481-21-0

Basic information

• Product Name: 5α-Cholestane
• Synonyms: ALPHA, ALPHA, ALPHA 20R-CHOLESTANE;(5A)-CHOLESTANE;5ALPHA-CHOLESTANE;CHOLESTANE;CHOLESTANE, (5A-)-;CHOLESTANE(5-ALPHA);10,13-Dimethyl-17-(1',5'-dimethylhexyl)-hexadecahydrocyclopenta(a)phenanthrene;28,29,30-Trinorlanostane
• CAS NO: 481-21-0
• Molecular Formula: C27H48
• Molecular Weight: 372.67
• EINECS: 207-562-8
• Product Categories: CHLipids;Cholesterol and DerivativesOther Lipid Related Products;SterolsFood&Beverage Standards;Alphabetic;C;FA/FAME/Lipids/Steroids;Lipid Analytical Standards;Cholesterol and Derivatives;Lipids;Sterols;Cholesterol and DerivativesAsymmetric Synthesis;Chiral Building Blocks;Complex Molecules
• Mol File: 481-21-0.mol
• Article Data: 73

Chemical Properties

• Melting Point: 78-80 °C
• Boiling Point: 250 °C (1 mmHg)
• Flash Point: 210.3 °C
• Appearance: White/Crystalline Powder
• Density: 0.9090
• Vapor Pressure: 1.47E-07mmHg at 25°C
• Refractive Index: 1.4887
• Storage Temp.: room temp
• Solubility: Do you have solubility information on this product that you woul
• Merck: 13,2219
• BRN: 2051806
• CAS DataBase Reference: 5α-Cholestane(CAS DataBase Reference)
• NIST Chemistry Reference: 5α-Cholestane(481-21-0)
• EPA Substance Registry System: 5α-Cholestane(481-21-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-40-48/20/22-67-36/38-20-63
• Safety Statements: 24/25-36/37-26
• RIDADR: UN 1888 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 481-21-0(Hazardous Substances Data)

Usage

Description

5α-Cholestane is a sterol that has been found in dust samples from urban and rural paved and agricultural and public unpaved roads. It has been used as an internal standard for the quantification of phytosterols by HPLC-MS/MS and fecal sterols by GC-FID and GC-MS.

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 481-21-0 differently. You can refer to the following data:
1. α-Cholestane is the trans-decalin homolog of Coprostane.
2. 5α-Cholestane was used as standard in cholesterol analysis by GC and HPLC.

Definition

ChEBI: The 5alpha-stereoisomer of cholestane.

Biochem/physiol Actions

5α-Cholestane is a sterol produced endogenously from cholesterol and has been isolated from human feces. It is derived from cholesterol by the action of intestinal microorganisms. Derivatives of 5α-cholestane in plants are called Brassinosteroids that selectively activate the PPI3K/Akt pathway.

Purification Methods

Crystallise 5-cholestane from Et2O/EtOH or EtOAc. [Ruzicka et al. Helv Chim Acta 16 327 1933, Beilstein 5 III 1132, 5 IV 1227.]

InChI:InChI=1/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20?,21-,22?,23?,24?,25?,26+,27-/m1/s1

Synthetic route

3-bromocholestane (97100-53-3) → cholestane (481-21-0)

Conditions	Yield
With triethyl borane; 1,1,2,2-tetraphenyldisilane In ethanol for 4h; Ambient temperature;	99%

3β-phenylselenenyl-5α-cholestane (75809-01-7) → cholestane (481-21-0)

Conditions	Yield
With triethyl borane; 1,1,2,2-tetraphenyldisilane In ethyl acetate at 20℃; for 1h; Reduction;	99%

cholest-2-ene (13901-19-4, 15910-23-3, 570-73-0) → cholestane (481-21-0)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating;	99%

(3R,5S,8R,9S,10S,13R,14S,17R)-3-bromo-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene (2309-03-7) → cholestane (481-21-0)

