Cholesteryl hemisuccinate

Catalog	DGS1510210
CAS	1510-21-0
Structure
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.
Synonyms	Cholesteryl hydrogen succinate
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.
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
Hygroscopic	No
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
Light Sensitive	No
Monoisotopic Mass	486.37091007
pKa	4.40±0.17 (Predicted)
Rotatable Bond Count	10
Shipping	Room temperature
Stability	≥2 years
Storage Conditions	-20 °C
Topological Polar Surface Area	63.6 Ų
XLogP3-AA	8.5