Cholestan-3-one, (5β)- supplier

Name
5BETA-CHOLESTAN-3-ONE
EINECS 210-003-0
CAS No. 601-53-6
Article Data151
CAS DataBase
Density 0.953 g/cm³
Solubility
Melting Point 62-63 °C
Formula C₂₇H₄₆O
Boiling Point 452.9 °C at 760 mmHg
Molecular Weight 386.662
Flash Point 219.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5β-Cholestan-3-one (8CI);(5β,17β)-17-Octylandrostan-3-one;3-Coprostanone;5β-Cholestanone;5β-Coprostan-3-one;Coprostanone;NSC 119031;
PSA 17.07000
LogP 7.67680

Synthetic route

: 80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5
Coprostanol

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With sodium bromate; ruthenium trichloride; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 1.5h;	98%
With oxygen; acetaldehyde; ruthenium trichloride; cobalt(II) acetate Ambient temperature; other reagent: peracetic acid, other catalyst: RuCl3*nH2O;	98%
With tert.-butylhydroperoxide; pentafluorobenzeneseleninic acid In benzene for 4h; Heating;	90%

: 25328-53-4
3,3-ethylenedioxy-5β-cholestane

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With Montmorillonite K 10; water In acetone for 3h; Heating;	97%

: 39854-45-0
1,3-dithiane of cholestanone

A: 557-22-2
1,2-dithiolane

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
With tetrafluoroboric acid; tris(2,2'-bipyridine)iron(III) perchlorate In tetrahydrofuran; water; acetonitrile for 0.0833333h; Ambient temperature;	A n/a B 96%

: 601-57-0
Cholest-4-en-3-one

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 1h; Heating;	95%
With sodium dithionite; 2-methyl-5-(prop-1-en-2-yl)cyclohexanone; sodium hydrogencarbonate In 1,4-dioxane at 50℃;	89%
With hydrogen; <((t-Bu)2PH)PdP(t-Bu)2>2 saturated with oxygen In tetrahydrofuran under 760 Torr; for 12h; Ambient temperature;	86%

: 3-nitrocholest-2-ene

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With water; magnesium; cadmium(II) chloride In tetrahydrofuran for 0.25h; Ambient temperature;	95%

: 566-84-7
5β-cholestan-3-ol

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In nitromethane at 20℃; for 18h;	92%
With nitroacetic acid ethyl ester; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran room temperature for 2 h, refluxed for 2 h;	77%
With C55H49N4OP2Ru In toluene under 750.075 Torr; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	76%
With tetrabutylammonium chlorochromate In chloroform for 32h; Heating;	75%
With jones reagent In acetone for 0.333333h; Ambient temperature;	3.6 mg

: 516-92-7
epicoprostanol

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With osmium(VIII) oxide; acetic acid In diethyl ether for 30h; Ambient temperature;	90%
With cyclohexanone; nickel; toluene

: N-[(5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-(3E)-ylidene]-N'-phenyl-hydrazine

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With BTIB In water; acetonitrile at 0℃; for 0.5h;	85%

: 287389-75-7
4β-Phenylsulfonyl-5β-cholestan-3-one

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With methanol; sodium amalgam In tetrahydrofuran Reduction;	80%

: 601-57-0
Cholest-4-en-3-one

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

C: 566-84-7
5β-cholestan-3-ol

Conditions

Conditions	Yield
With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr;	A 14% B 75% C 5%

...Expand

: 5493-36-7, 5493-37-8, 55955-17-4
3α-Cholestanylnitrit

A: 516-92-7
epicoprostanol

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
In solid for 142h; Irradiation;	A 8% B 65%

: (3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-3-nitrosooxy-hexadecahydro-cyclopenta[a]phenanthrene

A: 80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5
Coprostanol

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
In solid for 76h; Irradiation;	A 5% B 64%

