127512-29-2

Basic information

• Product Name: DODAP
• Synonyms: 18:1 DAP;1,2-DIOLEOYLOXY-3-(DIMETHYLAMINO)PROPANE;1,2-DIOLEOYL-3-DIMETHYLAMMONIUM-PROPANE;DODAP;9-Octadecenoic acid(9Z)-1,1'-[1-[(dimethylamino)methyl]-1,2-ethanediyl] ester
• CAS NO: 127512-29-2
• Molecular Formula: C₄₁H₇₇NO₄
• Molecular Weight: 648.05
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 127512-29-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 670.148°C at 760 mmHg
• Flash Point: 359.092°C
• Appearance: /
• Density: 0.916g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.476
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive; Hydroscopic; Store at -15 to -25°C
• CAS DataBase Reference: DODAP(CAS DataBase Reference)
• NIST Chemistry Reference: DODAP(127512-29-2)
• EPA Substance Registry System: DODAP(127512-29-2)

Safety Data

• Hazardous Substances Data: 127512-29-2(Hazardous Substances Data)

Usage

Description

DODAP (18:1) is an ionizable cationic lipid with lower cytotoxicity and high transfection efficiency. DODAP is neutral at physiological pH, but acquires a positive charge inside the endosome due to the protonation of free amines when pH is lower than its pKa (<7).

Chemical Properties

Light Yellow Oil

Uses

Cationic amphiphiles are being studied for their potential role in preparing liposomes for interaction with artificial and biological membranes and cellular transfection techniques. Cationic species with ester linkages to the hydrophobic portion are more easily degraded by recipient cells and more efficiently metabolized.

InChI:InChI=1/C41H77NO4/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-40(43)45-38-39(37-42(3)4)46-41(44)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2/h19-22,39H,5-18,23-38H2,1-4H3/b21-19-,22-20-

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 623-57-4 3-(dimethylamino)-1,2-propanediol 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 477274-39-8 N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride 

Relevant articles and documents

A simple approach to DOTAP and its analogs bearing different fatty acids

A simple synthesis of N-[1-(2,3-dioleoyloxy)propyl]-N,N,N- trimethylammonium methyl sulfate (DOTAP) and its analogs differing in the fatty acids is presented. The synthesis is designed as quasi-one-pot reaction and the precipitating products are purified by simple recrystallization. (C) 2000 Elsevier Science Ireland Ltd.

Liposome, preparation method, of liposome, liposome assembly and carrying liposome complex (by machine translation)

The liposome according, to the present invention has the properties such, as that of the. liposome according to the present invention in the form (I), of ,L a liposome according to the present invention in the form of, a liposome according to the L present invention, in the form of a. liposome according to the present (I) invention in the form, of a, liposome according to, and the present invention in the, form of a liposome according to the present, invention. (by machine translation)

MANUFACTURING METHOD OF CATIONIC LIPID

PROBLEM TO BE SOLVED: To provide a manufacturing method of industrial cationic lipid capable of efficiently providing high purity cationic lipid without needs for special facility. SOLUTION: A cationic lipid represented by the formula (2) is obtained by mixing cationic lipid represented by the formula (1) and a tetraalkylammonium salt having X- in an organic solvent, filtering deposited tetraalkylammonium iodide to obtain a filtrate and concentrating the filtrate to deposit tetraalkylammonium iodide. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and characterization of novel zwitterionic lipids with pH-responsive biophysical properties

We report the synthesis and biophysical characterization of a novel class of zwitterionic lipids (ZL) with head groups containing a 3° or 4° amine and carboxylate. ZL form stable liposomes that exhibit head group dependent, pH-responsive biophysical characteristics. These lipids may be suitable components for drug delivery applications due to their ease of synthesis and unique pH-dependent properties.