4-[(3β)-Cholest-5-en-3-yloxy]-4-oxobutanoic acid

Names

[ Name ]:
4-[(3β)-Cholest-5-en-3-yloxy]-4-oxobutanoic acid

[Synonym ]:
4-[(3β)-Cholest-5-en-3-yloxy]-4-oxobutanoic acid
3-cholesteryloxycarbonylpropanoic acid
Cholesteryl hydrogen succinate
EINECS 216-148-6
3-(3-cholesteryloxycarbonyl)propanoic acid
MONO-CHOLESTERYL-SUCCINATE
CHOLESTEROL HYDROGEN SUCCINATE
3β-Hydroxy-5-cholestene 3-hemisuccinate
MFCD00037705
cholesteryl hemisuccinate free acid
cholesterylsuccinate
5-Cholesten-3β-ol 3-hemisuccinate
Succinic Acid Monocholesterol Ester
5-CHOLESTEN-3BETA-OL 3-HEMISUCCINATE
Butanedioic acid, mono[(3β)-cholest-5-en-3-yl] ester

Biological Activity

[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[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vivo]

Cholesteryl hemisuccinate（100 mg/kg；ip；AAP 前单次给药）消除 AAP（350-500 mg/kg；ip；单次给药）在 ICR 小鼠 (CD-1) 中诱导的细胞凋亡和坏死的组织学和生化诊断[1]。

[References]

[1]. Ray SD, et al. Protection of acetaminophen-induced hepatocellular apoptosis and necrosis by cholesteryl hemisuccinate pretreatment. J Pharmacol Exp Ther. 1996 Dec;279(3):1470-83.

[2]. Varshosaz J, et al. Folated synperonic-cholesteryl hemisuccinate polymeric micelles for the targeted delivery of docetaxel in melanoma. Biomed Res Int. 2015;2015:746093.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
586.0±43.0 °C at 760 mmHg

[ Melting Point ]:
178 °C

[ Molecular Formula ]:
C₃₁H₅₀O₄

[ Molecular Weight ]:
486.73

[ Flash Point ]:
179.6±21.7 °C

[ Exact Mass ]:
486.370911

[ PSA ]:
63.60000

[ LogP ]:
10.32

[ Vapour Pressure ]:
0.0±3.5 mmHg at 25°C

[ Index of Refraction ]:
1.529

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Precursor & DownStream

Precursor

DownStream

Articles

Co-expression of human agouti-related protein enhances expression and stability of human melanocortin-4 receptor.

Biochem. Biophys. Res. Commun. 456(1) , 116-21, (2014)

G protein-coupled receptors (GPCRs) represent the largest family of transmembrane signaling proteins, and they are considered major targets of approximately half of all therapeutic agents. Human melan...

Solution structure of the transmembrane 2 domain of the human melanocortin-4 receptor in sodium dodecyl sulfate (SDS) micelles and the functional implication of the D90N mutant.

Biochim. Biophys. Acta 1848 , 1294-302, (2015)

The melanocortin receptors (MCRs) are members of the G protein-coupled receptor (GPCR) 1 superfamily with seven transmembrane (TM) domains. Among them, the melanocortin-4 receptor (MC4R) subtype has b...

Structural basis for the facilitative diffusion mechanism by SemiSWEET transporter.

Nat. Commun. 6 , 6112, (2015)

SWEET family proteins mediate sugar transport across biological membranes and play crucial roles in plants and animals. The SWEETs and their bacterial homologues, the SemiSWEETs, are related to the PQ...