: 29365-27-3
(5β-cholestan-3α-yl)-methyl ether

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;	57%

/PBKTC004-1560/: /PBKTC004-1560/

A: 601-57-0
Cholest-4-en-3-one

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
IrH5(P-(i-Pr)3)2 In various solvent(s) at 100℃; for 30h;	A 55% B 13%

/PBKTC004-1550/: /PBKTC004-1550/

A: 601-57-0
Cholest-4-en-3-one

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
IrH5(P-(i-Pr)3)2 In various solvent(s) at 100℃; for 20h;	A 52% B 41%

: 474-77-1
epicholesterol

A: 601-57-0
Cholest-4-en-3-one

B: 566-88-1
dihydrocholesterone

C: 601-53-6
coprostanone

Conditions

Conditions	Yield
nickel In xylene at 135 - 140℃; for 1h; Heating;	A 28% B 4.5% C 2.5%

...Expand

: 57-88-5
cholesterol

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
With nickel at 220℃;
With nickel at 240℃;

: 516-92-7
epicoprostanol

A: 601-53-6
coprostanone

B: 1177-97-5
3.4-seco-5β-cholestanedioic acid-(3.4)

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid at 60℃;
With chromium(VI) oxide; acetic acid

: 80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5
Coprostanol

A: 601-53-6
coprostanone

B: 1177-97-5
3.4-seco-5β-cholestanedioic acid-(3.4)

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid

: 57-88-5
cholesterol

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With hydrogenchloride; jones reagent; hydrogen 1.) acetone, r.t.; 2.) methanol; Multistep reaction;

: 601-54-7
Cholest-5-en-3-one

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
With hydrogen; Nic In tetrahydrofuran; ethanol at 25℃; under 760 Torr; for 0.533333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 601-57-0
Cholest-4-en-3-one

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
With hydrogen; palladium In pyridine at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With hydrogen bromide; hydrogen; palladium In tetrahydrofuran at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With hydrogen; Nic In tetrahydrofuran; ethanol at 25℃; under 760 Torr; for 0.6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 566-93-8
cholesta-4,6-dien-3-one

A: 601-57-0
Cholest-4-en-3-one

B: 566-88-1
dihydrocholesterone

C: 601-53-6
coprostanone

Conditions

Conditions	Yield
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 4h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 566-91-6
cholesta-1,4-dien-3-one

A: 601-57-0
Cholest-4-en-3-one

B: 566-88-1
dihydrocholesterone

C: 601-53-6
coprostanone

Conditions

Conditions	Yield
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 1h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 1-[(8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-ylidene]-pyrrolidinium; perchlorate

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide; water 1.) acetonitrile, 40 h, reflux 2.) acetonitrile, reflux, 1 h; Multistep reaction. Yields of byproduct given;

: 2791-51-7
Δ4-Cholesten-3-one ethylene dithioacetal

: 601-53-6
coprostanone

Conditions

Conditions	Yield
With dihydrogen peroxide; diborane 1.) THF, 0 deg C, 5 h, 2.) THF, 0 deg C, 5 min; Yield given. Multistep reaction;
With dihydrogen peroxide; diborane In tetrahydrofuran at 0℃; Mechanism; other Δ4-steroids;

: 57-88-5
cholesterol

A: 601-54-7
Cholest-5-en-3-one

B: 601-57-0
Cholest-4-en-3-one

C: 80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5
Coprostanol

D: 601-53-6
coprostanone

Conditions

Conditions	Yield
With sodium phosphate buffer; Eubacterium coprostanoligenes ATCC 51222; sodium pyruvate; sodium 2-mercaptoacetate In water at 37℃; for 120h; Product distribution; Mechanism;

...Expand

: 60-29-7
diethyl ether

: 601-57-0
Cholest-4-en-3-one

aged platinum: aged platinum

: 601-53-6
coprostanone

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 60-29-7
diethyl ether

: 601-57-0
Cholest-4-en-3-one

palladium: palladium

: 601-53-6
coprostanone

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 57-88-5
cholesterol

nickel: nickel

A: 566-88-1
dihydrocholesterone

B: 601-53-6
coprostanone

Conditions

Conditions	Yield
at 220℃; sowie auf 240grad;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 601-53-6
coprostanone

