5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 154212
• Molecular Formular: C20H20O5
• Molecular Mass: 340.3698
• Monoisotopic Mass: 340.13107374
• SMILES: CC(=CCc1c(cc(c2c1OC(CC2=O)c1ccc(cc1)O)O)O)C
• Canonical SMILES: CC(=CCc1c(O)cc(c2c1OC(CC2=O)c1ccc(cc1)O)O)C
• InChI: InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3
• InChIKey: LPEPZZAVFJPLNZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: sophoraflavanone B
• Synonyms: (+/-)-8-Prenylnaringenin; 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; 8-isopentenylnaringenin; (±)-8-Prenylnaringenin; (±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one; rac 8-Prenylnaringenin

Database IDs

• CAS Number: 68682-02-0
• MDL Number: MFCD00272175
• PubChem SID: 162248351
• PubChem CID: 509245

CALCULATED PROPERTIES

• Acid pKa: 7.729241
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 4.5611396
• LogD (pH = 7.4): 4.3970494
• Log P: 4.563675
• Molar Refractivity: 95.5326 cm^3
• Polarizability: 36.2246 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C20H20O5

DETAILS

Sigma Aldrich - P3496

Biochem/physiol Actions
8-Prenylnaringenin, a strong plant-derived estrogen receptor ligand, is a phytoestrogen that inhibits multidrug resistance-associated transporters, P-glycoprotein and MRP1. 8-Prenylnaringenin also inhibits EGF signaling at the level of phosphatidylinositol-3-OH kinase ((PI(3)K))activity.
Protocols & Applications
Hops (Humulus lupulus) Plant Profile: bioactives, mechanism of action, references

Toronto Research Chemicals - P712900

8-Prenylnaringenin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.

REFERENCES

• Miyamoto, M. et al.: Planta Med., 64, 516 (1998)
• Kim, H.J. et al.: Arch. Pharm. Res., 31, 1241 (1998)
• Zierau, O. et al.: Mol. Cell. Endocrinol., 294, 92 (1998)