Product Name

  • Name

    Sodium deoxycholate

  • EINECS 206-132-7
  • CAS No. 302-95-4
  • Article Data2
  • CAS DataBase
  • Density 1.129 g/cm3
  • Solubility 330 g/L (15 °C) in water
  • Melting Point 357-365 °C
  • Formula C24H39NaO4
  • Boiling Point 547.148 °C at 760 mmHg
  • Molecular Weight 414.561
  • Flash Point 298.768 °C
  • Transport Information
  • Appearance white to cream crystalline powder
  • Safety 22
  • Risk Codes 22-37
  • Molecular Structure Molecular Structure of 302-95-4 (Sodium deoxycholate)
  • Hazard Symbols HarmfulXn
  • Synonyms 5b-Cholan-24-oic acid, 3a,12a-dihydroxy-, monosodium salt (8CI);Deoxycholic acidmonosodium salt;Deoxycholic acid sodium salt;Desoxycholate sodium;Desoxycholic acid sodium salt;NSC 681065;Sodium 3a,12a-dihydroxy-5b-cholanate;Sodium 7-deoxycholate;Sodium deoxycholate;Sodium desoxycholate;Sodium Deoxycholic acid;
  • PSA 80.59000
  • LogP 3.14320

Synthetic route

insulin

insulin

sodium cholate
302-95-4

sodium cholate

Conditions
ConditionsYield
In tetrahydrofuran
Deoxycholic acid
83-44-3

Deoxycholic acid

sodium cholate
302-95-4

sodium cholate

Conditions
ConditionsYield
With disodium hydrogenphosphate; sodium hydroxide pH=8.3;
sodium cholate
302-95-4

sodium cholate

12α-hydroxy-3-oxochol-4-en-24-oic acid
13073-08-0

12α-hydroxy-3-oxochol-4-en-24-oic acid

Conditions
ConditionsYield
With Pseudomonas mendocina ECS10 In water at 28℃; for 24h; Microbiological reaction;95%
iron(III)phthalocyanine chloride
14285-56-4

iron(III)phthalocyanine chloride

sodium cholate
302-95-4

sodium cholate

C32H16FeN8(1+)*C24H39O4(1-)

C32H16FeN8(1+)*C24H39O4(1-)

Conditions
ConditionsYield
In dichloromethane; water for 48h;92%
methanol
67-56-1

methanol

sodium cholate
302-95-4

sodium cholate

methyl deoxycholate
3245-38-3

methyl deoxycholate

Conditions
ConditionsYield
With sulfuric acid for 3h; Heating;91%
sodium cholate
302-95-4

sodium cholate

1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene
181058-08-2

1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene

C87H138O12
1359731-67-1

C87H138O12

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 75 - 80℃; Inert atmosphere;87%
1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate
875341-39-2

1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate

sodium cholate
302-95-4

sodium cholate

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

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
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 7h;86%
sodium cholate
302-95-4

sodium cholate

triphenyltin chloride
639-58-7

triphenyltin chloride

(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

(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
ConditionsYield
In toluene Inert atmosphere; Reflux;84.6%
1,3,5-Tris(bromomethyl)benzene
18226-42-1

1,3,5-Tris(bromomethyl)benzene

sodium cholate
302-95-4

sodium cholate

C81H126O12
1359731-64-8

C81H126O12

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 75 - 80℃; Inert atmosphere;84%
tributyltin chloride
1461-22-9

tributyltin chloride

sodium cholate
302-95-4

sodium cholate

(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

(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
ConditionsYield
In toluene Inert atmosphere; Reflux;83.9%
sodium cholate
302-95-4

sodium cholate

12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid
66428-56-6

12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid

Conditions
ConditionsYield
With Pseudomonas fragi ECS9 In water at 28℃; for 48h; Microbiological reaction;80%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

sodium cholate
302-95-4

sodium cholate

(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

(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
ConditionsYield
In toluene Inert atmosphere; Reflux;73.4%
sodium cholate
302-95-4

sodium cholate

3-keto-12α-hydroxy-5β-cholan-24-oic acid
4185-01-7

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

Conditions
ConditionsYield
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

1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate

sodium cholate
302-95-4

sodium cholate

C113H168O20

C113H168O20

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃;66%
sodium cholate
302-95-4

sodium cholate

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3α,12α,24-trihydroxy-5β-cholane
2603-77-2

