1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) - Moligand™, ≥99% , CAS No.923-61-5

CAS: 923-61-5 Cat. No.: D130469 Molecular Weight: 691.96 Beilstein Registry Number: 1730601

GRADE & PURITY Moligand™, ≥99%

Synonyms

(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dipalmitate | CEPHALIN, L-ALPHA-DIPALMITOYL | EINECS 213-097-1 | Palmitin, 1,2-di-, 2-aminoethyl hydrogen phosphate, L- | PE(16:0/16:0) | D4213 | (2R)-3-{[(S)-(2-aminoethoxy)(hydroxy)phospho

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

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

Overview

1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), a phospholipid member of glycerophosphonoethanolamine family, is a major component in biological membranes. Studies focused on interactions between DPPE and cholesterol show that cholesterol induces condensation of DPPE monolayers in the presence of Ca2+ ions. Membranes containing a higher concentration of this compound contain more ordered lipid tails which results in a thicker membrane. Increasing DPPE concentrations has also been noted to cause competitive hydrogen bonding between amine groups and phosphate/carbonyl groups or water.
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine is used in model membrane.

Specifications

Synonyms

(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1, 2-diyl dipalmitate | CEPHALIN, L-ALPHA-DIPALMITOYL | EINECS 213-097-1 | Palmitin, 1, 2-di-, 2-aminoethyl hydrogen phosphate, L- | PE(16:0/16:0) | D4213 | (2R)-3-{[(S)-(2-aminoethoxy)(hydroxy)phospho

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

1, 2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine is a phospholipid, a lipid component in cell membrane.Phospholipid component in cell membranes. For use in lipid bilayer studies and biological systems.

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.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504758841
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758841
• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
• IUPAC Name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
• InChIKey: SLKDGVPOSSLUAI-PGUFJCEWSA-N
• INCHI: 1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
• WGK Germany: 3
• Molecular Weight: 691.96
• Beilstein: 1730601
• Reaxy-Rn: 1730602
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1730602&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphoethanolamines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphoethanolamines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphatidylethanolamines
• Alternative Parents: Phosphoethanolamines Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Carboxylic acid esters Amino acids and derivatives Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Diacylglycero-3-phosphoethanolamine - Phosphoethanolamine - Fatty acid ester - Dialkyl phosphate - Dicarboxylic acid or derivatives - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Organic nitrogen compound - Primary amine - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
• External Descriptors: Diacylglycerophosphoethanolamines

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

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Specific Rotation[α]: +6.0 to +8.0 deg(C=0.5,CHCL3:AcOH=1:1)
• Melt Point(°C): 195-199℃
• Molecular Weight: 692.000 g/mol
• XLogP3: 10.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 39
• Exact Mass: 691.515 Da
• Monoisotopic Mass: 691.515 Da
• Topological Polar Surface Area: 134.000 Ų
• Heavy Atom Count: 47
• Formal Charge: 0
• Complexity: 754.000
• 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

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