Cholesteryl hemisuccinate

Product Name: Cholesteryl hemisuccinate
CAS No.: 1510-21-0
Chemical Name: Cholesteryl hemisuccinate
Synonyms: CHOLESTERYL HYDROGEN SUCCINATE;cholesterylsuccinate;Cholesterol Succinate;Cholesteryl hemisuccite;CHOLESTERYL HEMISUCCINATE;MONO-CHOLESTERYL-SUCCINATE;CHOLESTEROL HYDROGEN SUCCINATE;5-CHOLESTEN-3β-OL HEMISUCCINATE;Cholesterol Hydrogen Succinate >5-CHOLESTEN-3-BETA-OL HEMISUCCINATE
CBNumber: CB0336321
Molecular Formula: C31H50O4
Formula Weight: 486.73
MOL File: 1510-21-0.mol

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Cholesteryl hemisuccinate Property

Melting point:: 178 °C
Boiling point:: 586.0±43.0 °C(Predicted)
Density: 1.06±0.1 g/cm3(Predicted)
refractive index: -34 ° (C=2, CHCl3)
storage temp.: -20°C
solubility: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
form: Solid
pka: 4.40±0.17(Predicted)
color: White to Off-White
InChIKey: WLNARFZDISHUGS-BLYFUZNHSA-N
SMILES: [C@@]12([H])CC=C3C[C@@H](OC(=O)CCC(=O)O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])[C@H](C)CCCC(C)C |&1:0,6,17,19,23,25,28,30,r|
LogP: 10.708 (est)
CAS DataBase Reference: 1510-21-0(CAS DataBase Reference)

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Safety

WGK Germany: 3
HS Code: 29171900

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C6512
Product name: Cholesteryl hemisuccinate
Packaging: 5g
Price: $280
Updated: 2025/07/31

Sigma-Aldrich

Product number: C6512
Product name: Cholesteryl hemisuccinate
Packaging: 25g
Price: $927
Updated: 2025/07/31

Cayman Chemical

Product number: 25698
Product name: Cholesteryl Hemisuccinate
Purity: ≥95%
Packaging: 1g
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 25698
Product name: Cholesteryl Hemisuccinate
Purity: ≥95%
Packaging: 5g
Price: $183
Updated: 2024/03/01

Cayman Chemical

Product number: 25698
Product name: Cholesteryl Hemisuccinate
Purity: ≥95%
Packaging: 10g
Price: $341
Updated: 2024/03/01

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Cholesteryl hemisuccinate Chemical Properties,Usage,Production

Description

Cholesteryl hemisuccinate is a cholesterol ester with anticancer activity. It inhibits the growth of murine C1498 myeloid and L1210 lymphocytic leukemia cells when used at concentrations of 50 and 150 μM, respectively. Cholesteryl hemisuccinate acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. It has also been used as an emulsifying agent in various vesicular drug delivery systems for anticancer drugs, antibiotics, and oligonucleotides and to solubilize various proteins including chemokine receptor 1 as well as erythrocyte ghosts.

Uses

Cholesteryl Hemisuccinate is an oxidation product of polyunsaturated fatty acid of cholesterol that alters lysosome structure and functions and induces proinflammatory cytokine production in macrophages.

Definition

ChEBI: Cholesteryl hemisuccinate is a dicarboxylic acid monoester resulting from the formal condensation of the hydroxy group of cholesterol with one of the carboxy groups of succinic acid. A detergent that is often used to replace cholesterol in protein crystallography, biochemical studies of proteins, and pharmacology. It has a role as a detergent. It is a cholestane ester, a dicarboxylic acid monoester and a hemisuccinate. It is functionally related to a cholesterol.

General Description

Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester.

Biochem/physiol Actions

CHEMS can help to maintain the stability of dioleoylphosphatidylethanolamine (DOPE). This amphipathic lipid is used in mixtures with dioleoylphosphatidylethanolamine (DOPE) to form ′pH sensitive′ fusogenic vesicles. It can control cell growth.

