34688-34-1

Basic information

• Product Name: glycerolcholine phosphate
• Synonyms: glycerolcholine phosphate
• CAS NO: 34688-34-1
• Molecular Weight: 257.224
• Mol File: 34688-34-1.mol

Chemical Properties

• CAS DataBase Reference: glycerolcholine phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: glycerolcholine phosphate(34688-34-1)
• EPA Substance Registry System: glycerolcholine phosphate(34688-34-1)

Safety Data

• Hazardous Substances Data: 34688-34-1(Hazardous Substances Data)

Upstream product

• 59414-92-5 2-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)-2-oxo-1,3,2-dioxaphospholane 
• 75-50-3 trimethylamine 
• 34688-39-6 Phosphoric acid 2-chloro-ethyl ester 2-chloromethyl-4-nitro-phenyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 107-73-3 phosphorylcholine chloride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 4826-71-5 phosphorylcholine chloride, calcium salt 
• 55357-38-5 choline tosylate 
• 556-52-5 oxiranyl-methanol 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 59414-94-7 choline-2,2-dimethyl-1,3-dioxolane-4-methyl phosphate 

Downstream Products

• 17364-19-1 1-stearoyl-sn-glycero-3-phosphocholine 
• 18194-24-6 dimyristoylphosphatidylcholine 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 
• 816-94-4 {2-[(2,3-bis-stearoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine 
• 57-11-4 stearic acid 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 57-10-3 1-hexadecylcarboxylic acid 
• 18656-40-1 1,2-dilauroylphosphatidylcholine 
• 39735-07-4 β-arachidonoyl-γ-palmitoyl-α-phosphatidylcholine 
• 6931-84-6 1-palmitoyl-2-lineleoylphosphatidylcholine 
• 4016-41-5 1-octadec-9'-enoyl-2-hydroxy-sn-glycero-3-phosphocholine 
• 13699-45-1 1-myristoyl-2-lyso-sn-glycero-3-phosphatidylcholine 
• 98819-78-4 1,2-dieicosapentanoylglycero-3-phophocholine 
• 273931-53-6 C₃₂H₅₃N₂O₁₂P 

Relevant articles and documents

Phospholipid Synthesis Based on New Sequential Phosphate and Carboxylate Ester Bond Formation Steps

A total synthesis of racemic phosphatidylcholine is based on two novel but straightforward reaction sequences.The phosphate diester portion is constructed by successive displacement of the chlorines on methyl dichlorophosphate by allyl alcohol and dimethylethanolamine.The resulting triester isomerizes smoothly to allyl choline phosphate.The double bond is then converted to the bromohydrin to allow the sequential introduction of the two acyl ester linkages.Esterification of the hydroxyl with palmitoyl chloride produces 2-bromo-2-deoxylysophosphatidylcholine as the only isomer.The bromide is displaced in the final step upon treatment with the carboxylate form of an anion-exchange resin.The distinctive 31P-13C coupling patterns in the 13C resonances of the glycerol backbone allow the regiochemistry of the various steps to be conveniently monitored.Also, employment of palmitic-1-13C acid in the final step indicated a 70percent rearrangement accompanied formation of the mixed acid phosphatidylcholine.

Lysophospholipases cooperate to mediate lipid homeostasis and lysophospholipid signaling

Abstract Lysophospholipids (LysoPLs) are bioactive lipid species involved in cellular signaling processes and the regulation of cell membrane structure. LysoPLs are metabolized through the action of lysophospholipases, including lysophospholipase A1 (LYPLA1) and lysophospholipase A2 (LYPLA2). A new X-ray crystal structure of LYPLA2 compared with a previously published structure of LYPLA1 demonstrated near-identical folding of the two enzymes; however, LYPLA1 and LYPLA2 have displayed distinct substrate specificities in recombinant enzyme assays. To determine how these in vitro substrate preferences translate into a relevant cellular setting and better understand the enzymes’ role in LysoPL metabolism, CRISPR-Cas9 technology was utilized to generate stable KOs of Lypla1 and/or Lypla2 in Neuro2a cells. Using these cellular models in combination with a targeted lipidomics approach, LysoPL levels were quantified and compared between cell lines to determine the effect of losing lysophospholipase activity on lipid metabolism. This work suggests that LYPLA1 and LYPLA2 are each able to account for the loss of the other to maintain lipid homeostasis in cells; however, when both are deleted, LysoPL levels are dramatically increased, causing phenotypic and morphological changes to the cells.—Wepy, J. A., James J. Galligan, P. J. Kingsley, S. Xu, M. C. Goodman, K. A. Tallman, C. A. Rouzer, and L. J. Marnett. Lysophospholipases cooperate to mediate lipid homeostasis and lysophospholipid signaling.

Method for Preparation of Choline alfoscerate

The present invention relates to a method for preparing a choline alfoscerate useful for the treatment of brain dysfunction caused by cerebrovascular diseases economically through a process suitable for mass production, and more particularly, to the method for preparing the choline alfoscerate, which comprises the following steps: (A) reacting phosphorylcholine chloride calcium salt with potassium oxalate to prepare an alkali metal-substituted salt; and (B) preparing the choline alfoscerate by a reaction of the alkali metal-substituted salt with (R)-(+)-3-chloro-1,2-propanediol.COPYRIGHT KIPO 2018

Method for Preparing Racemic or Optically Active α―Glycerophosphoryl choline

The present invention relates to a method for manufacturing racemic or optically active andalpha;-glycerophosphoryl choline, and, more specifically, to a method for manufacturing racemic and optically active D or L-andalpha;- glycerophosphoryl choline in bulk, with a substitution reaction of choline phosphate or a salt thereof, and racemic and optically highly pure (S) and (R)-3-halo-1,2-propanediol, by using an inorganic base, which increases the activity of the reaction, at high temperature in the presence of a medium. According to the present invention, the method for manufacturing the racemic or optically active andalpha;-glycerophosphoryl choline is economical by using a low cost starting material, compared to a conventional method; provides a simple manufacturing process by performing a one-pot reaction without a separate refining process; and can quantitatively mass-produce the racemic and optically active D or L-andalpha;- glycerophosphoryl choline and the salt thereof without a side reaction, under the presence of the medium, by using the inorganic base of increasing the activity of the reaction.COPYRIGHT KIPO 2015

A rapid condensation between lysophosphorylcholine and fatty acids with an easily separable amine base

With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system. Georg Thieme Verlag Stuttgart.

Nuclear Magnetic Resonance Evidence for Radiation Damage of Saturated Phosphatidylcholine in Bilayers

Multilayer membranes of 1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine were prepared in D2O and exposed to γ-radiation.Changes in the chemical structure due to irradiation were studied by (1)H, (13)C and (31)P NMR after lyophilization and dissolution in chloroform-methanol (1:2 v/v).One- and two-dimensional techniques were used. 1-Palmitoyl-sn-glycero-3-phosphorylcholine, 2-palmitoyl-sn-glycero-3-phosphorylcholine, glycero-3-phosphorylcholine and palmitic acid were identified as new components.Their development during irradiation was quantitatively determined.The results were discussed in terms of possible reaction steps responsible for the radiolytic decomposition. Key words: (1)H NMR, (13)C NMR, (31)P NMR, 1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine, bilayer, radiation damage