566-24-5

Basic information

• Product Name: (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoic acid
• Synonyms: (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoic acid;3b,7a-Dihydroxy-5b-cholanoic acid;3-epi-Chenodeoxycholic acid;Isochenodeoxycholic acid;3beta,7alpha-dihydroxy-5beta-cholan-24-oic acid
• CAS NO: 566-24-5
• Molecular Formula: C24H40O4
• Molecular Weight: 392.57
• Mol File: 566-24-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 547.1°Cat760mmHg
• Flash Point: 298.8°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 2.98E-14mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly, Heated), Methanol (Slightly)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoic acid(566-24-5)
• EPA Substance Registry System: (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoic acid(566-24-5)

Safety Data

• Hazardous Substances Data: 566-24-5(Hazardous Substances Data)

Usage

Uses

Isochenodeoxycholic Acid is an epimer of common bile acid Chenodeoxycholic Acid (C291900), present in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate.

Definition

ChEBI: A dihydroxy-5beta-cholanic acid in which the two hydroxy groups are located at positions 3beta and 7alpha. The 3beta-hydroxy epimer of chenodeoxycholic acid.

InChI:InChI=1/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20-,22+,23+,24-/m1/s1

Synthetic route

methyl 3β,7α-dihydroxy-5β-cholan-24-oate (28050-38-6) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
With sodium hydroxide In methanol; water Reflux;	89%
With potassium hydroxide In methanol

Dehydrochenodeoxycholic acid (4185-00-6) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
With 1,4-dihydronicotinamide adenine dinucleotide; DL-dithiothreitol In ethanol; water for 30h; 3β-hydroxysteroid dehydrogenase, formate/formate dehydrogenase, potassium phosphate buffer pH=7.2;	81%

methyl 3α-p-toluenesulfonyl-7α-hydroxy-5β-cholest-24-carboxylate (28192-93-0) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
With potassium superoxide; 18-crown-6 ether In 1,2-dimethoxyethane; dimethyl sulfoxide for 22h;	52%
Multi-step reaction with 3 steps 1: 80 °C 2: 56 percent / neutral alumina (grade I) / benzene / 18 h 3: KOH / methanol View Scheme
Multi-step reaction with 2 steps 1: potassium acetate / N,N-dimethyl-formamide; water / 2 h / Reflux 2: sodium hydroxide / methanol; water / Reflux View Scheme

sodium chenodeoxycholate (2646-38-0) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / NAD, DTT / ethyl acetate; H2O / 40 h / Ambient temperature; 3α-hydroxysteroid dehydrogenase, serum albumin, pyruvate/lactic dehydrogenase, potassium phosphate buffer pH=8.5 2: 81 percent / NADH, DTT / ethanol; H2O / 30 h / 3β-hydroxysteroid dehydrogenase, formate/formate dehydrogenase, potassium phosphate buffer pH=7.2 View Scheme

(R)-4-((3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-Formyloxy-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / neutral alumina (grade I) / benzene / 18 h 2: KOH / methanol View Scheme

5β-3,7-diacetoxycholanic acid isopropyl ester (944409-55-6) → chenodeoxycholic acid (474-25-9) + 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
Stage #1: 5β-3,7-diacetoxycholanic acid isopropyl ester With methanol; sodium hydroxide; water for 7h; Heating / reflux; Stage #2: With hydrogenchloride; water

chenodeoxycholic acid methyl ester (3057-04-3) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 4 h / 20 °C 2: potassium acetate / N,N-dimethyl-formamide; water / 2 h / Reflux 3: sodium hydroxide / methanol; water / Reflux View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl (5β)-3,7-bis[2-[(phenylamino)thioxomethyl]hydrazinylidene]-cholan-24-oate (1410795-76-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.08 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl (5)β-3,7-bis[2-[[(4-methoxyphenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate (1410795-77-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.09 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl (5β)-3,7-bis[2-[[(4-bromophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate (1410795-79-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.07 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl (5β)-3,7-bis[2-[[(3-fluorophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate (1410795-81-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.08 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → C33H47N3O4S (1346544-93-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.07 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → C32H44FN3O3S (1346544-94-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.09 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → C33H47N3O3S (1346544-96-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.07 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → C36H47N3O3S

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane 3: aluminum oxide; hydrogenchloride / neat (no solvent) / 0.09 h / Microwave irradiation View Scheme

3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl 3,7-dioxocholan-24-oate (7753-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid 2: pyridinium chlorochromate / dichloromethane View Scheme

methanol (67-56-1) + 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5) → methyl 3β,7α-dihydroxy-5β-cholan-24-oate (28050-38-6)

Conditions	Yield
With toluene-4-sulfonic acid

Upstream product

• 2646-38-0 sodium chenodeoxycholate 
• 944409-55-6 5β-3,7-diacetoxycholanic acid isopropyl ester 

Downstream Products

• 92054-20-1 5β-cholanic acid-3α,7α-diol di-p-fluorobenzoate 
• 88165-77-9 bis(3α-phenylsulfonyloxy-5β-cholansaeure-7α-yl)diester 
• 1410795-79-7 methyl (5β)-3,7-bis[2-[[(4-bromophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate 
• 1410795-81-1 methyl (5β)-3,7-bis[2-[[(3-fluorophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate 
• 1346544-93-1 C₃₃H₄₇N₃O₄S 
• 1346544-94-2 C₃₂H₄₄FN₃O₃S 
• 1346544-96-4 C₃₃H₄₇N₃O₃S 
• 28050-38-6 methyl 3β,7α-dihydroxy-5β-cholan-24-oate 

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