1-Myristoyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-Myristoyl-sn-glycero-3-phosphocholine
• CAS No.: 20559-16-4
• Molecular Formula: C₂₂H₄₆NO₇P
• Molecular Weight: 467.583
• Hs Code.: 2923900090
• UNII: 2T5V973UQY
• DSSTox Substance ID: DTXSID90942748
• Wikidata: Q27133313
• Metabolomics Workbench ID: 14991
• ChEMBL ID: CHEMBL462723
• Mol file: 20559-16-4.mol

Synonyms:1-Myristoyl-sn-glycero-3-phosphocholine;20559-16-4;LysoPC(14:0/0:0);1-tetradecanoyl-sn-glycero-3-phosphocholine;LPC(14:0);PC(14:0/0:0);LysoPC(14:0);[(2R)-2-hydroxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate;LPC(14:0/0:0);Myristoyl L-alpha-lysolecithin;1-Myristoyl-sn-glycero-3-phosphatidylcholine;LyPC(14:0);CHEBI:64489;1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine;LPC 14:0;1-myristoyl-glycero-3-phosphocholine;Lysophosphatidylcholine(14:0/0:0);1-Myristoyl-L-alpha-phosphorylcholine;LyPC(14:0/0:0);L-alpha-Myristoyllysophosphatidylcholine;Myristoyl L-alpha-lysophosphatidylcholine;1-Tetradecanoyl-sn-glycero-3-phosphorylcholine;1-Myristoyl-2-Hydroxy-sn-Glycero-3-Phosphatidylcholine;(R)-2-Hydroxy-3-(tetradecanoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate;Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monomyristin, L-;Myristin, 1-mono-, 3-(dihydrogen phosphate), monoester with choline hydroxide, inner salt, L-;M-LysoPC;LMPC;lysoPC a C14:0;lysoPC 14:0;14:0 Lyso PC;L--Myristoyl--lysolecithin;1-myristoylglycerophosphocholine;Lysophosphatidylcholine(14:0);2T5V973UQY;CHEMBL462723;SCHEMBL19787878;DTXSID90942748;1-14:0-2-lysophosphatidylcholine;EX-A5418;LMGP01050012;MFCD00036902;AKOS027328058;1-Myristoyl-sn-glycero-3-phosphocoline;GS-6041;1-C14:0-lysophosphatidylcholine betaine;1-Myristoyl-2-hydroxy-sn-glycero-3-PC;1-myristoyl-sn-glycero-3-phos-phocholine;BP-26336;Lyso-1-myristoyl-sn-3-phosphatidylcholine;HY-113123;CS-0059637;1-Myristoyl-2-lyso-sn-glycero-3-phosphocholine;1-myristoyl-sn-glycero-3-phosphocholine betaine;H10541;1-tetradecanoyl-sn-glycero-3-phosphocholine betaine;J-013420;Q27133313;14:0 Lyso PC, 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine, powder;2-Hydroxy-3-(tetradecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphatato;(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium;(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl 2-(trimethylammonio)ethyl phosphate;(R)-2-Hydroxy-3-(tetradecanoyloxy)propyl(2-(trimethylammonio)ethyl)phosphate;2-[hydroxy-[(2R)-2-hydroxy-3-tetradecanoyloxy-propoxy]phosphoryl]oxyethyl-trimethyl-ammonium;Myristoyl Lyso-phosphocholine ,1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine;3,5,9-TRIOXA-4-PHOSPHATRICOSAN-1-AMINIUM, 4,7-DIHYDROXY-N,N,N-TRIMETHYL-10-OXO-, INNER SALT, 4-OXIDE, (7R)-;3,5,9-Trioxa-4-phosphatricosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (R)-

Chemical Property of 1-Myristoyl-sn-glycero-3-phosphocholine

Chemical Property:

• PSA: 114.93000
• LogP: 4.86960
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 22
• Exact Mass: 467.30118980
• Heavy Atom Count: 31
• Complexity: 489

Purity/Quality:

98%Min ^*data from raw suppliers

L-a-Lysophosphatidylcholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Description: 1-MYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE is a lysophospholipid (LyP), which is a monoglycerophospholipid in which the phosphorylcholine moiety occupies the glycerol substitution site. LysoPC(14:0/0:0) has a potent antispasmodic effect.
• Physical properties: 1-MYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE is a Solid,it can insoluble in water.
• Uses: 1-Myristoyl-sn-glycero-3-phosphocholine is a derivative of sn-Glycero-3-phosphocholine (G598700) and can be used as a biomarker in biological studies.

Technology Process of 1-Myristoyl-sn-glycero-3-phosphocholine

There total 3 articles about 1-Myristoyl-sn-glycero-3-phosphocholine 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: 100.0%

dimyristoylphosphatidylcholine (18194-24-6) → 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (13699-45-1,20559-16-4,68852-66-4)

Guidance literature:

With calcium chloride; snake venom; In diethyl ether; water; at 35 ℃; for 6h; buffer systems;

Reference yield:

dimyristoylphosphatidylcholine (18194-24-6) → 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (13699-45-1,20559-16-4,68852-66-4) + n-tetradecanoic acid (544-63-8)

Guidance literature:

With phospholipase A₂; Tris buffer; calcium chloride; In water; at 23.5 ℃; for 1.5h; pH=8.0; Further Variations:; Temperatures; time; Kinetics;

DOI:10.1021/ac061049b

Reference yield:

1,2-dimyristoyl-sn-glycero-3-phosphocholine (18194-24-6) → L-λ-myristoyl lysolecithin (20559-16-4)

Guidance literature:

With phospholipase A₂; HEPES-buffer pH 7.2; water; In chloroform-d1; at 25 ℃; reaction rate; different cosolvents, other temperatures;

DOI:10.1016/S0040-4039(00)91974-9

upstream raw materials:

dimyristoylphosphatidylcholine

1,2-dimyristoyl-sn-glycero-3-phosphocholine

Downstream raw materials:

1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine

Refernces

• 1、 Cherney, Daniel P.,Myers, Grant A.,Horton, Robert A.,Harris, Joel M.. "Optically trapping confocal Raman microscopy of individual lipid vesicles: Kinetics of phospholipase A2-catalyzed hydrolysis of phospholipids in the membrane bilayer". . p. 6928 - 6935. Retrieved 2008/02/12.
• 2、 Yamamoto, Masakuni,Dolle, Valerie,Warnock, William,Diyizou, Yvonne,Yamada, Masashi,et al.. "Studies of the topography of biomembranes: the four-step synthesis of a photoactivatable transmembrane phospholipidic probe and its dideuterated analogue". . p. 317 - 329. Retrieved 2007/10/02.