159701-21-0

Basic information

• Product Name: 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine
• CAS NO: 159701-21-0
• Molecular Weight: 758.073
• Mol File: 159701-21-0.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine(159701-21-0)
• EPA Substance Registry System: 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine(159701-21-0)

Safety Data

• Hazardous Substances Data: 159701-21-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Used in Diagnostic Applications:
Used in Cosmetic Applications:
1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine is used as an ingredient in the cosmetic industry, particularly in the formulation of skincare products. It serves as an emollient, helping to moisturize and protect the skin by forming a protective barrier that prevents water loss. Additionally, its presence in the outer layer of the skin's stratum corneum makes it an ideal component for maintaining skin health and promoting a smooth, supple appearance.
Used in Food Industry:
In the food industry, 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine is used as an additive to improve the texture, stability, and shelf life of various products. It can be found in the formulation of spreads, margarines, and other fat-based products, where it contributes to a desirable mouthfeel and helps maintain the product's structure during storage.

Upstream product

• 60-33-3 linoleic acid 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1487-50-9 1-O-hexadecanoyl-3-O-benzyl-sn-glycerol 
• 256494-17-4 1-O-palmitoyl-3-[methyl α-(2,4-dinitrophenyl)acetate]glycerol 
• 256494-15-2 1-O-palmitoyl-2-arachidonoyl-3-benzylglycerol 
• 256494-19-6 1-O-palmitoyl-2-arachidonoyl-3-[methyl α-(2,4-dinitrophenyl)acetate]glycerol 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 51704-36-0 (9Z,12Z)-Octadeca-9,12-dienoic acid (R)-2-hexadecanoyloxy-1-hydroxymethyl-ethyl ester 
• 143003-65-0 (2R)-3-(benzyloxy)-2-hydroxypropyl hexadecanoate 
• 75-50-3 trimethylamine 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 1455-05-6 2-chloroethyl phosphorodichloridate 

Downstream Products

• 117205-52-4 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 

Relevant articles and documents

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.

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.

A rapid condensation between lysophosphorylcholine and fatty acids with an easily separable amine base

With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system. Georg Thieme Verlag Stuttgart.