14863-27-5

Basic information

• Product Name: 1-Palmitoyl-Lysolecithin,Synthetic
• Synonyms: 1-Palmitoyl-Lysolecithin,Synthetic;We 201;[O-(1-O-Palmitoyl-D-glycero-3-phospho)choline]anion;O-[[[(2S)-2-Hydroxy-3-(hexadecanoyloxy)propyl]oxy]oxylatophosphinyl]choline;1-Palmitoyllysolecithin;1-Palmitoylphosphatidylcholine;3,5,9-Trioxa-4-phosphapentacosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide;4,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphapentacosan-1-aminium inner salt, 4-oxide
• CAS NO: 14863-27-5
• Molecular Formula: C₂₄H₅₀NO₇P
• Molecular Weight: 495.633
• EINECS: 241-396-7
• Mol File: 14863-27-5.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Palmitoyl-Lysolecithin,Synthetic(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Palmitoyl-Lysolecithin,Synthetic(14863-27-5)
• EPA Substance Registry System: 1-Palmitoyl-Lysolecithin,Synthetic(14863-27-5)

Safety Data

• Hazardous Substances Data: 14863-27-5(Hazardous Substances Data)

Usage

Chemical derivation

Derived from lecithin, a natural substance found in plant and animal tissues.

Phospholipid class

Belongs to the lysophosphatidylcholine class of phospholipids.

Structural modification

Modified with a palmitoyl group attached to the hydroxyl group of the glycerol backbone.

Enhanced solubility

Improved solubility in both water and oil due to palmitoyl group attachment.

Application in products

Valued ingredient in cosmetic and pharmaceutical products.

Emulsifying properties

Helps to stabilize formulations and improve texture.

Moisturizing effects

Believed to possess moisturizing properties.

Surfactant properties

Acts as a surfactant in personal care products.

Versatility

Utilized in a wide range of personal care products due to its multiple beneficial properties.

InChI:InChI=1/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3

Upstream product

• 7501-44-2 hexadecanoic acid, glycidyl ester 
• 645-84-1 choline phosphate 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 525-66-6 propranolol 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 112-67-4 n-hexadecanoyl chloride 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 6931-84-6 lecithin 
• 408-35-5 sodium palmitate 
• 172794-56-8 Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester 
• 57-10-3 1-hexadecylcarboxylic acid 
• 18282-29-6 (S)-3-O-palmitoyl-2-O-benzylglycerol 
• 17618-07-4 2-O-Benzyl-3-O-palmitoyl-D-glycerinaldehyd 
• 55357-38-5 choline tosylate 

Downstream Products

• 875685-46-4 10-Nitrooleic Acid 
• 294659-11-3 (E)-methyl 10-nitrooctadec-9-enoate 
• 117205-52-4 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 
• 6931-84-6 lecithin 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1372802-60-2 C₇₉H₁₄₃F₄N₅O₁₆P₂S₂ 
• 1315501-24-6 C₃₉H₆₅F₄N₄O₉P 
• 1039749-81-9 C₅₅H₈₆NO₈PS 
• 116405-87-9 1-palmitoyl-2-<12-(lipoyloxy)dodecanoyl>-sn-glycero-3-phosphocholine 
• 865302-38-1 C₆₀H₉₆NO₁₁PSi 

Relevant articles and documents

Synthetic access to arsenic-containing phosphatidylcholines

We wish to disclose the first synthesis of 1-O-hexadecanoyl-2-O-((15-(dimethylarsinoyl)pentadecanoyl)oxy)-sn-glycero-3-phosphocholine, which belongs to the group of arsenic-containing phosphatidylcholines (AsPCs), recently discovered in herring caviar. The synthesized product will serve as a model compound to study biological and toxicological properties of arsenolipids in food.

Syntheses and antiproliferative activities of novel phosphatidylcholines containing dehydroepiandrosterone moieties

Dehydroepiandrosterone (DHEA) is a natural hormone with many beneficial properties including an anticancer activity. Unfortunately, DHEA is unstable in the body and exhibits cytotoxicity against healthy cells. In this study, a series of new phosphocholines containing DHEA at sn-1 and/or sn-2 positions were prepared. Succinic acid was used as a linker between the active drug and sn-glycero-3-phosphocholine. All the compounds were evaluated in vitro for their antiproliferative activities against four cell lines: Balb/3T3, HL-60, B16, and LNCaP. The results showed that phosphocholines with DHEA at sn-1 and/or sn-2 positions did not have cytotoxic effects on the normal cell line (Balb/3T3). Mixed-chain phospholipids with DHEA and fatty acid residues showed the highest activity against tumor cell lines. The most active compound, 11c, showed a moderate cytotoxic effect against the HL-60 and B16 cell lines.

Lytic reactions of drugs with lipid membranes

Propranolol is shown to undergo lipidation reactions in three types of lipid membrane: (1) synthetic single-component glycerophospholipid liposomes; (2) liposomes formed from complex lipid mixtures extracted from E. coli or liver cells; and (3) in cellulo in Hep G2 cells. Fourteen different lipidated propranolol homologues were identified in extracts from Hep G2 cells cultured in a medium supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products, but many of these drugs did affect the lysolipid levels in model membranes. The propensity for a compound to induce lysolipid formation in a model system was found to be a predictor for phospholipidosis activity in cellulo.

Tin-mediated synthesis of lyso-phospholipids

1-O-Acyl-sn-glycero-3-phosphocholine and 1-O-acyl-sn-glycero-3-phosphoric acid have been prepared selectively and with high yields from the corresponding diols, glycerophosphoryl choline and glycerol-3-phosphate. Starting from the diols, the activated tin ketals were prepared in 2-propanol by reaction with dialkyltin oxide. The intermediates were acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso- phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed. The Royal Society of Chemistry 2006.

Synthesis and biological evaluation of novel phosphatidylcholine analogues containing monoterpene acids as potent antiproliferative agents

The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59-87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards noncancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.