4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase编号: 107780
• 分子式: C23H34O4
• 平均质量: 374.51366
• 单一同位素质量: 374.24570957
• SMILES: C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1
• Canonical SMILES: O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
• InChI: InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
• InChIKey: XZTUSOXSLKTKJQ-CESUGQOBSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC传统名: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; digitoxigenin
• 别名: 洋地黄毒苷配基; (+)-毛地黄毒苷配基; 3,14,21-三羟基-20(22)-去甲胆烯酸内酯; 3β,14-二羟基-5β,20(22)-卡烯内酯; 5β,20(22)-卡烯内酯-3β,14-二醇; 洋地黄毒苷配基; 3β,14-Dihydroxy-5β,20(22)-cardenolide; 3,14,21-Trihydroxy-20(22)-norcholenic acid lactone; 5β,20(22)-Cardenolide-3β,14-diol; Digitoxigenin; (+)-Digitoxigenin; Thevetigenin; Cerberigenin; Echujetin; DIGITOXIGENIN; Digitoxigenin

登记号

• CAS号: 143-62-4
• EC号: 205-603-4
• MDL号: MFCD00003687
• Beilstein号: 95448
• PubChem SID: 24894291; 24863063; 162095458
• PubChem CID: 4369270

理论计算性质

• Acid pKa: 7.1826363
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.0584373
• LogD (pH = 7.4): 2.645005
• Log P: 3.0673547
• 摩尔折射率: 103.6406 cm^3
• 极化性: 41.212856 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 253 °C(lit.); 253-255 °C (dec.)(lit.)
• 比旋光度: [α]20/D +14.5±2°, c = 1% in methanol; [α]20/D +16.9°, c = 1.3 in methanol

安全信息

• RTECS编号: FH4975000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 3462
• 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): 2
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2

药理学性质

• 相关基因信息: rat ... Atp1a1(24211)
• 生物活性机理: Na-K-Atpase inhibitor

产品相关信息

• 纯度: ≥99.0% (HPLC); 98%
• 级别: puriss.
• 简要说明: non-ionic
• 生物来源: Isol. from Digitalis lanata, Pachycarpus schinzianus, Gongronema gazense and others
• 应用领域: Cardiotonic agent
• Empirical Formula (Hill Notation): C23H34O4

详细说明

MP Biomedicals - 05205013

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D103209

包装
10, 100 mg in glass bottle

参考文献

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1063A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 605A; 605B, (nmr)
• Fritsch, W. et al., Annalen, 1974, 621-629, (Digitoxigenin, synth)
• Yoshii, E. et al., Chem. Pharm. Bull., 1975, 23, 2496-2506, (Digitoxigenin, synth)
• Welzel, P. et al., Annalen, 1982, 2119-2134, (Digitoxigenin, synth)
• Milkova, T. et al., Tet. Lett., 1982, 23, 413-414, (Digitoxigenin, synth)
• Wicha, J. et al., J.C.S. Perkin 1, 1985, 1601-1605, (Digitoxigenin, synth)