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

• ChemBase编号: 126286
• 分子式: C15H12O5
• 平均质量: 272.25278
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: butein
• 别名: 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

登记号

• CAS号: 487-52-5
• EC号: 207-659-5
• MDL号: MFCD00017300
• PubChem SID: 24891611; 162220625
• PubChem CID: 5281222
• CHEMBL: 128000
• Chemspider ID: 4444634
• 维基百科标题: Butein

理论计算性质

• Acid pKa: 7.110532
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): 3.3156154
• LogD (pH = 7.4): 2.8432667
• Log P: 3.326064
• 摩尔折射率: 74.8006 cm^3
• 极化性: 27.768017 Å^3
• 极化表面积: 97.99 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >50 mg/mL; H2O: insoluble; Methanol
• 外观: Orange powder; yellow solid; Yellow Solid
• 熔点: 208-213°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: EGFR
• 相关基因信息: rat ... Alox5(25290)

产品相关信息

• 成盐信息: Free Base

详细说明

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.

参考文献

• 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)