17708-90-6

Basic information

• Product Name: 1,2-DIACYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: 3-sn-Phosphatidylcholine, 2-linoleoyl-1-palmitoyl;1-Palmitoyl-2-linoleoyl-sn-glycero-3-PC
• CAS NO: 17708-90-6
• Molecular Formula: C₄₂H₈₀NO₈P
• Molecular Weight: 758.067
• Mol File: 17708-90-6.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• BRN: 5209585
• CAS DataBase Reference: 1,2-DIACYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIACYL-SN-GLYCERO-3-PHOSPHOCHOLINE(17708-90-6)
• EPA Substance Registry System: 1,2-DIACYL-SN-GLYCERO-3-PHOSPHOCHOLINE(17708-90-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17708-90-6(Hazardous Substances Data)

Usage

General Description

1,2-Diacyl-sn-glycero-3-phosphocholine, also known as phosphatidylcholine, is a phospholipid molecule composed of a glycerol backbone, two fatty acid chains, a phosphate group, and choline. It is a major component of cell membranes and plays a crucial role in maintaining their structure and function. Phosphatidylcholine also serves as a source of the important neurotransmitter acetylcholine, which is involved in various physiological processes such as muscle movement, memory, and learning. Additionally, phosphatidylcholine has been used in the pharmaceutical and cosmetic industries due to its emulsifying and moisturizing properties. Its potential health benefits include liver protection, cognitive function improvement, and cardiovascular health support.

Upstream product

• 60-33-3 linoleic acid 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 256494-19-6 1-O-palmitoyl-2-arachidonoyl-3-[methyl α-(2,4-dinitrophenyl)acetate]glycerol 
• 256494-15-2 1-O-palmitoyl-2-arachidonoyl-3-benzylglycerol 
• 256494-17-4 1-O-palmitoyl-3-[methyl α-(2,4-dinitrophenyl)acetate]glycerol 
• 1487-50-9 1-O-hexadecanoyl-3-O-benzyl-sn-glycerol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 1455-05-6 2-chloroethyl phosphorodichloridate 
• 65886-78-4 1-O-palmitoyl-2-arachidonoyl-glycerol 
• 75-50-3 trimethylamine 

Downstream Products

• 54672-38-7 (R)-1,2-diacetoxy glycerylphosphoryl choline 
• 117205-52-4 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 10219-69-9 (R,S)-coriolic acid 
• 73543-67-6 (10E,12Z)-9-hydroxy-10,12-octadecadienoic acid 
• 115185-06-3 9-Hode 
• 32819-31-1 [14C]-13-Hydroxyoctadecadienoic acid 
• 26662-95-3 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine 

Relevant articles and documents

Synthesis of phosphatidylcholine with conjugated linoleic acid and studies on its cytotoxic activity

Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82%) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87% yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety

(Chemical Equation Presented) The two possible diastereomers of 5,6-epoxyisoprostane A2 were synthesized efficiently through aldol condensations of a substituted cyclopentenone and the corresponding epoxyaldehydes (see picture). The relative configurations of the products were assigned by comparing their 1H NMR spectra with literature data. Condensation of the epoxyisoprostane A2 with lysophosphorylcholine (lyso-PC) then furnished the title lipid.

Deuterated cyclosporine analogs and their use as immunomodulating agents

Cyclosporine derivatives are disclosed which possess enhanced efficacy and reduced toxicity over naturally occurring and other presently known cyclosporins and cyclosporine derivatives. The cyclosporine derivatives of the present invention are produced by chemical and isotopic substitution of the cyclosporine A (CsA) molecule by: (1) Chemical substitution and optionally deuterium substitution of amino acid 1; and (2) deuterium substitution at key sites of metabolism of the cyclosporine A molecule such as amino acids 1, 4, 9. Also disclosed are methods of producing the cyclosporine derivatives and method of producing immunosuppression with reduced toxicity with the disclosed cyclosporine derivatives.