Cholesteryl hemisuccinate supplier

Name
Cholesteryl hemisuccinate
EINECS 216-148-6
CAS No. 1510-21-0
Article Data52
CAS DataBase
Density 1.069 g/cm³
Solubility
Melting Point 178 °C
Formula C₃₁H₅₀O₄
Boiling Point 585.973 °C at 760 mmHg
Molecular Weight 486.736
Flash Point 179.603 °C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Cholest-5-en-3-ol(3b)-, hydrogen butanedioate (9CI);Cholesterol, hydrogen succinate (7CI,8CI);3-(3-Cholesteryloxycarbonyl)propionicacid;3-Cholesteryloxycarbonylpropanoic acid;3-[(Cholest-5-en-3b-yl)oxycarbonyl]propionic acid;Mono(cholesteryl) succinate;Succinicacid monocholesteryl ester;
PSA 63.60000
LogP 7.80440

Synthetic route

: 108-30-5
succinic acid anhydride

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With pyridine; dmap; dimethyl sulfoxide In chloroform at 110℃; for 3h;	97%
With pyridine; dmap at 20℃; for 168h;	96%
Stage #1: succinic acid anhydride; cholesterol; dmap In 1,4-dioxane at 20℃; for 24h; Stage #2: With hydrogenchloride In 1,4-dioxane; water	95%

: 92803-49-1
5-cholesten-3β-yl 2-(trimethylsilyl)ethyl butanedioate

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 2h;	95%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	81%

: 57-88-5
cholesterol

: 543-20-4
succinoyl dichloride

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
Stage #1: cholesterol; succinoyl dichloride In acetonitrile at 50℃; for 12h; Stage #2: With hydrogenchloride In water; acetonitrile	92%

: 108-30-5
succinic acid anhydride

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; benzene
With pyridine; toluene-4-sulfonic acid

: 57-88-5
cholesterol

: 543-20-4
succinoyl dichloride

A: 1510-21-0
cholesteryl hemisuccinate

B: 1510-20-9
cholesteryl 3-succinate

Conditions

Conditions	Yield
With benzene

...Expand

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / DCC, 4-dimethylaminopyridine / benzene / 5 h / 27 °C 2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 27 °C View Scheme

: 1510-21-0
cholesteryl hemisuccinate

: 87311-35-1
cholesteryloxycarbonylpropionyl chloride

Conditions

Conditions	Yield
With thionyl chloride In toluene at 90℃; for 2h;	100%
With oxalyl dichloride In dichloromethane at 20℃; for 12h;	98%
With thionyl chloride In toluene at 80℃; for 1h;

: 1510-21-0
cholesteryl hemisuccinate

: 96-53-7
2-mercaptothiazoline

: C34H53NO3S2

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	100%

: 3731-51-9
(2-aminomethylpyridine)

: 1510-21-0
cholesteryl hemisuccinate

: (3β)-cholest-5-en-3-yl 4-oxo-4-[(pyridin-2-ylmethyl)amino]butanoate

Conditions

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 75h; Reagent/catalyst; Solvent;	96%

: 108-30-5
succinic acid anhydride

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With pyridine; dmap; dimethyl sulfoxide In chloroform at 110℃; for 3h;	97%
With pyridine; dmap at 20℃; for 168h;	96%
Stage #1: succinic acid anhydride; cholesterol; dmap In 1,4-dioxane at 20℃; for 24h; Stage #2: With hydrogenchloride In 1,4-dioxane; water	95%

: 92803-49-1
5-cholesten-3β-yl 2-(trimethylsilyl)ethyl butanedioate

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 2h;	95%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	81%

: 57-88-5
cholesterol

: 543-20-4
succinoyl dichloride

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
Stage #1: cholesterol; succinoyl dichloride In acetonitrile at 50℃; for 12h; Stage #2: With hydrogenchloride In water; acetonitrile	92%

: 108-30-5
succinic acid anhydride

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; benzene
With pyridine; toluene-4-sulfonic acid

: 57-88-5
cholesterol

: 543-20-4
succinoyl dichloride

A: 1510-21-0
cholesteryl hemisuccinate

B: 1510-20-9
cholesteryl 3-succinate

Conditions

Conditions	Yield
With benzene

...Expand

: 57-88-5
cholesterol

: 1510-21-0
cholesteryl hemisuccinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / DCC, 4-dimethylaminopyridine / benzene / 5 h / 27 °C 2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 27 °C View Scheme

: 1510-21-0
cholesteryl hemisuccinate

: 87311-35-1
cholesteryloxycarbonylpropionyl chloride

Conditions

Conditions	Yield
With thionyl chloride In toluene at 90℃; for 2h;	100%
With oxalyl dichloride In dichloromethane at 20℃; for 12h;	98%
With thionyl chloride In toluene at 80℃; for 1h;

