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diosmetin
5,7,3'-trihydroxy-4'-methoxyflavone

Supplier Sponsors

Name:5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
CAS Number: 520-34-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-291-8
FDA UNII: TWZ37241OT
Nikkaji Web:J831A
Beilstein Number:294492
MDL:MFCD00017425
XlogP3:1.70 (est)
Molecular Weight:300.26684000
Formula:C16 H12 O6
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: 253.50 °C. @ 760.00 mm Hg
Boiling Point: 576.70 °C. @ 760.00 mm Hg (est)
Vapor Pressure:3.800000 mmHg @ 25.00 °C. (est)
Flash Point: 429.00 °F. TCC ( 220.30 °C. ) (est)
logP (o/w): 3.100
Soluble in:
 water, 104.7 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.
Diosmetin 98%
BOC Sciences
For experimental / research use only.
Diosmetin (Diosmin Impurity F) >98%
Odor: characteristic
Use: Diosmetin is a bioflavonoid found in spearmint, oregano, and many other plants.
ExtraSynthese
For experimental / research use only.
Diosmetin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Diosmetin ≥98%
Shaanxi Y-Herb Biotechnology
98% Diosmetin Monomer Powder CAS No. 520-34-3 Lemon Peel Citrus Limon Peel Extract
Sigma-Aldrich
For experimental / research use only.
Diosmetin
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 diosmetin usage levels up to:
 not for fragrance use.
 
Recommendation for diosmetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281612
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Chemidplus:0000520343
 
References:
 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:520-34-3
Pubchem (cid):5281612
Pubchem (sid):135025513
 
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):C10038
HMDB (The Human Metabolome Database):HMDB29676
FooDB:FDB000861
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
 dill leaf
Search Trop Picture
 hyssop oil
Search Trop Picture
 lemon peel
Search Trop Picture
 lemon plant
Search Trop Picture
 lippia citriodora
Search Trop Picture
 marjoram shoot
Search Trop Picture
 oregano plant
Search Trop Picture
 rosemary plant
Search Trop Picture
 sage plant
Search Trop Picture
 spearmint
Search Trop Picture
 spearmint plant
Search Trop Picture
 thyme plant
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
 flavone, 3',5,7-trihydroxy-4'-methoxy-
 luteolin 4'-methyl ether
 pillon
5,7,3'-trihydroxy-4'-methoxyflavone
 

Articles:

