5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron

Bezeichnung:5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron

CAS-Nr520-34-3

Englisch Name:Diosmetin

CBNumberCB2380858

SummenformelC16H12O6

Molgewicht300.26

MOL-Datei520-34-3.mol

Synonyma

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron physikalisch-chemischer Eigenschaften

Schmelzpunkt	256-258°C
Siedepunkt	576.7±50.0 °C(Predicted)
Dichte	1.512±0.06 g/cm3(Predicted)
Dampfdruck	0Pa at 20℃
storage temp.	Sealed in dry,2-8°C
Löslichkeit	Soluble in acetonitrile, DMSO (60 mg/ml), and ethanol (17 mg/ml), clear, light yellow to yellow.
Aggregatzustand	Solid
pka	6.50±0.40(Predicted)
Farbe	light yellow to yellow
Wasserlöslichkeit	19μg/L at 20℃
BRN	294492
Stabilität	Hygroscopic
InChIKey	MBNGWHIJMBWFHU-UHFFFAOYSA-N
LogP	3.1 at 20℃
CAS Datenbank	520-34-3(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	22
S-Sätze:	24/25
WGK Germany	3
HS Code	29329990
Giftige Stoffe Daten	520-34-3(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Diosmetin Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Diosmetin is a flavonoid compound that appears as a yellow powder. It is extracted from lemon and also found in various other natural plants, including spearmint and spider incense. Diosmetin is slightly soluble in methanol but readily dissolves in DMSO.
Verwenden
Diosmetin (Diosmin EP Impurity F) is a metabolite of Apigenin. It exhibits anticancer, antimicrobial, antioxidant, oestrogenic, and anti-inflamatory activities. Diosmetin can be used in the production of functional foods, cosmetics, and future drugs with antioxidant, anti-infective and anti-shock effects.
Definition
ChEBI: Diosmetin is a monomethoxyflavone that is the 4'-methyl ether derivative of luteolin. It is a natural product isolated from citrus fruits which exhibits a range of pharmacological activities. It has a role as an antioxidant, an antineoplastic agent, a plant metabolite, a tropomyosin-related kinase B receptor agonist, an apoptosis inducer, an angiogenesis inhibitor, a cardioprotective agent, a bone density conservation agent, an anti-inflammatory agent and a vasodilator agent. It is a monomethoxyflavone, a trihydroxyflavone and a 3'-hydroxyflavonoid. It is functionally related to a luteolin. It is a conjugate acid of a diosmetin-7-olate.
Flammability and Explosibility
Not classified
Biologische Aktivität
diosmetin (dio) is an agonist of the aryl hydrocarbon receptor (ahr). it potently inhibited the enzyme activity of cytochrome p450 1a1 (cyp1a1) in a dose-dependent manner with an ic50 value of approximately 30 nm, in microsomes from mcf-7 cells [1].ahr belongs to the per, arnt, sim/basic-helix-loop-helix superfamily of ligand-activated transcription factors. ahr mediates the toxic effects of polycyclic aromatic hydrocarbons, 2,3,7,8-tetrachlorodibenzo-p-dioxin (tcdd) and polychlorinated biphenyls. these chemicals all bind to ahr, and result in the activation of a battery of genes, including the cytochromes p450 cyp1a1, cyp1a2, and cyp1b1 [2].in mcf-7 cells, at 24 h after the incubation of diosmetin, cyp1a1 mrna was increased in a dose-dependent manner. in mcf-7 cells, diosmetin at 2.5 μm modestly increased cyp1a1 enzyme activity, with an activity increase in cells, while diosmetin at 5 μm did not increase the enzyme activity compared to controls in cells. compared with controls, diosmetin dose-dependently increased the capacity of nuclear extracts to bind an oligonucleotide containing the ahr-binding sequence of cyp1a1 [1].in the presence of cyp1a inhibitor, the concentration of diosmetin ranged from 25 μm at 0 h to 22 μm. in the absence of cyp1a inhibitor, the concentration of diosmetin ranged from 25 μm at 0 h to 15 μm [3].no in vivo result from the administration of diosmetin had been found.
Einzelnachweise
[1]. ciolino hp, wang tt and yeh gc. diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome p450 1a1 activity. cancer res, 1998, 58(13):2754-60. PMID: 9661887
[2]. gonzalez fj and fernandez-salguero p. the aryl hydrocarbon rreceptor studies using the ahr-null mice. drug metabolism and disposition, 1998, 26(12): 1194-1198. PMID: 9860927
[3]. and routsopoulos vp and spandidos da. 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. j nutr biochem, 2013, 24(2):496-504. DOI:10.1016/j.jnutbio.2012.01.012

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyron Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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