| Identification | More | [Name]
Glycocholic acid | [CAS]
475-31-0 | [Synonyms]
3a,7a,12a-trihydroxy-5b-cholan-24-oic acid n-(carboxymethyl)amide
3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-OIC ACID N-[CARBOXYMETHYL]AMIDE
3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-OIC ACID N-(CARBOXYMETHYL) AMIDE, HYDRATE
5BETA-CHOLANIC ACID-3ALPHA,7ALPHA,12ALPHA-TRIOL 24-N-(CARBOXYMETHYL)-AMIDE
5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL N-(CARBOXYMETHYL)-AMIDE
cholylglycine
CHOLYLGLYCINE HYDRATE
GLYCOCHOLIC
GLYCOCHOLIC ACID
GLYCOCHOLIC ACID HYDRATE
N-[3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-24-OXOCHOLAN-24-YL]GLYCINE
N-(3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-24-OXOCHOLAN-24-YL)-GLYCINE HYDRATE
n-(3-alpha,7-alpha,12-alpha-trihydroxycholan-24-oyl)glycine
[(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
N-Cholylglycine
glycocholic acid free acid
GLYCOCHOLIC ACID HYDRAT
Clycocholic acid | [EINECS(EC#)]
207-494-9 | [Molecular Formula]
C26H43NO6 | [MDL Number]
MFCD06408004 | [Molecular Weight]
465.62 | [MOL File]
475-31-0.mol |
| Chemical Properties | Back Directory | [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
| [form ]
Solid | [pka]
4.4(at 25℃) | [color ]
White to Off-White | [Water Solubility ]
329.9mg/L(20 ºC) | [Merck ]
13,4507 | [Stability:]
Hygroscopic | [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 | [LogP]
1.650 | [CAS DataBase Reference]
475-31-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Glycocholic acid(475-31-0) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332 | [Precautionary statements ]
P280 | [Hazard Codes ]
N | [Risk Statements ]
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
N-Cholylglycine. Bile salt, conjugate of cholate and glycine, usually
as the sodium salt. It acts as a detergent to solubilize fats for
absorption and is itself absorbed. It is used as a cholagogue and
choleretic. | [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]
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 |
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Henan yingchuang Gold
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16650708709 |
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www.hnyingchuang.com/ |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
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https://www.jkchemical.com |
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Spectrum Chemical Manufacturing Corp.
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