7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

• ChemBase ID: 106084
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: COc1cc2c(occ(c2=O)c2ccc(O)cc2)cc1O
• Canonical SMILES: COc1cc2c(cc1O)occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
• InChIKey: DXYUAIFZCFRPTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
• IUPAC Traditional name: glycitein
• Synonyms: 4,7-Dihydroxy-6-methoxyisoflavone; GLYCITEN; 4′,7-Dihydroxy-6-methoxyisoflavone; Glycetein; Glycitein; 4',7-Dihydroxy-6-methoxyisoflavone; Glycitein; 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; Glicetein; 7,4’-Dihydroxy-6-methoxyisoflavone

Database IDs

• CAS Number: 40957-83-3; 446-72-0
• EC Number: 207-174-9
• MDL Number: MFCD00016679
• PubChem SID: 162092888
• PubChem CID: 5317750
• CHEMBL: 513024
• Wikipedia Title: Glycitein

CALCULATED PROPERTIES

• Acid pKa: 6.919339
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.5566611
• LogD (pH = 7.4): 1.9694681
• Log P: 2.5727665
• Molar Refractivity: 76.1652 cm^3
• Polarizability: 29.011745 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Orange Solid
• Melting Point: >300°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: NR2392000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC); 99%

DETAILS

MP Biomedicals - 02199015

Purity: 99%

Sigma Aldrich - G2785

Biochem/physiol Actions
Glycitein is a soybean (yellow cultivar) isoflavonoid; its natural glycosides are synergistic with genistein in inducing specific gene expression. Glycitein may be used to study anti-oxidation processes at the level of gene transcription where it increases the binding of transcription factors [nuclear factor-E2-related factor 2 (Nrf2) and c-Jun] to the antioxidant response element (ARE) on HO-1 and NQO1 promoters. Glycitein may be used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis.

Toronto Research Chemicals - G635400

The compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss.

REFERENCES

• Whalley, J.L., et al.: Bioorg. Med. Chem. Lett., 8, 1569 (1998)
• Song, T., et al.: J. Agric. Food Chem., 47, 1607 (1998)