Dotap chloride

Base Information

• Chemical Name: Dotap chloride
• CAS No.: 132172-61-3
• Molecular Formula: C₄₂H₈₀NO₄*Cl
• Molecular Weight: 698.554
• UNII: 3R78UC794Z
• ChEMBL ID: CHEMBL133173
• Wikidata: Q27257930
• Mol file: 132172-61-3.mol

Synonyms:1,2-dioleoyl-3-trimethylammoniumpropane;1,2-dioleoyl-3-trimethylpropanammonium;1,2-dioleoyloxy-3-(trimethylammonium)propane;1,2-DOTAP;DOTAP;N,N,N-trimethyl-2,3-bis((-1-oxo-octadecenyl)oxy)-(Z,Z)-1-propanaminium;N-(1-(2,3-dioleoyloxy)propyl)-N,N,N-trimethylammonium methylsulfate

Chemical Property of Dotap chloride

Chemical Property:

• Melting Point: 35-38°C
• PSA: 52.60000
• LogP: 12.22260
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 37
• Exact Mass: 697.5775877
• Heavy Atom Count: 48
• Complexity: 754

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Dioleoyl-3-trimethylammonium-propane,Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC.[Cl-]
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC.[Cl-]
• Description: 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. 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.
• Uses: 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 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.

Technology Process of Dotap chloride

There total 9 articles about Dotap chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methylene chloride (74-87-3) + (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine (127512-29-2) → N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride (477274-39-8,132172-61-3)

Guidance literature:

In dichloromethane; at 85 ℃; under 11251.1 Torr; Solvent; Temperature;

Reference yield: 84.3%

cis-Octadecenoic acid (112-80-1,2027-47-6) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride (477274-39-8,132172-61-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 16h; Inert atmosphere;

Reference yield: 75.0%

(R,S) 1,2-dioleoyl-trimethylammonium propane tosylate → N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride (477274-39-8,132172-61-3)

Guidance literature:

With IRA 404 ion-exchange resin, chloride form; In methanol; Ion exchange;

upstream raw materials:

dichloromethane

(+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine

methylene chloride

cis-Octadecenoic acid

Refernces

• 1、 -. "Preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride)". Paragraph 0027; 0028; 0031; 0032. . Retrieved 2018/07/06.
• 2、 -. "STABLE CRYSTAL MODIFICATIONS OF DOTAP CHLORIDE". Page/Page column 25-27. . Retrieved 2012/12/13.