Glycocholic acid supplier | CasNO.475-31-0

Name
Glycocholic acid
EINECS 207-494-9
CAS No. 475-31-0
Article Data12
CAS DataBase
Density 1.213 g/cm³
Solubility methanol: 0.1 g/mL, clear, colorless
Melting Point 128 °C
Formula C₂₆H₄₃NO₆
Boiling Point 692.042 °C at 760 mmHg
Molecular Weight 465.631
Flash Point 372.334 °C
Transport Information UN 3077 9/PG 3
Appearance Off-white solid
Safety 61
Risk Codes 51/53
Molecular Structure
Hazard Symbols N
Synonyms Glycine,N-choloyl- (8CI);Glycoreductodehydrocholic acid (6CI);5b-Cholan-24-amide, N-(carboxymethyl)-3a,7a,12a-trihydroxy- (8CI);3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine;3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine;3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide;Cholylglycine;Glycine cholate;N-Choloylglycine;
PSA 127.09000
LogP 2.95580

Synthetic route

: 517904-33-5
glycocholic acid ethyl ester

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
Stage #1: glycocholic acid ethyl ester With water; sodium hydroxide at 20 - 28℃; Stage #2: With hydrogenchloride In water pH=7 - 7.5;	92.3%

: 81-25-4
cholic acid

: 623-33-6
glycine ethyl ester hydrochloride

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
Stage #1: cholic acid With triethylamine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Stage #2: glycine ethyl ester hydrochloride With pivaloyl chloride In tetrahydrofuran; water at 0 - 10℃; Reagent/catalyst;	78.3%

: 81-25-4
cholic acid

: 541-41-3
chloroformic acid ethyl ester

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
With 1,4-dioxane; tributyl-amine anschliessend Behandeln mit Glycin und wss. NaOH;

: 40248-73-5
3α,7α,12α-trihydroxy-5β-cholanoyl-(24)-azide

: 56-40-6
glycine

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 56-40-6
glycine

3α,7α,12α-triformyloxy-5β-cholanoic acid (24)-chloride: 3α,7α,12α-triformyloxy-5β-cholanoic acid (24)-chloride

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 80948-49-8
cholic acid hydrazide

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid; aqueous sodium nitrite solution 2: aq. NaOH solution View Scheme

: 81-25-4
cholic acid

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h 2: triethylamine; glycine / dimethyl sulfoxide / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 - 30 °C 2: potassium hydroxide / tetrahydrofuran; water / 10 h / 35 - 40 °C View Scheme

: 70090-26-5
cholic acid N-succinimidyl ester

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
With triethylamine; glycine In dimethyl sulfoxide at 20℃; for 4h;

: glycocholic acid methyl ester

: 475-31-0
glycocholic acid

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 35 - 40℃; for 10h;	0.8 g

: 475-31-0
glycocholic acid

: C30H56N2O14

: C56H97N3O19

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 24h;	90%

: 1-(2-(2-aminoethoxy)ethyl)-1H-pyrrole-2,5-dione

: 475-31-0
glycocholic acid

: C34H53N3O8

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 24h; Reagent/catalyst;	89%

: 475-31-0
glycocholic acid

: C12H20N2O5

: C38H61N3O10

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 24h;	88%

: 475-31-0
glycocholic acid

: 633-65-8
berberine chloride

: C26H42NO6(1-)*C20H18NO4(1+)

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8;	87%

: 475-31-0
glycocholic acid

: C24H44N2O11

: C50H85N3O16

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 24h;	87%

: 475-31-0
glycocholic acid

: C16H28N2O7

: C42H69N3O12

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 24h;	85%

: 475-31-0
glycocholic acid

: C20H36N2O9

: C46H77N3O14

Conditions

Conditions	Yield
With dmap; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 24h;	85%

: 475-31-0
glycocholic acid

: 76757-85-2
N-nitrosoglycocholic acid

Conditions

Conditions	Yield
With sodium acetate; acetic acid; nitrosylchloride at 10 - 15℃; for 0.5h;	75%

: 475-31-0
glycocholic acid

: 516493-93-9
α-amino,ω-azido,α,ω-dideoxy-hexaethyleneglycol

: C38H67N5O10

Conditions

Conditions	Yield
Stage #1: glycocholic acid With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: α-amino,ω-azido,α,ω-dideoxy-hexaethyleneglycol With triethylamine In N,N-dimethyl-formamide at 20℃;	55.56%

: 475-31-0
glycocholic acid

: 2-{2-[2-(2-{2-[2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethylamine

: C46H83N5O14

Conditions

Conditions	Yield
Stage #1: glycocholic acid With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-{2-[2-(2-{2-[2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethylamine With triethylamine In N,N-dimethyl-formamide at 20℃;	55%

: 64-17-5
ethanol

: 475-31-0
glycocholic acid

A: 621-79-4, 22031-64-7
cinnamamide

B: 62430-51-7
ethyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate

Conditions

Conditions	Yield
With 1.) KO2; phase-transfer catalyst 1.) ether, 40 deg C, 8 h; Yield given. Multistep reaction;	A 48% B n/a

...Expand

: 475-31-0
glycocholic acid

: C14H29NO6S*ClH

: C40H70N2O11S

Conditions

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	38.7%

: 475-31-0
glycocholic acid

A: 124-38-9
carbon dioxide

B: 6786-09-0
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-amide

C: 144-62-7
oxalic acid

Conditions

Conditions	Yield
With KO2; phase-transfer catalyst In tetrahydrofuran at 40℃; for 8h; Mechanism;	A n/a B 27% C n/a

...Expand

: 475-31-0
glycocholic acid

: 1115-70-4
metformin hydrochloride

: C30H50N6O4

Conditions

Conditions	Yield
Stage #1: glycocholic acid With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In ethanol at 60℃; for 4h; Stage #2: metformin hydrochloride In ethanol for 24h; Heating; Further stages.;	20%

: 475-31-0
glycocholic acid

: 56-40-6
glycine

Conditions

Conditions	Yield
With barium dihydroxide
With mineral acid

: 475-31-0
glycocholic acid

: 78537-20-9
7-ketodeoxycholic acid glycine-conjugate

Conditions

Conditions	Yield
With potassium phosphate; NAD; 2-oxo-propionic acid; diothiothreitol In water Ambient temperature; lactic dehydrogenase, 7α-hydroxysteroid dehydrogenase; Yield given;

: 475-31-0
glycocholic acid

NaHCO3: NaHCO3

bromine: bromine

water: water

N-<3,7,12-trioxo-5β-cholanoyl-(24)>-glycine: N-<3,7,12-trioxo-5β-cholanoyl-(24)>-glycine

...Expand

: 475-31-0
glycocholic acid

: 68753-51-5
glycoursodeoxycholic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate, pyruvate, dithiothreitol, NAD / H2O / Ambient temperature; lactic dehydrogenase, 7α-hydroxysteroid dehydrogenase 2: potassium phosphate, glucose, dithiothreitol, NADP / H2O / glucose dehydrogenase, 7β-hydroxysteroid dehydrogenase View Scheme

: 475-31-0
glycocholic acid

: 61869-08-7
paroxetine

: paroxetine glycocholate

Conditions

Conditions	Yield
In ethanol at 40℃; for 3h;

Glycocholic acid Specification

The Glycine, N-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-, with CAS registry number 475-31-0, belongs to the following product category: Miscellaneous Natural Products. It has the systematic name of N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine. Its classification codes are Cholagogues and choleretics, Detergents, Gastrointestinal Agents and Surface-Active Agents. And the chemical formula of this chemical is C₂₆H₄₃NO₆. The main use of this chemical is for the intermediate of Dehydrocholic Acid.

Physical properties of Glycine, N-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-: (1)ACD/LogP: 1.21; (2)# of Rule of 5 Violations: 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 7; (8)#H bond donors: 5; (9)#Freely Rotating Bonds: 9; (10)Polar Surface Area: 127.09 Å²; (11)Index of Refraction: 1.56; (12)Molar Refractivity: 124.131 cm³; (13)Molar Volume: 383.793 cm³; (14)Polarizability: 49.209×10^-24cm³; (15)Surface Tension: 52.798 dyne/cm; (16)Density: 1.213 g/cm³; (17)Flash Point: 372.334 °C; (18)Enthalpy of Vaporization: 115.95 kJ/mol; (19)Boiling Point: 692.042 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
The Glycine, N-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]- is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment, so avoid release it to the environment. Refer to special instructions / safety data sheets.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
(2)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-/m1/s1
(3)InChIKey: RFDAIACWWDREDC-FRVQLJSFBG
(4)Std. InChI: InChI=1S/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-/m1/s1
(5)Std. InChIKey: RFDAIACWWDREDC-FRVQLJSFSA-N

Product Name

Glycocholic acid

Synthetic route

Glycocholic acid Specification

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