PubMed:In Vitro Effects of Some Flavones on Human Pyruvate Kinase Isoenzyme M2.
PubMed:Determination of Metabolites of Diosmetin-7-O-glucoside by a Newly Isolated Escherichia coli from Human Gut Using UPLC-Q-TOF/MS.
PubMed:HPLC-UV-MS Profiles of Phenolic Compounds and Antioxidant Activity of Fruits from Three Citrus Species Consumed in Northern Chile.
PubMed:Modulation of (-)-epicatechin Metabolism by Co-administration with other Polyphenols in Caco-2 Cell Model.
PubMed:Structure activity relationships of flavonoids as potent alpha-amylase inhibitors.
PubMed:[Chemical constituents of Trichosanthes kirilowii peels].
PubMed:Flavones from Erythrina falcata are modulators of fear memory.
PubMed:Intracellular antioxidant detoxifying effects of diosmetin on 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative stress through inhibition of reactive oxygen species generation.
PubMed:An efficient preparative procedure for main flavonoids from the peel of Trichosanthes kirilowii Maxim. using polyamide resin followed by semi-preparative high performance liquid chromatography.
PubMed:Diosmetin ameliorates the severity of cerulein-induced acute pancreatitis in mice by inhibiting the activation of the nuclear factor-κB.
PubMed:Antitubercular constituents from Premna odorata Blanco.
PubMed:HPLC-DAD-ESI/MS(n) analysis of phenolic compounds for quality control of Grindelia robusta Nutt. and bioactivities.
PubMed:Flavonoid diosmetin increases ATP levels in kidney cells and relieves ATP depleting effect of ochratoxin A.
PubMed:Identification of quercitrin as a potential therapeutic agent for periodontal applications.
PubMed:Bioavailability of lemon verbena (Aloysia triphylla) polyphenols in rats: impact of colonic inflammation.
PubMed:Flavonoid and phenolic compounds from Salvia palaestina L. growing wild in Jordan and their antioxidant activities.
PubMed:HPLC-UV-ESI MS/MS identification of the color constituents of sawwort (Serratula tinctoria L.).
PubMed:Extraction process optimization of polyphenols from Indian Citrus sinensis - as novel antiglycative agents in the management of diabetes mellitus.
PubMed:Flavonoids from Sophora moorcroftiana and their synergistic antibacterial effects on MRSA.
PubMed:A review on pharmacological and analytical aspects of diosmetin: a concise report.
PubMed:Two new flavonol glycosides and a metabolite profile of Bryophyllum pinnatum, a phytotherapeutic used in obstetrics and gynaecology.
PubMed:Quercitrin and taxifolin stimulate osteoblast differentiation in MC3T3-E1 cells and inhibit osteoclastogenesis in RAW 264.7 cells.
PubMed:Confirmation of diosmetin 3-O-glucuronide as major metabolite of diosmin in humans, using micro-liquid-chromatography-mass spectrometry and ion mobility mass spectrometry.
PubMed:Identification and determination of major constituents in a traditional Chinese medicine compound recipe Xiongdankaiming tablet using HPLC-PDA/ESI-MS(n) and HPLC-UV/ELSD.
PubMed:Inhibition of c-Kit signaling by diosmetin isolated from Chrysanthemum morifolium.
PubMed:Chemical differentiation of Da-Cheng-Qi-Tang, a Chinese medicine formula, prepared by traditional and modern decoction methods using UPLC/Q-TOFMS-based metabolomics approach.
PubMed:[Chemical constituents of Rabdosia japonica var. glaucocalyx and their anti-complementary activity].
PubMed:Alkyl and phenolic glycosides from Saussurea stella.
PubMed:Synergistic effects of diosmetin with erythromycin against ABC transporter over-expressed methicillin-resistant Staphylococcus aureus (MRSA) RN4220/pUL5054 and inhibition of MRSA pyruvate kinase.
PubMed:Simultaneous quantification and validation of caffeoylquinic acids and flavonoids in Hemistepta lyrata and peroxynitrite-scavenging activity.
PubMed:[Flavonoid glycosides from dried and nearly ripe fruits of Evodia rutaecarpa].
PubMed:Induction of melanogenesis by 4'-O-methylated flavonoids in B16F10 melanoma cells.
PubMed:Novel macrocyclic monoterpene glycosides from bioactive extract of Parkinsonia aculeata L.
PubMed:Pharmacokinetic study of luteolin, apigenin, chrysoeriol and diosmetin after oral administration of Flos Chrysanthemi extract in rats.
PubMed:On line characterization of 58 phenolic compounds in Citrus fruit juices from Spanish cultivars by high-performance liquid chromatography with photodiode-array detection coupled to electrospray ionization triple quadrupole mass spectrometry.
PubMed:HPLC-PDA-MS and NMR characterization of a hydroalcoholic extract of Citrus aurantium L. var. amara peel with antiedematogenic activity.
PubMed:[Chemical constituents from Gueldenstaedtia stenophylla].
PubMed:Structure-activity relationship studies of 5,7-dihydroxyflavones as naturally occurring inhibitors of cell proliferation in human leukemia HL-60 cells.
PubMed:[Chemical constituents contained in seeds of Notopterygium franchetii].
PubMed:Bioactivity of diosmetin glycosides isolated from the epicarp of date fruits, Phoenix dactylifera, on the biochemical profile of alloxan diabetic male rats.
