Dehydrocholic acid supplier

Name
Dehydrocholic acid
EINECS 201-335-7
CAS No. 81-23-2
Article Data35
CAS DataBase
Density 1.172 g/cm³
Solubility 10 mg/mL in ethanol
Melting Point 238-240 °C
Formula C₂₄H₃₄O₅
Boiling Point 581.5 °C at 760 mmHg
Molecular Weight 402.531
Flash Point 319.5 °C
Transport Information
Appearance white to off-white amorphous powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5b-Cholan-24-oic acid,3,7,12-trioxo- (8CI);3,7,12-Tri-keto-5b-Cholan-24-oic acid;3,7,12-Triketo-5b-cholanic acid;3,7,12-Triketocholanic acid;3,7,12-Trioxo-5b-cholan-24-oic acid;3,7,12-Trioxo-5b-cholanic acid;3,7,12-Trioxocholanic acid;Acolen;Bilidren;Bilostat;Cholagon;Cholan DH;Cholepatin;Cholic acid, dehydro-;Cholimed;Chologon;DHC;Decholin;Dehychol;Dehycon;
PSA 88.51000
LogP 4.07330

Synthetic route

: 81-25-4
cholic acid

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With sodium hydroxide; sodium perchlorate; sodium chloride In water at 25℃; for 40h; pH=12; Electrochemical reaction; 50 mA;	100%
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; for 3h; Temperature; Green chemistry;	95%
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; for 3.3h;	95%

: 3,7,12-trihydroxy-5β-cholan-24-oic acid

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With jones' reagent In acetone for 0.0833333h;	100%

: C27H46O5

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Stage #1: C27H46O5 With potassium sulfate; cerous nitrate at 8℃; for 2.33333h; Large scale; Stage #2: With Tetradecanoic acid 1-methylethyl ester for 3h; Temperature; Large scale;	94%

: 81-25-4
cholic acid

A: 2458-08-4
3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid

B: 911-40-0
7-ketodeoxycholic acid

C: 517-33-9
7,12-dioxolitocholic acid

D: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With sodium hydroxide; sodium perchlorate; sodium chloride In water at 25℃; for 6h; pH=12; Product distribution; Further Variations:; electricity; Electrochemical reaction; 200 mA;	A 10% B 33% C 46% D 11%

...Expand

: 1100696-11-4
(24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With chromium(VI) oxide In water; acetic acid at 25℃; for 5h;	90 mg

: 361-09-1
sodium cholate

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With Pseudomonas fluorescens B26 broth In water at 30℃; for 48h;	41 % Chromat.

: 81-25-4
cholic acid

: 7732-18-5
water

: 7726-95-6
bromine

: 81-23-2
dehydrocholic acid

...Expand

: 81-25-4
cholic acid

: 7726-95-6
bromine

: 64-19-7
acetic acid

: 81-23-2
dehydrocholic acid

...Expand

: 81-25-4
cholic acid

: 7726-95-6
bromine

aqueous sodium hydrogencarbonate solution: aqueous sodium hydrogencarbonate solution

: 81-23-2
dehydrocholic acid

...Expand

: 81-25-4
cholic acid

: 64-19-7
acetic acid

chromium (VI)-oxide: chromium (VI)-oxide

: 81-23-2
dehydrocholic acid

...Expand

: 81-25-4
cholic acid

liver-substances: liver-substances

: 81-23-2
dehydrocholic acid

: 81-25-4
cholic acid

Alcaligenes faecalis: Alcaligenes faecalis

A: 911-40-0
7-ketodeoxycholic acid

B: 517-33-9
7,12-dioxolitocholic acid

C: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
unter aeroben Bedingungen;

...Expand

: 7647-01-0
hydrogenchloride

: 3.3-bis-(4-acetylamino-phenylsulfanyl)-7.12-dioxo-5β-cholanoic acid-(24)

: 81-23-2
dehydrocholic acid

: 1061-64-9, 23605-03-0, 73804-37-2, 73837-07-7, 73889-90-4, 85552-41-6, 85552-42-7, 85552-43-8, 85552-44-9
(25Ξ)-3ξ.7ξ.12ξ.24ξ-tetrahydroxy-5β-cholestanoic acid-(26)

