816-94-4

Basic information

• Product Name: L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL
• Synonyms: DSPC;DISTEAROYL LECITHIN;L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL;L-BETA,GAMMA-DISTEAROYL-ALPHA-LECITHIN;(R)-(7-lauroyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacosyl)trimethylammonium 4-oxide;L-A-PHOSPHATIDYLCHOLINE, DISTEAROYL;L-A-PHOSPHATIDYLCHOLINE DISTEAROYL*CRYST SYNTHETIC;Distearoyl-L-a-Lecithin
• CAS NO: 816-94-4
• Molecular Formula: C₄₄H₈₈NO₈P
• Molecular Weight: 790.15
• EINECS: 212-440-2
• Mol File: 816-94-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 236°C(lit.)
• Boiling Point: Vapour density:
• Appearance: solid
• Storage Temp.: −20°C
• Solubility: slightly sol. in Chloroform
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3923978
• CAS DataBase Reference: L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL(CAS DataBase Reference)
• NIST Chemistry Reference: L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL(816-94-4)
• EPA Substance Registry System: L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL(816-94-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 816-94-4(Hazardous Substances Data)

Usage

Description

1,2-Distearoyl-sn-glycero-3-PC (DSPC) is a phospholipid containing the saturated long-chain (18:0) stearic acid inserted at the sn-1 and sn-2 positions. It is commonly used in the generation of micelles, liposomes, and other types of artificial membranes.

Chemical Properties

solid

Uses

18:0 PC (DSPC) has been used:in the microbubble monolayer preparation for biomolecule delivery studies into protoplastsin the preparation of liposomes for immobilization studies in the generation of porphyrin-phospholipid (PoP) liposomes for irinotecan (IRT) and doxorubicin delivery

Definition

ChEBI: A phosphatidylcholine 36:0 in which both phosphatidyl acyl groups are specified as stearoyl (octadecanoyl).

General Description

1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) is a phospholtidylcholine with alkyl chain comprising 18 carbons. It has phophatidylcholine head group and its structure is similar to 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC).

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

• 66152-20-3 2-(1,2-Distearoyl-rac-3-glyceryl)-1,3,2-dioxaphospholan 
• 67-48-1 choline chloride 
• 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 
• 116953-95-8 diphenyl 1,2-distearoyl-sn-glycero-3-phosphate 
• 34487-26-8 1-stearoyl-2-linoleoyl-sn-glycerol 
• 40879-44-5 (R)-1,2-distearoyl-3-iodopropane 
• 107437-06-9 α-<α'-Linoleoyl-β-stearoyl>-phosphatidylcholin 
• 57-11-4 stearic acid 
• 1429-59-0 1,2-distearoyl-sn-glycerol 
• 10025-87-3 trichlorophosphate 

Downstream Products

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

Relevant articles and documents

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.

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.

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.