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  • 5255-17-4 Structure
  • Basic information

    1. Product Name: 3BETA-HYDROXY-DELTA5-CHOLENIC ACID
    2. Synonyms: CHOLESTEROL TRISNORCHOLENIC ACID;5-CHOLENIC ACID-3BETA-OL;5-CHOLENIC ACID-3-BETA-HYDROXY;3BETA-HYDROXY-5-CHOLEN-24-OIC ACID;3-BETA-HYDROXYCHOLENIC ACID;3BETA-HYDROXY-DELTA5-CHOLENIC ACID;3-beta-hydroxychol-5-en-24-oic acid;5-cholenic acid-3B-ol
    3. CAS NO:5255-17-4
    4. Molecular Formula: C24H38O3
    5. Molecular Weight: 374.56
    6. EINECS: N/A
    7. Product Categories: Bile Acids;Biochemistry;Steroids
    8. Mol File: 5255-17-4.mol
    9. Article Data: 4
  • Chemical Properties

    1. Melting Point: 232°C
    2. Boiling Point: 522.8 °C at 760 mmHg
    3. Flash Point: 284.1 °C
    4. Appearance: /
    5. Density: 1.11 g/cm3
    6. Vapor Pressure: 4.99E-17mmHg at 25°C
    7. Refractive Index: -39.5 ° (C=1, Dioxane)
    8. Storage Temp.: Refrigerator
    9. Solubility: Dioxane (Slightly, Sonicated), DMF (Slightly), DMSO (Slightly, Heated,. Sonicate
    10. PKA: 4.76±0.10(Predicted)
    11. CAS DataBase Reference: 3BETA-HYDROXY-DELTA5-CHOLENIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: 3BETA-HYDROXY-DELTA5-CHOLENIC ACID(5255-17-4)
    13. EPA Substance Registry System: 3BETA-HYDROXY-DELTA5-CHOLENIC ACID(5255-17-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5255-17-4(Hazardous Substances Data)

5255-17-4 Usage

Description

3BETA-HYDROXY-DELTA5-CHOLENIC ACID, also known as Cholic Acid, is a monohydroxy bile acid derived from the oxidation of cholesterol. It plays a crucial role in the metabolism of primary bile acids, such as lithocholic acid and chenodeoxycholic acid, in humans. Cholic Acid is formed through the 7α-hydroxylation of 27-hydroxycholesterol and serves as a precursor in the biosynthesis of chenodeoxycholic acid. Its levels are elevated in patients with neonatal liver disease and those with intrahepatic and extrahepatic cholestasis.

Uses

Used in Pharmaceutical Industry:
3BETA-HYDROXY-DELTA5-CHOLENIC ACID is used as a therapeutic agent for treating various liver-related conditions, such as neonatal liver disease and cholestasis. Its application is based on its role in bile acid metabolism and its ability to alleviate symptoms associated with these conditions.
Used in Diagnostics:
In the medical field, 3BETA-HYDROXY-DELTA5-CHOLENIC ACID is used as a diagnostic marker to identify and monitor the progression of liver diseases, particularly in newborns and infants. The increased levels of this bile acid in patients with liver disorders help healthcare professionals in diagnosing and managing these conditions effectively.
Used in Research:
3BETA-HYDROXY-DELTA5-CHOLENIC ACID is also utilized in scientific research to study the metabolism of bile acids and their role in various physiological processes. This knowledge contributes to the development of new therapeutic strategies and a better understanding of liver function and related diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 5255-17-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,5 and 5 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 5255-17:
(6*5)+(5*2)+(4*5)+(3*5)+(2*1)+(1*7)=84
84 % 10 = 4
So 5255-17-4 is a valid CAS Registry Number.
InChI:InChI=1/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)

5255-17-4 Well-known Company Product Price

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  • TCI America

  • (H0521)  3β-Hydroxy-Δ5-cholenic Acid  >97.0%(T)

  • 5255-17-4

  • 1g

  • 1,990.00CNY

  • Detail
  • TCI America

  • (H0521)  3β-Hydroxy-Δ5-cholenic Acid  >97.0%(T)

  • 5255-17-4

  • 5g

  • 6,990.00CNY

  • Detail
  • Sigma

  • (C2650)  5-Cholenic acid-3β-ol  ≥98%

  • 5255-17-4

  • C2650-1G

  • 6,780.15CNY

  • Detail

5255-17-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3BETA-HYDROXY-DELTA5-CHOLENIC ACID

