Cholesteryl benzoate supplier

Name
Cholesteryl benzoate
EINECS 210-064-3
CAS No. 604-32-0
Article Data51
CAS DataBase
Density 1.04 g/cm³
Solubility INSOLUBLE
Melting Point 148-150 °C(lit.)
Formula C₃₄H₅₀O₂
Boiling Point 563.6 °C at 760 mmHg
Molecular Weight 490.77
Flash Point 213.1 °C
Transport Information
Appearance white powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Cholest-5-en-3-ol(3b)-, benzoate (9CI);3b-(Benzoyloxy)cholest-5-ene;Benzoate cholesterol;(3β)-Cholest-5-en-3-yl benzoate;Cholest-5-en-3b-yl benzoate;Cholesterol 3b-benzoate;(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methyl-2-heptanyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl benzoate;
PSA 26.30000
LogP 9.25340

Synthetic route

: 93-58-3
benzoic acid methyl ester

: 57-88-5
cholesterol

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With iron(III)-acetylacetonate In n-heptane at 105℃; for 30h; Inert atmosphere;	97%
With tetramethylammonium methyl carbonate In hexane for 16h; Solvent; Molecular sieve; Reflux; Green chemistry;	94%
With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol In hexane Reflux; chemoselective reaction;	78%

: 57-88-5
cholesterol

: 85909-02-0
N-benzyl-N-(tert-butoxycarbonyl)-benzamide

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With sodium t-butanolate In toluene at 150℃; for 24h; Sealed tube;	96%

: 57-88-5
cholesterol

: Benzoyltriazole

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;	95%

: 1416720-35-8
cholester-3-yl 4-hydroxymethylbenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With oxygen; palladium diacetate; sodium carbonate In cyclohexane at 130℃; for 48h; Molecular sieve; Schlenk technique;	92%

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With 1,2-dibromo-1,1,2,2-tetrachloroethane; potassium carbonate; bis(4-methoxyphenyl)telluride In chloroform for 23h; Ambient temperature;	90%
With 1,2-dibromo-1,1,2,2-tetrachloroethane; K2CO3 or triethylamine; bis(4-methoxyphenyl)telluride In chloroform for 23h; Ambient temperature; different ratios of halogenating agent and catalyst; different reaction time; different concentrations of aqueous base;	90%
With benzeneseleninic anhydride In tetrahydrofuran for 24h; Ambient temperature;	73%

: 36228-61-2
4-(Benzoyloxy)pyridine

: 57-88-5
cholesterol

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 5h;	89%

: 57-88-5
cholesterol

: 36967-85-8
benzoyl triflate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
In dichloromethane at -78℃; for 0.5h;	89%

: 57-88-5
cholesterol

: 98-88-4
benzoyl chloride

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
In pyridine	89%
With silica gel HF-254/magnesium oxide at 20℃; for 4h; Green chemistry; chemoselective reaction;	82%
With picoline In dichloromethane for 1h; Reflux;

aqueous potassium carbonate: aqueous potassium carbonate

petroleum ether-ethyl acetate: petroleum ether-ethyl acetate

symdibromo-tetrachloroethane: symdibromo-tetrachloroethane

: 63971-78-8
tellurium dichloride

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
In Petroleum ether	88%

...Expand

: (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 4-bromobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
Stage #1: (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 4-bromobenzoate With palladium dichloride In water at 20℃; for 0.0333333h; Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 11.9667h;	86%

aqueous potassium carbonate: aqueous potassium carbonate

symdibromo-tetrachloroethane: symdibromo-tetrachloroethane

: 63212-69-1
p-dimethylaminophenyl(p-methoxyphenyl)tellurium(II)

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
	77%

...Expand

aqueous potassium carbonate: aqueous potassium carbonate

petroleum ether-ethyl acetate: petroleum ether-ethyl acetate

sym-tetrachloro dibromoethane: sym-tetrachloro dibromoethane

: 4456-34-2
bis(4-methoxyphenyl)telluride

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
	72%

...Expand

: 618-32-6
Benzoyl bromide

: 57-88-5
cholesterol

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With silica gel HF-254/magnesium oxide at 20℃; for 5.5h; Green chemistry; chemoselective reaction;	72%

: 57-88-5
cholesterol

: 65-85-0
benzoic acid

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; Bu3PI2 In diethyl ether for 6h;	71%
With potassium hypophosphite; iodine; sodium sulfate In neat (no solvent) at 20℃; for 0.333333h; Milling; Green chemistry;	53%

