998-06-1

Basic information

• Product Name: 1,2-DILINOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: 18:2 PC (CIS);1,2-DI[CIS-9,12-OCTADECADIENOYL]-SN-GLYCERO-3-PHOSPHOCHOLINE;1,2-DI9-CIS-12-CIS-OCTADECENOYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1,2-DILINOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE;[R-(all-Z)]-[4-oxido-10-oxo-7-[(1-oxooctadeca-9,12-dienyl)oxy]-3,5,9-trioxa-4-phosphaheptacosa-18,21-dienyl]trimethylammonium 4-oxide;L-A-PHOSPHATIDYLCHOLINE DILINOLEOYL SYNTHETIC;L-A-PHOSPHATIDYLCHOLINE DILINOLEOYL,*LYO PHILIZED;L-ALPHA-Dilinoleoylphosphatidyl choline
• CAS NO: 998-06-1
• Molecular Formula: C₄₄H₈₀NO₈P
• Molecular Weight: 782.08
• EINECS: 213-647-0
• Mol File: 998-06-1.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /lyophilized powder
• Density: g/cm³
• Storage Temp.: −20°C
• BRN: 5212188
• CAS DataBase Reference: 1,2-DILINOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DILINOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(998-06-1)
• EPA Substance Registry System: 1,2-DILINOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(998-06-1)

Safety Data

• WGK Germany: 1
• F: 1-8-10
• Hazardous Substances Data: 998-06-1(Hazardous Substances Data)

Usage

Uses

18:2 (Cis) PC (DLPC) has been used for liposome preparation.

Definition

ChEBI: A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at positions 1 and 2 are specified as linoleoyl [(9Z,12Z)-octadeca-9,12-dienoyl].

General Description

18:2 (Cis) PC (DLPC) is a synthetic phosphatidylcholine.

InChI:InChI=1/C44H80NO8P/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/h14-17,20-23,42H,6-13,18-19,24-41H2,1-5H3/b16-14-,17-15-,22-20-,23-21-/t42-/m1/s1

Upstream product

• 60-33-3 linoleic acid 
• 7459-33-8 linoleyl chloride 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 107-07-3 2-chloro-ethanol 
• 75-50-3 trimethylamine 
• 67-48-1 choline chloride 
• 24529-89-3 (2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl-(9Z,12Z)-octadeca-9,12-dienoate 

Downstream Products

• 22252-07-9 L-γ-linoleoyl-α-lysolecithin 
• 10219-69-9 (R,S)-coriolic acid 
• 73543-67-6 (10E,12Z)-9-hydroxy-10,12-octadecadienoic acid 
• 115185-06-3 9-Hode 
• 32819-31-1 [14C]-13-Hydroxyoctadecadienoic acid 
• 816-94-4 distearoylphosphatidylcholine 

Relevant articles and documents

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.

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.

Short-route Synthesis of a Glycerophospholipid Bearing an Unsaturated Acyl Group at the sn-1 Position

A short-route synthesis of an optically active phosphocholine bearing an unsaturated acyl group at the sn-1 position was developed via lipase-catalyzed enantioselective acylation of 2-O-methoxyethoxymethylglycerol, removal of the MEM group by employing catechol boron bromide, subsequent DCC-mediated acylation of the hydroxy group at the 2-position and final introduction of a choline phosphate moiety.