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

N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE, also known as DOTMA, is a cationic lipid that is commonly used in the formation of liposomes for gene delivery and transfection. It possesses two oleoyl chains and a trimethylammonium head group, which allows it to spontaneously interact with DNA and form lipid-DNA complexes with high entrapment efficiency. DOTMA is also a strong activator of the innate immune system in animal cells and has potential applications in the study of elicitors of plant immunity.

Uses

Used in Gene Delivery and Transfection:
N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE is used as a cationic lipid for the preparation of cationic liposomes and liposome-DNA complexes. It facilitates the fusion of the complex with the plasma membrane of tissue culture cells, resulting in both uptake and expression of the delivered genetic material.
Used in Immunology Research:
N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE is used as an immune system activator in animal cells. It has potential applications in the study of elicitors of plant immunity and can be used to assess tumor necrosis factor α (TNF-α) production.
Used in Drug Delivery Systems:
N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE is used in the development of drug delivery systems for nucleic acid and protein delivery. Its cationic nature allows for efficient interaction with negatively charged biological molecules, enhancing the delivery and therapeutic outcomes of various drugs.
Chemical Properties:
N-[1-(2,3-DIOLEYLOXY)PROPYL]-N,N,N-TRIMETHYLAMMONIUM CHLORIDE appears as a white foam and is a di-chain, or gemini, cationic surfactant.

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

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

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.