Chenodeoxycholic Acid 鹅去氧胆酸

CAS 474-25-9 MFCD00064142

化学结构图

474-25-9
SMILES: CC(CCC(=O)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C

化学属性

Mol. FormulaC24H40O4
Mol. Weight392.57
Melting Point165-167 °C
SolubilitySoluble in ethanol (~20 mg/ml), methanol, acetone, glacial acetic acid, DMF, DMSO, and 1:1 DMF:PBS(pH 7.2) (~0.5 mg/ml). Insoluble in water.
Density1.128
Stability对光敏感
Appearance 本品是由鸡、鸭、鹅等胆汁中提取。为白色或淡黄色结晶粉末；味苦，有异臭。Mp141-142℃。在乙醇、氯仿和冰醋酸中易溶，在水中几乎不溶。 本品能使胆固醇合成及分泌减少，使胆汁内总胆固醇的排出量减少，从而提高胆汁对胆固醇的溶解能力，促进已结石的胆固醇解离而达到溶石效应。本品口服后在胆囊中的浓度很高，且可多次肝肠循环。本品在肠道中易被细菌分解，产生具有肝毒性的代谢产物。
Boiling Point437.26 °C at 760 mmHg

别名和识别编码

Chemical NameChenodeoxycholic Acid
MDL NumberMFCD00064142
CAS Number474-25-9
Synonym Chenodeoxycholic Acid {LY} Chenodeoxycholic Acid {} {LY} Chenodeoxycholic Acid {} {} {LY} Chenodeoxycholic Acid {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Chenodeoxycholic Acid {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID10133
Beilstein Registry Number3219887
EC Number207-481-8
Chemical Name Translation鹅去氧胆酸
Reaxys-RN3219887
Merck Number2054
Wiswesser Line NotationL E5 B666TJ A1 E1 FY1&2VQ KQ OQ
LabNetwork Molecule IDLN00243122
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
Canonical SMILESO=C(O)CC[C@@H](C)[C@]1([H])[C@]2(C)[C@](CC1)([H])[C@]3([H])[C@H](O)C[C@@](C4)([H])[C@@](CC[C@H]4O)(C)[C@]([H])3CC2
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分类

  • {SNA} Anionic Detergents, Bile Salts, Bile acids and Derivatives, Bioactive Small Molecules, Biochemicals and Reagents, C-CH, Cell Culture, Detergents, Detergents A to M, Detergents by Applications, Drug Delivery-Liposomes, Lipids, Membrane Protein Solubilization, Sterol Lipids, 细胞生物学
  • {SNA} Anionic Detergents, Bile Salts, Bile acids and Derivatives, Cell Culture, Detergents A to M, Detergents by Applications, Drug Delivery-Liposomes, Membrane Protein Solubilization, Sterol Lipids, 去垢剂,
  • {SNA} Anionic Detergents,
  • {SNA} Anio

产品应用

  • 主要用于合成熊去氧胆酸。
  • 胆石溶解剂，用于胆固醇高而引起的结石、胆道炎和胆囊炎等。

相关文献及参考

  • [2]. Casaburi I, et al. Chenodeoxycholic acid through a TGR5-dependent CREB signaling activation enhances cyclin D1 expression and promotes human endometrial cancer cell proliferation. Cell Cycle. 2012 Jul 15;11(14):2699-710
  • [3]. Kawabe Y, et al. The molecular mechanism of the induction of the low density lipoprotein receptor by chenodeoxycholic acid in cultured human cells. Biochem Biophys Res Commun. 1995 Mar 8;208(1):405-11.
  • [4]. Ao M, et al. Chenodeoxycholic acid stimulates Cl(-) secretion via cAMP signaling and increases cystic fibrosis transmembrane conductance regulator phosphorylation in T84 cells. Am J Physiol Cell Physiol. 2013 Aug 15;305(4):C447-56
  • [5]. Noh K, et al. Farnesoid X receptor activation by chenodeoxycholic acid induces detoxifying enzymes through AMP-activated protein kinase and extracellular signal-regulated kinase 1/2-mediated phosphorylation of CCAAT/enhancer binding protein β. Drug Metab
  • [1]. Stauffer AT, et al. C

