3α,7β-Dihydroxy-5β-cholan-24-oate 3α,7β-二羟基-5β-胆碱-24-油酸

CAS 128-13-2 MFCD00003680

化学结构图

128-13-2
SMILES: CC(CCC(=O)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C

化学属性

Mol. FormulaC24H40O4
Mol. Weight393
Melting Point203-204
TSCANo
Appearance 本品为白色粉末;无臭,味苦。Mp 200-204℃。在乙醇和冰醋酸中易溶,在氢氧化钠试液中溶解,在氯仿中不溶。UDCA为CDCA的同分异构体,其溶石作用强于CDCA,无腹泻及肝脏毒性。UDCA能降低胆固醇的吸收,并能降低胆固醇的合成及胆汁中的胆固醇含量。另外,UDCA亦能降低伴刀豆蛋白A结合片段,该物质能促进胆汁结晶的形成,从而抑制结石的形成。UDCA和CDCA联合使用,可增强各自单独使用的溶石作用,同时减轻副作用。两者联用主要用于治疗胆囊胆固醇结石,患者胆石与胆汁等密度或者胆石CT值低于75单位时, UDCA的溶石速度最快。胆石症病人使用本品后,可增加外周血小板数量。
Density1.128
SolubilitySoluble in ethanol (79 mg/ml at 25 °C), alcohol (freely), chloroform (slightly), and DMSO (79 mg/ml at 25 °C). Insoluble in water.
Refractive index60.5 ° (C=2, EtOH)

别名和识别编码

Chemical Name3α,7β-Dihydroxy-5β-cholan-24-oate
MDL NumberMFCD00003680
CAS Number128-13-2
Synonym Actigall Cholit-ursan URSODESOXYCHOLIC ACID 3alpha,7beta-二羟基-5beta-胆甾烷-24-酸 3α,7β-Dihydroxy-5β-cholan-24-oic acid 5β-Cholan-24-oic acid-3α,7β-diol 7β-Hydroxylithocholic acid UDCS 3,7-Dihydroxy-5-cholan-24-oic acid, 5-Cholan-24-oic acid-3,7-diol, 7-Hydroxylithocholic acid 3-alpha,7-beta-Dioxycholanic acid Ursacol 3ALPHA,7BETA-DIHYDROXY-5BETA-CHOLAN-24-OIC ACID URSODEOXYCHOLOC ACID 3α,7β-Dihydroxy-5β-cholan-24-oic acid, 5β-Cholan-24-oic acid-3α,7β-diol, 7β-Hydroxylithocholic acid URSODEOXYCHOLIC ACID Litursol 5BETA-CHOLANIC ACID-3ALPHA,7BETA-DIOL 熊去氧胆酸 7-beta-Hydroxylithocholic acid 6BETA-CHOLANIC ACID-3A,7BETA-DIOL 熊果去氧胆酸 UDCA
PubChem Substance ID31401
Beilstein Registry Number3219888
EC Number204-879-3
Merck Number9889
Reaxys-RN3219888
Chemical Name Translation3α,7β-二羟基-5β-胆碱-24-油酸
Wiswesser Line NotationL E5 B666TJ A1 E1 FY1&2VQ KQ OQ
InChIInChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
LabNetwork Molecule IDLN00243877
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分类

  • {Chemicalbo
  • {SNA} Anionic Detergents, Bile Salts, Bile acids and Derivatives, Cell Culture, Chemical ER Chaperones, Detergents N to Z, Detergents by Applications, Endoplasmic Reticulum Stress, Gene Regulation, Phototherapy, Sterol Lipids, 代谢组学, 代谢通路, 化学预防剂, 去垢剂, 抗肿瘤药物, 生化试剂, 癌症研究, 细胞信号转导和神经科学, 细胞生物学, 胆汁酸代谢, 脂类
  • {SNA} Anionic Detergents, Antitumor Agents, Bile Acid Metabolism, Bile Salts, Bile acids and Derivatives,
  • {SNA} Analytical Standards,
  • {SNA} Anionic D

