302-95-4

Basic information

• Product Name: Sodium deoxycholate
• Synonyms: OXIDE EXTRACT;SODIUM CHOLEATE;SODIUM DESOXYCHOLATE;SODIUM DEOXYCHOLATE;CHOLEIC ACID SODIUM SALT;DESOXYCHOLIC ACID SODIUM SALT;DEOXYCHOLIC ACID NA-SALT;DEOXYCHOLIC ACID SODIUM SALT
• CAS NO: 302-95-4
• Molecular Formula: C₂₄H₃₉O₄*Na
• Molecular Weight: 414.55
• EINECS: 206-132-7
• Product Categories: Bile SaltsDetergents;Anionic;Detergents;Detergents A to Z;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 302-95-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 357-365 °C
• Boiling Point: 547.148 °C at 760 mmHg
• Flash Point: 298.768 °C
• Appearance: Yellow-tan/Powder
• Density: 1.129 g/cm³
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Store at RT.
• Solubility: water: soluble1 gm in 10 ml, clear, colorless to very faintly ye
• Water Solubility: 330 g/L (15 ºC)
• BRN: 3581950
• CAS DataBase Reference: Sodium deoxycholate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium deoxycholate(302-95-4)
• EPA Substance Registry System: Sodium deoxycholate(302-95-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: FZ2250000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 302-95-4(Hazardous Substances Data)

Usage

Chemical Properties

Sodium deoxycholate is white to cream crystalline powder

Uses

Different sources of media describe the Uses of 302-95-4 differently. You can refer to the following data:
1. Sodium deoxycholate is used as a component in cell lysis buffers.
2. Sodium deoxycholate is an ionic detergent for the solubilization of membrane-bound proteins.
3. Sodium deoxycholate is used as a choleretic and an anionic detergent. It is useful for the extraction of membrane receptors, plasma membrane proteins, nuclei isolation and solubilizes fats as well as membrane components. It acts as an intermediate for the production of corticosteroids and microbiological diagnostic media. In addition, it acts as a catalyst in the preparation of protein extracts for immunoblotting and immunoprecipitation of radiolabeled proteins.

General Description

Sodium deoxycholate is a bile salt and an ionic detergent. Bile salts work along with lipids/fats/cholesterol and form mixed micelles in the intestine. These micelles help in fat digestion and absorption through the intestinal wall.

Biochem/physiol Actions

Solubilizes fats for absorption in the intestines.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NasO.

Purification Methods

Recrystallise it from EtOH and dry it in an oven at 100o. The solution is freed from soluble components by repeated extraction with acid-washed charcoal. [Beilstein 10 IV 1608.]

InChI:InChI=1/CO/c1-2/q+1

Synthetic route

insulin → sodium cholate (302-95-4)

Conditions	Yield
In tetrahydrofuran

Deoxycholic acid (83-44-3) → sodium cholate (302-95-4)

Conditions	Yield
With disodium hydrogenphosphate; sodium hydroxide pH=8.3;

sodium cholate (302-95-4) → 12α-hydroxy-3-oxochol-4-en-24-oic acid (13073-08-0)

Conditions	Yield
With Pseudomonas mendocina ECS10 In water at 28℃; for 24h; Microbiological reaction;	95%

iron(III)phthalocyanine chloride (14285-56-4) + sodium cholate (302-95-4) → C32H16FeN8(1+)*C24H39O4(1-)

Conditions	Yield
In dichloromethane; water for 48h;	92%

methanol (67-56-1) + sodium cholate (302-95-4) → methyl deoxycholate (3245-38-3)

Conditions	Yield
With sulfuric acid for 3h; Heating;	91%

sodium cholate (302-95-4) + 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene (181058-08-2) → C87H138O12 (1359731-67-1)

Conditions	Yield
In N,N-dimethyl-formamide at 75 - 80℃; Inert atmosphere;	87%

1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate (875341-39-2) + sodium cholate (302-95-4) → 4-(3,12-bis-{[4-(3,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoyloxy]-acetoxy}-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylmethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 7h;	86%

sodium cholate (302-95-4) + triphenyltin chloride (639-58-7) → (R)-triphenylstannyl 4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions	Yield
In toluene Inert atmosphere; Reflux;	84.6%

1,3,5-Tris(bromomethyl)benzene (18226-42-1) + sodium cholate (302-95-4) → C81H126O12 (1359731-64-8)