安全信息

WGK Germany2
RTECSFZ1980000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Signal word Warning
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H303 May be harmfully swallowed 吞食可能有害
  • H312 Harmful in contact with skin 皮肤接触有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P312
  • P302+P352
  • P304+P312
  • P304+P340
  • P305+P351+P338
  • P308+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P322 Specific measures (see …on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
GHS Symbol
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Codes Xn
Risk Statements
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 24 gm/kg/5Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - tumors
REFERENCE :
   CLONEA Clinics in Oncology.  (W.B. Saunders Co., W. Washington Sq.,
   Philadelphia, PA 19105) V.1-    1982-  Volume(issue)/page/year: 7,245,1981

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >4 gm/kg
TOXIC EFFECTS :
   Blood - changes in spleen
   Skin and Appendages - hair
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: 11,2499,1977

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,397,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,397,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 86 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - hypermotility, diarrhea
   Gastrointestinal - other changes
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 15,915,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUT

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 10 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: 15,1911,1994

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 20 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           : 1100 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

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 1100 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

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 100 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            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 100 mg/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB81-127581

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Primate - monkey
DOSE                    : 1500 mg/kg
SEX/DURATION            : female 21-45 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - physical
REFERENCE :
   TXCYAC Toxicology.  (Elsevier Scientific Pub. Ireland, Ltd., POB 85,
   Limerick, Ireland) V.1-    1973-  Volume(issue)/page/year: 2,239,1974

TYPE OF T

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1375 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Primate - monkey
DOSE                    : 1500 mg/kg
SEX/DURATION            : female 21-45 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - hepatobiliary system
   Reproductive - Specific Developmental Abnormalities - endocrine system
   Reproductive - Specific Developmental Abnormalities - urogenital

