rhamnetin

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

CAS: 90-19-7 C16 H12 O7 MW: 316.26604000

Identification

Namerhamnetin
IUPAC2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
CAS Number90-19-7
EINECS201-974-1
FDA UNII71803L5F4S
Molecular FormulaC16 H12 O7
Molecular Weight316.26604000
MDL NumberMFCD00016931
Nikkaji NumberJ3.912H
Beilstein0047741
XlogP31.90 (est)

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for rhamnetin usage levels up tonot for fragrance use.
Recommendation for rhamnetin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

clove fruit coriander fruit pepper black pepper fruit tarragon plant

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 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.