1.2 Other means of identification

Product number -
Other names Cholenic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5255-17-4 SDS

5255-17-4Synthetic route

3β-acetoxy-5-cholenic acid
19462-13-6

3β-acetoxy-5-cholenic acid

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol for 4h; Ambient temperature;89.6%
methyl 5-cholenoate
20231-57-6

methyl 5-cholenoate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran Inert atmosphere;80%
methyl 3α,6α-ditosyloxy-5β-cholan-24-oate
1184-20-9

methyl 3α,6α-ditosyloxy-5β-cholan-24-oate

potassium acetate
127-08-2

potassium acetate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
With N,N-dimethyl-formamide Erwaermen des Reaktionsprodukts mit methanol. KOH;
Hyodeoxycholic Acid
83-49-8

Hyodeoxycholic Acid

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

3β-acetoxy-5α,6β-dibromocholestane
514-50-1

3β-acetoxy-5α,6β-dibromocholestane

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit methanol. Kalilauge;
With chromium(VI) oxide; acetic acid Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit wss. Natronlauge;
3β-hydroxy-24-nor-chol-5-ene-23,23-dicarboxylic acid
111823-89-3

3β-hydroxy-24-nor-chol-5-ene-23,23-dicarboxylic acid

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
at 200℃;
hyodeoxycholic acid-derivative

hyodeoxycholic acid-derivative

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

methyl hyodeoxycholate
2868-48-6

methyl hyodeoxycholate

A

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

B

4-(10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid

4-(10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid

Conditions
ConditionsYield
Stage #1: methyl hyodeoxycholate With pyridine; p-toluenesulfonyl chloride
Stage #2: With potassium acetate In N,N-dimethyl-formamide at 110℃;
Stage #3: With potassium hydroxide In methanol at 110℃;
3β-acetoxy-Δ5-cholenic aldehyde
86476-29-1

3β-acetoxy-Δ5-cholenic aldehyde

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74.2 percent / chromic acid / tetrahydrofuran / 0.17 h / 0 °C
2: 89.6 percent / NaOH (10percent) / methanol / 4 h / Ambient temperature
View Scheme
24,24-ethylenedioxy-Δ5-chol-3β,20-diol
86476-21-3

24,24-ethylenedioxy-Δ5-chol-3β,20-diol

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 94.1 percent / pyridine / 14 h / Ambient temperature
2: 88.5 percent / phosphoryl chloride / pyridine / 16 h / Ambient temperature
3: 96.8 percent / H2 / PtO2 / ethanol / 3 h / Ambient temperature
4: 91.7 percent / HCl (10percent) / acetone / 3 h / Ambient temperature
5: 74.2 percent / chromic acid / tetrahydrofuran / 0.17 h / 0 °C
6: 89.6 percent / NaOH (10percent) / methanol / 4 h / Ambient temperature
View Scheme
24,24-ethylenedioxy-Δ5-chola-3β-acetate
86476-27-9

24,24-ethylenedioxy-Δ5-chola-3β-acetate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91.7 percent / HCl (10percent) / acetone / 3 h / Ambient temperature
2: 74.2 percent / chromic acid / tetrahydrofuran / 0.17 h / 0 °C
3: 89.6 percent / NaOH (10percent) / methanol / 4 h / Ambient temperature
View Scheme
3β-acetoxy-24,24-ethylenedioxychol-Δ5,20(22)-diene
86476-25-7

3β-acetoxy-24,24-ethylenedioxychol-Δ5,20(22)-diene

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96.8 percent / H2 / PtO2 / ethanol / 3 h / Ambient temperature
2: 91.7 percent / HCl (10percent) / acetone / 3 h / Ambient temperature
3: 74.2 percent / chromic acid / tetrahydrofuran / 0.17 h / 0 °C
4: 89.6 percent / NaOH (10percent) / methanol / 4 h / Ambient temperature
View Scheme
24,24-ethylenedioxy-20-hydroxy-Δ5-chola-3β-acetate
86476-23-5