: 23400-63-7
[(5R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-trimethyl-silane

Conditions

Conditions	Yield
With chiral lithium amide ((R)-5b) In hexane; toluene at -78℃; for 0.333333h;	99%

: 601-53-6
coprostanone

: 109-94-4
formic acid ethyl ester

: 2493-32-5, 17130-63-1, 53585-15-2
2-hydroxymethylene-5β-cholestan-3-one

Conditions

Conditions	Yield
With ethanol; sodium In diethyl ether	99%

: 601-53-6
coprostanone

: 107-21-1
ethylene glycol

: 25328-53-4
3,3-ethylenedioxy-5β-cholestane

Conditions

Conditions	Yield
With montmorillonite K-10 In benzene for 2h; Heating;	98%

: 601-53-6
coprostanone

: 516-92-7
epicoprostanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 0.0833333h;	95%
With lithium aluminium tetrahydride; diethyl ether
Multi-step reaction with 2 steps 1: sodium; ethanol 2: sodium pentylate; amyl alcohol View Scheme
Multi-step reaction with 2 steps 2: sodium ethylate; ethanol / 180 - 210 °C View Scheme

: 601-53-6
coprostanone

: 54786-78-6
4β-chloro-5β-cholestan-3-one

Conditions

Conditions	Yield
With potassium chlorate; sulfuric acid In 1,4-dioxane at 45℃; for 0.833333h;	90.4%

: 601-53-6
coprostanone

: 108-24-7
acetic anhydride

: 2-cholestene-3-ol acetate

Conditions

Conditions	Yield
With iodine for 0.0833333h; Acetylation; microwave irradiation;	90%

: 601-53-6
coprostanone

: 4657-43-6
4β-bromo-5β-cholestan-3-one

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate; bromine In water; acetic acid at 20℃; for 16h; Bromination;	85%
With hydrogen bromide; bromine; acetic acid
With tetrachloromethane; N-Bromosuccinimide unter starker Belichtung;

: 67-56-1
methanol

: 601-53-6
coprostanone

: 18003-81-1
5β-cholestan-3-one dimethyl acetal

Conditions

Conditions	Yield
at 20℃; for 12h; acetalization; UV-irradiation;	85%
With toluene-4-sulfonic acid
With hydrogen; Wilkinson's catalyst

: 37891-79-5
bis(methylsulfanyl)trimethylsilylmethane

: 601-53-6
coprostanone

: 56772-73-7
3-[bis(methylthio)methylene]cholestane

Conditions

Conditions	Yield
Stage #1: bis(methylsulfanyl)trimethylsilylmethane With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 4h; Stage #2: coprostanone In tetrahydrofuran; hexane at 20℃; for 12h;	85%

: 601-53-6
coprostanone

: 540-63-6
ethane-1,2-dithiol

: 2791-44-8
5β-cholestan-3-one dithiolane

Conditions

Conditions	Yield
tin(ll) chloride for 0.0833333h; microwave irradiation;	84%

: 601-53-6
coprostanone

: 566-91-6
cholesta-1,4-dien-3-one

Conditions

Conditions	Yield
With benzeneseleninic anhydride In chlorobenzene at 132℃; for 3h;	83%
Multi-step reaction with 2 steps 1: 114 mg / pyridine hydrobromide perbromide / acetic acid / 0.5 h / 60 °C 2: CaCO3 / N,N-dimethyl-acetamide / 30 h / Heating View Scheme

: 601-53-6
coprostanone

: 881739-66-8
2α-Bromcholestan-3-on

Conditions

Conditions	Yield
With hexabromocyclopenta-1,3-diene In acetonitrile for 15h; Heating;	77%