: 64-19-7
acetic acid

chromium (VI)-oxide: chromium (VI)-oxide

: 81-23-2
dehydrocholic acid

...Expand

: (25Ξ)-24ξ-chloro-27-hydroxy-3,7,12-trioxo-5β-cholestanoic acid-(26)

: 64-19-7
acetic acid

chromium (VI)-oxide: chromium (VI)-oxide

: 81-23-2
dehydrocholic acid

...Expand

: 19964-67-1
(R)-methyl-4-((5R,8R,9S,10S,13R,14S,17R)-3,3-dimethoxy-10,13-dimethyl-7,12-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

ethanolic alkaline solution: ethanolic alkaline solution

: 81-23-2
dehydrocholic acid

: 3.3-bis-(4-acetylamino-phenylsulfanyl)-7.12-dioxo-5β-cholanoic acid-(24)

methanol. KOH-solution: methanol. KOH-solution

: 81-23-2
dehydrocholic acid

: C28H35O10(3-)*3Na(1+)

: 145-41-5
Biliton

A: C32H42O15

B: C32H42O15

C: 623552-24-9
C28H38O10

D: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With sulfuric acid; water In ethyl acetate pH=1 - 5;

...Expand

: C28H40O7

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 1.2: 0.5 h / 15 °C 2.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 3.1: sodium hydroxide / methanol / 2 h / 60 °C 4.1: Jones reagent / acetone / 20 °C View Scheme

: C32H46O8

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 2: sodium hydroxide / methanol / 2 h / 60 °C 3: Jones reagent / acetone / 20 °C View Scheme

: C32H50O8

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 2 h / 60 °C 2: Jones reagent / acetone / 20 °C View Scheme

: 71883-64-2
cholic acid

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
With Jones reagent In acetone at 20℃;	20 mg

: 633-34-1
androst-4,6-diene-3,17-dione

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 5 °C 2.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C 4.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark 5.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 6.2: 2 h / 70 °C / Inert atmosphere 7.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 8.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 9.2: -78 - 15 °C 10.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 10.2: 0.5 h / 15 °C 11.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 12.1: sodium hydroxide / methanol / 2 h / 60 °C 13.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 5 °C
2.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr
3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C
4.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark
5.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
6.2: 2 h / 70 °C / Inert atmosphere
7.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
8.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
9.2: -78 - 15 °C
10.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
10.2: 0.5 h / 15 °C
11.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
12.1: sodium hydroxide / methanol / 2 h / 60 °C
13.1: Jones reagent / acetone / 20 °C
View Scheme

: 50788-88-0
6α,7α-dihydrooxireno<6,7>androst-4-ene-3,17-dione

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C 3.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark 4.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 5.2: 2 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 7.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 8.2: -78 - 15 °C 9.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 9.2: 0.5 h / 15 °C 10.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 11.1: sodium hydroxide / methanol / 2 h / 60 °C 12.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr
2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C
3.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark
4.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
5.2: 2 h / 70 °C / Inert atmosphere
6.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
7.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
8.2: -78 - 15 °C
9.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
9.2: 0.5 h / 15 °C
10.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
11.1: sodium hydroxide / methanol / 2 h / 60 °C
12.1: Jones reagent / acetone / 20 °C
View Scheme

: 91378-51-7
7α-hydroxy-5β-androstane-3,17-dione

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C 2.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark 3.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 4.2: 2 h / 70 °C / Inert atmosphere 5.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 7.2: -78 - 15 °C 8.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 8.2: 0.5 h / 15 °C 9.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 10.1: sodium hydroxide / methanol / 2 h / 60 °C 11.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C
2.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark
3.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
4.2: 2 h / 70 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
7.2: -78 - 15 °C
8.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
8.2: 0.5 h / 15 °C
9.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
10.1: sodium hydroxide / methanol / 2 h / 60 °C
11.1: Jones reagent / acetone / 20 °C
View Scheme

