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42358

Sigma-Aldrich

Dioctadecylamine

≥99.0% (NT)

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Synonym(s):
DODA, Distearylamine
Linear Formula:
[CH3(CH2)17]2NH
CAS Number:
Molecular Weight:
521.99
Beilstein:
1801688
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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This Item
30539139423874750
Dioctadecylamine ≥99.0% (NT)

Sigma-Aldrich

42358

Dioctadecylamine

Octadecylamine ≥99% (GC)

Sigma-Aldrich

305391

Octadecylamine

Pyrrolidine ≥99.5%, purified by redistillation

Sigma-Aldrich

394238

Pyrrolidine

Octadecylamine ≥99.0% (GC)

Sigma-Aldrich

74750

Octadecylamine

mp

71-73 °C

mp

50-52 °C (lit.)

mp

-

mp

50-52 °C (lit.), 52-55 °C

solubility

water: soluble(lit.)

solubility

-

solubility

water: miscible

solubility

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

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 (bicyclo[6.1.0]nonyne) 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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Robert Pajewski et al.
Organic & biomolecular chemistry, 3(4), 619-625 (2005-02-11)
Heptapeptides having dioctadecyl, N-terminal hydrocarbon chains insert in phospholipid bilayer membranes and form pores through which at least chloride ions pass. Although amphiphilic, these compounds do not typically form vesicles themselves. They insert in the bilayers of phospholipid vesicles and
Self-assembling nanoscaled drug delivery systems composed of amphiphilic poly-N-vinylpyrrolidones.
Kuskov AN, et al.
Journal of Non-Crystalline Solids, 353(41), 3969-3975 (2007)
Yanmei Dong et al.
Molecular pharmaceutics, 9(6), 1654-1664 (2012-05-02)
Progress in the development of nonviral gene delivery vectors continues to be hampered by low transfection activity and toxicity. Here we proposed to develop a lipid prodrug based on a polyamine analogue bisethylnorspermine (BSP) that can function dually as gene
K Ohno et al.
Bioconjugate chemistry, 6(4), 361-366 (1995-07-01)
A galactose-containing monomer (2-(methacryloyloxy)ethyl beta-D-galactopyranoside, MEGal) was polymerized by using a lipophilic radical initiator. The amphiphile obtained formed a liposome by mixing with bis(trans,trans-2,4-dioctadecadienoyl)phosphatidylcholine (DDPC), and the liposome obtained was physically stabilized by the polymerization of DDPC by UV irradiation.

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