产品应用

  • 阴离子去垢剂,用于生化研究。

相关文献及参考

  • [2]. Kumar D, et al. Use of ursodeoxycholic acid in liver diseases. J Gastroenterol Hepatol. 2001 Jan;16(1):3-14.
  • [3]. Biao Nie, et al. Specific Bile Acids Inhibit Hepatic Fatty Acid Uptake in Mice. Hepatology. 2012 Oct;56(4):1300-10.
  • Merck: 14,9889
  • Merck: 14,9889 Beilstein:10(3)1635
  • [1]. Jackson H, et al. Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study. Hepatology. 2007 Oct;46(4):1131-7.
  • [1]. Jackson H, et al. Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study. Hepatology. 2007 Oct;46(4):1131-7.
  • [2]. Kumar D, et al. Use of ursodeoxycholic acid in liver diseases. J Gastroenterol Hepatol. 2001 Jan;16(1):3-14.
  • [3]. Biao Nie, et al. Specific Bile Acids Inhibit Hepatic Fatty Acid Uptake in Mice. Hepatology. 2012 Oct;56(4):1300-10.

安全信息

WGK Germany2
RTECSFZ2000000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Signal word
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
GHS Symbol
Safety Statements
Storage condition 充氩保存 充氩密封保存。
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85IQAH "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical,
   Medical and Dental Supply Exporters' Assoc., 1972  Volume(issue)/page/year:
   -,109,1972

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 310 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - convulsions or effect on seizure threshold
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 9,3159,1975

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 700 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   BCFAAI Bollettino Chimico Farmaceutico.  (Societa Editoriale Farmaceutica,
   Via Ausonio 12, 20123 Milan, Italy)  V.33-    1894- Volume(issue)/page/year:
   126,282,1987

TYPE OF TEST            : LD50 - Lethal dose, 5

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 4600 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   BCFAAI Bollettino Chimico Farmaceutico.  (Societa Editoriale Farmaceutica,
   Via Ausonio 12, 20123 Milan, Italy)  V.33-    1894- Volume(issue)/page/year:
   126,282,1987

{haza

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 51 mmol/L
REFERENCE :
   ARTODN Archives of Toxicology.  (Springer-Verlag, Heidelberger Pl. 3, D-1000
   Berlin 33, Fed. Rep. Ger.)  V.32-    1974-  Volume(issue)/page/year:
   60,192,1987

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 40 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 158,45,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1200 mg/kg
SEX/DURATION            : female 9-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 9

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 65 mg/kg
SEX/DURATION            : female 6-18

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 1200 mg/kg
SEX/DURATION            : female 7-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 9,3223,1975

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1200 mg/kg
SEX/DURATION            : female 9-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 9,3223,

