[3-(Dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate

Base Information

• Chemical Name: [3-(Dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate
• CAS No.: 127512-29-2
• Molecular Formula: C41H77 N O4
• Molecular Weight: 648.067
• DSSTox Substance ID: DTXSID10400693
• Mol file: 127512-29-2.mol

Synonyms:127512-29-2;[3-(dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate;DTXSID10400693;AKOS030241389;FT-0606429

Chemical Property of [3-(Dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.476
• Boiling Point: 670.148°C at 760 mmHg
• Flash Point: 359.092°C
• PSA: 55.84000
• Density: 0.916g/cm³
• LogP: 12.07800
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 15.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 37
• Exact Mass: 647.58525994
• Heavy Atom Count: 46
• Complexity: 717

Purity/Quality:

98%Min ^*data from raw suppliers

1,2-Dioleoyloxy-3-(dimethylamino)propane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(CN(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
• Description: DODAP (18:1) is an ionizable cationic lipid with lower cytotoxicity and high transfection efficiency. DODAP is neutral at physiological pH, but acquires a positive charge inside the endosome due to the protonation of free amines when pH is lower than its pKa (<7).
• Uses: Cationic amphiphiles are being studied for their potential role in preparing liposomes for interaction with artificial and biological membranes and cellular transfection techniques. Cationic species with ester linkages to the hydrophobic portion are more easily degraded by recipient cells and more efficiently metabolized.

Technology Process of [3-(Dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate

There total 3 articles about [3-(Dimethylamino)-2-octadec-9-enoyloxypropyl] octadec-9-enoate 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: 97.5%

→ (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine (127512-29-2)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

Reference yield: 95.0%

(Z)-9-octadecenoyl chloride (112-77-6) + 3-(dimethylamino)-1,2-propanediol (623-57-4) → (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine (127512-29-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -5 - 20 ℃; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale;

Reference yield: 91.0%

cis-Octadecenoic acid (112-80-1,2027-47-6) + 3-(dimethylamino)-1,2-propanediol (623-57-4) → (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine (127512-29-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/c2cc31710a

upstream raw materials:

cis-Octadecenoic acid

3-(dimethylamino)-1,2-propanediol

(Z)-9-octadecenoyl chloride

Downstream raw materials:

N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride

Refernces

• 1、 Perttu, Emily K.,Szoka, Francis C.. "Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties". . p. 12613 - 12615. Retrieved 2011.
• 2、 -. "(2,3-dioleoyl-propyl)trimethyl ammonium chloride as well as preparation method and application thereof". Paragraph 0017; 0018. . Retrieved 2018/05/16.
• 3、 Walsh, Colin L.,Nguyen, Juliane,Szoka, Francis C.. "Synthesis and characterization of novel zwitterionic lipids with pH-responsive biophysical properties". experimental part. p. 5575 - 5577. Retrieved 2012/07/27.