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
• Article Data: 3

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

• 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 
• 60-33-3 linoleic acid 
• 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

• 816-94-4 distearoylphosphatidylcholine 
• 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 
• 22252-07-9 L-γ-linoleoyl-α-lysolecithin 

Relevant articles and documents

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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.