(2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate | CAS No. 35418-59-8

(2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate

Basic Information

CAS Number

35418-59-8

Molecular Formula

C46H84NO8P

Molecular Weight

810.1 g/mol

AD

Basic Physical Properties

CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC

InChI

InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,44H,6-13,15,17-19,21,23-24,26,28-30,32,34-43H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t44-/m1/s1

InChIKey

PSVRFUPOQYJOOZ-QNPWAGBNSA-N

LogP

13.12660

Complexity

1090

Synonyms & References

English

  • 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(18:0/20:4omega6)
  • Phosphatidylcholine(18:0/20:4)
  • [(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxy-3-octadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  • Q27145040
  • PC 38:4
  • LMGP01010802
  • HY-126356
  • 1-stearoyl-2-arachidonoyl-GPC (18:0/20:4)
  • Phosphatidylcholine(18:0/20:4n6)
  • SAPC
  • (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
  • PC(18:0/20:4omega6)
  • 1-Stearoyl-2-Arachidonoyl PC
  • Phosphatidylcholine(18:0/20:4w6)
  • 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholine
  • 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
  • 1-stearoyl-2-arachidonoyl-GPC
  • 1-C18:0-2-C20:4(omega-6)-phosphatidylcholine
  • HMS3650D03
  • (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
  • PC(18:0/20:4w6)
  • Phosphatidylcholine(38:4)
  • (R)-2-((5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyloxy)-3-(stearoyloxy)propyl(2-(trimethylammonio)ethyl)phosphate
  • 35418-59-8
  • AKOS024418765
  • CHEBI:74965
  • DTXSID701344787
  • SCHEMBL79578
  • GPC(18:0/20:4)
  • 1-stearoyl-2-arachidonoyl-phosphatidylcholine

MDL Number

MFCD00082436

FAQ

What are the physical and chemical properties of (2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate (CAS: 35418-59-8)?

This compound is a complex phospholipid with a specific structure. It is typically crystalline at room temperature. The molecular weight is approximately 1016.6 g/mol. It is poorly soluble in water but soluble in organic solvents. The compound exhibits moderate reactivity, particularly towards nucleophiles, but is less reactive than typical phospholipids due to its unique hydrocarbon chains. It is stable under neutral and slightly basic conditions but can degrade under acidic conditions.

How is (2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate (CAS: 35418-59-8) typically synthesized?

This compound can be synthesized through a multi-step process involving the synthesis of the icosatetraenoyloxy and stearoyloxy moieties, followed by their conjugation with a phospholipid backbone. The synthesis typically requires the use of specific catalysts and reagents to achieve high selectivity and yield. Common methods include acid-catalyzed transesterification and phosphatidyltransferase enzyme methods, ensuring the desired stereochemistry is maintained.

What industries use (2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate (CAS: 35418-59-8)?

This compound is used in various industries due to its unique chemical structure. It is primarily used in pharmaceuticals for its potential as a drug delivery system, in polymers for its specific hydrophobic and hydrophilic properties, in sensors for its ability to detect specific chemical or biological analytes, and in semiconductors for its use in molecular electronics. Its versatility makes it a valuable component in advanced materials research and development.

What precautions should be taken when handling (2R)-2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate (CAS: 35418-59-8)?

When handling this compound, it is important to wear appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood due to its potential volatility. Spills should be cleaned up using appropriate absorbent materials and proper disposal methods. Always refer to the Safety Data Sheet (SDS) for detailed handling and storage instructions. This compound, while generally stable, should be stored in a cool, dry place away from direct sunlight and acidic environments.

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