Diosmetin Chemical Properties

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 

Soluble in acetonitrile, DMSO (60 mg/ml), and ethanol (17 mg/ml), clear, light yellow to yellow.

pka

6.50±0.40(Predicted)

color 

light yellow to yellow

Water Solubility 

19μg/L at 20℃

BRN 

294492

Stability:

Hygroscopic

InChIKey

MBNGWHIJMBWFHU-UHFFFAOYSA-N

LogP

3.1 at 20℃

CAS DataBase Reference

520-34-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29329990

Hazardous Substances Data

520-34-3(Hazardous Substances Data)

Diosmetin Usage And Synthesis

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: 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

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.

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

Diosmetin(520-34-3)Related Product Information

• Luteolin
• Eurycoma longifolia powder extract
• Coumarin 6
• Coumarin-3-carboxylic acid
• BETA-RHODINOL
• Coumarin 153
• Diosmetin 7-O-β-D-glucopyranoside,Diosmetin 7-O-glucoside
• DIOSMETIN-7-O-RUTINOSIDE,DIOSMETIN-7-RUTINOSIDE
• LUTEOLIN-4'-O-GLUCOSIDE
• 3,7,3',4'-TETRAMETHYLGOSSYPETIN
• 3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE
• 3',4',5,7-TETRAMETHOXYFLAVONE
• Diosmetin
• TAMARIXETIN
• QUERCETIN-3,7,3',4'-TETRAMETHYL ETHER
• 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE
• EUPATORIN-5-METHYL ETHER
• DIOSMETIN-7-NEOHESPERIDOSIDE