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57-88-5

Basic Information
CAS No.: 57-88-5
Name: Cholest-5-en-3-ol(3b)-
Molecular Structure:
Molecular Structure of 57-88-5 (Cholest-5-en-3-ol(3b)-)
Formula: C27H46O
Molecular Weight: 386.66
Synonyms: Cholesterol(8CI);5:6-Cholesten-3b-ol;Cholest-5-en-3b-ol;Cholesterin;Cholesteryl alcohol;Dythol;Lidinit;Lidinite;NSC 8798;Provitamin D;D5-Cholesten-3b-ol;
EINECS: 200-353-2
Density: 0.988 g/cm3
Melting Point: 148-150 °C
Boiling Point: 480.648 °C at 760 mmHg
Flash Point: 209.291 °C
Solubility: 0.002 mg/mL in water
Appearance: White to faintly yellow cryst. powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 10-48/20/22-40-38-22-36/37/38
Safety: 24/25-22-36/37-36-26
Transport Information: UN 1170 3/PG 3
PSA: 20.23000
LogP: 7.38870
Synthetic route
70650-16-7

cholesteryl-2-tetrahydrofuran

57-88-5

cholesterol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;95%
6252-45-5

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol

57-88-5

cholesterol

Conditions
ConditionsYield
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 40h; Hydrolysis;100%
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane at 55℃; for 0.5h;98%
With CuCl2*H2O In ethanol for 2h; Hydrolysis; Heating;98%
57711-50-9

3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene

57-88-5

cholesterol

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 32h;99%
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.7h;98%
With tetra-N-butylammonium tribromide In methanol; dichloromethane for 8h;97%

4-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile

57-88-5

cholesterol

Conditions
ConditionsYield
With Triethylgermyl-natrium In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 16h;99%
7604-85-5

cholesterol triethylsilyl ether

57-88-5

cholesterol

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 0.166667h;99%
604-32-0

cholesteryl benzoate

57-88-5

cholesterol

Conditions
ConditionsYield
With methanol; samarium(II) dibromide In tetrahydrofuran at 50℃; for 48h; Temperature;99%
604-35-3

Cholesteryl acetate

57-88-5

cholesterol

Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;98%
With potassium hydroxide In methanol at 35℃; for 1h;97%
With aluminum oxide at 130℃; for 0.116667h; Irradiation;96%
25092-65-3

allyl cholesteryl ether

57-88-5

cholesterol

Conditions
ConditionsYield
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Heating;98%
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Product distribution; Heating; or deprotection of other allyl ethers;98%
With diisobutylaluminium hydride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether; toluene at 0 - 20℃; for 2h;95%
1857-80-3

5α,6β-dibromocholestan-3β-ol

57-88-5

cholesterol

Conditions
ConditionsYield
With sodium selenite; rac-cysteine In tetrahydrofuran; water at 0℃; for 1h;98%
With samarium diiodide In tetrahydrofuran for 0.333333h; Ambient temperature;97%
With 2,2'-azobis(isobutyronitrile); diphenylstibane In toluene at 90℃; for 18h;97%
33999-75-6

1-((cholesteryloxy)methyl)-4-methoxybenzene

57-88-5

cholesterol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; p-toluenesulfonamide safety-catch resin In 1,4-dioxane98%
With trifluorormethanesulfonic acid; 1,3-Dimethoxybenzene In dichloromethane at 21℃; for 0.166667h;91%
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 10h;85%
54972-79-1

3β-(1-Ethoxyethoxy)-5-cholestene

57-88-5

cholesterol

Conditions
ConditionsYield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;98%
With CuCl2*H2O In water; acetone Hydrolysis; Heating;96%
With water; ammonium chloride In tetrahydrofuran at 150℃; for 1h; Glovebox; High pressure; Sealed tube;

Carbonic acid allyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

57-88-5

cholesterol

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;98%

C28H48O

57-88-5

cholesterol

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; water at 50℃; for 3h; Solvent;97.74%
27241-01-6

3β-hydroxycholest-5-en-23-one

57-88-5

cholesterol

Conditions
ConditionsYield
Wolff-Kishner reduction;97%
34103-99-6

cholester-3β-yl thiobenzoate

A

57-88-5

cholesterol

B

7278-60-6

benzyl 3-cholesteryl ether

C

570-74-1

cholest-5-ene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); triphenylstannane In toluene at 110℃; for 0.333333h; Yields of byproduct given;A n/a
B 97%
C n/a
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Product distribution; Mechanism; var. of reagent, its amount;A 38%
B 49%
C n/a
80667-96-5

Carbonic acid 2-benzenesulfonyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

57-88-5

cholesterol

Conditions
ConditionsYield
With triethylamine In pyridine at 20℃; for 70h; Product distribution;96.5%
78687-50-0

Carbonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 2-trimethylsilanyl-ethyl ester

A

74-85-1

ethene

B

420-56-4

trimethylsilyl fluoride

C

57-88-5

cholesterol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; for 0.166667h; deprotection of TMSEC derivat;A n/a
B n/a
C 94%
76514-42-6

{2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethoxy]-ethyl}-trimethyl-silane

57-88-5

cholesterol

Conditions
ConditionsYield
With 4 A molecular sieve; tetrabutyl ammonium fluoride 1.) THF; 2.) DMPU, 45 deg C, 9 h;94%
With 4 A molecular sieve; tetrabutyl ammonium fluoride Product distribution; 1.)THF; 2.) DMPU, 45 deg C, 9 h; deprotection of various ethers investigated;94%

Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

57-88-5

cholesterol

Conditions
ConditionsYield
In benzene for 1h; Irradiation;94%

cholesteryl 2,2,2-trichloroethyl carbonate

57-88-5

cholesterol

Conditions
ConditionsYield
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran; water for 0.75h;94%
2864-50-8

sodium (20R)-5-cholesten-3β-yl sulfate

57-88-5

cholesterol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 20℃; Hydrolysis;93%
77588-15-9

Cholesteryl-4-methoxybenzolsulfonat

57-88-5

cholesterol

Conditions
ConditionsYield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;92.7%
1182-65-6, 3381-56-4

cholesteryl p-toluenesulfonate

57-88-5

cholesterol

Conditions
ConditionsYield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;92%
With sodium tetrahydroborate In diethyl ether; water; N,N-dimethyl-formamide for 6h; Ambient temperature;86%
57-88-5

cholesterol

Conditions
ConditionsYield
With 1% Pd on activated carbon; ammonium acetate; hydrogen In ethanol at 50℃; under 2280.15 Torr; for 12h; Temperature;91.9%
With 5%-palladium/activated carbon; hydrogen In methanol at 15 - 20℃; for 24h;85%
2626-17-7

3β-methoxymethoxy-5-cholestene

57-88-5

cholesterol

Conditions
ConditionsYield
With trimethylsilyl bromide; 4 A molecular sieve In dichloromethane -30 deg C, 1 h, 0 deg C, 12 h;91%
67-56-1

methanol

1256491-32-3

cholesteryl oleate

A

112-62-9

octadec-9-enoic acid methyl ester

B

57-88-5

cholesterol

Conditions
ConditionsYield
With potassium hydrogensulfate; silica gel at 65℃; for 10h;A 71%
B 91%
103846-32-8

2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-[1,4]dioxane

57-88-5

cholesterol

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 2h; Heating;90%
66168-89-6

3β-(2-methoxyethoxymethoxy)-5-cholestene

89449-88-7

bis-i-propylthioboron bromide

A

57-88-5

cholesterol

B

89449-90-1

i-propylthiomethyl ether of cholesterol

Conditions
ConditionsYield
With dmap In dichloromethane 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and -50 deg C, 10 min;A 9%
B 89%
With dmap In dichloromethane Product distribution; Mechanism; 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and-50 deg C, 10 min;A 9%
B 89%
57-88-5

cholesterol

407-25-0

trifluoroacetic anhydride

2665-02-3

cholesteryl trifluoroacetate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 4h;100%
110-87-2

3,4-dihydro-2H-pyran

57-88-5

cholesterol

6252-45-5

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 6h; Ambient temperature;100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1.5h;99%
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane at 0℃; for 0.333333h;98%
112-80-1

cis-Octadecenoic acid

57-88-5

cholesterol

303-43-5

cholesterol oleate

Conditions
ConditionsYield
With TiO(acac)2 In xylene for 36h; Heating;100%
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;99%
With iron(III)-acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Inert atmosphere; Reflux;96%
4224-70-8

6-bromohexanoic acid

57-88-5

cholesterol

82962-33-2

cholesteryl ω-bromohexanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.33333h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;88%
With dmap; dicyclohexyl-carbodiimide In dichloromethane70%
57-88-5

cholesterol

86795-39-3

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran

(3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran

Conditions
ConditionsYield
With 2-methyl-but-2-ene; zinc(II) p-tert-butylbenzoate In dichloromethane for 1h; Ambient temperature;100%
57-88-5

cholesterol

601-54-7

Cholest-5-en-3-one

Conditions
ConditionsYield
With C40H36Cl2FeN2P2Ru; potassium tert-butylate In toluene; tert-butyl alcohol at 145℃; for 3h; Inert atmosphere;100%
With 1,4-butanediol dimethylacrylate crosslinked polyacenaphthylene supported t-butyl chromate In chloroform at 30℃; for 29h;92%
With water; Dess-Martin periodane In dichloromethane for 0.5h;91%
57-88-5