: 57857-70-2
di-(p-methoxyphenyl)tellurium oxide

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
	66%

: 57-88-5
cholesterol

: 848417-68-5
3,6-dibenzoyloxy-1,2-pyridazine

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 75 - 80℃; for 6h;	62%

aqueous potassium carbonate: aqueous potassium carbonate

petroleum ether-ethyl acetate: petroleum ether-ethyl acetate

: tetramethylenetellurium diiodide

: 34103-99-6
cholester-3β-yl thiobenzoate

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
In Petroleum ether	58%

...Expand

: 532-32-1
sodium benzoate

: 57-88-5
cholesterol

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide for 7h; Heating;	43%

: 57-88-5
cholesterol

: 140-29-4
phenylacetonitrile

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With pyridine; ferric(III) bromide; oxygen In chlorobenzene at 130℃; Sealed tube;	43%

: 76303-24-7
cholest-5-en-3β-yl N-trifluoroacetylbenzimidate

A: 604-32-0
cholesteryl benzoate

B: 76303-25-8
α-ethoxy-α-trifluoroacetamidotoluene

Conditions

Conditions	Yield
With sodium hydrogen telluride In ethanol; dichloromethane for 2h; Ambient temperature;	A 13% B n/a

: 57-88-5
cholesterol

: 99802-96-7
2-benzoyl-1,3-dimethyl-1H-imidazol-3-ium iodide

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 14h; Inert atmosphere; Sealed tube; regioselective reaction;	10%

: 57-88-5
cholesterol

: 614-28-8
N-benzoylbenzamide

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; toluene

: 26048-46-4
7α-bromocholest-5-en-3β-ol benzoate

A: 3,3'-bis-benzoyloxy-7ξH,7'ξH-[7,7']bicholest-5-enyl

B: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With copper; acetic acid; zinc
With nickel; ethyl acetate Hydrogenation.weiteres Reagens: Essigsaeure;
With Lindlar's catalyst; ethyl acetate Hydrogenation.weiteres Reagens: Essigsaeure;

: 57-88-5
cholesterol

: 98-88-4
benzoyl chloride

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With pyridine at 45 - 60℃;
at 160℃;

: 57-88-5
cholesterol

: 93-97-0
benzoic acid anhydride

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
at 150 - 160℃;

: 57-88-5
cholesterol

: 65-85-0
benzoic acid

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
at 200℃;

: 57-88-5
cholesterol

: 100936-11-6
2-methoxy-4-benzoyloxy-6-methyl pyrimidine

: 604-32-0
cholesteryl benzoate

Conditions

Conditions	Yield
With dmap Ambient temperature; Yield given;
Ambient temperature; Yield given;

: 67-66-3
chloroform

: 10034-85-2
hydrogen iodide

: 6557-19-3
5β,6β-epoxy-cholestan-3β-ol benzoate

: 604-32-0
cholesteryl benzoate

...Expand

: 110-86-1
pyridine

: 26048-47-5
5α,6β-dibromocholestan-3β-yl benzoate

: silver nitrate

: 604-32-0
cholesteryl benzoate

...Expand

: 604-32-0
cholesteryl benzoate

: 6557-19-3
5β,6β-epoxy-cholestan-3β-ol benzoate

Conditions

Conditions	Yield
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In fluorobenzene at 100℃; under 7600 Torr;	99%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In fluorobenzene at 100℃; under 7500.6 Torr; for 3h;	99%
With oxygen; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) In benzene at 20℃; for 144h;	93%

: 604-32-0
cholesteryl benzoate

: 57-88-5
cholesterol

Conditions

Conditions	Yield
With methanol; samarium(II) dibromide In tetrahydrofuran at 50℃; for 48h; Temperature;	99%

: 604-32-0
cholesteryl benzoate

: 6997-41-7
3β-benzoyloxy-cholest-5-en-7-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; bis(acetylacetonato) oxovanadium(IV) In benzene at 20℃; for 120h; Inert atmosphere;	98%
With 3 A molecular sieve; pyridinium chlorochromate In benzene for 24h; Heating;	89%
With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; magnesium acetate tetrahydrate In decane; butyl butyrate at 0℃; for 6h; regioselective reaction;	78%

: 604-32-0
cholesteryl benzoate

: 62307-95-3
3β-benzoyloxy-5α,6β-dichlorocholestane

Conditions

Conditions	Yield
With manganese(IV) oxide; acetic acid; acetyl chloride Ambient temperature;	95%
With chloroform; antimony(III) chloride; chlorine at -20℃;
With (Dichloroiodo)benzene In chloroform Heating;

: 604-32-0
cholesteryl benzoate

: 109003-94-3, 116780-59-7
Benzoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With oxygen; isopropyl alcohol; bis(trifluoroacetylacetonato)cobalt(II) at 75℃; for 8h;	91%

: 604-32-0
cholesteryl benzoate

A: 6557-19-3
5β,6β-epoxy-cholestan-3β-ol benzoate

B: 51646-05-0
5α,6α-epoxy-cholestan-3β-ol benzoate

Conditions

Conditions	Yield
With potassium permanganate; copper(II) sulfate In dichloromethane; water; tert-butyl alcohol for 2h; Yields of byproduct given;	A 90% B n/a
With monoperoxyphthalic acid; diethyl ether; chloroform
With potassium permanganate; chloroform; acetic acid

