Introduction：Basic information about Glycocholic acid CAS 475-31-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Glycocholic acid Basic information
| Product Name: | Glycocholic acid |
| Synonyms: | GLYCOCHOLIC ACID;GLYCOCHOLIC ACID HYDRATE;GLYCOCHOLIC;cholylglycine;CHOLYLGLYCINE HYDRATE;[(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acid;Glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-;N-((3,5,7,12)-3,7,12-Trihydroxy-24-oxocholan-24-yl)glycine |
| CAS: | 475-31-0 |
| MF: | C26H43NO6 |
| MW: | 465.63 |
| EINECS: | 207-494-9 |
| Product Categories: | Inhibitors;API;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Miscellaneous Natural Products |
| Mol File: | 475-31-0.mol |
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Glycocholic acid Chemical Properties
| Melting point | 128°C |
| Boiling point | 568.76°C (rough estimate) |
| density | 1.1336 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| storage temp. | Refrigerator |
| solubility | methanol: 0.1 g/mL, clear, colorless |
| pka | 4.4(at 25℃) |
| form | Solid |
| color | White to Off-White |
| Water Solubility | 329.9mg/L(20 ºC) |
| Merck | 13,4507 |
| Stability: | Hygroscopic |
| InChI | InChI=1/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/s3 |
| InChIKey | RFDAIACWWDREDC-NSPZZGDONA-N |
| SMILES | N(CC(=O)O)C(=O)CC[C@H]([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@H](C[C@H]3O)C[C@@H](CC4)O)C)C[C@@H]2O)CC1)C)C |
| SMILES | O[C@@H]1C[C@]2([H])C[C@H](O)CC[C@]2(C)[C@@]2([H])C[C@H](O)[C@@]3([C@@]([H])([C@H](C)CCC(=O)NCC(=O)O)CC[C@@]3([H])[C@]12[H])C |&1:1,3,6,10,12,15,17,18,20,33,35,r| |
| LogP | 1.650 |
| CAS DataBase Reference | 475-31-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Glycocholic acid(475-31-0) |
Safety Information
| Hazard Codes | N |
| Risk Statements | 51/53 |
| Safety Statements | 61 |
| RIDADR | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
Glycocholic acid Usage And Synthesis
| Description | N-Cholylglycine. Bile salt, conjugate of cholate and glycine, usuallyas the sodium salt. It acts as a detergent to solubilize fats forabsorption and is itself absorbed. It is used as a cholagogue andcholeretic. |
| Description | Glycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid and has roles in the emulsification of fats. It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml. Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin. It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases. Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals. |
| Chemical Properties | Off-White Solid |
| Uses | Labelled Glycocholic Acid. The product of conjugation of cholic acid with glycine; chief ingredient of the bile of herbivorous animals. In the weakly alkaline bile fluid glycocholic acid exists as the sodium salt. |
| Definition | ChEBI: A bile acid glycine conjugate having cholic acid as the bile acid component. |
| Synthesis | 517904-33-5 475-31-0 Example 3: General procedure for the synthesis of ((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren[a]ethene-17-yl)pentanoyl)glycine from glycocholic acid ethyl ester (GCAEE):1. 1.89 g of NaOH was dissolved in 189 ml of water at ambient temperature in a clean 1 liter dry glass flask and stirred until completely dissolved.2. 16.9 g of purified wet GCAEE was added to the above solution and the suspension was stirred at 20 to 28°C for about 12 hours.3. Adjust the pH of the clarified solution to between 7.0 and 7.5 using 50 ml of 1N HCl.4. wash the aqueous solution twice with 75 ml of ethyl acetate at 35 to 40 °C.5. Heat the separated aqueous solution under vacuum to remove the ethyl acetate.6. the resulting aqueous solution was diluted with 100 ml of water, heated at 35 to 40 °C and the pH was adjusted to between 2.0 and 2.5 with 1N HCl to precipitate pure GCA.7. The wet product was dried under vacuum at 50 to 60 °C to give 14 g of the sesquihydrate product in 92.3% dry yield.8. TLC analysis showed that the purity of CA was less than 0.4%, GGCAEE was less than 0.1%, total other impurities were less than 0.2%, and no glycine was observed. |
| Purification Methods | Glycocholic acid crystallises from hot water as the sesquihydrate. Dry it at 110o in vacuo. An analytical sample is prepared by suspending the acid (4g) in H2O (400mL) at ~20o, heating to boiling with slow stirring, filtering hot and allowing to cool to ~20o. The acid is filtered off, washed with H2O, dried in air, recrystallised from 5% aqueous EtOH, washed well and dried over P2O5 in a moderate vacuum to constant weight. Recrystallisation from EtOH/EtOAc, and drying, gave the anhydrous acid. [Cortese & Bauman J Am Chem Soc 57 1393 1935, Bergstrom & Norman Acta Chem Scand 7 1126 1953, Beilstein 10 IV 2077.] |
| References | [1] Patent: WO2010/128472, 2010, A1. Location in patent: Page/Page column 6 |
Glycocholic acid Preparation Products And Raw materials
| Raw materials | Cholic acid-->glycocholic acid ethyl ester-->Hydrochloric acid |
| Preparation Products | Dehydrocholic acid |
