ChemicalBook CAS DataBase List Chenodeoxycholic acid

Chenodeoxycholic acid synthesis

8synthesis methods

Product Name:Chenodeoxycholic acid
CAS Number:474-25-9
Molecular formula:C24H40O4
Molecular Weight:392.57

Cholan-24-oic acid, 3-(acetyloxy)-7-hydroxy-, methyl ester, (3α,5β,7α)-

19684-68-5
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474-25-9
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Yield:474-25-9 97%

Reaction Conditions:

with water;sodium hydroxide in methanol; for 1 h;Reflux;

Steps:

2.2.9. 2β, 3, 6α-Trihydroxyl-5β-cholanoate (H9/H10)

General procedure: To a stirred solution of compound H8 (3α)(0.1011g, 0.2mmol) in MeOH (4mL) and H₂O (1mL) was added NaOH (0.0441g, 1.1mmol) at room temperature. The mixture was heated at reflux for 1h, and then adjusted to pH 1-2 with 1M HCl aq to afford compound 2β, 3α, 6α-trihydroxyl-5β-cholanoate H9 (0.0794g, 90% yield) as white solid; mp 52-55°C; (α)20D αD20 =-9.2 (c=0.5, CH₂Cl₂); FTIR (KBr, cm^-1) 3443 (O-H), 1704 (C=O), 1025 and 1023 (C-O); HRMS (ESI, m/z) Calcd for C₂₄H₄₀O₅ 408.2876; found: 431.2751 [M+Na]⁺ (Calcd 431.2773). H9 ¹H NMR (600MHz, CD₃OD) δ 4.08 (dt, J=11.1, 4.2Hz, 1H, 6β-H), 4.02-3.96 (m, 1H, 2α-H), 3.68-3.61 (m, 1H, 3β-H), 1.00 (s, 3H, 19-H), 0.98 (d, J=6.5Hz, 3H, 21-H), 0.72 (s, 3H, 18-H); ¹³C NMR (151MHz, CD₃OD) δ 176.7 (C-24), 68.9 (C-3), 67.1 (C-6), 67.0 (C-2), 56.1, 55.9, 42.6, 42.1, 40.4, 39.9, 37.8, 37.7, 35.3, 34.8, 33.9, 30.9, 30.6, 27.8, 25.5, 23.8, 22.9, 20.9, 17.4, 11.0.