: 604-32-0
cholesteryl benzoate

: 570-74-1
cholest-5-ene

Conditions

Conditions	Yield
With magnesium(II) perchlorate; 9-ethyl-3,6-dimethyl-9H-carbazole In water; isopropyl alcohol at 23℃; for 2h; Irradiation;	90%

: 604-32-0
cholesteryl benzoate

: 250134-81-7
5,6-epoxycholestan-3β-ol benzoate

Conditions

Conditions	Yield
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine In various solvent(s) at -10℃; for 0.5h;	81%

: 604-32-0
cholesteryl benzoate

: 26048-46-4
7α-bromocholest-5-en-3β-ol benzoate

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In hexane for 0.5h; Heating;	74%
With N-Bromosuccinimide In tetrachloromethane for 0.5h; Heating;	40%
With N-Bromosuccinimide; Petroleum ether

: 604-32-0
cholesteryl benzoate

: 26048-47-5
5α,6β-dibromocholestan-3β-yl benzoate

Conditions

Conditions	Yield
With tetraethylammonium bromide In dichloromethane at 20℃; for 0.5h; Electrochemical reaction;	72%

: 614-45-9
tert-Butyl peroxybenzoate

: 604-32-0
cholesteryl benzoate

: 54758-42-8
7α-benzoyloxycholesteryl-3β-benzoate

Conditions

Conditions	Yield
Stage #1: cholesteryl benzoate With copper(I) bromide In dichloromethane for 0.25h; Heating; Stage #2: tert-Butyl peroxybenzoate In dichloromethane Heating;	69%

: 604-32-0
cholesteryl benzoate

: 50611-92-2
3β-benzoyloxycholest-5-ene-4-one

Conditions

Conditions	Yield
With perfluorooctylselenic acid; iodosylbenzene In various solvent(s) Heating;	65%

Cholesteryl benzoate Specification

The Cholesteryl benzoate with CAS registry number of 604-32-0 is also called Cholest-5-en-3-ol (3b)-,3-benzoate. The IUPAC name is[(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-yl] benzoate. Its EINECS registry number is 210-064-3. In addition, the molecular formula is C₃₄H₅₀O₂ and the molecular weight is 490.76. It is a kind of white solid and belongs to the classes of Cholesteryl Compounds (Liquid Crystals); Functional Materials; Liquid Crystals; Related Compounds; Intermediates; Fine Chemicals; Pharmaceuticals; Steroids; Chiral Building Blocks; Complex Molecules.

Physical properties about this chemical are: (1)ACD/LogP: 12.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 12.68; (4)ACD/LogD (pH 7.4): 12.68; (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)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.547; (14)Molar Refractivity: 149.64 cm³; (15)Molar Volume: 471.5 cm³; (16)Polarizability: 59.32×10^-24cm³; (17)Surface Tension: 41.2 dyne/cm; (18)Density: 1.04 g/cm³; (19)Flash Point: 213.1 °C; (20)Enthalpy of Vaporization: 84.69 kJ/mol; (21)Boiling Point: 563.6 °C at 760 mmHg; (22)Vapour Pressure: 1E-12 mmHg at 25°C.

Preparation of Cholesteryl benzoate: it can be prepared by benzoic acid-[4]pyridyl ester and cholest-5-en-3b-ol. This reaction will need solvent CH₂Cl₂. The reaction time is 5 hours at reaction temperature of 40 °C. The yield is about 89%.

Cholesteryl benzoate can be prepared by benzoic acid-[4]pyridyl ester and cholest-5-en-3b-ol

Uses of Cholesteryl benzoate: it can be used as intermediate of vitamin D3, and can be used in some hair colors, make-ups, and some other cosmetic preparations. Moreover, it can be used with cholesteryl nonanoate and cholesteryl oleyl carbonate in some thermochromic liquid crystals. In addition, it can be used to get 3b-benzoyloxy-cholest-5-en-7-one. This reaction will need reagent 3,5-dimethylpyrazolium fluorochromate and solvent acetonitrile. The reaction time is 10 hours by heating. The yield is about 70%.

Cholesteryl benzoate can be used to get 3b-benzoyloxy-cholest-5-en-7-one

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. In addition, you should not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4)c5ccccc5
(2)InChI: InChI=1/C34H50O2/c1-23(2)10-9-11-24(3)29-16-17-30-28-15-14-26-22-27(36-32(35)25-12-7-6-8-13-25)18-20-33(26,4)31(28)19-21-34(29,30)5/h6-8,12-14,23-24,27-31H,9-11,15-22H2,1-5H3/t24-,27+,28+,29-,30+,31+,33+,34-/m1/s1
(3)InChIKey: UVZUFUGNHDDLRQ-LLHZKFLPBM

Product Name

Cholesteryl benzoate

Synthetic route

Cholesteryl benzoate Specification

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