: 64144-66-7
(3α,5β,7α)-3,7-dihydroxyandrostan-17-one

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark 2.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 3.2: 2 h / 70 °C / Inert atmosphere 4.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 5.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 6.2: -78 - 15 °C 7.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 7.2: 0.5 h / 15 °C 8.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 9.1: sodium hydroxide / methanol / 2 h / 60 °C 10.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark
2.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
3.2: 2 h / 70 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
6.2: -78 - 15 °C
7.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
7.2: 0.5 h / 15 °C
8.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
9.1: sodium hydroxide / methanol / 2 h / 60 °C
10.1: Jones reagent / acetone / 20 °C
View Scheme

: 53-43-0
dehydroepiandrosterone

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 48 h / 0 - 25 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 5 °C 3.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr 4.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C 5.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark 6.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 7.2: 2 h / 70 °C / Inert atmosphere 8.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 9.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 10.2: -78 - 15 °C 11.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 11.2: 0.5 h / 15 °C 12.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 13.1: sodium hydroxide / methanol / 2 h / 60 °C 14.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 14 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 48 h / 0 - 25 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 5 °C
3.1: palladium 10% on activated carbon; hydrogen / pyridine / 12 h / 25 °C / 2585.81 Torr
4.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 5 °C
5.1: toluene-4-sulfonic acid / toluene / 2 h / 120 °C / Dean-Stark
6.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
7.2: 2 h / 70 °C / Inert atmosphere
8.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
9.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
10.2: -78 - 15 °C
11.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
11.2: 0.5 h / 15 °C
12.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
13.1: sodium hydroxide / methanol / 2 h / 60 °C
14.1: Jones reagent / acetone / 20 °C
View Scheme

: C25H36N2O2

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere 2.2: 2 h / 70 °C / Inert atmosphere 3.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 5.2: -78 - 15 °C 6.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 6.2: 0.5 h / 15 °C 7.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 8.1: sodium hydroxide / methanol / 2 h / 60 °C 9.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium L-ascorbate; oxygen; tetrakis(actonitrile)copper(I) hexafluorophosphate / acetone; methanol / 2.17 h / 25 - 50 °C / 775.74 Torr
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 70 °C / Inert atmosphere
2.2: 2 h / 70 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
5.2: -78 - 15 °C
6.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
6.2: 0.5 h / 15 °C
7.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
8.1: sodium hydroxide / methanol / 2 h / 60 °C
9.1: Jones reagent / acetone / 20 °C
View Scheme

: C21H34O3

: 81-23-2
dehydrocholic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 3.2: -78 - 15 °C 4.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C 4.2: 0.5 h / 15 °C 5.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr 6.1: sodium hydroxide / methanol / 2 h / 60 °C 7.1: Jones reagent / acetone / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: dmap; triethylamine / dichloromethane / 7 h / 25 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 15 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
3.2: -78 - 15 °C
4.1: sodium hydride / tetrahydrofuran / 0.17 h / 15 °C
4.2: 0.5 h / 15 °C
5.1: hydrogen; palladium on activated charcoal / ethanol / 4 h / 25 °C / 2585.81 Torr
6.1: sodium hydroxide / methanol / 2 h / 60 °C
7.1: Jones reagent / acetone / 20 °C
View Scheme

: 81-23-2
dehydrocholic acid

: 108-98-5
thiophenol

: 69577-96-4
(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanethioic acid S-phenyl ester

Conditions

Conditions	Yield
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;	95%
(i) Me2NPOCl2, Et3N, (ii) /BRN= 506523/; Multistep reaction;

: 81-23-2
dehydrocholic acid

: ferric dehydroxycholate

Conditions

Conditions	Yield
With iron(III) chloride; sodium hydroxide In water at 35℃; pH=8;	95%

: 81-23-2
dehydrocholic acid

: 74-88-4
methyl iodide

: 7727-82-4
methyl 3,7,12-trioxo-5β-cholan-24-oate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	94%

: 67-56-1
methanol

: 81-23-2
dehydrocholic acid

: 7727-82-4
methyl 3,7,12-trioxo-5β-cholan-24-oate

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 5h;	93%
With N-Bromosuccinimide at 70℃; for 1h; Time;	89%
With sulfuric acid
toluene-4-sulfonic acid In benzene Heating;

