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

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

Uses

Used in Pharmaceutical Industry:
DMPE is used as a component in the development of drug delivery systems, such as liposomes, to improve the solubility, stability, and targeted delivery of therapeutic agents.
Used in Cosmetic Industry:
DMPE is used as an emulsifying agent in cosmetic formulations to stabilize oil-water mixtures and enhance the texture and appearance of products.
Used in Food Industry:
DMPE is used as an ingredient in the production of artificial membranes and as a component in the formulation of food supplements and nutraceuticals.
Used in Biotechnology Industry:
DMPE is used in the development of biosensors and diagnostic tools, as well as in the study of membrane biophysics and the design of artificial cellular systems.

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

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

Downstream Products

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

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.

A diacyl phosphatidyl ethanolamine preparation method (by machine translation)

The invention provides a diacyl phosphatidyl ethanolamine preparation method, comprises the following steps: (1) solvent and organic/inorganic alkali under the action of, the formula I compound and phosphorus reagent undergo the substitution reaction, formula a intermediate 1; (2) in the same reaction system, intermediate 1 of an organic/inorganic the presence of an alkali, with 2 - (N - [...] carbonyl amino) ethanol or N - Boc protection of the ethanolamine undergo the substitution reaction, formula b intermediate 2; (3) in the same reaction system, intermediate 2 under the action of the oxidizing agent in the oxidation reaction, the compound of formula II; (4) the formula II compound in the solvent, under the action of alkali, phospholipid base hydrolysis, formula III compound. The advantage of this invention is characterized in that: the invention only needs two-step synthesis of the target product can be obtained, and the method is easy to control conditions, after treatment is simple, less side reaction, high yield, consistent with the requirements of industrial production. (by machine translation)

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