PubMed:The flavonoids diosmetin and luteolin exert synergistic cytostatic effects in human hepatoma HepG2 cells via CYP1A-catalyzed metabolism, activation of JNK and ERK and P53/P21 up-regulation.
PubMed:[Compounds from fraction with cardiovascular activity of Chrysanthemum indicum].
PubMed:[Chemical constituents from stems of Lonicera macranthoides].
PubMed:Simultaneous qualitative assessment and quantitative analysis of flavonoids in various tissues of lotus (Nelumbo nucifera) using high performance liquid chromatography coupled with triple quad mass spectrometry.
PubMed:A new flavonol glycoside from Hylomecon vernalis.
PubMed:A profile of bioactive compounds of Rumex vesicarius L.
PubMed:Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction.
PubMed:Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques.
PubMed:Antioxidant and anti-inflammatory activities of aqueous extracts of Schizonepeta tenuifolia Briq.
PubMed:A potent inhibitor of SIK2, 3, 3', 7-trihydroxy-4'-methoxyflavon (4'-O-methylfisetin), promotes melanogenesis in B16F10 melanoma cells.
PubMed:Flavonoids in tropical citrus species.
PubMed:Protective effects of diosmetin extracted from Galium verum L. on the thymus of U14-bearing mice.
PubMed:Inhibition of cytochrome P450 2C8-mediated drug metabolism by the flavonoid diosmetin.
PubMed:Flavonoid C- and O-glycosides from the Mongolian medicinal plant Dianthus versicolor Fisch.
PubMed:Effects of Teucrium polium spp. capitatum flavonoids on the lipid and carbohydrate metabolism in rats.
PubMed:Iron deficiency enhances bioactive phenolics in lemon juice.
PubMed:Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
PubMed:[Nonvolatile chemical constituents from Pogostemon cablin].
PubMed:Role of catechol-O-methyltransferase in the disposition of luteolin in rats.
PubMed:Tea prepared from Anastatica hirerochuntica seeds contains a diversity of antioxidant flavonoids, chlorogenic acids and phenolic compounds.
PubMed:Anti-inflammatory activity of Penstemon gentianoides and Penstemon campanulatus.
PubMed:Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.
PubMed:[Chemical constituents of Discocleidion rufescens].
PubMed:Beta-glucuronidase from Helix pomatia origin is not suitable for diosmetin analysis.
PubMed:New iridoid diesters of glucopyranose from Linaria canadensis (L.) Dum.
PubMed:Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts.
PubMed:Flavonoids and antioxidant activity of Rosa agrestis leaves.
PubMed:[Chemical constituents from stems of Lonicera japonica].
PubMed:[Chemical constituents of Galium verum].
PubMed:Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.
PubMed:[Studies on flavones from Flos Chrysanthemi Indici].
PubMed:Flavonoid glycosides of the black locust tree, Robinia pseudoacacia (Leguminosae).
PubMed:[Chemical constituents of Lobelia chinensis].
PubMed:Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study.
PubMed:[Studies on chemical components of Lobelia chinensis].
PubMed:Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.
PubMed:Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.
PubMed:Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.
PubMed:Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.
PubMed:Two new flavonoids from Origanum vulgare.
PubMed:Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?
PubMed:Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.
PubMed:A new ferulic acid ester and other constituents from Dracocephalum peregrinum.
PubMed:Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: in vivo metabolic reduction of diosmetin to hesperetin.
PubMed:Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
PubMed:The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece-Crete indicates a new commercial source of hesperidin.
PubMed:Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation.
PubMed:Flavonoids from Galium verum L.
PubMed:Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida.
PubMed:Effect of flavonoids on rat splenocytes, a structure-activity relationship study.
PubMed:[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].
PubMed:New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry.
PubMed:HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity.
PubMed:Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.
PubMed:Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.
PubMed:Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
PubMed:Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
PubMed:Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
PubMed:Complete assignments of NMR data of 13 hydroxymethoxyflavones.
PubMed:Raddeanalin, a new flavonoid glycoside from the leaves of Salix raddeana Laksh.
PubMed:A new flavone glycoside from the fruits of Luffa cylindrica.
PubMed:Pensteminoside, an unusual catalpol-type iridoid from Penstemon gentianoides HBK (Plantaginaceae).