24,24-ethylenedioxy-20-hydroxy-Δ5-chola-3β-acetate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 88.5 percent / phosphoryl chloride / pyridine / 16 h / Ambient temperature
2: 96.8 percent / H2 / PtO2 / ethanol / 3 h / Ambient temperature
3: 91.7 percent / HCl (10percent) / acetone / 3 h / Ambient temperature
4: 74.2 percent / chromic acid / tetrahydrofuran / 0.17 h / 0 °C
5: 89.6 percent / NaOH (10percent) / methanol / 4 h / Ambient temperature
View Scheme
methyl hyodeoxycholate
2868-48-6

methyl hyodeoxycholate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: DMF / Erwaermen des Reaktionsprodukts mit methanol. KOH
View Scheme
3β-acetoxy-23,24-bisnor-chol-5-en-22-yl p-toluenesulfonate
120664-97-3

3β-acetoxy-23,24-bisnor-chol-5-en-22-yl p-toluenesulfonate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: xylene / Erwaermen des Reaktionsprodukts mit KOH in Methanol und Isopropylalkohol
2: 200 °C
View Scheme
Cholesteryl acetate
604-35-3

Cholesteryl acetate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; glacial acetic acid; bromine
2: chromium (VI)-oxide; water containing acetic acid / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit wss. Natronlauge
View Scheme
Multi-step reaction with 2 steps
1: glacial acetic acid; bromine
2: chromium (VI)-oxide; water containing acetic acid / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit wss. Natronlauge
View Scheme
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

acetic anhydride
108-24-7

acetic anhydride

3β-acetoxy-5-cholenic acid
19462-13-6

3β-acetoxy-5-cholenic acid

Conditions
ConditionsYield
With pyridine100%
With acetic acid
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

methyl 5-cholenoate
20231-57-6

methyl 5-cholenoate

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 20℃; for 0.666667h;100%
98%
In diethyl ether; chloroform for 2.5h;77%
methanol
67-56-1

methanol

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester
114011-35-7

3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester

Conditions
ConditionsYield
Stage #1: methanol; 3β-hydroxy-5-cholenoic acid With toluene-4-sulfonic acid at 60℃;
Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole; dmap In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h;
99%
tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate
811442-84-9

tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

C39H68N2O8

C39H68N2O8

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;95%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

3β-hydroxy-5α-cholan-24-oic acid
2276-93-9

3β-hydroxy-5α-cholan-24-oic acid

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 48h; Inert atmosphere;93%
Multi-step reaction with 3 steps
1: hydrogen chloride
2: acetic acid; platinum / Hydrogenation
3: methanol. KOH-solution
View Scheme
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

3β-hydroxy-5-cholenamide
475102-50-2

3β-hydroxy-5-cholenamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With ammonia In tetrahydrofuran; water at 0 - 20℃;
93%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester
120876-14-4

3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane Ambient temperature;92%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

propargyl alcohol
107-19-7

propargyl alcohol

3-hydroxychol-5-en-24-oic acid propargyl ester

3-hydroxychol-5-en-24-oic acid propargyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;90%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

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

N,O-dimethylhydroxylamine*hydrochloride

5-cholenic acid-3β-ol N-methoxy-N-methylamide
219903-24-9

5-cholenic acid-3β-ol N-methoxy-N-methylamide

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;89%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;85%
Stage #1: 3β-hydroxy-5-cholenoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at 20℃; for 6h;
57%
Stage #1: 3β-hydroxy-5-cholenoic acid With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 1h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at 20℃; for 6h;
57%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

diethylamine
109-89-7

diethylamine

N,N-diethyl-3β-hydroxy-5-cholenamide

N,N-diethyl-3β-hydroxy-5-cholenamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: diethylamine In tetrahydrofuran at 0 - 20℃;
88%
formic acid
64-18-6

formic acid

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

3β-Formato-5-cholenic acid
119748-13-9

3β-Formato-5-cholenic acid

Conditions
ConditionsYield
In water at 90 - 95℃; for 3h;87%
tert-butyl 2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethylcarbamate
890091-43-7

tert-butyl 2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethylcarbamate

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

C49H88N2O13

C49H88N2O13

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;86%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

dibutylamine
111-92-2

dibutylamine

N,N-di-n-butyl-3β-hydroxy-5-cholenamide
1450593-71-1

N,N-di-n-butyl-3β-hydroxy-5-cholenamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: dibutylamine In tetrahydrofuran at 0 - 20℃;
85%
L-β-homo-tryptophan
192003-01-3

