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Basic Information
CAS No.: 57-88-5
Name: Cholesterol
Article Data: 150
Molecular Structure:
Molecular Structure of 57-88-5 (Cholesterol)
Formula: C27H46O
Molecular Weight: 386.662
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%
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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.