Methyl deoxycholate

Base Information

• Chemical Name: Methyl deoxycholate
• CAS No.: 3245-38-3
• Molecular Formula: C25H42O4
• Molecular Weight: 406.606
• European Community (EC) Number: 221-819-1
• NSC Number: 22957
• UNII: H1C2TVP7AQ
• DSSTox Substance ID: DTXSID70954203
• Nikkaji Number: J21.483C
• Wikidata: Q63396505
• ChEMBL ID: CHEMBL1078051
• Mol file: 3245-38-3.mol

Synonyms:Methyl desoxycholate;3245-38-3;Methyl deoxycholate;Methyl 7-Deoxycholate;NSC 22957;H1C2TVP7AQ;Deoxycholic Acid Methyl Ester;EINECS 221-819-1;NSC-22957;Cholan-24-oic acid, 3,12-dihydroxy-, methyl ester, (3.alpha.,5.beta.,12.alpha.)-;Methyl 3-alpha,12-alpha-dihydroxy-5-beta-cholan-24-oate;MLS002638913;Methyl 3,12-dihydroxycholan-24-oate;Deoxycholic acid methyl;Methyl 7-desoxycholate;ST024724;UNII-H1C2TVP7AQ;TimTec1_001899;SCHEMBL60803;Deoxycholic acid, methyl ester;CHEMBL1078051;DTXSID70954203;CHEBI:183913;HMS1539G07;NSC22957;Cholan-24-oic acid, 3,12-dihydroxy-, methyl ester, (3a,5b,12a)-;MFCD00046270;AKOS024278937;methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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;methyl 4-((1S,2S,11S,16S,5R,7R,10R,14R,15R)-5,16-dihydroxy-2,15-dimethyltetrac yclo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoate;F82321;J-018743;5beta-Cholanic acid-3alpha,12alpha-diol methyl ester;Q63396505;Methyl 3.alpha.,12.alpha.-dihydroxy-5.beta.-cholanoate;3alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid methyl ester;Methyl 3.alpha.,12.alpha.-dihydroxy-5.beta.-cholan-24-oate;5.beta.-Cholan-24-oic acid, 3.alpha.,12.alpha.-dihydroxy-, methyl ester;Methyl 3,12-dihydroxycholan-24-oate, (3.alpha.,5.beta.,12.alpha.)-;Cholan-24-oic acid, 3,12-dihydroxy-, methyl ester, (3alpha,5beta,12alpha)-;Cholan-24-oic acid,12-dihydroxy-, methyl ester, (3.alpha.,5.beta.,12.alpha.)-

Chemical Property of Methyl deoxycholate

Chemical Property:

• Appearance/Colour: Odourless Whitish Solid
• Vapor Pressure: 1.99E-12mmHg at 25°C
• Melting Point: 92-93 °C
• Refractive Index: 1.525
• Boiling Point: 507.6 °C at 760 mmHg
• PKA: 14.88±0.70(Predicted)
• Flash Point: 162.1 °C
• PSA: 66.76000
• Density: 1.089 g/cm³
• LogP: 4.56630
• Storage Temp.: -20°C Freezer
• Solubility.: Benzene, Chloroform, Methanol
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 406.30830982
• Heavy Atom Count: 29
• Complexity: 620

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

MethylDesoxycholate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: Methyl Desoxycholate (cas# 3245-38-3) is a compound useful in organic synthesis.

Technology Process of Methyl deoxycholate

There total 2 articles about Methyl deoxycholate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

methyl deoxycholate 3,12-bis(trimethylsilyl ether) (6818-41-3,20230-63-1,81519-43-9) → (R)-4-((3R,5R,8S,9S,10S,12S,13R,14S,17R)-3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (1912-56-7,1912-65-8,2569-05-3,2934-50-1,3245-38-3,20231-66-7,28050-36-4,60103-19-7,60103-20-0,60103-21-1,80225-61-2,81702-91-2) + (R)-4-((3R,5R,8S,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (1985-15-5,3623-41-4,18069-51-7,20231-68-9,28050-47-7) + (S)-4-((5R,8S,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (1174-86-3,28057-90-1,60103-18-6) + (R)-4-((5R,8S,9S,10S,12S,13R,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (10538-58-6,14772-89-5,99591-01-2,132089-92-0)

Guidance literature:

With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -40 deg C, 45 min; 2.) methanol;

Reference yield: 58.0%

methyl 3α,7α-diacetoxy-12α-hydroxy cholanate (3749-87-9) → Methyl 12α-hydroxy-5β-cholanate (1249-70-3) + methyl deoxycholate (3245-38-3) + methyl 7α,12a-dihydroxy-5β-cholan-24-oate (3701-54-0) + methyl cholate (1448-36-8)

Guidance literature:

With potassium Sodium; iso-butanol; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran; Yields of byproduct given; Ambient temperature; var. cat.: 18-crown-6;

DOI:10.1016/S0040-4039(00)95452-2

Reference yield: 98.0%

methyl deoxycholate (3245-38-3) → methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate (10538-58-6)

Guidance literature:

With Ag₂CO₃ on Celite; In toluene; Reflux; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.05.140

upstream raw materials:

methyl 3α,7α-diacetoxy-12α-hydroxy cholanate

methyl deoxycholate 3,12-bis(trimethylsilyl ether)

Downstream raw materials:

24,24-diphenyl-5β-cholanetriol-(3α,12α,24)

3-keto-12α-hydroxy-5β-cholan-24-oic acid

methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate

methyl 3α-cathyloxy-12α-hydroxy-5β-cholan-24-oate

Refernces

• 1、 Afonso, Carlos M.,Barros, M. Teresa,Maycock, Christopher D.. "The Reactivity of Silyl Ethers to the Swern Reagent". . p. 1221 - 1224. Retrieved 2007/10/02.