ChemicalBook > CAS DataBase List > Glycocholic acid

Glycocholic acid

Product Name
Glycocholic acid
CAS No.
475-31-0
Chemical Name
Glycocholic acid
Synonyms
GLYCITIN;cholylglycine;GLYCOCHOLIC ACID HYDRATE;N-Cholylglycine;[(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acid;GLYCOCHOLIC;N-cholyglycine;glycocholicaci;Cholylglycinate;lycocholic acid
CBNumber
CB8378590
Molecular Formula
C26H43NO6
Formula Weight
465.63
MOL File
475-31-0.mol
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Glycocholic acid Property

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
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)
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Safety

Hazard Codes 
N
Risk Statements 
51/53
Safety Statements 
61
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
20276
Product name
Glycocholic Acid
Purity
≥95%
Packaging
1g
Price
$48
Updated
2024/03/01
Cayman Chemical
Product number
20276
Product name
Glycocholic Acid
Purity
≥95%
Packaging
5g
Price
$152
Updated
2024/03/01
Cayman Chemical
Product number
20276
Product name
Glycocholic Acid
Purity
≥95%
Packaging
10g
Price
$278
Updated
2024/03/01
Usbiological
Product number
278290
Product name
Glycocholic acid
Packaging
1g
Price
$336
Updated
2021/12/16
TRC
Product number
G641370
Product name
GlycocholicAcid
Packaging
5g
Price
$185
Updated
2021/12/16
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Glycocholic acid Chemical Properties,Usage,Production

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.

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.

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.]

Glycocholic acid Preparation Products And Raw materials

Raw materials

Cholic acid

Preparation Products

Dehydrocholic acid
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View Lastest Price from Glycocholic acid manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Glycocholic acid 475-31-0
Price
US $990.00-800.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-19
HANGZHOU HAILAN CHEMICAL CO.,LTD.
Product
Glycocholic acid 475-31-0
Price
US $9.90-9.90/kg
Min. Order
0.10000000kg
Purity
99%min
Supply Ability
1ton
Release date
2024-11-26
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Glycocholic acid 475-31-0
Price
US $0.00/G
Min. Order
100G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-09

475-31-0, Glycocholic acidRelated Search:

Polyamide Diethylstilbestrol Stearic acid Folic acid Fomesafen Ethyl 2-(Chlorosulfonyl)acetate Rink Amide Linker N-Carbobenzyloxyglycine Ursodeoxycholic acid 4-Hydroxy-D-(-)-2-phenylglycine Glycine Betaine Chenodeoxycholic acid Citric acid Ascoric Acid GLYCOCHOLIC ACID-13C1 (GLYCYL-1-13C),GLYCOCHOLIC ACID-(GLYCINE-1-13C) MONO-HY DRATE, 99 ATOM % 13C SODIUM GLYCOCHOLATE HYDRATE, 98 5Β-CHOLANIC ACID

  • 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
  • 5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL N-(CARBOXYMETHYL)-AMIDE
  • 5BETA-CHOLANIC ACID-3ALPHA,7ALPHA,12ALPHA-TRIOL 24-N-(CARBOXYMETHYL)-AMIDE
  • 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
  • N-Cholylglycine
  • 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
  • glycocholic acid free acid
  • GLYCOCHOLIC ACID HYDRAT
  • Clycocholic acid
  • Taurocholic aicd sodium salt
  • GLYCITIN
  • Cholylglycine, 3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid N-(carboxymethyl)amide, N-(3α,7α,12α-Trihydroxy-24-oxocholan-24-yl)-glycine
  • 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid n-(carboxymethyl)amide
  • 2-[4-(3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoylamino]acetic acid
  • N-cholyglycine
  • 3,7,12-Trihydroxy-5-cholan-24-oic acid 24-glycinamide
  • 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)
  • 2-[[(4R)-1-oxo-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]amino]acetate
  • Ursodeoxycholic Impurity 11
  • 2-[(3α,7α,12α-Trihydroxy-24-oxo-5β-cholane-24-yl)amino]acetic acid
  • Cholylglycinate
  • N-(3α,7α,12α-Trihydroxy-24-oxo-5β-cholan-24-yl)glycine
  • N-Carboxymethyl-3α,7α,12α-trihydroxy-5β-cholane-24-amide
  • N-(3α,7α,12α-Trihydroxy-24-oxocholan-24-yl)-glycine
  • Glycocholic acid hydrate,3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid N-(carboxymethyl)amide, Cholylglycine, N-(3α,7α,12α-Trihydroxy-24-oxocholan-24-yl)-glycine
  • N-[(3α,5β,7α,12α)-3,7,12-Τrihydroxy-24-oxocholan-24-yl]glycine Hydrate
  • N-Choloylglycine
  • N-[(3α,5β,7α,12α)-3,7,12-Τrihydroxy-24-oxocholan-24-yl]glycine-d5
  • Glycocholic-d4 Acid
  • 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)acetic acid
  • Glycine, N-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-
  • lycocholic acid
  • Glycocholic acid USP/EP/BP
  • ((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycine
  • glycocholicaci
  • Glycine, N-[(3a,5b,7a,12a)-3,7,12-trihydroxy-24-oxocholan-24-yl]-
  • Glycocholic Acid MaxSpec Standard
  • Urosodeoxycholic Acid Impurity 11
  • 5β-CHOLANIC ACID-3α, 7α, 12α-TRIOL N-(CARBOXYMETHYL)-AMIDE
  • Glyceric acid (medicinal excipients)
  • Glycocholate|||cholylglycine
  • 475-31-0
  • C26H43NO6
  • C24H39O4NHCH2COOH
  • C26H45NO7
  • C26H43NO6xH2O
  • C26H43N06