Cholic acid 胆酸

CAS 81-25-4 MFCD00003672

化学结构图

81-25-4
SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O

化学属性

Mol. FormulaC24H40O5
Mol. Weight408.57
Density1.422
Melting Point200-201
TSCAYes
Solubility150 G/L (20 ºC)
Appearance 本品存在于牛、羊、猪的胆汁中。为无色片状物或白色结晶粉末。有些苦味,尝后又有些甜的感觉。Mp198℃,比旋度(c=0.6,乙醇)为+37°。1g胆酸约溶于300ml乙醇或丙酮,7ml冰醋酸,很少量溶于水。一水合物为白色片状结晶。1927年,H.Wieland(德国)研究胆酸组成,获诺贝尔化学奖。
Stability对湿度敏感

别名和识别编码

Chemical NameCholic acid
Synonym 12-三羟甾代异戊酸,3α,7α,12α-三羟基-5β-胆烷酸,(3α,5β,7α,12α)-3,7,12-三羟基胆(甾)烷-24-酸单钠盐 12α-Trihydroxy-5β-cholan-24-oic acid. 3α,7α,12α-三羟基-5β-胆烷酸 胆甾烷酸 3,7,12-TRIHYDROXYCHOLANIC ACID 3A,7A,12A-TRIHYDROXY-5B-CHOLAN-24-OIC ACID 3α,7α,12α-Trihydroxy-5α-cholanic acid, 3α,7α,12α-Trihydroxy-5β-cholanic acid, Cholanic acid 5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy- CA CHOLALIC ACID CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, (3,5,7,12)- Cholalin Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)- Cholic acid {} {} {Chemicalbook} Cyclosphorine {} {} {} {Chemblink} Cholic acid sodium salt; Sodium (3a,5b,7a,12a)-3,7,12-trihydroxycholan-24-oate
MDL NumberMFCD00003672
CAS Number81-25-4
EC Number201-337-8
Beilstein Registry Number2822009
Merck Number14,2203
PubChem Substance ID221493
Chemical Name Translation胆酸
Wiswesser Line NotationL E5 B666TJ A1 DQ E1 FY1&2VQ KQ OQ
LabNetwork Molecule IDLN00202370
InChIInChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
Canonical SMILESC[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C
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分类

  • {SNA} Analytical Reagents, Analytical/Chromatography, Anionic Detergents, Antigen-Vaccine Preparation, Application Specific Reagents, Bile Salts, Bile acids and Derivatives, Bioactive Small Molecules, Biochemicals and Reagents, C-CH, Cell Biology, Cell Culture, Core Bioreagents, Detergents, Detergents A to M, Detergents by Applications, Diagnostic Applications, Drug Delivery-Liposomes, Electrophoresis Chromatography, Enzymology, Lipids, Membrane Protein Solubilization, Molecular Biology, Reagents for Extraction Analysis,
  • {SNA} Anionic Detergents,
  • {SNA} Analytical Standards,

产品应用

  • 非变性离子去垢剂,用于抽提膜蛋白。用于生化研究,医药中间体。胆酸钠是利胆药,治疗胆囊炎;胆汁缺乏;肠道消化不良等症。

相关文献及参考

  • [2]. Pan X, et al. Cholic acid Feeding Leads to Increased CYP2D6 Expression in CYP2D6-Humanized Mice. Drug Metab Dispos. 2017 Apr;45(4):346-352.
  • Merck: 14,2203
  • Merck: 14,2203 Beilstein: 10,IV,2072
  • [1]. Li Y, et al. Mechanism of hepatic targeting via oral administration of DSPE-PEG-Cholic acid-modified nanoliposomes. Int J Nanomedicine. 2017 Feb 28;12:1673-1684.
  • [1]. Li Y, et al. Mechanism of hepatic targeting via oral administration of DSPE-PEG-Cholic acid-modified nanoliposomes. Int J Nanomedicine. 2017 Feb 28;12:1673-1684.
  • [2]. Pan X, et al. Cholic acid Feeding Leads to Increased CYP2D6 Expression in CYP2D6-Humanized Mice. Drug Metab Dispos. 2017 Apr;45(4):346-352.

安全信息

Signal word Warning
GHS Symbol
WGK Germany2
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Risk Statements
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
RTECSFZ9350000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 2-8°C Store at RT. 密封保存。
Hazard Codes Xi
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4950 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - ulceration or bleeding from stomach
   Gastrointestinal - hypermotility, diarrhea
REFERENCE :
   ESKHA5 Eisei Shikenjo Hokoku.  Bulletin of the Institute of Hygienic
   Sciences.  (Kokuritsu Eisei Shikenjo Kagaku, 18-1 Bushitsu Johobu,
   Setagaya-ku, Tokyo 158, Japan)  V.1-    1886-  Volume(issue)/page/year:
   (103),29,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 330 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 20,323,1970

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 400 mg/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 5,447,1984

TYPE OF TEST            : Morphological transformation
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 7560 mg/kg/6W
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 9,387,1988

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 50 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            : Gene conversion and mitotic recombination
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 93200 umol/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

Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛

其他信息

  • 鉴别试验:溶解性极难溶于水;溶于乙醇。按OT-42方法测定。 熔程 197~202℃。按常规方法测定。 用50%醋酸液配制0.02%试样液,取1m1,加1%糠醛溶液1ml、水6ml和浓硫酸5ml。此混合液在5min内应转变成玫瑰色后又转紫色。 取试样约10mg,加苯甲醛2滴和3:1硫酸3滴,在50℃下加热5min。再加冰醋酸约10ml,应呈棕色。
  • 上游原料:乙醇 --> 乙酸乙
  • 检测方法:Chromatography, colorimetry
  • 参考质量标准:FAO/WHO,1992 含量 ≥98.0% 干燥失重 ≤0.5% 硫酸盐灰分(GT-5试样2g) ≤0.1% 比旋光度[口]分(配2%试样乙醇液,w/y) ≥+37。 砷(GT-3) ≤3mg/kg 铅(GT-18) ≤10mg.kg 重金属(GT-16-2) ≤40mg/kg
  • 所属类别一:食品添加剂: 乳化剂、增稠剂和稳定剂
  • 含量分析:精确称取140℃真空干燥4h后的试样约400mg,放人250ml烧瓶中,加水20ml和乙醇40ml,盖上表面皿,在蒸汽浴上温和地加热至溶解后冷却。加酚酞试液(TS-167)5滴,用0.1mol/L氢氧化钠液滴定至粉红色并保持15s同时进行空白试验并作必要校正。每mL 0.1mol/L氢氧化钠相当于胆酸(C 24 H 40 O5)40.86mg。
  • 用途一:一种具有类固醇结构的有机酸,能乳化脂肪,促进其消化作用
  • 用途四:非变性离子去垢剂,用于抽提膜蛋白
  • 用途五:用于生化研究,医药中间体。胆酸钠是利胆药,治疗胆囊炎;胆汁缺乏;肠道消化不良等症。
  • 胆酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K2701001 胆酸BC,99.0% 25g 530元 2011/08/23 SC112901 胆酸 25g 215元 2010/06/21 159115000 胆酸 Cholic acid 97% 500 GR 3268元
  • 图谱信息:胆酸(81-25-4)红外图谱(IR1) 胆酸(81-25-4)红外图谱(IR2) 胆酸(81-25-4)Raman光谱 胆酸(81-25-4)核磁图( 13 CNMR)
  • Sigma Aldrich:81-25-4(sigmaaldrich)
  • 方法一:方法一、乙醇结晶法 粗牛羊胆酸的制备 取牛或羊胆汁,加100 g/L氢氧化钠,加热煮沸12-18h,得皂化液。冷却后加酸调pH 1,析出胆酸,将胆酸取出,经水煮、漂洗、于75℃干燥、磨粉,得粗牛羊胆酸。 牛、羊胆酸[NaOH]→[100℃, 12-18h]皂化液[H2SO4]→[pH1, 75℃]粗牛、羊胆酸 牛羊胆酸成品的制备 取粗胆酸,加0.5-1倍量的95%乙醇,加热回流至固体溶解,冷却。取出结晶捣碎,过滤,加95%乙醇洗涤至滤液无色。结晶再加4倍量乙醇,加100-150g/L活性炭,加热回流至结晶溶解,趁热过滤,滤液浓缩至原体积的1/4,冷却,结晶,过滤,加乙醇洗涤结晶,干燥,得牛羊胆酸成品。 粗牛、羊胆酸[乙醇,活性炭]→精制液[90℃以下]→牛、羊胆酸成品 方法二、乙酸乙酯分离法 粗制猪胆酸的制备 取新鲜猪胆汁,在搅拌下加3-3.5倍量饱和石灰水上清液,待加完后继续搅拌5-10min,加热至沸2min,冷却,过滤,滤液加盐酸调pH3.5,析出沉淀,静置12h以上,得粗胆酸。取出,水洗,加1.5倍氢氧化钠,加9倍水,加热煮沸12-18h,放冷,静置过夜,得膏状物。加水,加硫酸调pH 1,析出猪胆酸。取出,捣碎,漂洗至无酸性,过滤,得粗制猪胆酸。$猪胆汁[饱和石灰水]→[100℃, pH11-12]碱性滤液[HCl]→[pH3.5]粗胆酸[水,NaOH]→膏状物[H2SO4]→[pH1]粗制猪胆酸 猪胆酸成品的制备 取粗猪胆酸,加4倍量乙酸乙酯,加150-200g/L活性炭,加热回流0.5h,放冷,过滤,滤饼加1.5-2.5倍乙酸乙酯处理1次,合并两次滤液。加200g/L无水硫酸钠,静置过夜,浓缩至原体积的1/3,放出,冷却结晶,过滤,用乙酸乙酯洗涤结晶,干燥,得猪胆酸成品。 粗制猪胆酸[乙酸乙酯
  • 用途三:用于生化研究,医药中间体。胆酸钠是利胆药,治疗胆囊炎、胆汁缺乏、肠道消化不良等症。

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