: 81-23-2
dehydrocholic acid

: 2304-91-8
3,12-diketo-7α-hydroxy-5β-cholan-24-oic acid

Conditions

Conditions	Yield
With potassium phosphate; D-glucose; diothiothreitol In ethanol for 9h; Ambient temperature; NADH, 7α-hydroxysteroid dehydrogenase, glucose dehydrogenase; pH 6.8;	91%
Multi-step reaction with 2 steps 1: 30 h / Heating 2: NaBH4, 5percent aq. NaOH / 1 h / Ambient temperature View Scheme

: 14174-09-5
dibenzo-24-crown ether

: 81-23-2
dehydrocholic acid

: N-[4-(hydroxymethyl)benzyl]-3,5-dimethylbenzylammonium hexafluorophosphate

: C41H53NO5*C24H32O8*F6P(1-)*H(1+)

Conditions

Conditions	Yield
With tributylphosphine; dicyclohexyl-carbodiimide In chloroform at 0℃; for 3h;	91%

...Expand

: 81-23-2
dehydrocholic acid

: (2-(4-phenyl-1H-imidazol-1-yl)phenyl)methanol

: C40H46N2O5

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;	91%

: 81-23-2
dehydrocholic acid

: 2,2,2,-trichloroethoxycarbonyl azide

: 2,2,2-trichloroethyl ((R)-3-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)carbamate

Conditions

Conditions	Yield
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube;	91%

: 81-23-2
dehydrocholic acid

: 81873-91-8
3α,7β-dihydroxy-12-oxo-5β-cholane-24-oic acid

Conditions

Conditions	Yield
With potassium phosphate; NAD; sodium formate; NADPH at 24℃; for 12h; pH=6; Enzymatic reaction;	90.6%
With glucose dehydrogenase; D-glucose; NAD-dependent 3α-hydroxysteroid dehydrogenase from Pseudomonas testosteroni; NADP-dependent 7β-hydroxysteroid dehydrogenase from Collinsella aerofaciens; NADPH; NADH; magnesium chloride In aq. buffer at 25℃; for 19h; pH=8; Kinetics; Catalytic behavior; pH-value; Time; Enzymatic reaction; stereoselective reaction;	80 g

: 67-56-1
methanol

: 81-23-2
dehydrocholic acid

: 19964-67-1
(R)-methyl-4-((5R,8R,9S,10S,13R,14S,17R)-3,3-dimethoxy-10,13-dimethyl-7,12-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 4h; Reflux;	90%

: 81-23-2
dehydrocholic acid

: 517-33-9
7,12-dioxolitocholic acid

Conditions

Conditions	Yield
With potassium phosphate; formaldehyd; diothiothreitol In ethanol for 12h; Ambient temperature; NADH, 3α-hydroxysteroid dehydrogenase, formate dehydrogenase; pH 6.8;	89%
With acetic acid; platinum Hydrogenation;
With sodium hydroxide; platinum Hydrogenation;

: 14949-00-9
5-amino-1, 3, 4-thiadiazole-2-sulfonamide

: 81-23-2
dehydrocholic acid

: 5-(3,7,12-trioxo-5-β-cholan-24-amido)-1,3,4-thiadiazole-2-sulfonamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	89%
With thionyl chloride In tetrahydrofuran for 12h;	82%

: 81-23-2
dehydrocholic acid

: 633-65-8
berberine chloride

: C24H33O5(1-)*C20H18NO4(1+)

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8;	88%

: 624-76-0
Iodoethanol

: 81-23-2
dehydrocholic acid

: 2-iodoethyl (4R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions

Conditions	Yield
Stage #1: Iodoethanol; dehydrocholic acid With diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Steglich Esterification; Inert atmosphere; Stage #2: With dmap In dichloromethane at 20℃; for 14h; Steglich Esterification;	88%

: 81-23-2
dehydrocholic acid

: 2304-92-9
3,7-diketo-12α-hydroxy-5β-cholan-24-oic acid

Conditions

Conditions	Yield
With potassium phosphate; D-glucose; diothiothreitol In ethanol for 26h; Ambient temperature; NADPH, 12α-hydroxysteroid dehydrogenase, glucose dehydrogenase; pH 6.8;	87%