PubMed:Anti-proliferative and antioxidant constituents from Tecoma stans.
PubMed:Inhibition of pro-inflammatory markers in primary bone marrow-derived mouse macrophages by naturally occurring flavonoids: analysis of the structure-activity relationship.
PubMed:Rumex induratus leaves: interesting dietary source of potential bioactive compounds.
PubMed:Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.
PubMed:The efflux of flavonoids morin, isorhamnetin-3-O-rutinoside and diosmetin-7-O-beta-D-xylopyranosyl-(1-6) -beta-D-glucopyranoside in the human intestinal cell line caco-2.
PubMed:Antioxidant constituents in the fruits of Luffa cylindrica (L.) Roem.
PubMed:Flavonoid glycosides in bergamot juice (Citrus bergamia Risso).
PubMed:In vitro antioxidant activity of some Teucrium species (Lamiaceae).
PubMed:Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
PubMed:Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators.
PubMed:Determination of active components in rosemary by capillary electrophoresis with electrochemical detection.
PubMed:Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars.
PubMed:[Investigation of the hepatoprotector action of natural flavonoids].
PubMed:Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.
PubMed:A validated HPLC determination of the flavone aglycone diosmetin in human plasma.
PubMed:Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice.
PubMed:Metabolism of apigenin by rat liver phase I and phase ii enzymes and by isolated perfused rat liver.
PubMed:The beta-D-glucoside and sodium-dependent glucose transporter 1 (SGLT1)-inhibitor phloridzin is transported by both SGLT1 and multidrug resistance-associated proteins 1/2.
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:[A study on chemical constituents in the herb of Mentha spicata].
PubMed:Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
PubMed:Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action.
PubMed:Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry.
PubMed:Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
PubMed:Resistance of MCF-7 cells to dimethylbenz(a)anthracene-induced apoptosis is due to reduced CYP1A1 expression.
PubMed:A benzoquinone and flavonoids from Cyperus alopecuroides.
PubMed:Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
PubMed:[Chemical constituents of Taraxacum sinicum Kitag].
PubMed:New antimicrobial mono- and sesquiterpenes from Soroseris hookeriana subsp. erysimoides.
PubMed:Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum MIll. (Parsley) and structures of 6"-acetylapiin and a new monoterpene glycoside, petroside.
PubMed:Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1.
PubMed:Metabolites of orally administered Perilla frutescens extract in rats and humans.
PubMed:Anaerobic degradation of flavonoids by Eubacterium ramulus.
PubMed:Two new flavone glycosides from paullinia pinnata
PubMed:In vitro anti-Helicobacter pylori activity of some flavonoids and their metabolites.
PubMed:In vitro effects of selected flavonoids on the 5'-nucleotidase activity.
PubMed:Studies of structure activity relationship of flavonoids for the anti-allergic actions.
PubMed:Anti-inflammatory effects of South American Tanacetum vulgare.
PubMed:Two flavonoid triglycosides from Buddleja madagascariensis.
PubMed:Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity.
PubMed:The inhibition by flavonoids of 2-amino-3-methylimidazo[4,5-f]quinoline metabolic activation to a mutagen: a structure-activity relationship study.
PubMed:[Flavone constituents in the seeds of Sophora vicii folia Hance].
PubMed:Preventive effect of natural and synthetic antioxidants on lipid peroxidation in the mammalian eye.
PubMed:Role of flavonoids and iron chelation in antioxidant action.
PubMed:Pharmacokinetic studies of diosmin and diosmetin in perfused rat liver.
PubMed:In vivo and in vitro glucuronidation of the flavonoid diosmetin in rats.
PubMed:[Constituents of the leaves of Daphne pseudo-mezereum].
PubMed:Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures.
PubMed:Amine uptake inhibition by diosmin and diosmetin in human neuronal and neuroendocrine cell lines.
PubMed:Protective effect of diosmetin on in vitro cell membrane damage and oxidative stress in cultured rat hepatocytes.
PubMed:Pharmacokinetics and metabolism of oral diosmin in healthy volunteers.
PubMed:[A comparative study of the protective effect of various phlebotonic agents on hypoxic endothelial cells].
PubMed:Schizonodiol, Schizonol, and Schizonepetosides D and E, Monoterpenoids of Schizonepeta tenuifolia Spikes1.
PubMed:Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship.
PubMed:Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids.
PubMed:[Simultaneous assay of diosmin and diosmetin; application to biological milieux].
 
Notes:
a 5,7-dihydroxyflavone. Isol. from peel of lemon (Citrus limon) and others
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