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

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

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

• 112-77-6 (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.

Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties

We describe a class of zwitterionic sulfobetaine (SB) lipids with fascinating salt-dependent properties. SB lipids are zwitter-neutral across a broad pH range; however they have negative surface potentials in the presence of anions and two salt-dependent transition temperatures. These new SB lipids provide insight on the role of charge orientation at the membrane interface and may be useful components in drug delivery systems. The Royal Society of Chemistry 2011.

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)

(2,3-dioleoyl-propyl)trimethyl ammonium chloride as well as preparation method and application thereof

The invention discloses a preparation method of (2,3-dioleoyl-propyl)trimethyl ammonium chloride. The method comprises the steps as follows: firstly, 3-dimethylamino-1,2-propylene glycol reacts with oleic acid or oleoyl chloride to produce 1,2-dioleoyl-3-diamino-propane, then, 1,2-dioleoyl-3-diamino-propane reacts with chloromethane under 0.1-10 MPa to produce (2,3-dioleoyl-propyl)trimethyl ammonium chloride. The method is suitable for pilot-scale production, and the prepared (2,3-dioleoyl-propyl)trimethyl ammonium chloride is phospholipid for cationic liposome and can be applied to various types of drugs such as injections, tablets, capsules and the like as a pharmaceutical adjuvant.

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

STABLE CRYSTAL MODIFICATIONS OF DOTAP CHLORIDE

The present invention relates to crystal modifications of racemic (2R,S)- and enantiomerically pure (2R)- resp. (2S)-DOTAP chloride, to processes for the preparation thereof, and to the use thereof for the preparation of pharmaceutical compositions.

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.

Design and assembly of new nonviral RNAi delivery agents by microwave-assisted quaternization (MAQ) of tertiary amines

RNA interference (RNAi) is a gene-silencing phenomenon whereby double-stranded RNA (dsRNA) triggers the sequence-specific degradation of homologous mRNA. RNAi has been quickly and widely applied to discover gene functions and holds great potential to prov

METHODS AND COMPOSITIONS FOR THE EFFICIENT DELIVERY OF THERAPEUTIC AGENTS TO CELLS AND ANIMALS

The present invention provides methods of carrying out the safe and reliable preparation of lipids comprising quaternary amines. Such lipids are especially suited for introducing therapeutic agents into cells or organisms. In particular, the lipids of the invention are suitable for the efficient transfer of gene therapy agents into mammalian cells or organisms in a cell type specific or tissue specific manner.