Cholestane, (5α)- supplier

Name
5α-Cholestane
EINECS 207-562-8
CAS No. 481-21-0
Article Data163
CAS DataBase
Density 0.91 g/cm³
Solubility
Melting Point 78-80 °C
Formula C₂₇H₄₈
Boiling Point 440.9 °C at 760 mmHg
Molecular Weight 372.678
Flash Point 210.3 °C
Transport Information UN 1888 6.1/PG 3
Appearance White crystalline powder
Safety 24/25-36/37
Risk Codes 22-38-40-48/20/22
Molecular Structure
Hazard Symbols Xn
Synonyms 28,29,30-Trinorlanostane;NSC 224419;(20R)-5a(H),14a(H),17a(H)-Cholestane;5a-Cholestane (6CI,8CI);
PSA 0.00000
LogP 8.49780

Synthetic route

: 97100-53-3
3-bromocholestane

: 481-21-0
cholestane

Conditions

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

: 75809-01-7
3β-phenylselenenyl-5α-cholestane

: 481-21-0
cholestane

Conditions

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

: 13901-19-4, 15910-23-3, 570-73-0
cholest-2-ene

: 481-21-0
cholestane

Conditions

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

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

: 481-21-0
cholestane

Conditions

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%

: 73532-35-1
5α-cholestan-3β-yl adamantane-1-carboxylate

A: 770-71-8
1-adamantanemethanol

B: 828-51-3
1-Adamantanecarboxylic acid

C: 481-21-0
cholestane

D: 80-97-7
Cholestanol

Conditions

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%

...Expand

: 1981-90-4
(5α-cholestan-3β-yl)-methyl ether

: 481-21-0
cholestane

Conditions

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%

: 130534-82-6
O-cholestan-3β-yl-O'-(4-fluorophenyl)thionocarbonate

: 481-21-0
cholestane

Conditions

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%

: 73532-35-1
5α-cholestan-3β-yl adamantane-1-carboxylate

A: 770-71-8
1-adamantanemethanol

B: 1501-94-6
N-ethyl-1-adamantanecarboxamide

C: 481-21-0
cholestane

D: 80-97-7
Cholestanol

Conditions

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

...Expand

: 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

: 481-21-0
cholestane

Conditions

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

: 75-04-7
ethylamine

: 73532-35-1
5α-cholestan-3β-yl adamantane-1-carboxylate

A: 828-51-3
1-Adamantanecarboxylic acid

B: 1501-94-6
N-ethyl-1-adamantanecarboxamide

C: 481-21-0
cholestane

D: 80-97-7
Cholestanol

Conditions

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

...Expand

: 73532-34-0
5α-cholestane-3β,6β-diyl bis-(adamantane-1-carboxylate)

A: 828-51-3
1-Adamantanecarboxylic acid

B: 481-21-0
cholestane

C: 80-97-7
Cholestanol

D: 35490-51-8
5α-cholestan-6β-ol

Conditions

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

...Expand

: 145345-67-1
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

: 481-21-0
cholestane

Conditions

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

: 481-21-0
cholestane

Conditions

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

: 57700-97-7
1-(5α-cholestan-3β-yloxythiocarbonyl)imidazole

: 481-21-0
cholestane

Conditions

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

: 5211-17-6
3β-(methylthio)thiocarbonyloxy-5α-cholestane

: 481-21-0
cholestane

Conditions

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

: 73532-35-1
5α-cholestan-3β-yl adamantane-1-carboxylate

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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

: 566-88-1
dihydrocholesterone

: 481-21-0
cholestane

Conditions

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

: 5211-17-6, 16734-07-9, 70286-38-3
O-cholestanyl-S-methyl dithiocarbonate

: 481-21-0
cholestane

Conditions

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%

: 2839-20-5
trifluoroacetoxy-3β 5α-cholestane

: 481-21-0
cholestane

Conditions

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

: 73532-43-1
3β-(NN-diethylaminothiocarbonyloxy)-5α-cholestane

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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

: 481-21-0
cholestane

Conditions

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

: 3381-51-9
(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

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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;

: 75250-34-9
3β-phenylselenenyl-5α-cholestane

: 481-21-0
cholestane

Conditions

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

: 78916-32-2
3β-(isopropyloxycarbonyloxy)-5α-cholestane

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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

: 73532-44-2
N-methyl-N-<2-(NN-dimethylamino)ethyl>aminothiocarbonyloxy-5α-cholestane

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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

: 130534-82-6
O-cholestan-3β-yl-O'-(4-fluorophenyl)thionocarbonate

A: 481-21-0
cholestane

B: 57701-04-9
O-cholestanyl thionoformate

Conditions

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

: 51154-61-1
neocholesteryl bromide

: 481-21-0
cholestane

Conditions

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

: 78916-31-1
3β-(NN-diethylaminocarbonyloxy)-5α-cholestane

A: 481-21-0
cholestane

B: 80-97-7
Cholestanol

Conditions

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

: 10437-24-8
3β-formyloxy-5αH-cholestane

A: 64-18-6
formic acid

B: 481-21-0
cholestane

C: 80-97-7
Cholestanol

Conditions

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

...Expand

: N-(3β-cholestanyloxythiocarbonyl)imidazole

: 481-21-0
cholestane

Conditions

Conditions	Yield
	79%

: 481-21-0
cholestane

: α-cholestane-d48

Conditions

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

Cholestane, (5α)- Specification

The CAS register number of Cholestane, (5α)- is 481-21-0. It also can be called as 28,29,30-Trinorlanostane and the systematic name about this chemical is (5α)-cholestane. The molecular formula about this chemical is C₂₇H₄₈ and the molecular weight is 372.67. It belongs to the following product categories which include 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 and so on.

Physical properties about Cholestane, (5α)- are: (1)ACD/LogP: 12.26; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 12.26; (4)ACD/LogD (pH 7.4): 12.26; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.492; (11)Molar Refractivity: 118.76 cm³; (12)Molar Volume: 409.1 cm³; (13)Polarizability: 47.08x10^-24cm³; (14)Surface Tension: 31.8 dyne/cm; (15)Density: 0.91 g/cm³; (16)Flash Point: 210.3 °C; (17)Enthalpy of Vaporization: 67.13 kJ/mol; (18)Boiling Point: 440.9 °C at 760 mmHg; (19)Vapour Pressure: 1.47E-07 mmHg at 25 °C.

Preparation: this chemical can be prepared by b-dihydrocholesterol methoxymethyl ether. This reaction will need reagents of 2,2-bis(tert-butylperoxy)butane, tri-tert-butoxysilanethiol and solvent of octane. This reaction needs heating. The reaction time is 160 mins. The yield is about 72%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and by inhalation. It is irritating to skin. It may also cause damage to health and danger of serious damage to health by prolonged exposure. There is limited evidence of a carcinogenic effect. However, if you want to store this chemical, please wear suitable protective clothing and gloves. When you are using it, avoid contact with skin and eyes. If you want to store it, you should keep the container tightly sealed in dry, cool places. It should be kept away from oxide. If you store and use this chemical according the rule, it will not be decomposed.

You can still convert the following datas into molecular structure:
(1)SMILES: [C@@H]41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)[C@H](C)CCCC(C)C)CC4)C
(2)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
(3)InChIKey: XIIAYQZJNBULGD-XWLABEFZBM
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: XIIAYQZJNBULGD-XWLABEFZSA-N

Product Name

5α-Cholestane

Synthetic route

Cholestane, (5α)- Specification

Related Products

Hot Products