其他信息

  • 用途三:该品为胆固醇性胆结石的溶解剂。主要用于预防和治疗胆
  • 方法一:方法一、氯化钡盐法 总胆汁酸的制备 新鲜或冷冻鸡(或鸭、鹅)胆汁，加1/10倍量的工业氢氧化钠，加热煮沸20-24h，不断补充蒸发的水量，冷却，加等体积的盐酸，调pH2-3，出现黑色膏状物，取出，水洗至近中性，得总胆汁酸。 鸡（鹅、鸭）胆汁[NaOH, 煮沸]→皂化液[HCl, pH2]→总胆汁酸 CDCA钡盐的制备 取总胆汁酸加2倍量95%乙醇，加50-100g/L的活性炭，加热回流2h，趁热过滤，滤液放冷后，加等体积的120号汽油萃取2-3次，静置分层，下层减压浓缩，回收乙醇，得膏状物。加大量水，析出沉淀，沉淀物用水洗至洗涤液近无色，加2倍量乙醇，加50g/L氢氧化钠醇溶液，加热回流1-2h，
  • 方法二:用鹅（鸡）胆汁制取脱氧鹅胆酸的过程：鹅（鸡）胆汁经NaOH水解得水解液，再经HCI酸化得总胆汁酸，用脱脂汽油、乙醇脱脂得脱氧鹅胆酸粗品在乙醇与氯化钡成盐得脱氧鹅胆酸钡盐用乙酸乙酯及HCI脱钡得结晶经过乙酸乙酯洗涤干燥得脱氧鹅胆酸。总收率（对鸡或鹅胆汁计）1.92%。
  • 类别:有毒物质
  • {
  • {Chemic
  • 参考质量标准:原料药 中国药典1995年版978页 指标名称 指标 指标名称 指标 含量(C24H40O4)/% ≥98.0/干燥失重/% ≤2.0 比旋度(10mg/ml乙醇)/+11°-+13°/炽灼残渣/% ≤0.2 酸度(消耗NaOH)/(mmol/g)
  • MOL 文件:474-25-9.mol
  • 方法一:方法一、氯化钡盐法 总胆汁酸的制备 新鲜或冷冻鸡(或鸭、鹅)胆汁，加1/10倍量的工业氢氧化钠，加热煮沸20-24h，不断补充蒸发的水量，冷却，加等体积的盐酸，调pH2-3，出现黑色膏状物，取出，水洗至近中性，得总胆汁酸。 鸡（鹅、鸭）胆汁[NaOH, 煮沸]→皂化液[HCl, pH2]→总胆汁酸 CDCA钡盐的制备 取总胆汁酸加2倍量95%乙醇，加50-100g/L的活性炭，加热回流2h，趁热过滤，滤液放冷后，加等体积的120号汽油萃取2-3次，静置分层，下层减压浓缩，回收乙醇，得膏状物。加大量水，析出沉淀，沉淀物用水洗至洗涤液近无色，加2倍量乙醇，加50g/L氢氧化钠醇溶液，加热回流1-2h，调pH8-8.5，加膏状物2倍量的150g/L氯化钡溶液，加热回流2h，趁热过滤，滤液蒸馏回收乙醇，至内容物出现晶膜或混浊时，停止加热，放冷，析出针状结晶，待晶体完全后，抽滤，得白色CDCA钡盐结晶，水洗，必要时以65%-70%的乙醇重结晶，减压干燥，得CDCA钡盐。 总胆汁酸[乙醇]→[120#汽油]CDCA粗品[BaCl 2 , pH8]→CDCA钡盐 CDCA成品的制备 将CDCA钡盐研细，悬浮与15倍量水中，加稍过量的碳酸钠，加热回流，趁热过滤，冷却，再过滤1次，滤液加盐酸调pH2-3，析出沉淀，过滤，沉淀用水洗至近中性，真空干燥，得CDCA精品。加乙酸乙酯重结晶1-2次，得CDCA结晶，真空干燥，得CDCA成品。 CDCA钡盐[Na 2 CO 3 , HCl]→CDCA精品[乙酸乙酯]CDCA结晶[干燥]→CDCA成品 方法二、氯化钙盐法 总胆酸钙盐的制备 新鲜鸡(或鸭、鹅)胆汁100kg，置于不锈钢锅内，按胆汁量100g/L加氢氧化钠固体，搅拌溶解，加热煮沸24h，
  • 用途四:主要用于合成熊去氧胆酸。胆石溶解剂，用于胆固醇高而引起的结石、胆道炎和胆囊炎等。
  • 图谱信息:鹅去氧胆酸(474-25-9)红外图谱(IR1) 鹅去氧胆酸(474-25-9)红外图谱(IR2)
  • 毒性分级:中毒
  • 鹅去氧胆酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C0750 鹅去氧胆酸 Chenodeoxycholic Acid 25G 2910元 2014/06/02 C0750 鹅去氧胆酸 Chenodeoxyc
  • MSDS 信息:3alpha,7alpha-Dihydroxy-5beta-cholanic acid(474-25-9).msds
  • Sigma Aldrich:474-25-9(sigmaaldrich)
  • 下游产品:熊去氧胆酸 --> (3Β,5Α,7Α)-3-[[3-((4-氨基丁基)氨

系列性分类

  1. Application Areas 应用领域分类
  2. Detergents 去污剂洗净剂
  1. Application Areas 应用领域分类
  2. Detergents 去污剂洗净剂
  3. Detergents A to M - Detergents
  1. Application Areas 应用领域分类
  2. Detergents 去污剂洗净剂
  3. Anionic Detergents - Detergents
  1. Application Areas 应用领域分类
  2. Detergents 去污剂洗净剂
  3. Anionic Detergents - Detergents
  4. Bile Salts - Anionic Detergents
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Sterol Lipids - Lipids
  5. Bile acids and Derivatives - Sterol Lipids
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. G Proteins and Cyclic Nucleotides - Cell Signaling and Neuroscience
  5. Cyclic Nucleotide Metabolism - G Proteins and Cyclic Nucleotides
  6. Phosphodiesterase Inhibitors - Cyclic Nucleotide Metabolism
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Steroids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Sterols
  1. Medical Research Areas
  2. Metabolism
  3. FXR  (法尼酯X受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)