17364-18-0

Basic information

• Product Name: DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN
• Synonyms: 1-PALMITOYL-RAC-GLYCERO-3-PHOSPHOCHOLINE;DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN;DL-ALPHA-LYSOPHOSPHATIDYLCHOLINE, PALMITOYL;PALMITOYLDL-ALPHA-LYSOPHOSPHATIDYLCHOLINE;PALMITOYL-LDL-ALPHA-LYSOPHOSPHATIDYLCHOLINE;RAC-LYSOPHOSPHATIDYLCHOLINE, 1-PALMITOYL;RAC-1-PALMITOYL-GLYCERO-3-PHOSPHOCHOLINE;(±)-(7-hydroxy-4-oxido-10-oxo-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide
• CAS NO: 17364-18-0
• Molecular Formula: C₂₄H₅₀NO₇P
• Molecular Weight: 495.63
• EINECS: 241-396-7
• Mol File: 17364-18-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: −20°C
• CAS DataBase Reference: DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN(CAS DataBase Reference)
• NIST Chemistry Reference: DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN(17364-18-0)
• EPA Substance Registry System: DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN(17364-18-0)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 17364-18-0(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN is used as an emulsifier to improve the stability and texture of food products. It helps in maintaining a uniform distribution of ingredients, preventing separation and improving the overall quality and shelf life of the food.
Used in Cosmetic Industry:
In cosmetics, DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN serves as an emulsifying agent, allowing for the combination of ingredients that would otherwise not mix well. This results in improved product consistency and performance, as well as enhanced skin feel and absorption.
Used in Pharmaceutical Industry:
DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN is utilized as a solubilizer in pharmaceutical formulations, enhancing the solubility of drugs and improving their bioavailability. This property is particularly beneficial for drugs that are poorly soluble in water, thus aiding in their absorption and therapeutic efficacy.
Used in Cell Culture Media:
In the field of cell culture, DL-GAMMA-PALMITOYL-ALPHA-LYSOLECITHIN acts as a growth aid, promoting cell growth and proliferation. Its presence in the culture media helps to maintain the integrity and functionality of the cells, supporting their growth and development in a controlled laboratory environment.

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

• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 112-67-4 n-hexadecanoyl chloride 
• 26227-65-6 palmitic acid carboimidazolide 
• 34688-34-1 glycerolcholine phosphate 
• 23470-00-0 2-palmitoylglycerol 
• 62106-90-5 rac.-1-Palmitoyl-glycerin-benzylether-⁽²⁾ 
• 67-56-1 methanol 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 786704-19-6 Hexadecanoic acid (R)-2-(4-nitro-phenoxycarbonyl)-2-(tetrahydro-pyran-2-yloxy)-ethyl ester 
• 786704-18-5 Hexadecanoic acid (R)-2-hydroxy-2-(4-nitro-phenoxycarbonyl)-ethyl ester 
• 605680-00-0 1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol 
• 57984-42-6 1-palmitoyl-3-(p-toluenesulfonyl)-sn-glycerol 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 

Downstream Products

• 79512-78-0 1-palmitoyl-2-O-acetyl-sn-glycero-3-phosphocholine 
• 6931-84-6 lecithin 
• 1039749-81-9 C₅₅H₈₆NO₈PS 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 89947-79-5 2-(4-hydroxycarbonylbutyroyl)lysophosphatidylcholine palmitoyl 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 39735-07-4 β-arachidonoyl-γ-palmitoyl-α-phosphatidylcholine 
• 6931-84-6 1-palmitoyl-2-lineleoylphosphatidylcholine 
• 875685-46-4 10-Nitrooleic Acid 

Relevant articles and documents

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.

A high-purity dissolved blood phosphatidyl choline and its preparation method (by machine translation)

The present invention provides a high purity dissolved blood phosphatidyl choline and its preparation, wherein the preparation method at least comprises the following steps: synthetic phosphatidyl choline, 1st mixed solvent and inorganic alkali; hydrolytic reaction, to be synthetic phosphatidyl choline reaction is complete; through the column chromatography purification, to obtain high-purity hemolyzed phosphatidyl choline. The present invention provides a high purity of chancing of the preparation method, the method for preparing the chancing high purity, and the fatty acid purity is greater than 99%, mild reaction conditions and the production cycle is comparatively short, low production cost, simple process, easy to industrial production. (by machine translation)

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.

Near-infrared light-sensitive liposomes for controlled release

A photoresponsive amphiphilic lipid molecule with phosphatidylcholine as the headgroup and a near-infrared (NIR) light-responsive unit on the hydrophobic moiety was synthesized. Liposomes constituting the NIR-responsive lipid, cholesterol and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, were constructed and applied as a photocontrolled release system. The precisely controlled release of the loaded cargo was demonstrated by adjusting the irradiation parameters and content of the photoresponsive species. The low cytotoxicity and good biocompatibility of the photoresponsive lipid was demonstrated by MTT assay. This study provides us with a new choice for developing a photoresponsive drug delivery system.

NOVEL GENE DERIVED FROM MUD FLAT METAGENOME AND NOVEL PROTEIN OBTAINED THEREFROM SHOWING COACTIVITY OF PHOSPHOLIPASE AND LIPASE

The present invention relates to a novel gene derived from a tidal flat metagenome, and a novel protein obtained therefrom showing the coactivity of phospholipase and lipase. Specifically, the novel gene isolated from the metagenome library of tidal flat sedimentsand the protein having phospholipase and lipase activities encoded from the novel gene: are expressed in a water-soluble form to be mass-producible; enable ultra high-purity protein to be obtained through single step purification using an Ni-NTA column; show good activity in the pH range of 5 ?? 10; maintain good low temperature activity and stability up to a temperature of 3°C to 40°C; and have high resistance against various organic solvents. Therefore, the novel gene and the protein can be usefully used for various industrial fields such as the purification and conversion of oil and fat, bio-medicine, and fine chemistry.

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.

Peptidophospholipids: Synthesis, phospholipase A2 catalyzed hydrolysis, and application to development of phospholipid prodrugs

New phospholipid analogues incorporating sn-2-peptide substituents have been prepared to probe the fundamental structural requirements for phospholipase A2 catalyzed hydrolysis of PLA2-directed synthetic substrates. Two structurally

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.

Acyl transfer from phosphocholine lipids to melittin

Transfer of fatty acyl groups from membrane phospholipids to melittin, a commonly studied membrane-active peptide, has been observed to occur over extended time periods. Transfer can be detected after 1-2 days and selectively targets amino groups at the N-terminal end of the peptide.