Conditions	Yield
With water; zinc In acetonitrile at 80℃; for 30h; Sealed tube; Inert atmosphere;	97%
With water; zinc In acetonitrile at 80℃; for 30h; Inert atmosphere; Sealed tube;	97%
With triethylsilane; 2,3,3,4,4,5-hexamethyl-2-hexanethiol In cyclohexane Heating;	86%

5α-cholestan-3β-yl adamantane-1-carboxylate (73532-35-1) → 1-adamantanemethanol (770-71-8) + 1-Adamantanecarboxylic acid (828-51-3) + cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran at 46℃; further reagent;	A 2% B 96% C 43% D 57%
With lithium; ethylamine at 17℃; further reagent;	A 65% B 4% C 4% D 94%

(5α-cholestan-3β-yl)-methyl ether (1981-90-4) → cholestane (481-21-0)

Conditions	Yield
With triethylsilane; (η4-1,5-cyclooctadiene)bis(triphenylphosphine)iridium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In dichloromethane-d2 at 50℃; for 2h; Reagent/catalyst;	95%

O-cholestan-3β-yl-O'-(4-fluorophenyl)thionocarbonate (130534-82-6) → cholestane (481-21-0)

Conditions	Yield
With triethyl borane; diphenylsilane; oxygen In hexane; benzene at 80℃; for 0.5h;	93%
With triethylsilane; Perbenzoic acid for 1.5h; Heating;	93%
With 2,2'-azobis(isobutyronitrile); phosphoric acid In 1,4-dioxane Heating;	93%
With Perbenzoic acid; phenylsilane In toluene for 1.33333h; Heating;	87%

5α-cholestan-3β-yl adamantane-1-carboxylate (73532-35-1) → 1-adamantanemethanol (770-71-8) + N-ethyl-1-adamantanecarboxamide (1501-94-6) + cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With lithium; ethylamine In tetrahydrofuran at -73℃; further reagent;	A 69% B 0.5% C 1% D 93%

Thiocarbonic acid O-[(5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester O-(4-fluoro-phenyl) ester → cholestane (481-21-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; triethylamine In 1,4-dioxane; water for 2.5h; Heating;	93%

ethylamine (75-04-7) + 5α-cholestan-3β-yl adamantane-1-carboxylate (73532-35-1) → 1-Adamantanecarboxylic acid (828-51-3) + N-ethyl-1-adamantanecarboxamide (1501-94-6) + cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With lithium In tetrahydrofuran at 17℃; Further byproducts given;	A 4% B 92% C 7% D 85%

5α-cholestane-3β,6β-diyl bis-(adamantane-1-carboxylate) (73532-34-0) → 1-Adamantanecarboxylic acid (828-51-3) + cholestane (481-21-0) + Cholestanol (80-97-7) + 5α-cholestan-6β-ol (35490-51-8)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine Further byproducts given;	A 92% B 45% C 27% D 6%

Thiocarbonic acid O-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester O-phenyl ester (145345-67-1) → cholestane (481-21-0)

Conditions	Yield
With triethylsilane; dibenzoyl peroxide at 110℃; for 3h;	91%
With 5,10-dihydro-silanthrene; ABIN In cyclohexane at 80℃; for 1h;	85%

1-(cholestan-3β-yloxymethyl)pyrrolidin-2-one → cholestane (481-21-0)

Conditions	Yield
With 2,2-bis(tert-butylperoxy)butane; tri-tert-butoxysilanethiol In octane for 4h; Heating;	91%

1-(5α-cholestan-3β-yloxythiocarbonyl)imidazole (57700-97-7) → cholestane (481-21-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); 2,2-di-Me-5-[3-(diphenylstannyl)propyl]-1,3-dioxolan-4-one In toluene for 10h; Heating;	91%
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo<5.4.0>undec-7-ene 2: 75 percent / Bu3SnH / azoisobutyronitrile / benzene / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo<5.4.0>undec-7-ene 2: 29 percent / Bu3SnH / azoisobutyronitrile / benzene / 80 °C View Scheme

