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 that exhibits lower cytotoxicity and high transfection efficiency. It is a light yellow oil at room temperature and remains neutral at physiological pH. However, it acquires a positive charge inside the endosome due to the protonation of free amines when the pH is lower than its pKa (<7).

Uses

Used in Pharmaceutical Industry:
DODAP is used as a cationic amphiphile for the preparation of liposomes, which are essential in interacting with artificial and biological membranes and cellular transfection techniques. The cationic nature of DODAP with ester linkages to the hydrophobic portion allows for easier degradation by recipient cells and more efficient metabolism.
Used in Gene Delivery:
DODAP is used as a component in the formulation of lipoplexes and polyplexes for gene delivery. Its cationic properties facilitate the binding and condensation of nucleic acids, enhancing the efficiency of gene transfer and expression.
Used in Drug Delivery Systems:
DODAP is utilized as a carrier in drug delivery systems, particularly for the encapsulation and delivery of therapeutic agents. Its ability to form liposomes and interact with biological membranes makes it a valuable component in the development of targeted drug delivery systems.
Used in Cosmetic Industry:
DODAP can be used as an ingredient in cosmetic formulations due to its cationic nature, which can help in the delivery of active ingredients to the skin and improve the overall effectiveness of the product.
Used in Biomedical Research:
DODAP is employed in the field of biomedical research for the development of novel drug delivery systems and as a tool for studying cellular uptake and intracellular trafficking mechanisms.

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

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

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.