: 601-53-6
coprostanone

: 80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5
Coprostanol

Conditions

Conditions	Yield
With hydrogen; carbon monoxide In methanol at 30 - 35℃; under 51485.6 - 73550.8 Torr; for 2.5h;	75%
With hydrogen bromide; acetic acid; platinum at 60 - 65℃; Hydrogenation.Behandlung des Reaktionsprodukts mit aethanol. Alkalilauge;
With intestine bacteria
Reduktion unter Einwirkung von Darm-Bakterien;

: 601-53-6
coprostanone

: 540-63-6
ethane-1,2-dithiol

: 2791-43-7
5α-cholestan-3-one ethanediyl S,S-acetal

Conditions

Conditions	Yield
With boron trifluoride diacetate for 0.25h;	70%

: 601-53-6
coprostanone

: 5β-cholestane-3,4-dione 4-oxime

Conditions

Conditions	Yield
With n-Butyl nitrite; potassium tert-butylate In tert-butyl alcohol for 0.5h; Ambient temperature;	66%
Multi-step reaction with 2 steps 1: 22 percent / potassium t-butoxide, propyl nitrate / tetrahydrofuran / 2.5 h / Ambient temperature 2: 50.4 percent / ethanol / 3 h / Irradiation View Scheme
Multi-step reaction with 3 steps 1: 22 percent / potassium t-butoxide, propyl nitrate / tetrahydrofuran / 2.5 h / Ambient temperature 2: 25.2 percent / ethanol / 3 h / Irradiation 3: 140 °C View Scheme

: 601-53-6
coprostanone

: 78806-58-3
4β-iodo-5β-cholestan-3-one

Conditions

Conditions	Yield
With copper diacetate; iodine In acetic acid at 60℃; for 6h;	65%
With ammonium cerium(IV) nitrate; iodine In water; acetic acid at 50℃; for 2.5h;	60%

: 601-53-6
coprostanone

: 108-98-5
thiophenol

: 88904-77-2
(5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-3-phenylsulfanyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Conditions

Conditions	Yield
Montmorillonite KSF In toluene for 6h; Heating;	62%

: 601-53-6
coprostanone

: (5S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-4-iodo-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate; iodine In water; acetic acid at 50℃; for 2.5h; Iodination;	60%

Cholestan-3-one, (5β)- Specification

This chemical is called Cholestan-3-one, (5β)-, and its systematic name is 5-beta-Cholestan-3-one. With the molecular formula of C₂₇H₄₆O, its molecular weight is 386.65. The CAS registry number of this chemical is 601-53-6.

Other characteristics of the Cholestan-3-one, (5β)- can be summarised as followings: (1)ACD/LogP: 9.64; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.64; (4)ACD/LogD (pH 7.4): 9.64; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 4178283.5; (8)ACD/KOC (pH 7.4): 4178283.5; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.497; (14)Molar Refractivity: 118.89 cm³; (15)Molar Volume: 405.6 cm³; (16)Polarizability: 47.13×10^-24cm³; (17)Surface Tension: 33.6 dyne/cm; (18)Density: 0.953 g/cm³; (19)Flash Point: 219.3 °C; (20)Enthalpy of Vaporization: 71.22 kJ/mol; (21)Boiling Point: 452.9 °C at 760 mmHg; (22)Vapour Pressure: 2.16E-08 mmHg at 25°C.

Production method of this chemical: The Cholestan-3-one, (5β)- could be obtained by the reactant of cholest-4-en-3-one. This reaction needs the reagent of diethyl ether, platinum. The other condition is Hydrogenation.

Uses of this chemical: The 5b-cholestan-3b-ol could be obtained by the Cholestan-3-one, (5β)-. This reaction needs the reagent of intestine bacteria.

You can still convert the following datas into molecular structure:
1.SMILES: O=C4C[C@H]3CC[C@@H]1[C@H](CC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)[C@@]3(C)CC4
2.InChI: InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1
3.InChIKey: PESKGJQREUXSRR-JDIFZLMIBL

Product Name

5BETA-CHOLESTAN-3-ONE

Synthetic route

Cholestan-3-one, (5β)- Specification

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