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rhamnetin
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy- (9CI)

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Name:2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
CAS Number: 90-19-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-974-1
FDA UNII: 71803L5F4S
Nikkaji Web:J3.912H
Beilstein Number:0047741
MDL:MFCD00016931
XlogP3:1.90 (est)
Molecular Weight:316.26604000
Formula:C16 H12 O7
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
Melting Point: 295.00 °C. @ 760.00 mm Hg
Boiling Point: 627.90 °C. @ 760.00 mm Hg (est)
Flash Point: 462.00 °F. TCC ( 239.00 °C. ) (est)
logP (o/w): 2.580 (est)
Soluble in:
 water, 678.5 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Rhamnetin 97%
Odor: characteristic
Use: Rhamnetin is a natural compound isolated from the branch of Rhamnus cathartica
ExtraSynthese
For experimental / research use only.
Rhamnetin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Rhamnetin ≥97%
Sigma-Aldrich
For experimental / research use only.
Rhamnetin
analytical standard
 
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 rhamnetin usage levels up to:
 not for fragrance use.
 
Recommendation for rhamnetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281691
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
Chemidplus:0000090197
RTECS:LK8748000 for cas# 90-19-7
 
References:
 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281691
Pubchem (sid):134970788
 
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):C10176
HMDB (The Human Metabolome Database):Search
FooDB:FDB002829
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
 clove fruit
Search Trop Picture
 coriander fruit
Search Trop Picture
 pepper black pepper fruit
Search Trop Picture
 tarragon plant
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy- (9CI)
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
 flavone, 3,3',4',5-tetrahydroxy-7-methoxy- (8CI)
 flavone, 7-methoxy-3,3',4',5-tetrahydroxy-
7-methoxyquercetin
7-methylquercetin
7-O-methylquercetin
 quercetin 7-methyl ether
beta-rhamnocitrin
3,5,3',4'-tetrahydroxy-7-methoxyflaone
3,3',4',5-tetrahydroxy-7-methoxyflavone
 

Articles:

PubMed:Silicon, endophytes and secondary metabolites as grass defenses against mammalian herbivores.
PubMed:Flavonoids enhance melanogenesis in human melanoma cells.
PubMed:A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.
PubMed:Chemical investigation of the roots of Polygala sibirica L.
PubMed:E-Pharmacophore and Molecular Dynamics Study of Flavonols and Dihydroflavonols as Inhibitors Against DiHydroOrotate DeHydrogenase.
PubMed:Cardioprotective effects of rhamnetin in H9c2 cardiomyoblast cells under H₂O₂-induced apoptosis.
PubMed:Anti-inflammatory activity of rhamnetin and a model of its binding to c-Jun NH2-terminal kinase 1 and p38 MAPK.
PubMed:Characterisation of honeys according to their content of phenolic compounds using high performance liquid chromatography/tandem mass spectrometry.
PubMed:Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines.
PubMed:Rhamnetin attenuates melanogenesis by suppressing oxidative stress and pro-inflammatory mediators.
PubMed:[Chemical constituents from leaves of Nelumbo nucifera].
PubMed:Anti-inflammatory effect of O-methylated flavonol 2-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-7-methoxy-chromen-4-one obtained from Cassia sophera Linn in rats.
PubMed:[Chemical constituents contained in aerial parts of Emilia sonchifolia].
PubMed:Differential in vitro and cellular effects of iron chelators for hypoxia inducible factor hydroxylases.
PubMed:Aggregating behavior of phenolic compounds--a source of false bioassay results?
PubMed:Rhamnetin-induced suppression of clonal expansion during early stage of adipogenesis.
PubMed:[Non-alkaloid chemical constituents from Coptis chinensis].
PubMed:[Preparative isolation and purification of five non-volatile compounds from Fructus caryophylli and Flos caryophylli by high-speed counter-current chromatography].
PubMed:Tyrosinase inhibitor and radical scavenger fractions and isolated compounds from aerial parts of Peucedanum knappii Bornm.
PubMed:Small molecule inhibitors of the HPV16-E6 interaction with caspase 8.
PubMed:[Simultaneous determination of seven flavonoids in Nervilia fordii with HPLC].
PubMed:[Studies on the chemical constituents of the herb of Antenoron filiforme].
PubMed:Effects of coadministration of natural polyphenols with doxycycline or calcium modulators on acute Chlamydia pneumoniae infection in vitro.
PubMed:Optimization of rhamnetin production in Escherichia coli.
PubMed:Phenolic compounds from the aqueous extract of Acacia catechu.
PubMed:Isolation of biologically active constituents from Moringa peregrina (Forssk.) Fiori. (family: Moringaceae) growing in Egypt.
PubMed:Rhamnetin production based on the rational design of the poplar O-methyltransferase enzyme and its biological activities.
PubMed:Simultaneous quantification of eight major constituents in Herba Siegesbeckiae by liquid chromatography coupled with electrospray ionization time-of-flight tandem mass spectrometry.
PubMed:Influence of extraction methods on stability of flavonoids.
PubMed:Ultrasound-assisted extraction of phenolic antioxidants from Acacia confusa flowers and buds.
PubMed:Total extract of Beta vulgaris var. cicla seeds versus its purified phenolic components: antioxidant activities and antiproliferative effects against colon cancer cells.
PubMed:HPLC-DAD-MS analysis of dyes identified in textiles from Mount Athos.
PubMed:3-Hydroxymethylglutaryl flavonol glycosides from a Mongolian and Tibetan medicine, Oxytropis racemosa.
PubMed:Xanthine oxidase inhibitory activities of extracts and flavonoids of the leaves of Blumea balsamifera.
PubMed:Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative.
PubMed:Flavonoids from the aerial parts of Diplomorpha canescens.
PubMed:Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.
PubMed:Screening for fractions of Oxytropis falcata Bunge with antibacterial activity.
PubMed:Polyphenolic profile and bioactivity study of Oenothera speciosa Nutt. aerial parts.
PubMed:Flavonoid-induced morphological modifications of endothelial cells through microtubule stabilization.
PubMed:Cytotoxic constituents of chinese propolis.
PubMed:Flavonoids inhibit the AU-rich element binding of HuC.
PubMed:In vitro anti-influenza viral activities of constituents from Caesalpinia sappan.
PubMed:Antioxidant activities of extracts and flavonoid compounds from Oxytropis falcate Bunge.
PubMed:Determination of rutin and other flavonoids by flow-injection/adsorptive stripping voltammetry using nujol-graphite and diphenylether-graphite paste electrodes.
PubMed:Silicon-mediated accumulation of flavonoid phytoalexins in cucumber.
PubMed:[A new flavonoid from heartwood of Caesalpinia sappan].
PubMed:Online RP-HPLC-DPPH screening method for detection of radical-scavenging phytochemicals from flowers of Acacia confusa.
PubMed:[Studies on flavonoids of Eupatorium odoratum L].
PubMed:[Studies on flavonoid constituents from herbs of Artemisia ordosica II].
PubMed:New flavonol glycosides and new xanthone from Polygala japonica.
PubMed:[Studies on chemical constituents in herb of Myricaria bracteata].
