CHOLESTERYL TOSYLATE

Base Information

• Chemical Name: CHOLESTERYL TOSYLATE
• CAS No.: 1182-65-6
• Molecular Formula: C₃₄H₅₂O₃S
• Molecular Weight: 540.851
• European Community (EC) Number: 214-657-8
• NSC Number: 134905,132807
• DSSTox Substance ID: DTXSID90922626
• Mol file: 1182-65-6.mol

Synonyms:Cholest-5-en-3-ol(3b)-, 4-methylbenzenesulfonate(9CI); Cholesterol, p-toluenesulfonate (6CI,7CI,8CI); 3b-Tosyloxycholest-5-ene;Chloest-5-en-3b-tosylate;Cholest-5-en-3b-ylp-toluenesulfonate; Cholesterol 3-tosylate; Cholesterol tosylate; Cholesterylp-toluenesulfonate; Cholesteryl p-toluenesulphonate; Cholesteryl tosylate; NSC132807; NSC 134905

Chemical Property of CHOLESTERYL TOSYLATE

Chemical Property:

• Vapor Pressure: 1.63E-14mmHg at 25°C
• Boiling Point: 617.5°C at 760 mmHg
• Flash Point: 327.2°C
• PSA: 51.75000
• Density: 1.09g/cm³
• LogP: 10.19110
• Storage Temp.: -20°C
• XLogP3: 10.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 540.36371669
• Heavy Atom Count: 38
• Complexity: 955

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cholesterylp-toluenesulfonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2CCC3(C4CCC5(C(C4CC=C3C2)CCC5C(C)CCCC(C)C)C)C

Technology Process of CHOLESTERYL TOSYLATE

There total 21 articles about CHOLESTERYL TOSYLATE 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: 90.0%

Δ5-cholesten-3β-ol (57-88-5,474-77-1,14868-17-8,23820-70-4,34026-89-6,57759-45-2,71869-93-7,121155-47-3,138456-89-0) + p-toluenesulfonyl chloride (98-59-9) → p-Toluol-sulfonsaeure-(cholesteryl-ester) (1182-65-6,3381-56-4)

Guidance literature:

With pyridine; at 0 - 55 ℃;

DOI:10.1016/j.ejmech.2019.111720

Reference yield: 88.0%

cholesterol (57-88-5) + toluene-4-sulfonic acid (104-15-4) → cholesteryl p-toluenesulfonate (1182-65-6,3381-56-4)

Guidance literature:

cobalt(II) chloride; In 1,2-dichloro-ethane; for 1h; Heating;

DOI:10.1016/j.tetlet.2003.10.106

Reference yield: 88.0%

cholesteryl methyl ether (1174-92-1) + p-toluenesulfonyl chloride (98-59-9) → cholesteryl p-toluenesulfonate (1182-65-6,3381-56-4)

Guidance literature:

With pyridine;

DOI:10.3390/60100052

upstream raw materials:

p-toluenesulfonyl chloride

Δ₅-cholesten-3β-ol

toluene-4-sulfonic acid

6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane

Downstream raw materials:

1-cholest-5-en-3β-yl-4-methyl-pyridinium; toluene-4-sulfonate

3,5-cholestadiene

cholesteryl methyl ether

6β-phenylsulfanyl-3α,5α-cyclo-cholestane

Refernces

• 1、 Yang, Xiwen,Chen, Shaonan,Luo, Hang,Xu, Haoran,Chen, Sheng. "Self-organization of cholesterol-side-chain liquid crystalline polymers by tailoring the main chain structure and flexible spacer length". . p. 5429 - 5440. Retrieved 2019.
• 2、 Tang, Jie,Zhang, Li,Liu, Yayuan,Zhang, Qianyu,Qin, Yao,Yin, Yujia,Yuan, Wenmin,Yang, Yuting,Xie, Yafei,Zhang, Zhirong,He, Qin. "Synergistic targeted delivery of payload into tumor cells by dual-ligand liposomes co-modified with cholesterol anchored transferrin and TAT". . p. 31 - 40. Retrieved 2013.
• 3、 Ren, Yuchun,Wang, Bin,Zhang, Xiuqing. "Synthesis of photoresponsive cholesterol-based azobenzene organogels: Dependence on different spacer lengths". . p. 1089 - 1095. Retrieved 2015.
• 4、 Chen, Qifan,Liu, Xiaofeng,Guo, Zhihao,Xu, Xiaoxu,Lu, Yanhua. "Synthesis and characterization of new chiral liquid crystal monomers containing steroid unit". . p. 1 - 11. Retrieved 2018.
• 5、 Felekis, Theodores,Tziveleka, Leto,Tsiourvas, Dimitris,Paleos, Constantinos M.. "Liquid crystals derived from hydrogen-bonded supramolecular complexes of pyridinylated hyperbranched polyglycerol and cholesterol-based carboxylic acids". . p. 1705 - 1710. Retrieved 2005.
• 6、 Reich,Lardon. "-". . p. 671,680. Retrieved 1946.
• 7、 Ju, Jia,Huan, Meng-Lei,Wan, Ning,Hou, Yi-Lin,Ma, Xi-Xi,Jia, Yi-Yang,Li, Chen,Zhou, Si-Yuan,Zhang, Bang-Le. "Cholesterol derived cationic lipids as potential non-viral gene delivery vectors and their serum compatibility". . p. 2401 - 2407. Retrieved 2016.
• 8、 Behera, Harekrushna,Madhavan, Nandita. "Anion-Selective Cholesterol Decorated Macrocyclic Transmembrane Ion Carriers". . p. 12919 - 12922. Retrieved 2017.
• 9、 Wang, Zhao,Luo, Ting,Sheng, Ruilong,Li, Hui,Sun, Jingjing,Cao, Amin. "Amphiphilic diblock terpolymer PMAgala-b-P(MAA-co-MAChol)s with attached galactose and cholesterol grafts and their intracellular pH-responsive doxorubicin delivery". . p. 98 - 110. Retrieved 2016.
• 10、 Misra, Santosh K.,Kondaiah, Paturu,Bhattacharya, Santanu,Boturyn, Didier,Dumy, Pascal. "Co-liposomes comprising a lipidated multivalent RGD-peptide and a cationic gemini cholesterol induce selective gene transfection in αvβ3 and αvβ5 integrin receptor-rich cancer cells". . p. 5758 - 5767. Retrieved 2014.