132172-61-3

Basic information

• Product Name: N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE
• Synonyms: N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE;N-[1-(2,3-DIOLEOYLOXY)PROPYL]-N,N,N-TRIMETHYL-AMMONIUM CHLORIDE SALT;N-[1-(2,3-DIOLEOYLOXY) PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE;TRIMETHYL[2,3-(DIOLEYLOXY)PROPYL]AMMONIUM CHLORIDE;1,2-DIOLEOYL-3-TRIMETHYLAMMONIUM-PROPANE, CHLORIDE;DOTMA;DOTAP CHLORIDE SALT;DOTAP
• CAS NO: 132172-61-3
• Molecular Formula: C₄₂H₈₀NO₄*Cl
• Molecular Weight: 698.54
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 132172-61-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 35-38°C
• Appearance: /lyophilized powder
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly)
• Stability: Store in Freezer, Hygroscopic
• CAS DataBase Reference: N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE(132172-61-3)
• EPA Substance Registry System: N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE(132172-61-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 132172-61-3(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 132172-61-3 differently. You can refer to the following data:
1. DOTAP chloride (1,2-Dioleoyl-3-trimethylammonium-propane chloride) is a potent cationic lipid widely used as a liposomal transfection reagent. DOTAP is also a strong activator of the innate immune system in animal cells and could serve as a potential candidate for the study of elicitors of plant immunity.
2. DOTAP, 1,2-Dioleoyl-3-trimethylammonium propane is a di-chain, or gemini, cationic surfactant. DOTAP has been used for in vitro and in vivo nucleic acid and protein delivery.

Chemical Properties

White Foam

Uses

Different sources of media describe the Uses of 132172-61-3 differently. You can refer to the following data:
1. Small unilamellar liposomes containing DOTMA interact spontaneously with DNA to form lipid-DNA complexes with 100% entrapment of DNA. Facilitates fusion of the complex with the plasma membrane of tissue culture cells, resulting in both uptake and
2. 1,2-dioleoyloxy-3-(trimethylammonium)propane (DOTAP) chloride has been used for the preparation of cationic liposome and liposome-DNA complex. It has also been used to assess tumor necrosis factor α (TNF- α) production.

Biochem/physiol Actions

18:1 TAP (DOTAP) is a cationic lipid structure, used for in vitro and in vivo nucleic acid and protein delivery. The lipid composition and cell type affects the transfection potential of DOTAP(1,2-dioleoyl-3-trimethylammonium-propane). 18:1 TAP (DOTAP) mediates gene knockdown technique in hematopoietic stem cells (HSCs).

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 34004-36-9 N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride 
• 112-80-1 cis-Octadecenoic acid 
• 623-57-4 3-(dimethylamino)-1,2-propanediol 
• 74-87-3 methylene chloride 
• 127512-29-2 (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine 
• 75-09-2 dichloromethane 

Relevant articles and documents

Preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride)

The invention discloses a preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride). The preparation method of the positive liposome DOTAP comprises preparation methods of (+/-)-DOTAP, (S)-DOTAP and (R)-DOTAP. The DOTAP product is synthesized by taking cheap 3,-chlorine-1,2-propylene glycol a starting material and by a two-step method, and high-purity positiveliposome DOTAP can be obtained through silica gel column purification. The invention provides a preparation method of the DOTAP, which is low in cost and simple in process. The method is low in raw material cost, mild in reaction condition and simple in aftertreatment, does not need an ion exchange process and has economic property, environmental friendliness and high efficiency.

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

PROCESS FOR THE SYNTHESIS OF CATIONIC LIPIDS

A process for the synthesis of lipid cations having general formula (6) in which: R1 represents a lipophilic chain; R2, R3, R4, which are identical or different from one another, represent C1-C10 alkyl, C1-C10 alkenyl, or C1-C10 alkynyl radicals, optionally containing hydroxyl, ether, halogen and acyloxy functions, and X- is an oxy-anion or a halide; in which a compound of formula (2) in which R5 and R6, which are identical or different from one another, represent a C1-C5 acyl, a benzyl group or a diolprotective group, is reacted in an alcoholic solvent with from 1 to 6 equivalents of NR2R3R4.