55357-38-5

Basic information

• Product Name: Choline tosylate
• Synonyms: [2-HYDROXYETHYL]TRIMETHYLAMMONIUM P-TOLUENESULFONATE SALT;CHOLINE P-TOLUENESULFONATE SALT;CHOLINE TOSYLATE;Choline 4-methylbenzenesulphonate salt;Choline 4-methylbenzenesulphonate salt 99%;2-Hydroxy-N,N,N-trimethyl-ethanaminium 4-methylbenzenesulfonic acid salt;Choline p-toluenesulfonate;(2-Hydroxyethyl)trimethylammonium toluene-4-sulphonate 99%
• CAS NO: 55357-38-5
• Molecular Formula: C₅H₁₄NO*C₇H₇O₃S
• Molecular Weight: 275.36
• Product Categories: Quarternary ammonium salts
• Mol File: 55357-38-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 95°C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive: Light Sensitive/Hygroscopic
• CAS DataBase Reference: Choline tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: Choline tosylate(55357-38-5)
• EPA Substance Registry System: Choline tosylate(55357-38-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 55357-38-5(Hazardous Substances Data)

Usage

Uses

Choline p-Toluenesulfonate Salt is a useful intermediate as well as a choline acetyltransferase (CHAT) substrate.

Synthesis

A 500 mL reactor was charged at 25 °C with 50 g (268.5 mmol) methyl tosylate and 100 mL acetone to which a solution of 25.1 g (281.6 mmol) N,N-dimethyl ethanolamine in 50.3 g acetone was added continuously at 25 °C over 3 h. The dropping funnel was rinsed with additional acetone. The reaction mixture was stirred at 25 °C for 20 h and the reaction progress was monitored by HPLC. When the level of methyltosylate was lower than 500 ppm the resulting suspension was cooled to 0 °C over 150 min and the suspension was stirred at 0 °C for 60 min. The product was collected by fdtration, washed two times with 175 mL acetone and dried under vacuum at 25 °C to obtain 73.1 g (99 %) of choline tosylate as a white crystalline solid.

InChI:InChI=1/C7H8O3S.C5H14NO/c1-6-2-4-7(5-3-6)11(8,9)10;1-6(2,3)4-5-7/h2-5H,1H3,(H,8,9,10);7H,4-5H2,1-3H3/q;+1/p-1

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 18678-98-3 Rac_. 1-O-Hexadecyl-2-O-benzylglycero-3-phosphocholin 
• 69483-37-0 1,2-di-O-hexadecyl-3-O-<<2-(trimethylamino)ethyl>phosphoryl>-rac-glycerol 
• 108587-39-9 C₂₉H₃₉N₂O₅P 
• 172363-11-0 1-O-<2'-(R,S)-benzyloxyhexadecyl>-2-chloro-2-deoxy-rac-glycero-3-phosphocholine 
• 172363-10-9 1-O-<2'-(R,S)-benzyloxyhexadecyl>-2-O-methyl-rac-glycero-3-phosphocholine 
• 174501-61-2 C₆₀H₈₈NO₁₂P 
• 253603-09-7 p-nitrophenyl 2,3,4-tri-O-benzyl-6-O-phosphorylcholine-α-D-glucopyranoside 
• 34688-34-1 glycerolcholine phosphate 
• 853997-34-9 (S)-1-O-hexadecyl-3-O-benzyl-glycero-2-phosphocholine 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 102152-55-6 Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-phosphoryloxy]-ethyl}-trimethyl-ammonium; 
• 102152-57-8 Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-thiophosphoryloxy]-ethyl}-trimethyl-ammonium; 
• 1063698-10-1 2,3,4-tri-O-benzoyl-6-O-phosphocholine-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-3-O-benzoyl-2-hexadecanamido-4-octadecene-1,3-diol 

Relevant articles and documents

Synthesis of sulfur-containing cationic lipids of the 1,3-dioxolane type

A series of cationic acetal lipids containing different spacer and cationic groups were synthesized starting from 1,2-O-hexadecylidene-3-thioglycerol.

Synthesis, physicochemical properties and biological activities of novel alkylphosphocholines with foscarnet moiety

A series of alkylphosphocholines with foscarnet moiety was synthesized. The structure of these zwitterionic amphiphiles was modified in both polar and non-polar parts of surfactant molecule. Investigations of physicochemical properties are represented by the determination of critical micelle concentration, the surface tension value at the cmc and the surface area per surfactant head group utilising surface tension measurements. Hydrodynamic diameter of surfactant micelles was determined using the dynamic light scattering technique. Alkylphosphocholines exhibit significant cytotoxic, anticandidal (Candida albicans) and antiamoebal (Acanthamoeba spp. T4 genotype) activity. The relationship between the structure, physicochemical properties and biological activity of the tested compounds revealed that lipophilicity has a significant influence on biological activity of the investigated surfactants. More lipophilic alkylphosphocholines with octadecyl chains show cytotoxic activity against cancer cells which is higher than that of the compounds with shorter alkyl chains. The opposite situation was observed in case of anticandidal and antiamoebal activity of these surfactants. The most active compounds were found to have pentadecyl chains. The foscarnet analogue of miltefosine C15-PFA-C showed the highest anticandidal activity. The minimum value of anticandidal activity of this compound is 1,4 μM thus representing the highest anticandidal activity found within the group of alkylphosphocholines.

The silane compound surface modification material phosphorylcholine-

PROBLEM TO BE SOLVED: To provide a novel compound serving as a surface modifying material for a high sensitivity biosensing element, which enables forming of a monomolecular film capable of inhibiting nonspecific adsorption of protein. SOLUTION: The compound is a phosphorylcholine-silane compound represented by chemical formula 1, wherein X1to X3each independently represent halogen, 1-3C alkoxy or 1-3C alkyl, provided that at least one of X1to X3is halogen or 1-3C alkoxy; R1represents -(CH2)m- or -(CH2CH2O)n-(CH2)2-; R2represents -(CH2)s- or -(CH2)3-(OCH2CH2)p-; m is an integer of 2-20, n is an integer of 1-5, s is an integer of 3-20, and p is an integer of 1-5. COPYRIGHT: (C)2013,JPOandINPIT