其他信息

  • MSDS 信息:3alpha,7beta-Dihydroxy-6beta-cholan-24-oic acid(128-13-2).msds
  • 上游原料:甲醇 --> 二乙二醇 --> 2,3-丁二酮 --> 铬酸钾 --> 鹅去氧胆酸 --> 5-Β-胆烷酸 --> 胆酸甲酯 --> 乙酰胆酸
  • 味苦。易溶于乙醇、冰乙酸,微溶于氯仿、乙醚,几乎不溶于水。半数致死量1000mg/kg(大鼠,腹腔)、310mg/kg(大鼠,静脉)。
  • 用途二:胆石溶解药。主要用于不宜手术治疗的胆固醇型胆结石,尤其是胆囊功能基本正常、结石直径在15mm以下、透X线、非钙化型的浮动胆固醇结石的治愈率高。对中毒性肝炎、胆囊炎、原发性硬化性胆管炎、原发性胆汁淤积性肝硬化也有一定的治疗效果。提高α-干扰素治疗慢性丙型肝炎的疗效。有腹泻,罕见便秘、过敏反应、瘙痒、头痛、头晕、胃痛、胰腺炎及心动过缓等。胆道完全阻塞和严重
  • Acros Organics:熊果去氧胆酸/熊去氧胆酸 Ursodeoxycholic acid, 99%(128-13-2)
  • 熊去氧胆酸价格(试剂
  • 方法一:方法一、以鹅去氧胆酸为原料 3α, 7α-二乙酰胆酸甲酯的制备 取无水甲醇36ml,通入1g干燥氯化氢气体,加胆酸12g,搅拌,加热回流20-30min,室温放置数小时后析出晶体,冷冻,过滤,用乙醚洗涤,干燥,得胆酸甲酯。取胆酸甲酯2g,加苯9.6ml,加吡啶2.4ml,加乙酐2.4ml,振摇10-15min,室温放置20h,将反应液倒入100ml水中,除去苯层,反复用蒸馏水洗涤,回收溶剂,固体残渣用石油醚洗涤1次,用甲醇-水溶液重结晶,得3α,7α-二乙酰胆酸甲酯。 胆酸→胆酸甲酯→3α,7α-二乙酰胆酸甲酯 鹅去氧胆酸的制备 取二乙酰胆酸甲酯1.5g,加乙酸24 ml,加铬酸钾溶液(取铬酸钾0.76g溶于1.8ml水中),加热至40℃,反应8h,加水120ml,振摇片刻,放置12h,过滤,用蒸馏水洗至中性,干燥,得3α,7α-二乙酰氧基- 12-酮基胆烷酸甲酯,简称12-酮。取12-酮15g,加二乙二醇醚150ml,加80%水合肼溶液15ml,加氢氧化钾15g,加热至30℃回流15h,升温至195-200℃,回流2.5h,升温至217℃反应片刻,冷却至190℃,加水合肼溶液0.7ml,在3h内由215℃升温至220℃,冷却,加蒸馏水600ml,加10%硫酸调pH 3,析出结晶,过滤,水洗至中性,加乙酸乙酯,弃去水层,有机层用水洗1-2次,减压蒸馏,得白色3α,7α-二羟基胆烷酸,即鹅去氧胆酸。 3α,7α-二乙酰胆酸甲酯→3α,7α-二乙酰氧基-12-酮基胆烷酸甲酯→3α,7α-二羟基胆烷酸(鹅去氧胆酸) 熊去氧胆酸精品的制备 取鹅去氧胆酸2g,加100ml乙酸,加乙酸钾20g,振摇溶解,加铬酸钾1.5g(溶于10ml水中),室温放置过夜,加水200ml,析出结晶,过滤,水洗,干燥,得3α-羟基-7-酮基胆烷酸。取3α-羟基-7-酮基胆烷酸4g,加正丁醇100ml,加热至约115℃,分次加入金属钠8g,逐渐有白色浆状物析出,继续反应30min,加水120ml,搅拌升温溶解透明,减压蒸去有机层,残渣加水500ml,溶解,过滤,滤液加10%硫酸调pH3,有白色絮状物沉淀,过滤,水洗至中性,干燥,加乙酸乙酯洗涤,稀乙醇结晶,得3α,7β-二羟基胆烷酸,即熊去氧胆酸精品。 鹅去氧胆酸[铬酸钾]→3α-羟基-7-酮基胆酸[金属钠,115℃]→3α, 7β-二羟基胆烷酸(熊去氧胆酸) 方法二、以猪胆
  • 参考质量标准:原料药 中国药典2000年版1006页 指标名称 指标 指标名称 指标 含量(C24H40O4)/% ≥98.5/干燥失重/% ≤1.0 比旋度(40mg/ml无水乙醇)/+59.0°-+62.0°/炽灼残渣/% ≤0.2 重金属 ≤百万分之二十 异臭/无/砷盐/% ≤0.0002 氯化物/% ≤0.02/硫酸盐/% ≤0.05 钡盐 无 片剂 中国药典2000年版1006页 指标名称 指标 指标名称 指标 含量(C24H40O4)/% 95.0-105.0/检查/符合片剂规定
  • 熊去氧胆酸,主要成分是3a,7β- 二羟基-5β- 胆甾烷-24-酸,为有机化合物,无臭,味苦。本品在乙醇中易溶,在氯仿中不溶;在冰醋酸中易溶,在氢氧化钠试液中溶解。医学上用于增加胆汁酸分泌,并使胆汁成分改变,降低胆汁中胆固醇及胆固醇脂,有利于胆结石中的胆固醇逐渐溶解。

系列性分类