816-94-4

Usage

Biochem/physiol Actions

1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) is used in combination with other members of phosphatidylcholine for the generation of mixed bilayer system. It is majorly used in conventional and stealth liposome preparation for drug delivery studies.

InChI:InChI=1/C44H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h42H,6-41H2,1-5H3/t42-/m1/s1

Upstream product

• 6542-05-8 1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine 
• 4167-02-6 2-bromoethylphosphoric acid dichloride 
• 51063-97-9 DL-α,β-distearin 
• 75-50-3 trimethylamine 
• 18498-22-1 DL-1.2-Distearoyl-glycerin-phosphorsaeure-⁽³⁾-mono-2-brom-aethylester 
• 67-48-1 choline chloride 
• 57-11-4 stearic acid 
• 998-06-1 (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 112-76-5 Stearoyl chloride 
• 17966-16-4 1,2-Distearoyl-sn-glycero-3-phosphoric acid 
• 55357-38-5 choline tosylate 
• 34487-26-8 1-stearoyl-2-linoleoyl-sn-glycerol 
• 40879-44-5 (R)-1,2-distearoyl-3-iodopropane 

Downstream Products

• 17364-19-1 1-stearoyl-sn-glycero-3-phosphocholine 
• 67-48-1 choline chloride 
• 19420-57-6 1-stearoyl-sn-glycero-3-phosphocholine 
• 83214-11-3 1-β-D-arabinofuranosylcytosine 5'-diphosphate-L-1,2-distearin 
• 18892-74-5 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine 
• 6753-53-3 1-octadecanoyl-2-[cis-9,12]-octadecadienoyl-glycero-3-phosphocholine 

Relevant academic research and scientific papers

Method for preparing difatty acyl phosphatidylcholine by solid-phase reaction

The invention relates to a method for preparing difatty acyl phosphatidylcholine by a solid-phase reaction. Glycerol phosphatidylcholine is subjected to wet-process loading by using a high-activity solid adsorbent, and then a condensation reaction is carried out on the glycerol phosphatidylcholine with fatty acid to obtain the difatty acyl phosphatidylcholine. The method comprises the following steps: dissolving glyceryl phosphatidylcholine in an organic solvent, adding a high-activity solid adsorbent, carrying out adsorbing dispersion while stirring, removing the organic solvent by vacuum evaporation, and carrying out vacuum drying on the obtained solid-phase loaded mixed material; dissolving fatty acid in an organic solvent, adding a condensation coupling agent, carrying out heating reflux to prepare active ester of fatty acid, adding the solid-phase loaded glyceryl phosphatidylcholine, and continuing reflux to prepare a difatty acyl phosphatidylcholine crude product; and carrying out filtering to recover the high-activity solid adsorbent, desolventizing mother liquor, pulping a crude product by using an organic solvent, and carrying out recrystallizing to obtain the high-puritydifatty acyl phosphatidylcholine. According to the method, the reaction yield reaches 65% or above, the product purity reaches 99% or above, the process is simple, the production period is short, andindustrial production is easy to achieve.

A (R)- 1, 2 - b stearyl acyl phosphatidyl choline preparation method

The invention discloses a preparation method of (R)-1,2-distearoyl phosphatidylcholine. The preparation method of (R)-1,2-distearoyl phosphatidylcholine comprises the following steps of: with 3-halogenated propylene as a raw material, carrying out an oxidation reaction under the catalytic action of a chiral catalyst, carrying out an addition reaction on the obtained (S)-1,2-diol-3-halogenated propane and stearic anhydride or stearic acid halide to obtain (R)-1,2-distearoyl-3-halogenated propane; then carrying out a reflux reaction on the (R)-1,2-distearoyl-3-halogenated propane and 3,4-dimethoxy benzyl silver phosphate to obtain (R)-1,2-distearoyl-3-(3,4-dimethoxy benzyl) phosphate propane; carrying out reaction on the (R)-1,2-distearoyl-3-(3,4-dimethoxy benzyl) phosphate propane and a phase transfer catalyst to remove phosphorus protecting group, so as to obtain (R)-1,2-glycerol distearate-glycerol-3- phosphatidic acid; finally carrying out the addition reaction on the (R)-1,2-glycerol distearate-glycerol-3-phosphatidic acid and choline tosilate in anhydrous pyridine under the catalytic action of trichloroacetonitrile to obtain (R)-1,2-distearoyl phosphatidylcholine. The preparation method of (R)-1,2-distearoyl phosphatidylcholine is simple in steps, mild in reaction and applicable to industrial production.

