1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine - 69747-55-3

1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine

Catalog Number: EVT-3565420
CAS Number: 69747-55-3
Molecular Formula: C23H48NO7P
Molecular Weight: 481.6 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine is a phospholipid molecule that plays a crucial role in various biological processes. It is a key component of cell membranes and is involved in cell signaling, membrane trafficking, and lipid metabolism. This paper aims to provide an overview of the synthesis/extraction methods, chemical structure, biological activity, biological effects, applications, and future perspectives of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine.
Applications in Various Fields
In medical research, 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine plays a crucial role in drug development. It serves as a target for drug discovery and as a potential therapeutic agent itself. Clinical trials have shown promising results in various disease models, but more research is needed to determine its safety and efficacy in humans.
In environmental research, the effects of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine on ecosystems and pollution management are not well-studied. However, its role in lipid metabolism and membrane dynamics suggests potential implications in environmental processes and sustainability.
In industrial research, 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine can be used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations should be taken into account due to the use of hazardous chemicals in its synthesis.

Properties

CAS Number

69747-55-3

Product Name

1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine

IUPAC Name

2-azaniumylethyl [(2R)-2-hydroxy-3-octadecanoyloxypropyl] phosphate

Molecular Formula

C23H48NO7P

Molecular Weight

481.6 g/mol

InChI

InChI=1S/C23H48NO7P/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/h22,25H,2-21,24H2,1H3,(H,27,28)/t22-/m1/s1

InChI Key

BBYWOYAFBUOUFP-JOCHJYFZSA-N

SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[NH3+])O

Canonical SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)O

Isomeric SMILES

CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O
Method of Synthesis or Extraction
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine can be synthesized using various methods. One commonly used method involves the reaction between stearic acid and 2-hydroxyethylamine, followed by phosphorylation using phosphorus oxychloride. This method yields a moderate to high efficiency, with yields ranging from 50% to 80%. However, it requires the use of toxic and hazardous chemicals, such as phosphorus oxychloride, which poses environmental and safety considerations.
Another method involves the enzymatic synthesis of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine using phospholipase D. This method offers a more environmentally friendly approach and can achieve high yields. However, it requires the availability of specific enzymes and may have limitations in scalability for industrial production.
Chemical Structure and Biological Activity
The chemical structure of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine consists of a stearoyl fatty acid chain attached to a glycerol backbone, with a phosphorylethanolamine headgroup. This structure allows it to integrate into cell membranes and participate in various cellular processes.
The biological activity of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine is primarily attributed to its role in cell signaling and membrane dynamics. It acts as a precursor for the synthesis of bioactive lipid mediators, such as lysophosphatidic acid and platelet-activating factor, which regulate cell proliferation, migration, and inflammation. Additionally, it modulates membrane fluidity and lipid rafts, influencing membrane protein function and signal transduction.
Biological Effects
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine has been implicated in various biological effects on cell function and signal transduction. It regulates cell growth, differentiation, and apoptosis through its involvement in intracellular signaling pathways. It also plays a role in membrane trafficking and vesicular transport, contributing to cellular homeostasis.
In terms of therapeutic effects, 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine has shown potential in drug development. It has been studied for its anti-inflammatory, anti-cancer, and neuroprotective properties. Clinical trials have demonstrated its efficacy in certain disease models, such as cancer and neurodegenerative disorders. However, further research is needed to fully understand its therapeutic potential and potential toxic effects.
Future Perspectives and Challenges
The current limitations in the use and study of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine include the lack of comprehensive understanding of its biological functions and mechanisms of action. Further research is needed to elucidate its role in cellular processes and its potential therapeutic applications.
Possible solutions and improvements include the development of more efficient and environmentally friendly synthesis methods, as well as the identification of specific biological targets and signaling pathways associated with 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine.
Future trends and prospects in the application of 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine in scientific research include its potential as a therapeutic target for various diseases, as well as its role in lipid metabolism and membrane dynamics. Further studies are needed to fully explore its therapeutic potential and understand its impact on cellular processes.
In conclusion, 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine is a phospholipid molecule with diverse biological functions and potential therapeutic applications. Its synthesis methods, chemical structure, biological activity, and applications have been discussed in this paper. Further research is needed to fully understand its mechanisms of action and explore its potential in various scientific fields.

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