(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

• ChemBase ID: 126286
• Molecular Formular: C15H12O5
• Molecular Mass: 272.25278
• Monoisotopic Mass: 272.06847348
• SMILES: c1cc(c(cc1/C=C/C(=O)c1c(cc(cc1)O)O)O)O
• Canonical SMILES: Oc1ccc(c(c1)O)C(=O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H
• InChIKey: AYMYWHCQALZEGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
• IUPAC Traditional name: butein
• Synonyms: 1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; 2′,3,4,4′-Tetrahydroxychalcone; Butein; (2E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; 3,4,2',4'-Tetrahydroxychalcone; 2′,4′,3,4-Tetrahydroxychalcone; Butein; 2',3,4,4'-Tetrahydroxychalcone; 2',4',3,4-Tetrahydroxychalcone

Database IDs

• CAS Number: 487-52-5
• EC Number: 207-659-5
• MDL Number: MFCD00017300
• PubChem SID: 162220625; 24891611
• PubChem CID: 5281222
• CHEMBL: 128000
• Chemspider ID: 4444634
• Wikipedia Title: Butein

CALCULATED PROPERTIES

• Acid pKa: 7.110532
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.3156154
• LogD (pH = 7.4): 2.8432667
• Log P: 3.326064
• Molar Refractivity: 74.8006 cm^3
• Polarizability: 27.768017 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >50 mg/mL; H2O: insoluble; Methanol
• Apperance: Orange powder; yellow solid; Yellow Solid
• Melting Point: 208-213°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: EGFR
• Gene Information: rat ... Alox5(25290)

Product Information

• Salt Data: Free Base

DETAILS

Sigma Aldrich - B178

Biochem/physiol Actions
Inhibits EGFR and Src tyrosine kinase activities; inhibits cAMP-dependent PDE-IV. Induces apoptosis in B16 melanoma cells and HL-60 human leukemia cells.
Caution
Photosensitive
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B178.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - B690125

Butrin, isobutrin, and butein from medicinal plant Butea monosperma selectively inhibit nuclear factor-κB in activated human mast cells: suppression of tumor necrosis factor-α, interleukin (IL)-6, and IL-8. Anti-inflammatory agent.

REFERENCES

• Woolley, D., et al.: Arthritis Res., 2, 65 (2000)
• Huang, D., et al.: J. Agric. Food Chem., 50, 4437 (2000)
• Lee, D., et al.: Science, 297, 1689 (2000)