4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

• ChemBase编号: 102407
• 分子式: C19H12O6
• 平均质量: 336.29498
• 单一同位素质量: 336.0633881
• SMILES: Oc1c(Cc2c(O)c3c(oc2=O)cccc3)c(=O)oc2c1cccc2
• Canonical SMILES: O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)O
• InChI: InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
• InChIKey: DOBMPNYZJYQDGZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
• IUPAC传统名: dicoumarol; 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
• 别名: Dicoumarol; Dicumarol; 3,3′-Methylene-bis(4-hydroxycoumarin); 3,3'-Methylene-bis[4-hydroxycoumarin]; DICOUMAROL; 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one); Bishydroxycoumarin; Dicoumarin; Cumid; Dufalone; Melitoxin; Dicoumarol; 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

登记号

• CAS号: 66-76-2
• EC号: 200-632-9
• MDL号: MFCD00006857
• PubChem SID: 24896643; 162089593
• PubChem CID: 54676038

理论计算性质

• Acid pKa: -11.9426155
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -1.6014295
• LogD (pH = 7.4): -1.6019053
• Log P: -1.5927894
• 摩尔折射率: 89.1928 cm^3
• 极化性: 33.760597 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 290 - 292°C; 290-292 °C(lit.); 290-292°C
• 疏水性(logP): 2.315

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: GN7875000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-48/25-51/53; R:22-48/25-51/53
• 安全公开号: 37-45-61; S:37-45-61
• GHS危险品标识: GHS07; GHS08; GHS09
• GHS警示词: Danger
• GHS危险声明: H302-H372-H411
• GHS警示性声明: P273-P314
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 相关基因信息: human ... CYP2C9(1559)
• 生物活性机理: Depletes clotting factor-IX; Depletes clotting factor-VII; depletes clotting factor-X; Depletes prothrombin; Interferes with synthesis of vitamin K dependent clotting-factors; Vitamin K antagonist

产品相关信息

• 纯度: 95%
• 生物来源: Isol. from Melilotus alba and Anthoxanthum spp.
• 应用领域: Antibacterial agent; Anticoagulant; Haemorrhagic agent causing ``sweet clover'' disease in cattle; Orally active anticoagulant

详细说明

MP Biomedicals - 02101555

Crystalline
Vitamin K antagonist.

Sigma Aldrich - M1390

Biochem/physiol Actions
Prototype of the 4-hydroxycoumarin class of anticoagulants, which act as vitamin K antagonists, preventing formation of prothrombin. There are many reports that dicumarol also inhibits NADPH:quinone oxidoreductase (NQO(1)). In one1, it inhibited NQO(1) in a pancreatic cancer cell line, causing increased formation of superoxide and inhibiting cell growth.

参考文献

• Hutchinson, D.W. et al., Tetrahedron, 1969, 25, 2531, (ir, pmr, struct)
• Levy, G., J. Pharmacokinet. Biopharm., 1973, 1, 541, (rev)
• Owen, C.A., Mayo Clin. Proc., 1974, 49, 912, (rev, pharmacol)
• Kirkiacharian, B.S. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1977, 284, 697, (cmr)
• Alcock, N.W. et al., Acta Cryst. B, 1978, 28, 1957, (cryst struct)
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, 271, (biochem)
• Hayward, R.C., J. Chem. Educ., 1984, 61, 87, (synth)
• Griminger, P., J. Nutr., 1987, 117, 1325, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5099
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 225
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BJZ000
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 325A, (ir)
• Stahmann, M.A. et al., J. Biol. Chem., 1941, 138, 21; 513; 529, (isol, synth, uv)
• Wittmann, H. et al., Monatsh. Chem., 1965, 96, 1200, (synth)
• Korenmann, I.M. et al., Zh. Anal. Khim., 1967, 22, 1305, (use)