| Identification | More | [Name]
DIOSMETIN | [CAS]
520-34-3 | [Synonyms]
3',5,7-TRIHYDROXY-4'METHOXYFLAVONE
4'-METHOXY-5,7,3'-TRIHYDROXYFLAVONE
4-METHOXY-5,7,3'-TRIHYDROXYFLAVONE
5,7,3'-TRIHYDROXY-4'-METHOXYFLAVONE
DIOSMETIN
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
5,7-Dihydroxy-2-[3-hydroxy-4-methoxyphenyl]-[4H]-1-benzopyran-4-one
4'-Methylluteolin
Diosmetine
Diosmetol
Luteolin 4'-Methyl Ether
Pillon
DIOSMETIN(P)
DIOSMETIN WITH HPLC
2-(3-Hydroxy-4-methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | [EINECS(EC#)]
208-291-8 | [Molecular Formula]
C16H12O6 | [MDL Number]
MFCD00017425 | [Molecular Weight]
300.26 | [MOL File]
520-34-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Powder | [Melting point ]
256-258°C | [Boiling point ]
576.7±50.0 °C(Predicted) | [density ]
1.512±0.06 g/cm3(Predicted) | [vapor pressure ]
0Pa at 20℃ | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: soluble1mg/mL, clear, light yellow to yellow | [form ]
neat | [pka]
6.50±0.40(Predicted) | [color ]
light yellow to yellow | [Water Solubility ]
19μg/L at 20℃ | [Usage]
A metabolite of Apigenin. Antibacterial | [BRN ]
294492 | [Stability:]
Hygroscopic | [InChIKey]
MBNGWHIJMBWFHU-UHFFFAOYSA-N | [LogP]
3.1 at 20℃ | [CAS DataBase Reference]
520-34-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
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. | [Uses]
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: A monomethoxyflavone that is the 4'-methyl ether derivative of luteolin. | [Flammability and Explosibility]
Notclassified | [Biological Activity]
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. | [storage]
Store at -20°C | [References]
[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 |
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