Cholesterol hemisuccinate

Base Information

• Chemical Name: Cholesterol hemisuccinate
• CAS No.: 1510-21-0
• Molecular Formula: C31H50O4
• Molecular Weight: 486.736
• Hs Code.: 29171900
• European Community (EC) Number: 216-148-6
• UNII: T3J4KS4201
• DSSTox Substance ID: DTXSID10934145
• Nikkaji Number: J206.716A
• Wikidata: Q27289619
• Mol file: 1510-21-0.mol

Synonyms:cholesterol hydrogen succinate;cholesterol-hemisuccinate;cholesteryl hemisuccinate;cholesteryl succinate;cholesteryl succinate, sodium salt, (3beta)-isomer

Chemical Property of Cholesterol hemisuccinate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.99E-15mmHg at 25°C
• Melting Point: 178 °C
• Refractive Index: -34 ° (C=2, CHCl3)
• Boiling Point: 585.973 °C at 760 mmHg
• PKA: 4.40±0.17(Predicted)
• Flash Point: 179.603 °C
• PSA: 63.60000
• Density: 1.069 g/cm³
• LogP: 7.80440
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 486.37091007
• Heavy Atom Count: 35
• Complexity: 815

Purity/Quality:

Cholesteryl hemisuccinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCC(=O)O)C)C
• 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
• 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.

Technology Process of Cholesterol hemisuccinate

There total 9 articles about Cholesterol hemisuccinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

succinic acid anhydride (108-30-5) + cholesterol (57-88-5) → cholesteryl hemisuccinate (1510-21-0)

Guidance literature:

With pyridine; dmap; dimethyl sulfoxide; In chloroform; at 110 ℃; for 3h;

DOI:10.1023/A:1020961812347

Reference yield: 95.0%

5-cholesten-3β-yl 2-(trimethylsilyl)ethyl butanedioate (92803-49-1) → cholesteryl hemisuccinate (1510-21-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 27 ℃; for 2h;

Reference yield: 92.0%

cholesterol (57-88-5) + succinoyl dichloride (543-20-4) → cholesteryl hemisuccinate (1510-21-0)

Guidance literature:

cholesterol; succinoyl dichloride; In acetonitrile; at 50 ℃; for 12h;

With hydrogenchloride; In water; acetonitrile;

upstream raw materials:

5-cholesten-3β-ol 3-<4-(2,2,2-trichloroethoxy)-4-oxobutanoate>

cholesterol

succinic acid anhydride

cholesterol

Downstream raw materials:

cholesterol-NHS ester

C₃₉H₅₂F₆O₄

Refernces

• 1、 Cai, Lulu,Qiu, Neng,Li, Xia,Luo, Kaili,Chen, Xiang,Yang, Li,He, Gu,Wei, Yuquan,Chen, Lijuan. "A novel truncated basic fibroblast growth factor fragment-conjugated poly (ethylene glycol)-cholesterol amphiphilic polymeric drug delivery system for targeting to the FGFR-overexpressing tumor cells". . p. 173 - 182. Retrieved 2011.
• 2、 Radwan, Awwad A.,Alanazi, Fares K.. "Design and synthesis of new cholesterol-conjugated 5-fluorouracil: A novel potential delivery system for cancer treatment". . p. 13177 - 13187. Retrieved 2014.
• 3、 Pescador, Paula,Brodersen, Nicolai,Scheidt, Holger A.,Loew, Martin,Holland, Gudrun,Bannert, Norbert,Liebscher, Juergen,Herrmann, Andreas,Huster, Daniel,Arbuzova, Anna. "Microtubes self-assembled from a cholesterol-modified nucleoside". . p. 5358 - 5360. Retrieved 2010.
• 4、 Konstantinova,Klykov,Maslov,Serebrennikova. "Synthesis of cationic cholesterol derivatives with succinyl spacer group". . p. 1189 - 1191. Retrieved 2002.
• 5、 Kumar, Prabhat,Shankar Rao,Krishna Prasad,Jayaraman. "In-plane modulated smectic ? vs smectic 'A' lamellar structures in poly(ethyl or propyl ether imine) dendrimers". . p. 98 - 104. Retrieved 2016.
• 6、 Yin, Xuelei,Chi, Yingying,Guo, Chuanyou,Feng, Shuaishuai,Liu, Jinhu,Sun, Kaoxiang,Wu, Zimei. "Chitooligosaccharides Modified Reduction-Sensitive Liposomes: Enhanced Cytoplasmic Drug Delivery and Osteosarcomas-Tumor Inhibition in Animal Models". . p. 2172 - 2184. Retrieved 2017.
• 7、 Wei, Renbo,Xu, Zeda,Liu, Xiyang,He, Yaning,Wang, Xiaogong. "Liquid-crystalline compounds containing both a strong push-pull azo chromophore and a cholesteryl unit as photoresponsive molecular glass materials". . p. 10925 - 10933. Retrieved 2015.
• 8、 Chen, Daquan,Yu, Hongyun,Mu, Hongjie,Wei, Junhua,Song, Zhenkun,Shi, Hong,Liang, Rongcai,Sun, Kaoxiang,Liu, Wanhui. "Novel chitosan derivative for temperature and ultrasound dual-sensitive liposomal microbubble gel". . p. 17 - 23. Retrieved 2013.
• 9、 Drasar,Cerny,Pouzar,Havel. "New preparation of steroidal 3-hemisuccinates". . p. 306 - 312. Retrieved 1984.
• 10、 Luo, Miao,Wang, Sheng,Wang, Meiling,Huang, Shaorong,Li, Chengpeng,Chen, Lin,Ma, Xiang. "Novel organogel harnessing Excited-State Intramolecular Proton Transfer process with aggregation induced emission and photochromism". . p. 48 - 57. Retrieved 2016.