3α,12α,24-trihydroxy-5β-cholane

Conditions
ConditionsYield
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

sodium cholate

A

3-keto-12α-hydroxy-5β-cholan-24-oic acid
4185-01-7

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

B

3,12-dioxo-7-deoxycholic acid
2958-05-6

3,12-dioxo-7-deoxycholic acid

Conditions
ConditionsYield
With Rhodococcus erythropolis ECS25 In water at 28℃; for 24h; Microbiological reaction;A 61%
B 30%
sodium cholate
302-95-4

sodium cholate

A

(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,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

B

(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

(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
ConditionsYield
With Rhodococcus rubber for 24h;A 55%
B 20%
sodium cholate
302-95-4

sodium cholate

A

3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid
88725-42-2

3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid

B

(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

(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
ConditionsYield
With Bacillus mycoides B23 broth In water at 32℃; for 24h;A 34%
B 50%
sodium cholate
302-95-4

sodium cholate

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

C26H45NO4

C26H45NO4

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;42%
sodium cholate
302-95-4

sodium cholate

A

3-keto-12α-hydroxy-5β-cholan-24-oic acid
4185-01-7

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

B

12α-hydroxy-3-oxochol-4-en-24-oic acid
13073-08-0

12α-hydroxy-3-oxochol-4-en-24-oic acid

Conditions
ConditionsYield
With Pseudomonas prosekii ECS1 In water at 28℃; for 72h; Microbiological reaction;A 20%
B 22%
methanol
67-56-1

methanol

sodium cholate
302-95-4

sodium cholate

A

12α-hydroxypregn-4-en-3-one-20-carboxylic acid methyl ester
80374-03-4

12α-hydroxypregn-4-en-3-one-20-carboxylic acid methyl ester

B

methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate
10538-58-6

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

C

(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

(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

D

methyl 12α-hydroxy-3-ketochola-1,4-dienoate
106759-10-8

methyl 12α-hydroxy-3-ketochola-1,4-dienoate

Conditions
ConditionsYield
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;
...Expand
sodium cholate
302-95-4

sodium cholate

δ-Aminophalloin
87876-22-0

δ-Aminophalloin

Nδ-Desoxycholyl-δ-aminophalloin
87876-29-7

Nδ-Desoxycholyl-δ-aminophalloin

Conditions
ConditionsYield
With isobutyl chloroformate 1) THF, -15 deg C, 8 min, 2) DMF, RT, 2 h; Yield given. Multistep reaction;
sodium cholate
302-95-4

sodium cholate

A

12β-hydroxy-1,4-androstadiene-3,17-dione
28840-96-2

12β-hydroxy-1,4-androstadiene-3,17-dione

B

12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid
66428-56-6

12β,17β-dihydroxypregna-1,4-dien-3-one-20-carboxylic acid

C

12β,17β-dihydroxyandrosta-1,4-dien-3-one
80227-48-1

12β,17β-dihydroxyandrosta-1,4-dien-3-one

D

12α-hydroxyandrosta-1,4-dien-3,17-dione
59531-53-2

12α-hydroxyandrosta-1,4-dien-3,17-dione

Conditions
ConditionsYield
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
...Expand
sodium cholate
302-95-4

sodium cholate

3,12β-dihydroxy-9,10-seco-1,3,5(10)-androstatriene-9,17-dione
79683-94-6

3,12β-dihydroxy-9,10-seco-1,3,5(10)-androstatriene-9,17-dione

Conditions
ConditionsYield
Pseudomonas putida ATCC 31752;
sodium cholate
302-95-4

sodium cholate

3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid
88725-42-2

3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid

Conditions
ConditionsYield
With Pseudomonas fluorescens BS7 broth In water at 30℃; for 48h;96 % Chromat.
sodium cholate
302-95-4

sodium cholate

12-oxolithocholic acid
5130-29-0

12-oxolithocholic acid

Conditions
ConditionsYield
With Acinetobacter calcoaceticus lwoffii BS11 broth In water at 30℃; for 48h;98 % Chromat.
sodium cholate
302-95-4

