1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
• CAS No.: 22252-07-9
• Molecular Formula: C₂₆H₅₀NO₇P
• Molecular Weight: 519.659
• UNII: 58529WFZ36
• DSSTox Substance ID: DTXSID101334833
• Wikidata: Q27103871
• Metabolomics Workbench ID: 15003
• Mol file: 22252-07-9.mol

Synonyms:lysophosphatidylcholine 18:2;22252-07-9;LPC(18:2/0:0);PC(18:2(9Z,12Z)/0:0);1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine;1-Linoleoyl-sn-glycero-3-phosphorylcholine;1-linoleoyl-phosphatidylcholine;18:2 LYSO-PC;1-Linoleoylglycerophosphocholine;LysoPC(18:2(9Z,12Z)/0:0);(7R,18Z,21Z)-4,7-dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphaheptacosa-18,21-dien-1-aminium, 4-oxide, inner salt;LPC 18:2;1-Linoleoyl-sn-glycero-3-phosphocholine;(R)-2-Hydroxy-3-((9Z,12Z)-octadeca-9,12-dienoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate;1-linoleoyl-GPC;lysoPC a C18:2;1-linoleoyl-GPC (18:2);Linoleyl lysophosphatidylcholine;CHEBI:28733;LysoPC(18:2w6/0:0);2-linoleoyl-lysophosphatidylcholine;DTXSID101334833;1-18:2-2-lysophosphatidylcholine;HY-N9410;LyPC(18:2w6/0:0);2-18:2(9Z,12Z)-lysoPC;GPC(18:2);LMGP01050035;LyPC(18:2/0:0);AKOS040755460;LPC(18:2w6/0:0);58529WFZ36;Lysophosphatidylcholine(18:2w6/0:0);1-lyso-2-18:2(9Z,12Z)-lysoPC;LysoPC 18:2(9Z,12Z)/0:0;1-Linoleoyl-sn-glycero-3-phosphorylcholin;2-18:2(9Z,12Z)-lysophosphatidylcholine;GPC(18:2/0:0);CS-0159737;LPC 18:2(9Z,12Z)/0:0;lysophosphatidylcholine(18:2(9Z,12Z)/0:0);PC 18:2(9Z,12Z)/0:0;Q27103871;1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine;1-(9Z,12Z-Octadecadienoyl-2-hydroxy-sn-glycero-3-phosphocholine;Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with L-1-monolinolein;(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl 2-(trimethylammonio)ethyl phosphate;(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate;3,5,9-Trioxa-4-phosphaheptacosa-18,21-dien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,18Z,21Z)-;3,5,9-Trioxa-4-phosphaheptacosa-18,21-dien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, [R-(Z,Z)]-;Linolein, 1-mono-, 3-(dihydrogen phosphate), monoester with choline hydroxide, inner salt, L-

Chemical Property of 1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 24
• Exact Mass: 519.33248993
• Heavy Atom Count: 35
• Complexity: 623

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O

Technology Process of 1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine

There total 5 articles about 1-(9Z,12Z-octadecadienoyl)-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: 95.0%

(R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate (998-06-1) → L-γ-linoleoyl-α-lysolecithin (22252-07-9)

Guidance literature:

With tris hydrochloride; sodium docusate; calcium chloride; In 2,2,4-trimethylpentane; at 40 ℃; for 0.5h; pH=8.5; Enzymatic reaction;

DOI:10.1071/CH14606

Reference yield:

C63H116O16P2(2-)*2H4N(1+) + (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate (998-06-1) → C81H146O17P2(2-)*2H4N(1+) + L-γ-linoleoyl-α-lysolecithin (22252-07-9)

Guidance literature:

With tafazzin from Saccharomyces cerevisiae; In aq. buffer; at 37 ℃; pH=7.4; Kinetics; Enzymatic reaction;

DOI:10.1074/jbc.M116.718510

Reference yield:

C30H58NO9P → L-γ-linoleoyl-α-lysolecithin (22252-07-9) + 1-linoleoyl-sn-glycero-3-phosphocholine (22252-07-9)

Guidance literature:

With bromocatecholborane; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

upstream raw materials:

(R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate

Refernces

• 1、 Niezgoda, Natalia,Gliszczyńska, Anna,G?adkowski, Witold,Kempińska, Katarzyna,Wietrzyk, Joanna,Wawrzeńczyk, Czes?aw. "Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies". . p. 1065 - 1075. Retrieved 2016/01/15.
• 2、 Eriksson, Per-Olof,Lindblom, Goeran,Arvidson, Goesta. "NMR Studies of Micellar Aggregates in 1-Acyl-sn-glycerophosphocholine Systems. The Formation of a Cubic Liquid Crystalline Phase". . p. 846 - 853. Retrieved 2007/10/02.