77060-26-5

Basic information

• Product Name: methyl 4-(10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
• Synonyms: 7b-Hydroxy-3-oxo-5b-cholanoic acid;methyl 4-(10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate;Cholan-24-oic acid,7-hydroxy-3-oxo-, (5b,7b)-;7b-Hydroxy-3-oxo-5b-cholan-24-oic acid;KNVADAPHVNKTEP-AQHAYLOVSA-N
• CAS NO: 77060-26-5
• Molecular Formula: C₂₄H₃₈O₄
• Molecular Weight: 390.56
• Product Categories: Steroids
• Mol File: 77060-26-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 503.8°C at 760 mmHg
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 2.82E-10mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: methyl 4-(10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(77060-26-5)
• EPA Substance Registry System: methyl 4-(10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(77060-26-5)

Safety Data

• Hazardous Substances Data: 77060-26-5(Hazardous Substances Data)

Usage

Uses

3-Oxo-7β-hydroxy-5β-cholanoic Acid is a keto bile acid derivative.

InChI:InChI=1/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1

Synthetic route

3-keto-7β-succinyloxy-5β-cholan-24-oic acid (459840-75-6) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With 20percent NaOH for 1h; Heating;	95%

ursodeoxycholic acid (128-13-2) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With dipotassium hydrogenphosphate; D-glucose; Pseudomonas paucimobilis; yeast extracxt; peptone In water at 28℃; for 24h;	90%
Multi-step reaction with 4 steps 1: triethylamine; DMAP / ethyl acetate / 10 h / Heating 2: 5percent NaOH / methanol / 1 h 3: Jones' reagent / acetone / 0.08 h 4: 95 percent / 20percent NaOH / 1 h / Heating View Scheme

Lithocholic acid (434-13-9) → ursodeoxycholic acid (128-13-2) + 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With Gibberella zeae VKM F-2600 extract In methanol; aq. phosphate buffer at 29℃; for 122h; pH=7; Microbiological reaction;	A 83% B n/a

7β-formyloxy-3-oxo-5β-cholanoic acid-(24) (106351-12-6) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With potassium hydroxide

3,7-dihydroxycholan-24-oic acid, monosodium salt (2646-38-0, 2898-95-5, 31687-63-5, 31687-65-7, 108609-27-4) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With DL-dithiothreitol; NAD In water; ethyl acetate for 40h; Ambient temperature; 3α-hydroxysteroid dehydrogenase, puryvate/lactic dehydrogenase, serum albumin, potassium phosphate buffer pH=8.5; Yield given;

Succinic acid mono-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-carboxy-1-methyl-propyl)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl] ester (459840-78-9) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones' reagent / acetone / 0.08 h 2: 95 percent / 20percent NaOH / 1 h / Heating View Scheme

Succinic acid mono-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-carboxy-1-methyl-propyl)-3-(3-carboxy-propionyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl] ester (103767-93-7) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5percent NaOH / methanol / 1 h 2: Jones' reagent / acetone / 0.08 h 3: 95 percent / 20percent NaOH / 1 h / Heating View Scheme

3α-hydroxy-7β-formyloxy-5β-cholanoic acid-(24) (64986-84-1) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; acetic acid 2: aqueous KOH-solution View Scheme

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid (6058-15-7, 6159-50-8) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH solution 2: chromium (VI)-oxide; acetic acid 3: aqueous KOH-solution View Scheme

Lithocholic acid (434-13-9) → 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5)

Conditions	Yield
With Cunninghamella echinulata VKM F-470 extract In methanol; aq. phosphate buffer at 29℃; pH=7; Microbiological reaction;

sarcosine (107-97-1) + 3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5) → sarco-7β-hydroxy-3-oxo-5β-cholan-24-oate (96158-42-8)

Conditions	Yield
With sodium hydroxide; tributyl-amine; chloroformic acid ethyl ester Ambient temperature;

3-keto-7β-hydroxy-5β-cholan-24-oic acid (77060-26-5) → 3β,7β-dihydroxy-5β-cholan-24-oic acid (78919-26-3)

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;

Upstream product

• 434-13-9 Lithocholic acid 
• 6058-15-7 (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid 
• 64986-84-1 3α-hydroxy-7β-formyloxy-5β-cholanoic acid-(24) 
• 128-13-2 ursodeoxycholic acid 
• 2646-38-0 3,7-dihydroxycholan-24-oic acid, monosodium salt 
• 106351-12-6 7β-formyloxy-3-oxo-5β-cholanoic acid-(24) 
• 103767-93-7 Succinic acid mono-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-carboxy-1-methyl-propyl)-3-(3-carboxy-propionyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl] ester 
• 459840-78-9 Succinic acid mono-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-carboxy-1-methyl-propyl)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl] ester 
• 459840-75-6 3-keto-7β-succinyloxy-5β-cholan-24-oic acid 

Relevant articles and documents

Hydroxylation of lithocholic acid by selected actinobacteria and filamentous fungi

Selected actinobacteria and filamentous fungi of different taxonomy were screened for the ability to carry out regio- and stereospecific hydroxylation of lithocholic acid (LCA) at position 7β. The production of ursodeoxycholic acid (UDCA) was for the first time shown for the fungal strains of Bipolaris, Gibberella, Cunninghamella and Curvularia, as well as for isolated actinobacterial strains of Pseudonocardia, Saccharothrix, Amycolatopsis, Lentzea, Saccharopolyspora and Nocardia genera. Along with UDCA, chenodeoxycholic (CDCA), deoxycholic (DCA), cholic (CA), 7-ketodeoxycholic and 3-ketodeoxycholic acids were detected amongst the metabolites by some strains. A strain of Gibberella zeae VKM F-2600 expressed high level of 7β-hydroxylating activity towards LCA. Under optimized conditions, the yield of UDCA reached 90% at 1 g/L of LCA and up to 60% at a 8-fold increased substrate loading. The accumulation of the major by-product, 3-keto UDCA, was limited by using selected biotransformation media.

Regiospecific oxidoreductions catalyzed by a new Pseudomonas paucimobilis hydroxysteroid dehydrogenase

The preparative-scale regio- and stereo-specific oxidation of hydroxy groups and reduction of keto functions at C(3) of several C21 bile acids, catalyzed by a new 3α-hydroxysteroid dehydrogenase (3α-HSDH) is reported. The crude enzyme, isolated from the cells of Pseudomonas paucimobilis, revealed the presence of a further enzymatic fraction containing a secondary alcohol dehydrogenase (SADH), that has been used to recycle the cofactor.