1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine - ≥99% , CAS No.123060-40-2

CAS: 123060-40-2 Cat. No.: M130503 Molecular Weight: 425.497

GRADE & PURITY ≥99%

Synonyms

1-myristoylglycerophosphoethanolamine | 2-azaniumylethyl (2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphate | RPXHXZNGZBHSMJ-GOSISDBHSA-N | 1-myristoyl-sn-glycero-3-phosphoethanolamine zwitterion | 2-azaniumylethyl [(2R)-2-hydroxy-3-tetradecanoyloxypropy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

1-Myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine (14:0 Lyso PE) is a lysophospholipid with a phosphoethanolamine head and a myristoyl tail. The free amine group can conjugate with NHS active ester or coupled with carboxylic acid in the presence of a coupling agent. It also induces transient increases in intracellular calcium in PC12 cells. Serum levels of 1-Myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine are elevated in patients with malignant breast cancer compared to healthy controls.
Application
14:0 Lyso PE has been used for lipidomic profiling. It has also been used for the preparation of lipids.

Specifications

Synonyms

1-myristoylglycerophosphoethanolamine | 2-azaniumylethyl (2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphate | RPXHXZNGZBHSMJ-GOSISDBHSA-N | 1-myristoyl-sn-glycero-3-phosphoethanolamine zwitterion | 2-azaniumylethyl [(2R)-2-hydroxy-3-tetradecanoyloxypropy

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[NH3+])O
• IUPAC Name: 2-azaniumylethyl [(2R)-2-hydroxy-3-tetradecanoyloxypropyl] phosphate
• InChIKey: RPXHXZNGZBHSMJ-GOSISDBHSA-N
• INCHI: 1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/t18-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[NH3+])O
• Molecular Weight: 425.497
• Reaxy-Rn: 37924654
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37924654&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphoethanolamines
        • Level5 Lysophosphatidylethanolamines
          • Level6 1-acyl-sn-glycero-3-phosphoethanolamines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphoethanolamines
• Intermediate Tree Nodes: Lysophosphatidylethanolamines
• Direct Parent: 1-acyl-sn-glycero-3-phosphoethanolamines
• Alternative Parents: Phosphoethanolamines Fatty acid esters Dialkyl phosphates Secondary alcohols Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-monoacyl-sn-glycero-3-phosphoethanolamine - Phosphoethanolamine - Fatty acid ester - Dialkyl phosphate - Organic phosphoric acid derivative - Fatty acyl - Alkyl phosphate - Phosphoric acid ester - Amino acid or derivatives - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organonitrogen compound - Hydrocarbon derivative - Alcohol - Primary aliphatic amine - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Amine - Organooxygen compound - Primary amine - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine.
• External Descriptors: Monoacylglycerophosphoethanolamines

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