Conditions	Yield
In N,N-dimethyl-formamide at 75 - 80℃; Inert atmosphere;	84%

tributyltin chloride (1461-22-9) + sodium cholate (302-95-4) → (R)-tributylstannyl 4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions	Yield
In toluene Inert atmosphere; Reflux;	83.9%

sodium cholate (302-95-4) → 12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid (66428-56-6)

Conditions	Yield
With Pseudomonas fragi ECS9 In water at 28℃; for 48h; Microbiological reaction;	80%

trimethyltin(IV)chloride (1066-45-1) + sodium cholate (302-95-4) → (R)-trimethylstannyl 4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions	Yield
In toluene Inert atmosphere; Reflux;	73.4%

sodium cholate (302-95-4) → 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7)

Conditions	Yield
With phosphate buffer; 3α-HSDH from Pseudomonas paucimobilis; sodium pyruvate; NAD In water at 22℃; for 48h;	72%
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;
With Bacillus mycoides B23 broth In water at 30℃; for 48h;	91 % Chromat.

1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate (875341-40-5) + sodium cholate (302-95-4) → C113H168O20

Conditions	Yield
In N,N-dimethyl-formamide at 60℃;	66%

sodium cholate (302-95-4) + chloroformic acid ethyl ester (541-41-3) → 3α,12α,24-trihydroxy-5β-cholane (2603-77-2)

Conditions	Yield
Stage #1: sodium cholate; chloroformic acid ethyl ester In tetrahydrofuran at 50℃; for 20h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; for 3h; Inert atmosphere;	63%

sodium cholate (302-95-4) → 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7) + 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Conditions	Yield
With Rhodococcus erythropolis ECS25 In water at 28℃; for 24h; Microbiological reaction;	A 61% B 30%

sodium cholate (302-95-4) → (αS,1R,3aS,4S,7S,7aS)-octahydro-7-hydroxy-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-α,7a-dimethyl-5-oxo-1H-indene-1-acetic acid + (αS,4S,7aS)-2,3,3a,4,5,7a-hexahydro-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-α,7a-dimethyl-5-oxo-1H-indene-1-acetic acid

Conditions	Yield
With Rhodococcus rubber for 24h;	A 55% B 20%

sodium cholate (302-95-4) → 3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid (88725-42-2) + (R)-4-((5R,6R,8S,9S,10R,13R,14S,17R)-6-Hydroxy-10,13-dimethyl-3,7-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid

Conditions	Yield
With Bacillus mycoides B23 broth In water at 32℃; for 24h;	A 34% B 50%

sodium cholate (302-95-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → C26H45NO4

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;	42%

sodium cholate (302-95-4) → 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7) + 12α-hydroxy-3-oxochol-4-en-24-oic acid (13073-08-0)

Conditions	Yield
With Pseudomonas prosekii ECS1 In water at 28℃; for 72h; Microbiological reaction;	A 20% B 22%

methanol (67-56-1) + sodium cholate (302-95-4) → 12α-hydroxypregn-4-en-3-one-20-carboxylic acid methyl ester (80374-03-4) + methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate (10538-58-6) + (S)-2-((8R,9S,10R,12S,13S,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-propionic acid methyl ester (86496-41-5) + methyl 12α-hydroxy-3-ketochola-1,4-dienoate (106759-10-8)

Conditions	Yield
With boron trifluoride 1.) water, 28 deg C, 16 h, Pseudomonas NCIB 10590, K2HPO4, KHPO4, KNO3, FeSO4*7H2O, ZnSO4*7H2O, MnSO4*4H2O, MgSO4*7H2O, pH=7, aeration; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

sodium cholate (302-95-4) + δ-Aminophalloin (87876-22-0) → Nδ-Desoxycholyl-δ-aminophalloin (87876-29-7)

Conditions	Yield
With isobutyl chloroformate 1) THF, -15 deg C, 8 min, 2) DMF, RT, 2 h; Yield given. Multistep reaction;

sodium cholate (302-95-4) → 12β-hydroxy-1,4-androstadiene-3,17-dione (28840-96-2) + 12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid (66428-56-6) + 12β,17β-dihydroxyandrosta-1,4-dien-3-one (80227-48-1) + 12α-hydroxyandrosta-1,4-dien-3,17-dione (59531-53-2)