: 1510-21-0
cholesteryl hemisuccinate

: 96-53-7
2-mercaptothiazoline

: C34H53NO3S2

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	100%

: 3731-51-9
(2-aminomethylpyridine)

: 1510-21-0
cholesteryl hemisuccinate

: (3β)-cholest-5-en-3-yl 4-oxo-4-[(pyridin-2-ylmethyl)amino]butanoate

Conditions

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 75h; Reagent/catalyst; Solvent;	96%

: 1510-21-0
cholesteryl hemisuccinate

: 17364-19-1
1-stearoyl-sn-glycero-3-phosphocholine

: 1-stearoyl-2-cholesterylhemisuccinoyl-sn-glycero-3-phosphocholine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 24h;	90%

: 1510-21-0
cholesteryl hemisuccinate

: 10157-97-8
5α,6β-dihydroxycholestan-3β-yl-hemisuccinate

Conditions

Conditions	Yield
Stage #1: cholesteryl hemisuccinate With monoperoxyphthalic acid magnesium salt hexahydrate In acetone at 57℃; for 0.5h; Stage #2: With bismuth(lll) trifluoromethanesulfonate In acetone at 20℃; for 0.5h;	90%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 1510-21-0
cholesteryl hemisuccinate

: 88848-79-7
cholesterol-NHS ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at -10 - 20℃; for 4h;	89%
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1.5h;

: C17H20ClNO4S

: 1510-21-0
cholesteryl hemisuccinate

: 104495-49-0
Ethyl-diisopropylphosphoramidochloridit

: 107-21-1
ethylene glycol

: C52H77ClNO11PS

Conditions

Conditions	Yield
at 20℃; for 10h;	85.7%

...Expand

monomethoxypolyethylene glycol-polylactide: monomethoxypolyethylene glycol-polylactide

: 1510-21-0
cholesteryl hemisuccinate

mPEG-PLA-cholesterol: mPEG-PLA-cholesterol

Conditions

Conditions	Yield
dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 24h; Product distribution / selectivity;	85%

: 188478-29-7
8-dioxane-3-cobalt-bis(1,2-dicarbollide)

: 1510-21-0
cholesteryl hemisuccinate

: 584-08-7
potassium carbonate

: C39H78B18CoO6(1-)*K(1+)

Conditions

Conditions	Yield
In 1,2-dimethoxyethane for 6h; Reflux;	83%

...Expand

: 1510-21-0
cholesteryl hemisuccinate

: 530-62-1
1,1'-carbonyldiimidazole

: C34H52N2O3

Conditions

Conditions	Yield
In chloroform at 38℃; for 8h;	81%

: 1510-21-0
cholesteryl hemisuccinate

: 39160-70-8
3,6,9,12,15,18-hexaoxa-1-octadecyl amine

: 878049-46-8
N-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl}-succinamic acid 17-(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

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 20h;	80%

: 926890-48-4
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-propanol

: 1510-21-0
cholesteryl hemisuccinate

A: 926890-49-5
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane

B: 2387-23-7
1,3-Dicyclohexylurea

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 6.08333h; Product distribution / selectivity;	A 79% B n/a

...Expand

: 926890-48-4
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-propanol

: 1510-21-0
cholesteryl hemisuccinate

: 926890-49-5
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h; Product distribution / selectivity;	79%

: 1510-21-0
cholesteryl hemisuccinate

: 174221-86-4
5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine

: C61H79N3O10

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	79%

: 3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-propanol

: 1510-21-0
cholesteryl hemisuccinate

: 926890-49-5
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6h; Cooling with ice;	79%

: (Bu4N)3{(MnMo6O18)3[(OCH2)3CNH2]2}

: 1510-21-0
cholesteryl hemisuccinate

: C8H16MnMo6N2O24(3-)*C16H36N(1+)*C31H50O4

Conditions

Conditions	Yield
Stage #1: cholesteryl hemisuccinate With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In acetonitrile at 81℃; for 0.583333h; Stage #2: (Bu4N)3{(MnMo6O18)3[(OCH2)3CNH2]2} In acetonitrile for 24h; Reflux;	79%

: 1510-21-0
cholesteryl hemisuccinate

: 405906-58-3
6A,6D-diamino-6A,6D-dideoxy-2A,D,3A,D-di-O-methylhexakis-(2A-G,3B-G,6B,C,E,F,G-tri-O-methyl)cyclomaltoheptaose

