5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 73004
• Molecular Formular: C16H12O6
• Molecular Mass: 300.26288
• Monoisotopic Mass: 300.0633881
• SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(c(c1)O)OC)O)O
• Canonical SMILES: COc1ccc(cc1O)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
• InChIKey: MBNGWHIJMBWFHU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: diosmetin; 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
• Synonyms: Luteolin 4-methyl ether; Diosmetin(Luteolin 4-methyl ether); Luteolin 4'-methyl ether; Diosmetin; 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one; ′,5,7-Trihydroxy-4′-methoxyflavone; 4′-Methylluteolin; 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one; Luteolin 4′-methyl ether; Diosmetin; Salinigricoflavonol; Vitamin P

Database IDs

• CAS Number: 520-34-3
• EC Number: 208-291-8
• MDL Number: MFCD00017425
• Beilstein Number: 294492
• PubChem SID: 162037924
• PubChem CID: 5281612
• CHEMBL: 90568
• Chemspider ID: 4444931
• Unique Ingredient Identifier: TWZ37241OT
• Wikipedia Title: Diosmetin

CALCULATED PROPERTIES

• Acid pKa: 6.637302
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.5186806
• LogD (pH = 7.4): 1.7277517
• Log P: 2.549018
• Molar Refractivity: 79.3771 cm^3
• Polarizability: 29.651005 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble1 mg/mL, clear, light yellow to yellow
• Apperance: light yellow to yellow

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Antioxidant

Product Information

• Purity: ≥95% (HPLC); ≥98% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Biological Source: Isol. from aerial parts of Valeriana spp., leaves of Digitalis spp., peel of lemon (Citrus limon) and others
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antioxidant
• Empirical Formula (Hill Notation): C16H12O6

DETAILS

Selleck Chemicals - S2380

Research Area: Cancer
Biological Activity:
Diosmetin (Luteolin 4-methyl ether) is a bioflavonoid found in spearmint, oregano, and many other plants. Like all bioflavonoids, diosmetin helps maintain normal capillary permeability and fragility. Diosmetin is called a bioflavonoid because of its chemical structure which is similar to the chemical structure of flavones, as well as for its biological activity. [1,2]

Sigma Aldrich - D7321

Biochem/physiol Actions
Flavonoid from Citrus limon. Antioxidant. Inhibits carcinogen activation by inhibiting the CYP1A1 enzyme.1

Sigma Aldrich - 90985

Biochem/physiol Actions
Flavonoid from Citrus limon. Antioxidant. Inhibits carcinogen activation by inhibiting the CYP1A1 enzyme.1

REFERENCES

• http://en.wikipedia.org/wiki/Diosmetin
• Oustrin, J. et al., Arzneim.-Forsch., 1977, 27, 1688