1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine - ≥99% , CAS No.20559-16-4

CAS: 20559-16-4 Cat. No.: M130491 Molecular Weight: 467.577 Beilstein Registry Number: 5776231

GRADE & PURITY ≥99%

Synonyms

14:0 Lyso PC | PC(14:0/0:0) | 1-Myristoyl-sn-glycero-3-phosphocoline | Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monomyristin, L- | 1-myristoyl-glycero-3-phosphocholine | DTXSID90942748 | CHEBI:64489 | LysoPC(14:0/0:0) | 3,5,9-T

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

228,229

Specifications

Synonyms

14:0 Lyso PC | PC(14:0/0:0) | 1-Myristoyl-sn-glycero-3-phosphocoline | Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monomyristin, L- | 1-myristoyl-glycero-3-phosphocholine | DTXSID90942748 | CHEBI:64489 | LysoPC(14:0/0:0) | 3, 5, 9-T

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• IUPAC Name: [(2R)-2-hydroxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: VXUOFDJKYGDUJI-OAQYLSRUSA-N
• INCHI: 1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Molecular Weight: 467.577
• Beilstein: 5776231
• Reaxy-Rn: 5776230
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5776230&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphocholines
        • Level5 Lysophosphatidylcholines
          • Level6 1-acyl-sn-glycero-3-phosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: Lysophosphatidylcholines
• Direct Parent: 1-acyl-sn-glycero-3-phosphocholines
• Alternative Parents: Phosphocholines Fatty acid esters Dialkyl phosphates Tetraalkylammonium salts Secondary alcohols Carboxylic acid esters Monocarboxylic acids and derivatives Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-acyl-sn-glycero-3-phosphocholine - Phosphocholine - Fatty acid ester - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Tetraalkylammonium salt - Quaternary ammonium salt - Secondary alcohol - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organic oxide - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Alcohol - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic salt - Amine - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
• External Descriptors: Monoacylglycerophosphocholines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 467.600 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 22
• Exact Mass: 467.301 Da
• Monoisotopic Mass: 467.301 Da
• Topological Polar Surface Area: 105.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 488.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jinlei Yang, Jing Wang, Runsong Cheng, Tianyi Liao, Siyuan Pan, Murong Du, Weiliang Liu, Liying Yan, Sichun Zhang, Xinrong Zhang.  (2025)  Microseparation of Lipophilic and Hydrophilic Metabolites for Single Oocyte Mass Spectrometry Analysis.  ANALYTICAL CHEMISTRY,      [PMID:39800910] [10.1021/acs.analchem.4c04900]

2. Zhuo Li, Zixin Huo, Shanshan Yao, Xianmeng Liang, Yiran Zhao, Yanxin Wang, Shifeng Guo, Caihuan Ke, Pei Su, Danqing Feng.  (2025)  Intertidal Warfare: Synergistic Allelopathy Mediates Spatial Competition between Two Marine Calcareous-Shelled Sessile Organisms.  Advanced Science,      [PMID:41355076] [10.1002/advs.202512644]