Hazard Codes | Xi |
Safety Statements | 22-24/25 |
Conditions | Yield |
---|---|
With diazomethyl-trimethyl-silane In methanol; toluene at 20℃; for 2h; | 100% |
With acetyl chloride at 20℃; for 72h; | 100% |
With acetyl chloride at 20℃; for 0.75h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran | A 100% B n/a |
Conditions | Yield |
---|---|
In methanol; hexane; toluene at 20℃; | 100% |
Conditions | Yield |
---|---|
In methanol for 12.5h; Cooling with ice; | 99% |
In methanol |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 97% |
With cesium fluoride In N,N-dimethyl-formamide |
7-α,12-α-dihydroxycholin-4-ene-3-one carboxylic acid methyl ester
A
methyl 3β,7α,12α-trihydroxy-5α-cholan-24-oate
B
methyl cholate
Conditions | Yield |
---|---|
With sodium tetrahydroborate In pyridine for 20h; Ambient temperature; | A 77% B 23% |
With sodium tetrahydroborate In pyridine for 20h; Ambient temperature; | A 77% B 23% |
methyl 3α,7α-diacetoxy-12α-hydroxy cholanate
B
Methyl 12α-hydroxy-5β-cholanate
C
methyl 7α,12a-dihydroxy-5β-cholan-24-oate
D
methyl cholate
Conditions | Yield |
---|---|
With potassium Sodium; iso-butanol; Tris(3,6-dioxaheptyl)amine In tetrahydrofuran Ambient temperature; var. cat.: 18-crown-6; Yield given. Yields of byproduct given; | A n/a B 58% C n/a D n/a |
methyl 3α,7α-diacetoxy-12α-hydroxy cholanate
A
Methyl 12α-hydroxy-5β-cholanate
B
methyl deoxycholate
C
methyl 7α,12a-dihydroxy-5β-cholan-24-oate
D
methyl cholate
Conditions | Yield |
---|---|
With potassium Sodium; iso-butanol; Tris(3,6-dioxaheptyl)amine In tetrahydrofuran Ambient temperature; var. cat.: 18-crown-6; Yields of byproduct given; | A 58% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate |
methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate
A
methyl cholate
Conditions | Yield |
---|---|
With borane tert-butylamine In methanol for 3h; Ambient temperature; Yield given. Yields of byproduct given; |
3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester
A
methyl cholate
B
methyl 3α,12α-dihydroxy-7-oxo-5β-cholanate
Conditions | Yield |
---|---|
With N-Bromosuccinimide Multistep reaction; |
Conditions | Yield |
---|---|
at 85℃; Rate constant; Kinetics; Thermodynamic data; Heating; Ea; var. temp.; |
methyl cholate
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate |
A
methyl cholate
B
3β,7α,12α-trihydroxy-5β-cholan-24-oic acid methyl ester
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate |
3-oxo cholic acid methyl ester
methyl cholate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 25 percent / DDQ / dioxane / 10 h / Heating 2: H2 / tris(triphenylphosphine)-rhodium chloride / benzene 3: 23 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 25 percent / DDQ / dioxane / 10 h / Heating 2: NaBH4 / methanol / 2 h / Ambient temperature 3: MnO2 / CHCl3 / 60 h 4: 23 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme |
methyl 3-oxo-7α,12α-dihydroxy-1,4-choladienate
methyl cholate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / tris(triphenylphosphine)-rhodium chloride / benzene 2: 23 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: NaBH4 / methanol / 2 h / Ambient temperature 2: MnO2 / CHCl3 / 60 h 3: 23 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme |
(R)-4-((7R,8R,9S,10R,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
methyl cholate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: MnO2 / CHCl3 / 60 h 2: 23 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
In methanol |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 12h; |
Conditions | Yield |
---|---|
With pyridinium dichromate | 100% |
With pyridinium dichromate | 100% |
With pyridinium dichromate | 100% |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 1h; | 100% |
With pyridine; dmap at 20℃; for 1h; | 100% |
With pyridine; dmap at 20℃; for 3h; | 98% |
methyl n-dodecanoate
methyl cholate
Dodecanoic acid (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
Conditions | Yield |
---|---|
at 60℃; under 8 Torr; for 20h; Candida antarctica lipase immobilized on Florisil with Triton X-100; | 100% |
Conditions | Yield |
---|---|
at 60℃; under 8 Torr; for 20h; Candida antarctica lipase immobilized on Florisil with Triton X-100; | 100% |
Conditions | Yield |
---|---|
at 60℃; under 8 Torr; for 20h; Candida antarctica lipase immobilized on Florisil with Triton X-100; | 99% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water for 0.0666667h; microwave irradiation; | 99% |
methyl cholate
tert-butyldimethylsilyl chloride
methyl 3α-O-(tert-butyl-dimethylsilanyloxy)-7α,12α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h; | 99% |
With pyridine; 1H-imidazole In dichloromethane at 50℃; for 18h; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; | 92% |
methyl cholate
