42358

Sigma-Aldrich

Dioctadecylamine

≥99.0% (NT)

Synonym(s):
DODA, Distearylamine
Linear Formula:
CH3(CH2)172NH
CAS Number:
Molecular Weight:
521.99
Beilstein/REAXYS Number:
1801688
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥99.0% (NT)

mp

71-73 °C

solubility

water: soluble(lit.)

SMILES string

CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC

InChI

1S/C36H75N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37H,3-36H2,1-2H3

InChI key

HKUFIYBZNQSHQS-UHFFFAOYSA-N

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General description

Dioctadecylamine (DODA), a secondary amine, is a fatty amine derivative. Its biodegradation potential has been assessed. It has been observed that in aqueous medium DODA self organizes into plate like structures. Its partial charge distribution as a function of its conformation has been analyzed. The phase diagram of dioctadecylamine Langmuir monolayers has been determined and investigations show it does not form a monolayer above pH 3.9. DODA has been utilized in forming liposomes, cationic lipids or lipid chelating agents.

Application

Dioctadecylamine (DODA) is suitable reagent used in the synthesis of the following:
  • Dioctadecylamine-BCN (bicyclo6.1.0nonyne) conjugate.
  • Lipid derivatives of bisethylnorspermine (BSP).
  • Functional VP (N-vinylpyrrolidone ) polymers.
It may be used in the following studies:
  • As a reactant in the synthesis of 4,4′-azobis(4-cyano-N,N-dioctadecyl)pentanamide (DODA-501) by reacting with disuccinimidyl 4,4′-azobis(4-cyanovalerate).
  • As a reagent in the synthesis of dioctadecyl heptapeptides.
  • As a phase transfer and stabilizer agent for gold nanoparticles (AuNPs) in non-polar solvent.

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Stefan Bleher et al.
Small (Weinheim an der Bergstrasse, Germany), 15(50), e1904716-e1904716 (2019-11-14)
Circulation lifetime is a crucial parameter for a successful therapy with nanoparticles. Reduction and alteration of opsonization profiles by surface modification of nanoparticles is the main strategy to achieve this objective. In clinical settings, PEGylation is the most relevant strategy...
Erik Oude Blenke et al.
Journal of controlled release : official journal of the Controlled Release Society, 202, 14-20 (2015-01-28)
The modification of liposomal surfaces is of interest for many different applications and a variety of chemistries are available that makes this possible. A major disadvantage of commonly used coupling chemistries (e.g. maleimide-thiol coupling) is the limited control over the...
Glycosidation of alkylamino-alkan-1-ol. A simple and convenient synthesis of glycosylated cationic lipids.
Jacopin C, et al.
Bioorganic & Medicinal Chemistry, 12(11), 1447-1450 (2002)
Emmanuelle Roux et al.
Journal of pharmaceutical sciences, 91(8), 1795-1802 (2002-07-13)
The aim of this study was to characterize a pH-sensitive liposome formulation bearing a terminally alkylated N-isopropylacrylamide (NIPAM) copolymer with regard to its pH responsiveness, surface properties, and pharmacokinetics. The interacting forces between two lipid bilayers bearing the anchored NIPAM...
Ab initio study of the influence of conformation on partial charge distribution of dioctadecylamine.
Huetz P, et al.
Chemical Physics Letters, 380(3), 424-434 (2003)

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