: 6(I),6(IV)-(β-cholesteryl)-succinylamido-6(I),6(IV)-6-deoxy-per(2,3,6-O-methyl)cycloheptaose

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 3h;	78%

: 1510-21-0
cholesteryl hemisuccinate

: 86639-52-3, 110714-48-2, 130144-34-2
7-ethyl-10-hydroxycamptothecin

: cholesterol succinate-10-(7-ethyl-10-hydroxycamptothecin)

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	78%
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃;	71.8%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 2.5h;	70%

: 524-38-9
N-hydroxyphthalimide

: 1510-21-0
cholesteryl hemisuccinate

: (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 (1,3-dioxoisoindolin-2-yl) succinate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	75%

: 868-77-9
2-methyl-2-propenoic acid 2-hydroxyethyl ester

: 1510-21-0
cholesteryl hemisuccinate

: 107674-10-2
2-(3-((cholesteryl)oxycarbonyl)propionyloxy)ethyl methacrylate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;	74%

: 51-21-8
5-fluorouracil

: 1510-21-0
cholesteryl hemisuccinate

: cholesteryl 4-(2,4-dioxo-5-fluoro-(1H,3H)-pyrimidin-1-yl)-4-oxobutanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 48h;	72%

: 1510-21-0
cholesteryl hemisuccinate

: 69515-74-8, 628317-17-9
mitomycin-C

: 118022-81-4
3-(cholesteryloxycarbonyl)propanoyl MMC

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; chloroform for 48h; Ambient temperature;	71%

: 92-50-2
2-( N-ethylanilino)ethanol

: 1510-21-0
cholesteryl hemisuccinate

: 2-(N-ethyl-N-phenylamino)ethyl 3'-((cholesteryl)oxycarbonyl)propionate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	70%

: radicicol

: 1510-21-0
cholesteryl hemisuccinate

: C49H65ClO9

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h;	70%

: 1198587-13-1
4-{[(2-hydroxyethyl)(2-naphthylmethyl)amino]methyl}-N-(tetrahydro-2H-pyran-2-yloxy)benzamide

: 1510-21-0
cholesteryl hemisuccinate

: 1198587-15-3
1-cholest-5-en-3-yl 4-{2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl} succinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	65.8%

: 54714-11-3
4,6-diphenylthieno-[3,4-d]-1,3-dioxol-2-one-5,5-dioxide

: 1510-21-0
cholesteryl hemisuccinate

: 127619-26-5
Succinic 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 1,1,4-trioxo-2,5-diphenyl-4,5-dihydro-1H-1λ6-thiophen-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h;	64%

: 1510-21-0
cholesteryl hemisuccinate

: 107-21-1
ethylene glycol

: 204652-39-1
Succinic 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-hydroxy-ethyl ester

Conditions

Conditions	Yield
Stage #1: cholesteryl hemisuccinate With thionyl chloride In toluene at 65℃; Stage #2: ethylene glycol With triethylamine In dichloromethane at 20℃;	63%
Stage #1: cholesteryl hemisuccinate With thionyl chloride In toluene Stage #2: ethylene glycol With triethylamine In dichloromethane at 20℃;

Cholesteryl hemisuccinate Specification

The Cholesteryl hemisuccinate, with the CAS registry number 1510-21-0, is also known as Cholest-5-en-3beta-yl hydrogen succinate. It belongs to the product categories of Cholesteryl Compounds (Liquid Crystals); Functional Materials; Liquid Crystals & Related Compounds. Its EINECS registry number is 216-148-6. This chemical's molecular formula is C₃₁H₅₀O₄ and molecular weight is 486.73. Its IUPAC name is called 4-[[(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]oxy]-4-oxobutanoic acid. This chemical is white powder.

Physical properties about Cholesteryl hemisuccinate are: (1)ACD/LogP: 10.32; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.19; (4)ACD/LogD (pH 7.4): 7.39; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 48165.85; (7)ACD/KOC (pH 5.5): 721507.88; (8)ACD/KOC (pH 7.4): 11509.87; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.528; (13)Molar Refractivity: 140.47 cm³; (14)Molar Volume: 455.5 cm³; (15)Surface Tension: 42.6 dyne/cm; (16)Density: 1.06 g/cm³; (17)Melting Point: 178 °C; (18)Flash Point: 179.6 °C; (19)Enthalpy of Vaporization: 95.62 kJ/mol; (20)Boiling Point: 586 °C at 760 mmHg; (21)Vapour Pressure: 2.99E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC(=O)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
(2)InChI: InChI=1/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
(3)InChIKey: WLNARFZDISHUGS-MIXBDBMTBW

Product Name

Cholesteryl hemisuccinate

Synthetic route

Cholesteryl hemisuccinate Specification

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