3-oxo cholic acid methyl ester
Conditions | Yield |
---|---|
With Ag2CO3 on Celite In toluene Reflux; Inert atmosphere; | 98% |
With silver carbonate In toluene for 12h; Reflux; Dean-Stark; | 94% |
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 35℃; for 4h; Inert atmosphere; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran | 98% |
With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating / reflux; | 98% |
With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating / reflux; | 98% |
methyl cholate
ethylenediamine
N-(2-aminoethyl)(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-amide
Conditions | Yield |
---|---|
In methanol at 20℃; for 48h; | 98% |
In methanol at 69 - 71℃; | 93% |
at 73℃; for 16h; | 93% |
methyl cholate
chloromethyl methyl ether
methyl 3α,7α,12α-tri(methoxymethoxy)-5β-cholan-24-oate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In benzene at 20℃; for 240h; | 98% |
Conditions | Yield |
---|---|
at 20℃; for 72h; | 96% |
With perchloric acid at 50℃; for 1.5h; | 86% |
Conditions | Yield |
---|---|
With pyridine at -10 - -6℃; for 15h; | 95.3% |
methyl cholate
dimethyl sulfoxide
3α,7α,12α-trihydroxy-24-methylsulfinylmethyl-5β-cholan-24-one
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; | 95% |
methyl cholate
methanesulfonyl chloride
Methyl 3α-methanesulphonyloxy-7α,12α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; Cooling with ice; | 95% |
With triethylamine In dichloromethane at 0℃; for 0.166667h; | 87% |
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere; | 84% |
1,6-Hexanediamine
methyl cholate
N-hexylamino-3α,7α,12α-trihydroxy-5β-cholan-24-cholanoamide
Conditions | Yield |
---|---|
In methanol at 69 - 71℃; | 95% |
at 73℃; for 16h; | 95% |
bis(trichloromethyl) carbonate
methyl cholate
Conditions | Yield |
---|---|
With pyridine In benzene at 25℃; for 24h; | 95% |
methyl cholate
methyl iodide
methyl 3α,7α-dimethoxy-12α-hydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 94% |
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 94% |
Stage #1: methyl cholate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 94% |
methyl cholate
acetic anhydride
methyl 3α,7α-diacetoxy-12α-hydroxy cholanate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 25℃; for 5h; | 92% |
With dmap; triethylamine In dichloromethane at 28℃; | 92% |
With dmap; triethylamine In dichloromethane at 0 - 28℃; | 92% |
methyl cholate
ethanolamine
N-(2-hydroxyethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide
Conditions | Yield |
---|---|
In methanol Heating; | 92% |
methyl cholate
methanesulfonyl chloride
methyl 3α-methanesulfonyl-7α,12α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With pyridine at 20℃; Inert atmosphere; | 92% |
methyl cholate
p-toluenesulfonyl chloride
7α,12α-dihydroxy-3α-(toluene-sulfonyl-(4)-oxy)-5β-cholanoic acid-(24)-methyl ester
Conditions | Yield |
---|---|
In pyridine; benzene Ambient temperature; | 91% |
In pyridine at 10℃; for 16h; | 90% |
With pyridine | 88% |
Conditions | Yield |
---|---|
In chloroform for 16h; | 91% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 40℃; for 24h; | 90% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 40 - 50℃; for 24h; | |
With dmap; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 48h; Mitsunobu reaction; | |
With dmap; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 40℃; for 8h; Mitsunobu Displacement; | |
With di-isopropyl azodicarboxylate; triphenylphosphine |
Conditions | Yield |
---|---|
In methanol at 65℃; for 72h; | 89% |
at 20℃; for 168h; |
Molecular Structure of Methyl cholate (CAS NO.1448-36-8):
IUPAC Name: Methyl(4R)-4-[(3R,5S,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]pentanoate
Molecular Weight: 422.59798 [g/mol]
Molecular Formula: C25H42O5
XLogP3-AA: 3.9
H-Bond Donor: 3
H-Bond Acceptor: 5
EINECS: 215-903-7
Appearance: Off-White Solid
Melting Point: 155-156 °C
Index of Refraction: 1.539
Molar Refractivity: 116.08 cm3
Molar Volume: 370.2 cm3
Surface Tension: 46 dyne/cm
Density: 1.141 g/cm3
Flash Point: 174.9 °C
Enthalpy of Vaporization: 94.23 kJ/mol
Boiling Point: 541.6 °C at 760 mmHg
Vapour Pressure: 5.49E-14 mmHg at 25 °C
Product Categories: Steroids; Steroids & Hormones - 13C & 2H
Safety Information of Methyl cholate (CAS NO.1448-36-8):
Hazard Codes: Xi
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
Methyl cholate (CAS NO.1448-36-8), its Synonyms are Methyl 4-(3,7,12-trihydroxy-10,13-dimethylperhydrocyclopenta[a]phenanthren-17-yl)pen ; 5(beta)-Cholmic acid-3alpha,7alpha,12alpha-triol methyl ester ; 5-beta-Cholanic acid-3-alpha, 7-alpha, 12-alpha-triol methyl ester ; Methyl 4-(3,7,12-trihydroxy-10,13-dimethylperhydrocyclopenta[a]phenanthren-17-yl)pentanoate ; Cholic acid methyl ester .
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