: 81-23-2
dehydrocholic acid

: 3615-35-8
3β-hydroxy-7,12-diketo-5β-cholan-24-oic acid

Conditions

Conditions	Yield
With potassium phosphate; formaldehyd; diothiothreitol In ethanol for 25h; Ambient temperature; NADH, 3β-hydroxysteroid dehydrogenase, formate dehydrogenase; pH 6.8;	86%

: 81-23-2
dehydrocholic acid

: 102649-81-0
7β-hydroxy-3,12-dioxo-5β-cholan-24-oic acid

Conditions

Conditions	Yield
With potassium phosphate; D-glucose; diothiothreitol In ethanol for 30h; Ambient temperature; NADPH, 7β-hydroxysteroid dehydrogenase, glucose dehydrogenase; pH 6.8;	86%

: 81-23-2
dehydrocholic acid

: 20667-12-3
silver(l) oxide

: 623935-15-9
silver dehydrocholate

Conditions

Conditions	Yield
In water for 5 - 6h; Heating / reflux;	86%

: 81-23-2
dehydrocholic acid

: 149-73-5
trimethyl orthoformate

A: (R)-methyl-4-((5S,8R,9S,10S,13R,14S,17R)-3,3,7,7-tetramethoxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

B: 19964-67-1
(R)-methyl-4-((5R,8R,9S,10S,13R,14S,17R)-3,3-dimethoxy-10,13-dimethyl-7,12-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions

Conditions	Yield
Stage #1: dehydrocholic acid With toluene-4-sulfonic acid In methanol for 4h; Reflux; Stage #2: trimethyl orthoformate at 40℃; for 4.2h; Temperature;	A 84% B 7%

...Expand

: 81-23-2
dehydrocholic acid

: acido 3β-amino-7,12-dicheto-5β-colanico

Conditions

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol Ambient temperature;	82%

: 81-23-2
dehydrocholic acid

: 98-80-6
phenylboronic acid

: 5739-38-8
1-(4-methoxyphenyl)-3-phenylpropan-1-one

Conditions

Conditions	Yield
With P(p-CH3OC6H4)3; 2,2-dimethylpropanoic anhydride In tetrahydrofuran; water at 60℃; for 16h;	81%

: 81-23-2
dehydrocholic acid

: 98-80-6
phenylboronic acid

: (8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxo-5-phenylpentan-2-yl)dodecahydro-3H-cyclopenta[a]phenanthrene-3,7,12(2H,4H)-trione

Conditions

Conditions	Yield
With P(p-CH3OC6H4)3; 2,2-dimethylpropanoic anhydride In tetrahydrofuran; water at 60℃; for 16h;	81%

: 81-23-2
dehydrocholic acid

: 593-51-1
methylamine hydrochloride

: (4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-methylpentanamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	80%

: 81-23-2
dehydrocholic acid

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 5β-cholanic acid-3,7,12-trione 3'-azido-3'-deoxythymidin-5'-yl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 72h;	78%

: 98-00-0
(2-furyl)methyl alcohol

: 81-23-2
dehydrocholic acid

: furan-2-ylmethyl 3,7,12-trioxocholanoate

Conditions

Conditions	Yield
Stage #1: (2-furyl)methyl alcohol; dehydrocholic acid With dmap In dichloromethane at 0℃; for 0.5h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃;	76.7%

: 81-23-2
dehydrocholic acid

: 100-51-6
benzyl alcohol

: benzyl 3,7,12-trioxocholanoate

Conditions

Conditions	Yield
Stage #1: dehydrocholic acid; benzyl alcohol With dmap In dichloromethane at 0℃; for 0.5h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃;	76.5%

: 495-76-1
piperonol

: 81-23-2
dehydrocholic acid

: 3,4-methylenedioxybenzyl 3,7,12-trioxocholanoate

Conditions

Conditions	Yield
Stage #1: piperonol; dehydrocholic acid With dmap In dichloromethane at 0℃; for 0.5h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃;	75.6%

Dehydrocholic acid Chemical Properties

IUPAC Name: (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic Acid
Formula: C₂₄H₃₄O₅
Molecular weight: 402.52 g/mol
The Molecular Structure of Dehydrocholic acid (CAS NO.81-23-2):

