4-[[17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxo-butanoic acid

HCID 500055CAS 1510-21-0
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)CCCC(C)C1CCC2C3CC=C4CC(OC(=O)CCC(=O)O)CCC4(C)C3CCC12C
InChIKey
WLNARFZDISHUGS-UHFFFAOYSA-N
Molecular formula
C31H50O4
Average molar mass
486.7 g/mol

Names & identifiers

Preferred name
4-[[17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxo-butanoic acid
IUPAC
4-[[10,13-dimethyl-17-(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
English name
Cholesteryl hemisuccinate
Molecular formula
C31H50O4
Molecular weight
486.73

Names & synonyms

4-(Cholest-5-en-3-yloxy)-4-oxobutanoic acid4-[[17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxo-butanoic acidNSC628321SCHEMBL463416orb3033164AKOS0243195204-[[10,13-dimethyl-17-(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 acidLS-15319DB-043075CHOLESTERYL HYDROGEN SUCCINATEcholesterylsuccinateCholesterol Succinate
Show more names
Cholesteryl hemisucciteCHOLESTERYL HEMISUCCINATEMONO-CHOLESTERYL-SUCCINATECHOLESTEROL HYDROGEN SUCCINATE5-CHOLESTEN-3β-OL HEMISUCCINATECholesterol Hydrogen Succinate >5-CHOLESTEN-3-BETA-OL HEMISUCCINATE

Database identifiers

CAS
1510-21-0
PubChem CID
500055

Properties

Computed structural properties

XLogP
8.5
Topological polar surface area
63.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
10
Heavy atoms
35

Physicochemical properties

Melting point
178 °C · 178 °C
Boiling point
586 · 586.0±43.0 °C(Predicted)
Density
1.06 · 1.06±0.1 g/cm3(Predicted)
refractive index
-34 ° · -34 ° (C=2, CHCl3)
storage temp.
-20 °C · -20°C
solubility
Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29171900
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications · 3 items

DescriptionCholesteryl 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.

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

General DescriptionCholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

2 records
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