cholesterol

80-97-7

Cholestanol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethyl acetate100%
With hydrogen; palladium dichloride In dichloromethane at 20℃; under 760 Torr;99%
With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; under 760.051 Torr; for 12h;99%
57-88-5

cholesterol

108-24-7

acetic anhydride

604-35-3

Cholesteryl acetate

Conditions
ConditionsYield
With iodine for 0.166667h; Ambient temperature;100%
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;100%
[(nBu2Sn)12(μ3-O)14(μ2-OH)6](2+)*2C6H5SO3(1-) at 20℃; for 0.416667h;100%
57-88-5

cholesterol

108-24-7

acetic anhydride

809-51-8

7-ketocholesteryl acetate

Conditions
ConditionsYield
With pyridine at 37℃; Inert atmosphere;100%
With pyridine; chromium trioxide-3,5-dimethylpyrazole
Stage #1: cholesterol; acetic anhydride With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With potassium dichromate; 1-hydroxy-pyrrolidine-2,5-dione; acetic acid In acetone at 50℃; for 48h;
2.03 g
57-88-5

cholesterol

98-59-9

p-toluenesulfonyl chloride

1182-65-6, 3381-56-4

cholesteryl p-toluenesulfonate

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 12h;100%
With pyridine at 0 - 20℃;98%
With aluminum dodecatungstophosphate at 20℃; for 0.1h;96%
57-88-5

cholesterol

1005-56-7

phenylcarbonochloridothioate

85335-71-3

cholest-5-en-3-ol (3β)-(O-phenyl carbonothioate)

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.833333h; Inert atmosphere;100%
With pyridine In dichloromethane for 2h;96%
With pyridine In chloroform-d1 at 25℃; half-life time of acylation of cholesterol with other chlorothionoformates;84%
With pyridine In chloroform-d1 at 25℃;84%
With sodium hydride
57-88-5

cholesterol

563-76-8

α-bromopropionyl bromide

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-bromopropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane Acylation;100%
57-88-5

cholesterol

149707-75-5, 149707-76-6, 138479-78-4

2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose

51704-23-5

1-O-cholesteryl-β-D-galactopyranoside

Conditions
ConditionsYield
Stage #1: cholesterol; 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
57-88-5

cholesterol

C41H40Cl3NO16

C39H66O10

Conditions
ConditionsYield
Stage #1: cholesterol; C41H40Cl3NO16 With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
57-88-5

cholesterol

107-13-1

acrylonitrile

71507-47-6

(3S,8S,9S,10R,13R,14S,17R)-3-(2-isocyanoethoxy)-10,13-dimethyl-17((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium hydroxide In dichloromethane; water at 20℃;100%
With water; potassium hydroxide In 1,4-dioxane at 20℃; for 120h;100%
With N-benzyl-trimethylammonium hydroxide at 20℃; Michael Addition;92%
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; benzylamine; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 4℃; for 1h; Inert atmosphere; chemoselective reaction;54%
With 18-crown-6 ether; potassium hydroxide In dichloromethane at 20℃; for 12h; Time;
57-88-5

cholesterol

podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate

3-O-(epi)-podophyllotoxylcholesterol

Conditions
ConditionsYield
Stage #1: cholesterol; podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;
Stage #2: With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere;
100%
57-88-5

cholesterol

55700-78-2

(6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;99.8%
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol at 20℃; for 1h; Green chemistry;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ambient temperature;97%
57-88-5

cholesterol

21615-34-9

2-Methoxybenzoyl chloride

cholester-3-yl 2-methoxybenzoate

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;99.8%
57-88-5

cholesterol

124-63-0

methanesulfonyl chloride

3381-54-2

cholesterol mesylate

Conditions
ConditionsYield
With pyridine at 20 - 25℃; for 20h; Inert atmosphere;99.1%
With triethylamine In dichloromethane at 4 - 22℃; Inert atmosphere;98%
With triethylamine In diethyl ether at 0℃; for 1h;98%
143-07-7

lauric acid

57-88-5

cholesterol

1908-11-8

cholesteryl laurate

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
With dmap; dicyclohexyl-carbodiimide
57-88-5

cholesterol

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

1856-05-9, 16134-40-0

cholesterol trimethylsilyl ether

Conditions
ConditionsYield
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.416667h;99%
With silica-FeCl3 at 20℃; for 0.85h; neat (no solvent);98%
With trichloromelamine In dichloromethane; acetonitrile at 20℃; for 0.416667h;98%
674-82-8

4-methyleneoxetan-2-one

57-88-5

cholesterol

1473-23-0

(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl 3-oxobutanoate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 48℃; for 0.0833333h;99%
6564-72-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose

57-88-5

cholesterol

208523-33-5

cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides

Conditions
ConditionsYield
With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 4h; Heating;99%
112-62-9

