovial phospholipases A2 and inflammatory responses in mice.
PubMed:New Flavonoid Glycosides from Arnicae Flos DAB 91.
PubMed:Site-specific DNA cleavage by mammalian DNA topoisomerase II induced by novel flavone and catechin derivatives.
PubMed:Inhibition of rat lens aldose reductase by quercetagetin and patuletin.
PubMed:Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids.
PubMed:Mechanisms of inhibition of various cellular DNA and RNA polymerases by several flavonoids.
PubMed:Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases.
PubMed:Inhibition of sheep platelet arachidonate metabolism by flavonoids from Spanish and Indian medicinal herbs.
PubMed:C18 solid-phase isolation and high-performance liquid chromatography/ultraviolet diode array determination of fully methoxylated flavones in citrus juices.
PubMed:Screening of the influence of flavonoids on lipoxygenase and cyclooxygenase activity, as well as on nonenzymic lipid oxidation.
PubMed:Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids. A structure-activity study.
PubMed:The flavonoids of Parthenium L.
PubMed:Flavonols: pigments responsible for ultraviolet absorption in nectar guide of flower.
PubMed:Quercetagetin 3,6-dimethyl ether.
 
Notes:
inhibits aldose reductase in rat lens.
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