3β-(methylthio)thiocarbonyloxy-5α-cholestane (5211-17-6) → cholestane (481-21-0)

Conditions	Yield
With HSiPh3 In 1,4-dioxane at 60℃; for 2.5h;	90%
With triethylsilane; bis(1-methyl-1-phenylethyl)peroxide; 2,3,3,4,4,5-hexamethyl-2-hexanethiol In octane at 140℃; for 4h; also with di-t-butyl peroxide (DTBP) (initiator);	86%
With 2,2'-azobis(isobutyronitrile); Tris(trimethylsilyl)methane In benzene at 80℃; for 12h;	86%
With tri-n-butyl-tin hydride In benzene-d6 at 80℃;	61%
Multi-step reaction with 3 steps 2: 31 percent / phenylseleninic acid / tetrahydrofuran; diethyl ether / -78 °C 3: 49 percent / t-butylmercaptan / toluene / 1 h / Heating View Scheme

5α-cholestan-3β-yl adamantane-1-carboxylate (73532-35-1) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With sodium-potassium alloy; 18-crown-6 ether; tert-butylamine In tetrahydrofuran at 25℃; further reagent;	A 90% B 6%

dihydrocholesterone (566-88-1) → cholestane (481-21-0)

Conditions	Yield
With zinc In acetic acid at 15℃; for 0.25h; ultrasonic irradiation;	89%
With chloro-trimethyl-silane; zinc In dichloromethane; isopropyl alcohol at 0℃; for 3h; Clemmensen reaction;	86%
With hydrogenchloride; amalgamated zinc; acetic acid

O-cholestanyl-S-methyl dithiocarbonate (5211-17-6, 16734-07-9, 70286-38-3) → cholestane (481-21-0)

Conditions	Yield
With triethylsilane; 2,3,3,4,4,5-hexamethyl-2-hexanethiol; bis(1-methyl-1-phenylethyl)peroxide In octane for 4h; Mechanism; Product distribution; Heating;	89%

trifluoroacetoxy-3β 5α-cholestane (2839-20-5) → cholestane (481-21-0)

Conditions	Yield
With di-tert-butyl peroxide; diphenylsilane at 140℃; for 15h;	87%

3β-(NN-diethylaminothiocarbonyloxy)-5α-cholestane (73532-43-1) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature;	A 86% B 8%
With 18-crown-6 ether In tetrahydrofuran; 1,2-dimethoxyethane	A 74% B 14%
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature; further conditions;	A 58% B 40%

3β-Cholestanyl phenyl telluride → cholestane (481-21-0)

Conditions	Yield
With triethyl borane; Tetrakis-(p-fluorphenyl)-disilan In ethyl acetate at 20℃; for 1h; Reduction;	85%

(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate (3381-51-9) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With sodium tetrahydroborate In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide for 15h; Irradiation;	A 14% B 84%
With sodium cyanide In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide for 15h; Irradiation;	A 21% B 75%
With potassium Sodium; tert-butyl alcohol; 18-crown-6 ether In tetrahydrofuran Ambient temperature; var. cat.: tris(3,6-dioxaheptyl)amine;	A 8 % Chromat. B 72%
With potassium Sodium; tert-butyl alcohol; 18-crown-6 ether In tetrahydrofuran Ambient temperature; var. cat.: tris(3,6-dioxaheptyl)amine;	A 8% B 72 % Chromat.
for 15h; Product distribution; Mechanism; Irradiation; different solvents and additives;

3β-phenylselenenyl-5α-cholestane (75250-34-9) → cholestane (481-21-0)

Conditions	Yield
With triphenylstannane In benzene at 120℃; for 0.5h;	84%

3β-(isopropyloxycarbonyloxy)-5α-cholestane (78916-32-2) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature;	A 12% B 83%

