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Name |
Cholesteryl benzoate |
EINECS | 210-064-3 |
CAS No. | 604-32-0 | Density | 1.04 g/cm3 |
PSA | 26.30000 | LogP | 9.25340 |
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 | N/A | Appearance | white powder |
Safety | 22-24/25 | Risk Codes | N/A |
Molecular Structure | Hazard Symbols | N/A | |
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; |
Article Data | 51 |
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% |
Conditions | Yield |
---|---|
With sodium t-butanolate In toluene at 150℃; for 24h; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature; | 95% |
cholester-3-yl 4-hydroxymethylbenzoate
cholesteryl benzoate
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; sodium carbonate In cyclohexane at 130℃; for 48h; Molecular sieve; Schlenk technique; | 92% |
cholester-3β-yl thiobenzoate
cholesteryl benzoate
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% |
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 5h; | 89% |
Conditions | Yield |
---|---|
In dichloromethane at -78℃; for 0.5h; | 89% |
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; |
Conditions | Yield |
---|---|
In Petroleum ether | 88% |
cholesteryl benzoate
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% |
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%.
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%.
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