1-oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine - ≥99% , CAS No.89576-29-4

CAS: 89576-29-4 Cat. No.: O130377 Molecular Weight: 479.588

GRADE & PURITY ≥99%

Synonyms

18:1 Lyso PE | PE(18:1(9Z)/0:0) | LysoPE(18:1omega9/0:0) | Lyso-PE(18:1omega9/0:0) | (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl oleate | 9-Octadecenoic acid (Z)-, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

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

Overview

Lysophosphatidyletnolamine (LPE), an enigmatic lipid of bacteria is obtained from phosphatidylethanolamine during various fluctuations of the bacterial growth conditions

18:1 Lyso PE is suitable for use in the synthesis of lipid molecules. It is also suitable to use as a standard in the study of systematic optimization of hydrophilic interaction liquid chromatography-mass spectrometry (HILIC/MS) separation of acidic lipid classes

Specifications

Synonyms

18:1 Lyso PE | PE(18:1(9Z)/0:0) | LysoPE(18:1omega9/0:0) | Lyso-PE(18:1omega9/0:0) | (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl oleate | 9-Octadecenoic acid (Z)-, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-

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: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)O
• IUPAC Name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] (Z)-octadec-9-enoate
• InChIKey: PYVRVRFVLRNJLY-MZMPXXGTSA-N
• INCHI: 1S/C23H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h9-10,22,25H,2-8,11-21,24H2,1H3,(H,27,28)/b10-9-/t22-/m1/s1
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O
• Molecular Weight: 479.588
• Reaxy-Rn: 7496297
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7496297&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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 479.600 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 24
• Exact Mass: 479.301 Da
• Monoisotopic Mass: 479.301 Da
• Topological Polar Surface Area: 128.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 517.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Xuan Liu, Weifei Wang, Zexin Zhao, Long Xu, Bo Yang, Dongming Lan, Yonghua Wang.  (2022)  Monoacylglycerol lipase from marine Geobacillus sp. showing lysophospholipase activity and its application in efficient soybean oil degumming.  FOOD CHEMISTRY,      [PMID:36463594] [10.1016/j.foodchem.2022.134506]