N-methyl-N-<2-(NN-dimethylamino)ethyl>aminothiocarbonyloxy-5α-cholestane (73532-44-2) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature;	A 83% B 12%

O-cholestan-3β-yl-O'-(4-fluorophenyl)thionocarbonate (130534-82-6) → cholestane (481-21-0) + O-cholestanyl thionoformate (57701-04-9)

Conditions	Yield
With triethyl borane; diphenylsilane; oxygen In hexane; benzene at 25℃; for 0.5h;	A 82% B 8%

neocholesteryl bromide (51154-61-1) → cholestane (481-21-0)

Conditions	Yield
With potassium Sodium; tert-butyl alcohol; Tris(3,6-dioxaheptyl)amine In tetrahydrofuran Ambient temperature; var. cat.: 18-crown-6;	80%

3β-(NN-diethylaminocarbonyloxy)-5α-cholestane (78916-31-1) → cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature;	A 4% B 80%

3β-formyloxy-5αH-cholestane (10437-24-8) → formic acid (64-18-6) + cholestane (481-21-0) + Cholestanol (80-97-7)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide; water for 5h; Irradiation;	A n/a B 79% C 19%

N-(3β-cholestanyloxythiocarbonyl)imidazole → cholestane (481-21-0)

Conditions	Yield
	79%

cholestane (481-21-0) → α-cholestane-d48

Conditions	Yield
With d8-isopropanol; 5% rhodium-on-charcoal; 10% Pt/activated carbon; water-d2 In cyclohexane at 120℃; for 24h; Sealed tube;	90%

Upstream product

• 97100-53-3 3-bromocholestane 
• 14582-65-1 3β-phenylthio-5α-cholestane 
• 57-88-5 cholesterol 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 604-35-3 Cholesteryl acetate 
• 71-41-0 pentan-1-ol 
• 101470-39-7 4α-acetoxy-5α-cholestan-3-one; compound of 4α-acetoxy-5α-cholestanone-(3) with 2α-acetoxy-5α-cholestanone-(3) 
• 7803-57-8 hydrazine hydrate 
• 57700-97-7 1-(5α-cholestan-3β-yloxythiocarbonyl)imidazole 
• 5211-17-6 β-Cholestanyl-S-methyl-xanthat 
• 64-17-5 ethanol 
• 106094-56-8 hydrazone of 3-cholestanone 
• 141-52-6 sodium ethanolate 

Downstream Products

• 963-74-6 5alpha-androstan-17-one 
• 468-98-4 5α-cholan-24-oic acid 
• 17669-94-2 cholestane-3β-thiol 
• 1055-44-3 cholestane-2α-thiol 
• 1055-19-2 (3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3-thiol 
• 358731-18-7 α-cholestane-d₄₈ 
• 5847-30-3 3α-chloro-5α-cholestane 
• 1474-58-4 3β-chloro-5α-cholestane 
• 4405-84-9 2α-chlorocholestane 

Relevant articles and documents

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ASTEROSAPONIN P1 FROM THE STARFISH PATIRIA PECTINIFERA

A novel steroidal glycoside has been isolated from the starfish Patiria pectinifera and its structure was determined as 5'-O-sulfate 24-(α-3-O-methyl-L-arabinofuranosyl)-3β,6α,8β,15α,24ξ-pentaoxy-5α-cholestane.

Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts

A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.

Method for hydrogenolysis of halides

The invention discloses a method for hydrogenolysis of halides. The invention discloses a preparation method of a compound represented by a formula I. The preparation method comprises the following step: in a polar aprotic solvent, zinc, H2O and a compound represented by a formula II are subjected to a reaction as shown in the specification, wherein X is halogen; Y is -CHRR or R; hydrogenin H2O exists in the form of natural abundance or non-natural abundance. According to the preparation method, halide hydrogenolysis can be simply, conveniently and efficiently achieved through a simple and mild reaction system, and good functional group compatibility and substrate universality are achieved.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.