Synthesis

108-30-5

57-88-5

1510-21-0

GENERAL METHOD: Succinic anhydride (14.7 mmol, 1.57 eq.) and 4-dimethylaminopyridine (DMAP, 1.584 mmol, 0.17 eq.) were sequentially added to a solution of (3β)-cholest-5-en-3-ol (9.37 mmol) in pyridine (28 mL). The reaction mixture was stirred at room temperature for 7 days. Upon completion of the reaction, the mixture was poured into ice water and the pH was adjusted to 7 with dilute hydrochloric acid and subsequently extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford the target compounds in 79% or 96% yield and >99.9% analytical purity (see Scheme 1-2). Analytical data for compounds 2 and 12 are detailed in the Supplementary Material.

References

[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 8, p. 1189 - 1191
[2] Steroids, 2013, vol. 78, # 14, p. 1347 - 1352
[3] Patent: US2005/201972, 2005, A1. Location in patent: Page/Page column 15
[4] Polymer, 2016, vol. 86, p. 98 - 104
[5] Arzneimittel-Forschung/Drug Research, 1994, vol. 44, # 11, p. 1259 - 1264

Cholesteryl hemisuccinate Preparation Products And Raw materials

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View Lastest Price from Cholesteryl hemisuccinate manufacturers

Shenzhen Nexcon Pharmatechs Ltd.

Product: Cholesteryl hemisuccinate 1510-21-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 97%
Supply Ability: 2000
Release date: 2025-08-22

Hebei Zhuanglai Chemical Trading Co Ltd

Product: Cholesteryl hemisuccinate 1510-21-0
Price: US $45.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20 tons
Release date: 2024-12-05

Henan Aochuang Chemical Co.,Ltd.

Product: Cholesteryl hemisuccinate 1510-21-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-10-09

1510-21-0, Cholesteryl hemisuccinateRelated Search:

6alpha-Methylprednisolone sodium succinate Disodium succinate Hydrogen Hydrogen Sulfide iron succinate CHLOROPHOSPHONAZO III Dimethyl succinate Succinic acid Cholesteryl oleate HYDROGEN CYANIDE Hydrogen peroxide Cholesterol (-)-Cholesterol sulfo-NHS succinate CHOLESTERYL HEMISUCCINATE F & D VERSION&,CHOLESTERYL HEMISUCCINATE TRIS,CHOLESTERYL HEMISUCCINATE TRIS SALT,CHOLESTERYL HYDROGEN SUCCINATE TRIS SALT (-)-Cholesterol NHS succinate hydrogen fluoride 5-CHOLESTENE Cholesteryl hemisuccinate

3β-(1,4-Dioxo-4-hydroxybutoxy)cholesta-5-ene

Butanedioic acid hydrogen 1-(cholest-5-en-3β-yl) ester

Succinic acid 1-(3β-cholesteryl) ester

Succinic acid hydrogen 3β-cholesteryl ester

Succinic acid hydrogen cholest-5-en-3β-yl ester

Cholest-5-en-3-ol (3b)-, 3-(hydrogen butanedioate)

CHOLESTEROL HYDROGEN SUCCINATE

CHOLESTERYL HYDROGEN SUCCINATE

CHOLESTERYL HEMISUCCINATE

3BETA-HYDROXY-5-CHOLESTENE 3-HEMISUCCINATE

5-CHOLESTER-3BETA-YL HYDROGEN SUCCINATE

5-CHOLESTEN-3-BETA-OL HEMISUCCINATE

5-CHOLESTEN-3BETA-OL 3-HEMISUCCINATE

SUCCINIC ACID MONOCHOLESTEROL ESTER

MONO-CHOLESTERYL-SUCCINATE

cholesterylsuccinate

cholesteryl hemisuccinate free acid

Cholesteryl hydrogen succinate Cholesteryl hemisuccinate

cholest-5-en-3beta-yl hydrogen succinate

Cholesterol Hydrogen Succinate &gt

Cholest-5-en-3-ol (3β)-, 3-(hydrogen butanedioate)

Cholesterol Succinate

6-Amino-2,4-dichloro-26-methylphenol&hydrochloride

5-CHOLESTEN-3β-OL HEMISUCCINATE

3β-Hydroxy-5-Cholestene 3-Hemisuccinate

Cholesteryl hemisuccite

1510-21-0

C31H50O4

Cholesteryl Compounds (Liquid Crystals)

Functional Materials

Liquid Crystals & Related Compounds