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42358

Sigma-Aldrich

Dioctadecylamine

≥99.0% (NT)

Synonym(s):

DODA, Distearylamine

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About This Item

Linear Formula:
[CH3(CH2)17]2NH
CAS Number:
Molecular Weight:
521.99
Beilstein:
1801688
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay:
≥99.0% (NT)

Quality Level

Assay

≥99.0% (NT)

mp

71-73 °C

solubility

water: soluble(lit.)

functional group

amine

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

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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K Tagawa et al.
Bioconjugate chemistry, 10(3), 354-360 (1999-05-29)
Novel amphiphiles which carry many mannose residues as side chains were prepared by telomerization of N-methacryloylaminopropyl D-mannopyranoside (alpha:beta = 20:1), N-methacryloylaminohexyl D-mannopyranoside (alpha:beta = 20:1), or 3-(2-methacryloylaminoethylthio)propyl D-mannopyranoside (alpha:beta = 4:1) using a lipophilic radical initiator. The mannose-carrying amphiphiles incorporated
The dioctadecylamine monolayer: Textures, phase transitions, and dendritic growth.
Flores A, et al.
J. Chem. Phys. , 119(11), 5644-5653 (2003)
Samuel F Brockington et al.
The New phytologist, 207(4), 1170-1180 (2015-05-15)
Betalain pigments are unique to the Caryophyllales and structurally and biosynthetically distinct from anthocyanins. Two key enzymes within the betalain synthesis pathway have been identified: 4,5-dioxygenase (DODA) that catalyzes the formation of betalamic acid and CYP76AD1, a cytochrome P450 gene
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
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)

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