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42358

Sigma-Aldrich

Dioctadecylamine

≥99.0% (NT)

Sinónimos:

DODA, Distearylamine

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About This Item

Fórmula lineal:
[CH3(CH2)17]2NH
Número de CAS:
112-99-2
Peso molecular:
521.99
Beilstein/REAXYS Number:
1801688
EC Number:
204-020-2
MDL number:
MFCD00048494
UNSPSC Code:
12352100
PubChem Substance ID:
57650109
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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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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Cong-Anh-Khanh Le et al.
International journal of biological macromolecules, 119, 555-564 (2018-07-31)
The crystallization of amylose from dilute solutions in the presence of a series of linear saturated fatty acids (C3 to C20) was investigated by varying the fatty acid concentration, crystallization temperature and solvent composition (DMSO:water in various ratios). The morphology
Biomimetic lipoglycopolymer membranes: photochemical surface attachment of supramolecular architectures with defined orientation.
Stefan M Schiller et al.
Angewandte Chemie (International ed. in English), 48(37), 6896-6899 (2009-08-19)
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.
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)
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
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