L-β-homo-tryptophan

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-β-homotryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-β-homotryptophan

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: L-β-homo-tryptophan In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
85%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

C37H76N2O17

C37H76N2O17

C61H112N2O19

C61H112N2O19

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;85%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

dimethyl amine
124-40-3

dimethyl amine

Cholenic acid dimethylamide
79066-03-8

Cholenic acid dimethylamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: dimethyl amine In tetrahydrofuran at 0 - 20℃;
84%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate

tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate

C32H37Cl4NO5

C32H37Cl4NO5

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;84%
L-methionine
63-68-3

L-methionine

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-methionine

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-methionine

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: L-methionine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
83%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

methyl iodide
74-88-4

methyl iodide

methyl 5-cholenoate
20231-57-6

methyl 5-cholenoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;82%
With diethyl ether; silver(l) oxide
With sodium hydroxide 1.) MeOH, 2.) DMF; Yield given. Multistep reaction;
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

propargyl alcohol
107-19-7

propargyl alcohol

prop-2-ynyl 4-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

prop-2-ynyl 4-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;82%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

di-n-propylamine
142-84-7

di-n-propylamine

N,N-di-n-propyl-3β-hydroxy-5-cholenamide
1450593-70-0

N,N-di-n-propyl-3β-hydroxy-5-cholenamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: di-n-propylamine In tetrahydrofuran at 0 - 20℃;
82%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

D-tryptophan
153-94-6

D-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-D-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-D-tryptophan

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: D-tryptophan In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
82%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

methylamine
74-89-5

methylamine

Cholenic acid monomethylamide

Cholenic acid monomethylamide

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: methylamine In tetrahydrofuran at 0 - 20℃;
81%
L-phenylalanine
63-91-2

L-phenylalanine

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-phenylalanine

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-phenylalanine

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: L-phenylalanine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
81%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

L-1-naphthylalanine
55516-54-6

L-1-naphthylalanine

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-3-(α-naphthyl)alanine

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-3-(α-naphthyl)alanine

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: L-1-naphthylalanine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
81%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

5-bromo-DL-tryptophan
6548-09-0, 25197-99-3, 93299-40-2

5-bromo-DL-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-5-bromo-L-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-5-bromo-L-tryptophan

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: 5-bromo-DL-tryptophan In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
80%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

L-Tryptophan
73-22-3

L-Tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-L-tryptophan

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: L-Tryptophan In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
79%
3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

N-(3β-hydroxy-Δ5-cholen-24-oyl)-1-methyl-L-tryptophan

N-(3β-hydroxy-Δ5-cholen-24-oyl)-1-methyl-L-tryptophan

Conditions
ConditionsYield
Stage #1: 3β-hydroxy-5-cholenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: 1-methyl-L-tryptophan In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; chemoselective reaction;
77%

5255-17-4Relevant articles and documents

Marine and semi-synthetic hydroxysteroids as new scaffolds for pregnane X receptor modulation

Sepe, Valentina,Di Leva, Francesco Saverio,D'Amore, Claudio,Festa, Carmen,De Marino, Simona,Renga, Barbara,D'Auria, Maria Valeria,Novellino, Ettore,Limongelli, Vittorio,D'Souza, Lisette,Majik, Mahesh,Zampella, Angela,Fiorucci, Stefano

, p. 3091 - 3115 (2014/07/08)

In recent years many sterols with unusual structures and promising biological profiles have been identified from marine sources. Here we report the isolation of a series of 24-alkylated-hydroxysteroids from the soft coral Sinularia kavarattiensis, acting as pregnane X receptor (PXR) modulators. Starting from this scaffold a number of derivatives were prepared and evaluated for their ability to activate the PXR by assessing transactivation and quantifying gene expression. Our study reveals that ergost-5-en-3β-ol (4) induces PXR transactivation in HepG2 cells and stimulates the expression of the PXR target gene CYP3A4. To shed light on the molecular basis of the interaction between these ligands and PXR, we investigated, through docking simulations, the binding mechanism of the most potent compound of the series, 4, to the PXR. Our findings provide useful functional and structural information to guide further investigations and drug design.

An efficient synthesis of cholanic acids from 20-ketopregnanes

Fukumoto,Suzuki,Nemoto,et al.

, p. 3701 - 3704 (2007/10/02)

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