Density: 1.172 g/cm³
Melting Point: 238-240 °C
Flash Point: 319.5 °C
Boiling Point: 581.5 °C at 760 mmHg
Index of Refraction: 1.534
Molar Refractivity: 106.86 cm³
Molar Volume: 343.3 cm³
Surface Tension: 45.4 dyne/cm
Enthalpy of Vaporization: 95 kJ/mol
Vapour Pressure: 4.96E-15 mmHg at 25 °C
Solubility Ethanol: 10 mg/mL
Appearance: white to off-white amorphous powder
XLogP3-AA: 2.6
H-Bond Donor: 1
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Tautomer Count: 18
Exact Mass: 402.240624
MonoIsotopic Mass: 402.240624
Topological Polar Surface Area: 88.5
Heavy Atom Count: 29
Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
InChI: InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
InChIKey: OHXPGWPVLFPUSM-KLRNGDHRSA-N
EINECS: 201-335-7
Product Categories: Bile Acids;Biochemistry;Steroids

Dehydrocholic acid Uses

Dehydrocholic acid (CAS NO.81-23-2) can be used as a gallbladder drug and very useful for the gallbladder and biliary tract dysfunction, post-cholecystectomy syndrome, chronic cholecystitis and cholelithiasis and chronic hepatitis.

Dehydrocholic acid Production

Dehydrocholic acid is manufactured by the oxidation of cholic acid.

Dehydrocholic acid Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	1492mg/kg (1492mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Japanese Journal of Pharmacology. Vol. 22, Pg. 235, 1972.
mouse	LD50	oral	3100mg/kg (3100mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 857, 1962.
mouse	LD50	subcutaneous	1620mg/kg (1620mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958.
rat	LD50	intramuscular	1500mg/kg (1500mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 244, 1954.
rat	LD50	intravenous	750mg/kg (750mg/kg)		Drugs in Japan Vol. 6, Pg. 495, 1982.
rat	LD50	oral	4gm/kg (4000mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958.

Dehydrocholic acid Consensus Reports

Reported in EPA TSCA inventory.

Dehydrocholic acid Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: FZ2300000
Moderately toxic by ingestion, intravenous, intramuscular, and subcutaneous routes. When heated to decomposition it emits acrid smoke and fumes.

Dehydrocholic acid Specification

The chemical synonyms of Dehydrocholic acid (CAS NO.81-23-2) are 3,7,12-Triketo-5beta-cholanoic acid ; 3,7,12-Triketocholanic acid ; 3,7,12-Trioxo-5-beta-cholan-24-oic acid ; 3,7,12-Trioxo-5beta-cholan-24-oic acid ; 3,7,12-Trioxo-5beta-cholanic acid ; 3,7,12-Trioxocholanic acid ; 4-10-00-03478 (Beilstein Handbook Reference) ; 5beta-Cholanic acid, 3,7,12-trioxo- ; Acide dehydrocholique ; Acide dehydrocholique [French] ; Acide dehydrocholique [INN-French] ; Acido dehidrocolico ; Acido dehidrocolico [INN-Spanish] ; Acido dehidrocolico [Spanish] ; Acido deidrocolico ; Acido deidrocolico [DCIT] ; Acidum dehydrocholicum ; Acidum dehydrocholicum [INN-Latin] ; Chologon ; DHC ; Decholin ; Dee-Co ; Dehychol ; Erebile ; Felacrinos ; Hykolex ; Ketochol ; Ketocholanic acid ; Khologon ; NSC 8796 ; Novocolin ; Oxycholin ; Procholon ; Sanocholen ; Triketocholanic acid ; UNII-NH5000009I . Dehydrocholic acid (CAS NO.81-23-2) is dissolved in sodium hydroxide, slightly soluble in chloroform, slightly soluble in ethanol, practically insoluble in water.

Product Name

Dehydrocholic acid

Synthetic route

Dehydrocholic acid Chemical Properties

Dehydrocholic acid Uses

Dehydrocholic acid Production

Dehydrocholic acid Toxicity Data With Reference

Dehydrocholic acid Consensus Reports

Dehydrocholic acid Safety Profile

Dehydrocholic acid Specification

Related Products

Hot Products