Conditions	Yield
In water at 28℃; for 16h; Pseudomonas NCIB 10590, K2HPO4, KHPO4, KNO3, FeSO4*7H2O, ZnSO4*7H2O, MnSO4*4H2O, MgSO4*7H2O, pH=7, aeration; Further byproducts given;	A 7.6 g B 5 g C 150 mg D 30 mg

sodium cholate (302-95-4) → 3,12β-dihydroxy-9,10-seco-1,3,5(10)-androstatriene-9,17-dione (79683-94-6)

Conditions	Yield
Pseudomonas putida ATCC 31752;

sodium cholate (302-95-4) → 3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid (88725-42-2)

Conditions	Yield
With Pseudomonas fluorescens BS7 broth In water at 30℃; for 48h;	96 % Chromat.

sodium cholate (302-95-4) → 12-oxolithocholic acid (5130-29-0)

Conditions	Yield
With Acinetobacter calcoaceticus lwoffii BS11 broth In water at 30℃; for 48h;	98 % Chromat.

sodium cholate (302-95-4) → 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Conditions	Yield
With Pseudomonas fluorescens B25 broth In water at 30℃; for 48h;	98 % Chromat.

sodium cholate (302-95-4) + erythromycin (114-07-8) → C37H67NO13*C24H40O4

Conditions	Yield
With phosphate buffer pH=5.5; ion pair formation;

sodium cholate (302-95-4) → methyl 3α,12α-bis(1-imidazolylcarbonyloxy)-5β-cholan-24-oate (317806-84-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / H2SO4 / 3 h / Heating 2: 97 percent / triethylamine / CH2Cl2 / 5 h / 40 °C View Scheme

sodium cholate (302-95-4) → methyl 3α,12α-bis(N,N-dimethylaminoethylcarbamoyloxy)-5β-cholan-24-oate (847983-29-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / H2SO4 / 3 h / Heating 2: 97 percent / triethylamine / CH2Cl2 / 5 h / 40 °C 3: 66 percent / CH2Cl2 / 8 h / 25 °C View Scheme

sodium cholate (302-95-4) → methyl 3α,12α-bis(5-bromopentanoyloxy)-5β-cholan-24-oate

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / H2SO4 / 3 h / Heating 2: 81 percent / pyridine / CHCl3 / 1 h / 25 °C View Scheme

sodium cholate (302-95-4) → methyl 3α,12α-bis(N-tert-butyloxycarbonylamidocapronoyloxy)-5β-cholan-24-oate (847983-33-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / H2SO4 / 3 h / Heating 2: 64 percent / DCC; DMAP / CH2Cl2 / 23 h / 25 °C View Scheme

Upstream product

• 83-44-3 Deoxycholic acid 

Downstream Products

• 5130-29-0 12-oxolithocholic acid 
• 2958-05-6 3,12-dioxo-7-deoxycholic acid 
• 4185-01-7 3-keto-12α-hydroxy-5β-cholan-24-oic acid 
• 79683-94-6 3,12β-dihydroxy-9,10-seco-1,3,5(10)-androstatriene-9,17-dione 
• 28840-96-2 12β-hydroxy-1,4-androstadiene-3,17-dione 
• 66428-56-6 12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid 
• 80227-48-1 12β,17β-dihydroxyandrosta-1,4-dien-3-one 
• 59531-53-2 12α-hydroxyandrosta-1,4-dien-3,17-dione 
• 80374-03-4 12α-hydroxypregn-4-en-3-one-20-carboxylic acid methyl ester 
• 10538-58-6 methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate 
• 86496-41-5 (S)-2-((8R,9S,10R,12S,13S,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-propionic acid methyl ester 
• 106759-10-8 methyl 12α-hydroxy-3-ketochola-1,4-dienoate 

Relevant articles and documents

USE OF DEOXYCHOLIC ACID, DERIVATIVES, OR SALTS THEREOF IN MANAGING BACTERIAL INFECTIONS AND COMPOSITIONS RELATED THERETO

This disclosure relates to uses of deoxycholic acid, salts, or derivatives thereof in managing bacterial infections and compositions related thereto. In certain embodiments, this disclosure relates to methods of treating or preventing a bacterial infection comprising administering an effective amount of a deoxycholic acid, salts, or derivatives thereof to a subject in need thereof. In certain embodiments, this disclosure relates to methods of treating or preventing streptococcus pneumoniae comprising administering an effective amount of a deoxycholic acid salt to a subject in need thereof.