998-07-2

Basic information

• Product Name: 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
• Synonyms: 14:0 PE;1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE;1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHATIDYLETHANOLAMINE;1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHORYLETHANOLAMINE;1,2-DITETRADECANOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE;3-SN-PHOSPHATIDYLETHANOLAMINE, 1,2-DIMYRISTOYL;L-A-PHOSPHATIDYL-ETHANOLAMINE,*DIMYRISTO YL;L-A-PHOSPHATIDYLETHANOLAMINE,*DIMYRISTOY
• CAS NO: 998-07-2
• Molecular Formula: C₃₃H₆₆NO₈P
• Molecular Weight: 635.85
• Mol File: 998-07-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 191.0 to 195.0 °C
• Boiling Point: 685.634 °C at 760 mmHg
• Flash Point: 368.458 °C
• Appearance: /
• Density: 1.028 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: −20°C
• PKA: 1.17±0.50(Predicted)
• BRN: 1730529
• CAS DataBase Reference: 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(998-07-2)
• EPA Substance Registry System: 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(998-07-2)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 998-07-2(Hazardous Substances Data)

Usage

Description

Phosphatidylethanolamines (PEs) are phospholipids found in biological membranes, serving both structural and functional roles. Different types of PEs are commonly used in the generation of micelles, liposomes, and other types of artificial membranes. 1,2-Dimyristoyl-sn-glycero-3-PE (DMPE) is a phospholipid containing the long-chain (14:0) myristic acid inserted at the sn-1 and sn-2 positions.

Uses

Tetradecanoic Acid (1R)-1-[[[(2-Aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl Ester is a phospholipid serving both structural and functional roles in biological membranes.

Purification Methods

Recrystallise the kephalin from EtOH [Bevan & Malkin J Chem Soc 2667 1951]. The R-isomer has m 195-196o (sintering at 130-135o) after recrystallisation from CHCl3/MeOH, and [] D 26 +6.7o (c 8.5, CHCl3/AcOH 9:1). [Baer Can J Biochem Physiol 35 239 1957, Baer et al. J Am Chem Soc 74 152 1952, Beilstein 4 IV 1463.]

InChI:InChI=1/C33H66NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(35)39-29-31(30-41-43(37,38)40-28-27-34)42-33(36)26-24-22-20-18-16-14-12-10-8-6-4-2/h31H,3-30,34H2,1-2H3,(H,37,38)/t31-/m1/s1

Upstream product

• 60562-16-5 1,2-dimyristoyl-sn-glycerol 
• 28874-52-4 L-α-dimyristoylphosphatidic acid 
• 149183-57-3 (N-tert-butyloxy)carbonyl-dimyristoylphosphatidylethanolamine 

Downstream Products

• 18194-24-6 dimyristoylphosphatidylcholine 
• 544-63-8 n-tetradecanoic acid 

Relevant articles and documents

Preparation method of disaturated acyl phosphatidylethanolamine

The invention discloses a preparation method of disaturated acyl phosphatidylethanolamine, relates to the field of compound preparation, and aims at solving the problems of low yield and high cost ofan existing synthesis method of disaturated acyl phosphatidylethanolamine, wherein the preparation method comprises the following steps: (1) carrying out phosphorylation reaction by using a one-pot method to generate a compound I; (2) mixing the compound I with acid, and carrying out hydrolysis reaction to generate a compound II; (3) carrying out esterification reaction on the compound II and saturated chain acid, namely myristic acid, palmitic acid and stearic acid to generate a compound III; (4) mixing the compound III with DBU, namely 1,8-diazabicyclo undec-7-ene, and carrying out a deprotection reaction to generate a compound IV; and (5) mixing the compound IV with zinc powder and acetic acid, and carrying out a deprotection reaction to generate the disaturated acyl phosphatidylethanolamine. The method is short in synthetic route, mild in reaction condition, wide in application range and high in yield.

Total synthesis of perdeuterated phospholipids

A general method for the total synthesis of various perdeuterated phospholipids (DMPA, DMPG, DMPE, DMPC) is described.Starting from simple and easily obtainable deuterated precursors, perdeuterated phosphatidic acid (DMPA-d59) was synthesized.DMPA-d59 was coupled to various perdeuterated alcohols in the presence of alkylsulfonyl chlorides as condensing agents.The preparation of the perdeuterated alcohols is also presented.The major advantage of this method lies in the independent synthesis of DMPA and the alcohol moieties, allowing the transformation to the desired phospholipid class in the final reaction step.The reaction scheme presented here can also be used for the synthesis of selectively deuterated phospholipids.Keywords - perdeuterated phospholipids / phosphatidic acid-d59 / phosphatidylglycerol-d64 / phosphatidylcholine-d72 / phopshatidylethanolamine-d63 / total synthesis