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Cholesteryl hemisuccinate

Catalog Number
ACM1510210
CAS Number
1510-21-0
Product Name
Cholesteryl hemisuccinate
Structure
Category
Liquid Crystal (LC) Materials
Synonyms
Cholesteryl hydrogen succinate
Description
Cholesteryl hemisuccinate is a with hepatoprotective an anticancer activity. Cholesteryl hemisuccinate inhibits Acetaminophen (AAP, HY-66005) hepatotoxicity, and prevents AAP-induced hepatic apoptosis and necrosis. Cholesteryl hemisuccinate inhibits DNA polymerase and DNA topoisomerase to inhibit DNA replication and repair and cell division. Thus, Cholesteryl hemisuccinate inhibits tumor growth.
IUPAC Name
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
Molecular Weight
486.7
Molecular Formula
C31H50O4
Canonical SMILES
CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCC(=O)O)C)C
InChI
InChI=1S/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
InChI Key
WLNARFZDISHUGS-MIXBDBMTSA-N
Boiling Point
586.0±43.0 °C (Predicted)
Melting Point
178 °C
Flash Point
179.6°C
Purity
≥95%
Density
1.06±0.1 g/cm³ (Predicted)
Solubility
Chloroform: 10 mg/mL
Appearance
A crystalline solid
Application
Cholesteryl hemisuccinate serves as a versatile compound with diverse applications in biochemical and pharmacological studies. It is primarily used as a detergent to replace cholesterol in protein crystallography, which aids in the structural analysis of proteins. Its function extends to stabilizing unilamellar vesicles and liposomes, essential for various drug delivery systems involving anticancer drugs, antibiotics, and oligonucleotides. Additionally, cholesteryl hemisuccinate exhibits anticancer properties by inhibiting the growth of certain leukemia cells. It also acts as an emulsifying agent, facilitating the solubilization of proteins, such as chemokine receptor 1 and erythrocyte ghosts, enhancing their study and application in research and therapeutic contexts.
Storage
Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
Assay
0.99
Complexity
815
EC Number
216-148-6
Exact Mass
486.37091007
Formal Charge
0
Heavy Atom Count
35
Hydrogen Bond Acceptor Count
4
Hydrogen Bond Donor Count
1
Isomeric SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)CCC(=O)O)C)C
Monoisotopic Mass
486.37091007
Packaging
10 g
Rotatable Bond Count
10
Stability
≥2 years
Storage Conditions
-20 °C
Topological Polar Surface Area
63.6 Ų
WGK Germany
3
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