Methyl oleate

57-88-5

cholesterol

303-43-5

cholesterol oleate

Conditions
ConditionsYield
With iron(III)-acetylacetonate In n-heptane at 105℃; for 22h; Inert atmosphere;99%
In hexane at 30℃; for 72h; Corynebacterium sp. S-401;16%
With Candida rugosa lipase at 40℃; under 15.0012 - 30.0024 Torr; for 48h;
With Lipozyme IM at 80℃; under 15.0012 - 30.0024 Torr; for 48h;
57-88-5

cholesterol

601-57-0

Cholest-4-en-3-one

Conditions
ConditionsYield
With aluminum tris(iso-propoxide) In cyclohexanone; toluene for 10h; Reflux;99%
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;98%
With Chromosorb; catalase; cholesterol oxidase In acetic acid butyl ester for 72h;95%
57-88-5

cholesterol

109-92-2

ethyl vinyl ether

54972-79-1

3β-(1-Ethoxyethoxy)-5-cholestene

Conditions
ConditionsYield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 2h;99%
With acetonyltriphenylphosphonium bromide In dichloromethane for 0.0833333h; Ambient temperature;97%
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 2h;77%
With toluene-4-sulfonic acid In dichloromethane
75-15-0

carbon disulfide

57-88-5

cholesterol

74-88-4

methyl iodide

53496-46-1

O-((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl) S-methyl carbonodithioate

Conditions
ConditionsYield
Stage #1: cholesterol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h;
Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 0 - 20℃; for 15h;
Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 2h;
99%
With sodium hydride92%
Stage #1: carbon disulfide; cholesterol In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: With N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 20℃; for 1h;
Stage #3: methyl iodide In dimethyl sulfoxide at 20℃; for 5h;
70%
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Chemistry


IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Empirical Formula: C27H46O
Molecular Weight: 386.6535
EINECS: 200-353-2
Classification Code: Mutation data; Natural Product; Pharmaceutic aid [emulsifying agent]; Reproductive Effect; Tumor data
Melting Point: 148-150 °C
alpha: -36 °(c=2, dioxane)
storage temp.: 2-8 °C
solubility: H2O: 0.002 mg/mL
Water Solubility: negligible
Index of Refraction: 1.525
Molar Refractivity: 119.97 cm3
Molar Volume: 391.4 cm3
Surface Tension: 38.1 dyne/cm
Density: 0.98 g/cm3
Flash Point: 209.3 °C
Enthalpy of Vaporization: 85.88 kJ/mol
Boiling Point: 480.6 °C at 760 mmHg
Vapour Pressure of (CAS NO.57-88-5): 2.95E-11 mmHg at 25 °C

History

The name Cholesterol originates from the Greek chole- and stereos, and the chemical suffix -ol for an alcohol, as Francois Poulletier de la Salle first identified cholesterol in solid form in gallstones, in 1769. However, it was only in 1815 that chemist Eugène Chevreul named the compound "cholesterine".

Uses

 Cholesterol (CAS NO.57-88-5) is used as pharmaceutic aid. It is an essential structural component of mammalian cell membranes, where it is required to establish proper membrane permeability and fluidity. In addition, cholesterol is an important component for the manufacture of bile acids, steroid hormones, and fat-soluble vitamins including Vitamin A, Vitamin D, Vitamin E, and Vitamin K. Cholesterol is the principal sterol synthesized by animals, but small quantities are synthesized in other eukaryotes, such as plants and fungi. It is almost completely absent among prokaryotes, which include bacteria.

Safety Profile

Hazard Codes : HarmfulXn,IrritantXii
Risk Statements : 10-48/20/22-40-38-22-36/37/38 
R10:Flammable. 
R48:Danger of serious damage to health by prolonged exposure. 
R20/22:Harmful by inhalation and if swallowed. 
R40:Limited evidence of a carcinogenic effect. 
R38:Irritating to skin. 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements : 24/25-22-36/37-36-26 
S24/25:Avoid contact with skin and eyes. 
S22:Do not breathe dust. 
S36/37:Wear suitable protective clothing and gloves. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR : UN 1170 3/PG 3
WGK Germany : 1
RTECS : FZ8400000

Specification

 Cholesterol (CAS NO.57-88-5), its Synonyms are 3-beta-Hydroxycholest-5-ene ; 3beta-Hydroxycholest-5-ene ; 5:6-Cholesten-3beta-ol ; AI3-03112 ; CCRIS 2834 ; Cholest-5-en-3-beta-ol ; Cholest-5-en-3-ol, (3beta)- ; Cholest-5-en-3beta-ol ; Cholesterin ; Cholesterine ; Cholesterol ; Cholesterol base H ; Cholesteryl alcohol ; Cholestrin ; Cholestrol ; Cordulan ; Dusoline ; Dusoran ; Dythol . It is white to faintly yellow cryst. powder. Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and fluidity.