(3α,5β)-3-Hydroxycholan-24-oic acid 3α-羟基-5β-胆烷酸

CAS 434-13-9 MFCD00003682

化学结构图

434-13-9
SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C

化学属性

Mol. FormulaC24H40O3
Mol. Weight376.58
Melting Point185.0 to 190.0 deg-C
Density1.073
Refractive index35.5 ° (C=1, EtOH)

别名和识别编码

Chemical Name(3α,5β)-3-Hydroxycholan-24-oic acid
CAS Number434-13-9
Synonym ######## 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol 17beta-(1-methyl- 17β-(1-Methyl-3-carboxypropyl)etiocholan-3α-ol 3α-羟基-5β-胆烷酸 3α-羟基-5β-胆甾烷-24-酸 5β-胆甾烷-24-酸-3α-醇 3-HYDROXYCHOLANIC ACID 3-Hydroxycholan-24-oic acid 3-alpha-Hydroxy-5-beta-cholanic acid 3-hydroxy-,(3alpha,5beta)-cholan-24-oicaci 3A-Hydroxy-5B-cholansäure 3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID 3ALPHA-HYDROXY-5BETA-CHOLANIC ACID 3ALPHA-HYDROXYCHOLANIC ACID 3alpha-hydroxy-5beta-cholan-24-oicaci 3alpha-hydroxy-5beta-cholanoicacid 3α-Hy 3α-Hydro 3α-Hydroxy-5β-cholan-24-oic acid 3α-Hydroxy-5β-cholanic acid 3α-Hydroxy-5β-cholansäure 3α-hydroxycholan-24-oic acid 3α-羟基-5
MDL NumberMFCD00003682
Beilstein Registry Number10(3)687
EC Number207-099-1
PubChem Substance ID9903
Merck Number5545
Chemical Name Translation3α-羟基-5β-胆烷酸
Reaxys-RN3217757
Wiswesser Line NotationL E5 B666TJ A E FY&2VQ OQ -B&AEFMO
LabNetwork Molecule IDLN00196693
InChIInChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
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分类

  • {SNA} Analytical Standards, EP Standards, EP Standards L - M, Pharmacopeia Metrological Institutes Standards,
  • {SA} Bile acids and Derivatives, Biochemicals and Reagents,
  • {SNA} Analytical Standards,
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards L - M, Pharmaceutical Standards, Pharmacopeia Standards
  • {uni_hamburg} no charge; carbocycle; alicycle; large ring; fused rings; 5ring; 6ring; 9ring; 10ring; 13ring; 14ring; 17ring; carboxylic acid; alcohol; chiral; 1fragment
  • {SNA} Bile acids and Derivatives, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, L, Lipids, Sterol Lipids
  • Steroids
  • Pharmaceuticals
  • Intermediates & Fine Chemicals
  • {SNA} Bile acids and Derivatives, Sterol Lipids, 生化试剂, 脂类

产品应用

  • A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

相关文献及参考

  • [2]. Yang R, et al. Metabolomic analysis of cholestatic liver damage in mice. Food Chem Toxicol. 2018 Jul 14;120:253-260.
  • [3]. Goldberg, A.A., et al., Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget, 2011. 2(10): p. 761-82.
  • [4]. Matsubara, T., et al., TGF-beta-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. J Lipid Res, 2012. 53(12): p. 2698-707.
  • Brindle, J., et al.: Nat. Med., 12, 1439
  • Merck: 14,5545 Beilstein:10(3)687
  • Short: EINECS
  • Short: III/35E
  • [1]. Jenkins, D.J., et al., Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol. N Engl J Med, 1993. 329(1): p. 21
  • [1]. Jenkins, D.J., et al., Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol. N Engl J Med, 1993. 329(1): p. 21-6.

安全信息

WGK Germany2
RTECSFZ2275000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
GHS Symbol
Signal word
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • 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。
  • P302+P350
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+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)。
  • 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
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 3900 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCILB* Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to
   the National Cancer Institute by Litton Bionetics, Inc.  (Bethesda, MD)
   Volume(issue)/page/year: NCI-E-C-72-3252,1973

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Embryo
DOSE/DURATION           : 5 mg/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - rat Embryo
DOSE/DURATION           : 8 ug/plate
REFERENCE :
   JJATDK JAT, Journal of Applied Toxicology.  (John Wiley & Sons Ltd., Baffins
   Lane, Chichester, W. Sussex PO19 1UD, UK)  V.1-    1981-
   Volume(issue)/page/year: 1,190,1981

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 83300 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

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            : DNA damage
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 2500 umol/L
REFERENCE :
   CBINA8 Chemico-Biological Interactions.  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1969-  Volume(issue)/page/year:
   52,311,1985

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 75 umol/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   24,181,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 8800 mg/kg
SEX/DURATION            : female 0-21 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
   Reproductive - Effects on Newborn - physical
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 43,355,1991

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 16 gm/kg
SEX/DURATION            : female 0-19 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
   (e.g., placenta, umbilical cord)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - hepatobiliary system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 43,355,1991

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 30160 ug/kg
SEX/DURATION            : female 12-19 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 42,215,1990

TYPE OF TEST            : TDLo - Low

其他信息

  • Sigma Aldrich:434-13-9(sigmaaldrich)
  • TCI Shanghai:石胆酸 Lithocholic Acid,>;97.0%(GC)(T)(434-13-9)
  • 石胆酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 69015080 石胆酸;3-羟基胆基酸;石胆甾酸;胆石酸 10g 107.8元 2011/08/23 SL625001 石胆酸;3-羟基胆基酸;石胆甾酸;胆石酸 10g 605元 2011/04/16 L0089 石胆酸 Lithocholic Acid 5G 495元
  • Acros Organics:石胆酸 Lithocholic acid, 98%(434-13-9)
  • 外观性质:胆汁酸之一。不是由胆甾醇在肝中直接生物合成的,而是由鹅脱氧胆酸在肠内通过细菌代谢产生的物质。在肠内生成的这种物质大部分与粪便一起排出,极少一部分被吸收,在肝中发生结合反应,以牛磺石胆酸(taurolithocholic acid)或甘氨石胆酸(glyclithocholic acid)形态出现于胆汁中。比其它胆汁酸毒性强,大量饲实验动物能引起肝胆道系统的种种障害。熔点: 183-188 °C
  • MOL 文件:434-13-9.mol
  • 图谱信息:石胆酸(434-13-9)质谱(MS) 石胆酸(434-13-9)红外图谱(IR2) 石胆酸(434-13-9)红外图谱(IR1) 石胆酸(434-13-9)核磁图( 13 CNMR)
  • 胆汁酸之一。不是由胆甾醇在肝中直接生物合成的,而是由鹅脱氧胆酸在肠内通过细菌代谢产生的物质。在肠内生成的这种物质大部分与粪便一起排出,极少一部分被吸收,在肝中发生结合反应,以牛磺石胆酸(taurolithocholic acid)或甘氨石胆酸(glyclithocholic acid)形态出现于胆汁中。比其它胆汁酸毒性强,大量饲实验动物能引起肝胆道系统的种种障害。

系列性分类


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