1,2-Diacrylglycerol and wherein the intermediate preparation method

The invention discloses a preparation method for diacylglycero and an intermediate thereof. The preparation method for diacylglycero comprises the following steps: in an ether solvent and/or an alcohol solvent, in the present of an alkali, performing hydrolysis reaction on a compound shown as a formula 5, so as to obtain diacylglycero which is 1 shown in a formula 1. R in the formula 5 and 5 is C14-C18 saturated or unsaturated aliphatic acyl. The preparation method is cheap in raw materials, mild in reaction conditions, safe in operation, simple in postprocessing operation, high in reaction conversion rate, high in yield and suitable for large-scale production.

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Novel phosphatidylcholines and lysophosphatidylcholines with cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acid (CLA) were synthesized in high yields (75-99%). The in vitro cytotoxic activities of these compounds against three human cancer cell lines (HL-60, MCF-7, and HT-29) were evaluated. The results revealed that there are differences in the activity between phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 CLA acyl groups. 1,2-Di(9Z,11E)-octadecadienoyl-sn-glycero-3-phosphocholine was the most potent cytotoxic agent among all tested CLA derivatives and its IC50 (concentration of a compound that inhibits the proliferation of 50% of the cancer cell population) was 29.4M against HL-60. Moreover, phosphatidylcholines with CLA acyls exhibited much lower cytotoxicity against non-cancer cells (Balb/3T3) than free CLA isomers.

Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

Process for the production of phospholipids

A new enzymatic process for preparing 1,2-diacylated phospholipids using an enzyme preparation possessing phospholipase activity towards acylation at the sn-1 and sn-2 sites in a microaqueous reaction system. More particularly, the 1,2-diacyl-phospholipids produced according to the esterification/transesterification process are obtainable in high yield and purity and carry identical desired carboxylic acid, preferably fatty acid, acyl groups at the sn-1 and sn-2 positions. The process involves esterification/transesterification (acylation) of a glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of the above mentioned appropriate enzyme preparation. The process of the invention further relates to a process for the production of 1-acyl-2-lyso-glycerophospholipid, preferably 2-lyso-PC by reacting glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of a sn-1 specific phospholipase (PLA1 or PLA1,2) and a solvent, in a microaqueous medium.

Method for producing liposomes with increased percent of compound encapsulated

The efficiency of encapsulating a drug into a liposomal formulation is increased by use of a lipid having a carbon chain containing from about 13 to about 28 carbons during preparation of the liposomes. Preferably the liposomes are multivesicular liposomes.

Method for loading lipid vesicles

Methods for the preparation of stable liposome formulations of protonatable therapeutic agents. The methods involve loading a therapeutic agent into preformed liposomes having a methylamine concentration gradient across the lipid bilayer of the liposomes. These methods provide liposome formulations which are more stable, more cost effective, and easier to prepare in a clinical environment than those previously available. The present invention also provides the pharmaceutical compositions prepared by the above methods, a kit for the preparation of liposome formulations of therapeutic agents, and methods for their use.

Facile and useful synthesis of enantiomeric phosphatidylcholines

The synthesis of optically active phosphatidylcholines (D- and L-4) containing two of the same fatty acid moieties in a molecule is described. Optically pure D-enantiomers (D-4) were obtained from 2,3-di-O-acyl-sn- glycerol (D-1) in high yield by phosphorylation with phosphorus oxychloride and subsequent treatment with choline tosylate (11a). L-Enantiomers (L-4) were also prepared in a similar manner from 1,2-di-O-acyl-sn-glycerol (L-1). The whole procedure is easy and useful for the synthesis of enantiomeric phosphatidylcholines.

Process of producing phosphatidylcholine derivatives

A process of producing phosphatidylcholine derivatives by the reaction of glycerophosphatidylcholine with at least one fatty acid anhydride in the presence of a pyridine catalyst is described. The reaction is carried out in a melt of the glycerophosphatidylcholine, the at least one fatty acid anhydride and the catalyst.