PubMed:Antioxidant activity of coumarins and flavonols from the resinous exudate of Haplopappus multifolius.
PubMed:Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: in vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies.
PubMed:Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid.
PubMed:[Study on flavonoids from leaf of Ipomoea batatas].
PubMed:Arbuscular mycorrhizal colonization of tomato by Gigaspora and Glomus species in the presence of root flavonoids.
PubMed:Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins, and pectin.
PubMed:On-line characterisation of apple polyphenols by liquid chromatography coupled with mass spectrometry and ultraviolet absorbance detection.
PubMed:Profiling glucosinolates, flavonoids, alkaloids, and other secondary metabolites in tissues of Azima tetracantha L. (Salvadoraceae).
PubMed:Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices.
PubMed:Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
PubMed:Allelochemicals of Polygonella myriophylla: chemistry and soil degradation.
PubMed:Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines.
PubMed:Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.
PubMed:Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection.
PubMed:Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
PubMed:Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. "Tommy Atkins") peels by high-performance liquid chromatography-electrospray ionization mass spectrometry.
PubMed:Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
PubMed:Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L.
PubMed:Flavonol glycosides from Cadaba glandulosa.
PubMed:Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. "Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS.
PubMed:Four new flavonol glycosides from the leaves of Astragalus caprinus.
PubMed:Characterization of flavonoid--biomembrane interactions.
PubMed:Inhibitory effects of naturally occurring compounds on aflatoxin B(1) biotransformation.
PubMed:Foliar flavonoids of Annonaceae from Brazil: taxonomic significance.
PubMed:Inhibition of beta-carotene-15,15'-dioxygenase activity by dietary flavonoids.
PubMed:Lipid peroxidation inhibitory activity of some constituents isolated from the stem bark of Eucalyptus globulus.
PubMed:Constituents in watercress: inhibitors of histamine release from RBL-2H3 cells induced by antigen stimulation.
PubMed:Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid peroxidation in human low-density lipoprotein.
PubMed:Alkylperoxyl radical-scavenging activity of various flavonoids and other phenolic compounds: implications for the anti-tumor-promoter effect of vegetables.
PubMed:Protective effects of some flavonoids on the renal cellular membrane.
PubMed:5-Methylflavasperone and rhamnetin from Guiera senegalensis and their antioxidative and 5-lipoxygenase inhibitory activity.
PubMed:Characterization of flavonoids as monofunctional or bifunctional inducers of quinone reductase in murine hepatoma cell lines.
PubMed:Phytochemical and biological study of radal Lomatia hirsuta (Proteaceae).
PubMed:Effects of isorhamnetin, rhamnetin, and quercetin on the concentrations of cholesterol and lipoperoxide in the serum and liver and on the blood and liver antioxidative enzyme activities of rats.
PubMed:Cloning and regulation of flavonol 3-sulfotransferase in cell-suspension cultures of Flaveria bidentis.
PubMed:Rhamnetin 3-p-coumaroylrhamninoside from Rhamnus petiolaris.
PubMed:Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids.
PubMed:Studies of the ability of rhamnetin and isorhamnetin to alkylate bacterial DNA.
PubMed:Antiplatelet effects and vasorelaxing action of some constituents of Formosan plants.
PubMed:A study of the genotoxic potential of flavonoids using short-term bacterial assays.
PubMed:The effect of flavonoids on the mutagenic activity of aromatic amines.
PubMed:Flavonoid glycosides from Cassia alata.
PubMed:Three saponins from Oxytropis species.
PubMed:Isolation and studies of the mutagenic activity in the Ames test of flavonoids naturally occurring in medical herbs.
PubMed:Identification of mutagens in Japanese pickles.
PubMed:The effect of some flavonoids on non-enzymatic lipid oxidation and enzymatic oxidation of arachidonic acid.
PubMed:Rhamnetin-3-O-neohesperidoside, a new flavonoid from the leaves of Derris trifoliata.
PubMed:In vivo exposure to plant flavonols. Influence on frequencies of micronuclei in mouse erythrocytes and sister-chromatid exchange in rabbit lymphocytes.
PubMed:Mutagenicity of plant flavonols in the Salmonella/mammalian microsome test: activation of flavonol glycosides by mixed glycosidases from rat cecal bacteria and other sources.
PubMed:Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium.
PubMed:Products of anaerobic phloroglucinol degradation by Coprococcus sp. Pe15.
PubMed:The partial demethylation of flavones. 3. Preparation of rhamnetin and 7-O-methylmyricetin.
PubMed:The antibacterial effect of the flavonol-dyestuff, rhamnetin.
 
Notes:
aglycone of xanthorhamnin; from rhamnus.
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