sodium cholate

3,12-dioxo-7-deoxycholic acid
2958-05-6

3,12-dioxo-7-deoxycholic acid

Conditions
ConditionsYield
With Pseudomonas fluorescens B25 broth In water at 30℃; for 48h;98 % Chromat.
sodium cholate
302-95-4

sodium cholate

erythromycin
114-07-8

erythromycin

C37H67NO13*C24H40O4

C37H67NO13*C24H40O4

Conditions
ConditionsYield
With phosphate buffer pH=5.5; ion pair formation;
sodium cholate
302-95-4

sodium cholate

methyl 3α,12α-bis(1-imidazolylcarbonyloxy)-5β-cholan-24-oate
317806-84-1

methyl 3α,12α-bis(1-imidazolylcarbonyloxy)-5β-cholan-24-oate

Conditions
ConditionsYield
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

sodium cholate

methyl 3α,12α-bis(N,N-dimethylaminoethylcarbamoyloxy)-5β-cholan-24-oate
847983-29-3

methyl 3α,12α-bis(N,N-dimethylaminoethylcarbamoyloxy)-5β-cholan-24-oate

Conditions
ConditionsYield
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

sodium cholate

methyl 3α,12α-bis(5-bromopentanoyloxy)-5β-cholan-24-oate

methyl 3α,12α-bis(5-bromopentanoyloxy)-5β-cholan-24-oate

Conditions
ConditionsYield
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

sodium cholate

methyl 3α,12α-bis(N-tert-butyloxycarbonylamidocapronoyloxy)-5β-cholan-24-oate
847983-33-9

methyl 3α,12α-bis(N-tert-butyloxycarbonylamidocapronoyloxy)-5β-cholan-24-oate

Conditions
ConditionsYield
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

Sodium deoxycholate Specification

The IUPAC name of Sodium deoxycholate is sodium (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. With the CAS registry number 302-95-4 and EINECS 206-132-7, it is also named as 3-alpha,12-alpha-Dihydroxy-5-beta-cholan-24-oic acid sodium salt. The product's categories are Bile Salts Detergents; Anionic; Detergents; Detergents A to Z; Steroids. It is white to cream crystalline powder which is a bile acid formed by bacterial action from cholate. What's more, it is used in the preparation of bacteria culture medium. Additionally, this chemical should be sealed in the container and stored in the cool and dry place at the normal temperature.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.946; (4)ACD/LogD (pH 7.4): 2.149; (5)ACD/BCF (pH 5.5): 374.136; (6)ACD/BCF (pH 7.4): 5.973; (7)ACD/KOC (pH 5.5): 1416.189; (8)ACD/KOC (pH 7.4): 22.61; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 77.76 Å2; (13)Index of Refraction: 1.543; (14)Molar Refractivity: 109.65 cm3; (15)Molar Volume: 347.857 cm3; (16)Polarizability: 43.469×10-24 cm3; (17)Surface Tension: 46.016 dyne/cm; (18)Density: 1.129 g/cm3; (19)Flash Point: 298.768 °C; (20)Enthalpy of Vaporization: 95.005 kJ/mol; (21)Boiling Point: 547.148 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also very toxic in contact with skin. So people should not breathe dust.

People can use the following data to convert to the molecule structure. 
1. SMILES:C[C@H](CCC(=O)O)[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
2. InChI:InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
3. InChIKey:KXGVEGMKQFWNSR-LLQZFEROBK

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 36mg/kg (36mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. Vol. (103), Pg. 29, 1985.
mouse LD50 intravenous 107mg/kg (107mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 90, Pg. 18, 1952.
mouse LD50 oral 1050mg/kg (1050mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE		 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. Vol. (103), Pg. 29, 1985.
mouse LD50 subcutaneous 815mg/kg (815mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 45, 1969.
rabbit LDLo intravenous 15mg/kg (15mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BLOOD: OTHER CHANGES		 Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 52, Pg. 779, 1926.
rat LD50 intraperitoneal 123mg/kg (123mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 45, 1969.
rat LD50 intravenous 150mg/kg (150mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 323, 1970.
rat LD50 oral 1370mg/kg (1370mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 45, 1969.
rat LD50 subcutaneous 2430mg/kg (2430mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 45, 1969.

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