Lauryldimethylamine oxide

Lauryldimethylamine oxide
Names
Preferred IUPAC name
N,N-Dimethyldodecan-1-amine N-oxide
Other names
Lauramine oxide; Dodecyldimethylamine oxide; Dimethyldodecylamine-N-oxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.183 Edit this at Wikidata
EC Number
  • 216-700-6
UNII
  • InChI=1S/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3 ☒N
    Key: SYELZBGXAIXKHU-UHFFFAOYSA-N ☒N
  • InChI=1/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3
    Key: SYELZBGXAIXKHU-UHFFFAOYAJ
  • CCCCCCCCCCCC[N+](C)(C)[O-]
Properties
C14H31NO
Molar mass 229.408 g·mol−1
Appearance White solid
Density 0.996 g/ml
Melting point 132–133 °C (270–271 °F; 405–406 K)
Boiling point 320 °C (608 °F; 593 K)
Surface tension:
1.70 mM[1][2]
Hazards
GHS labelling:
GHS05: Corrosive[3]
Danger[3]
H314[3]
P280, P305+P351+P338, P310[3]
Safety data sheet (SDS) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lauryldimethylamine oxide (LDAO), also known as dodecyldimethylamine oxide (DDAO), is an amine oxide–based zwitterionic surfactant, with a C12 (dodecyl) alkyl tail. It is one of the most frequently-used surfactants of this type.[4] Like other amine oxide–based surfactants it is antimicrobial, being effective against common bacteria such as S. aureus and E. coli,[1] however, it is also non-denaturing and can thus be used for protein purification.

At high concentrations, LDAO forms liquid crystalline phases.[5] Despite having only one polar atom that is able to interact with water – the oxygen atom (the quaternary nitrogen atom is hidden from intermolecular interactions), DDAO is a strongly amphiphilic surfactant: it forms normal micelles and normal liquid crystalline phases. High amphiphilicity of this surfactant can be explained by the fact that it forms not only very strong hydrogen bonds with water: the energy of DDAO – water hydrogen bond is about 50 kJ/mol,[6] but it also has high experimental partition coefficient in non-polar medium, as characterized by experimental logP 5.284[7]

See also

References

  1. ^ a b Birnie, C. R.; Malamud, D.; Schnaare, R. L. (1 September 2000). "Antimicrobial Evaluation of N-Alkyl Betaines and N-Alkyl-N,N-Dimethylamine Oxides with Variations in Chain Length". Antimicrobial Agents and Chemotherapy. 44 (9): 2514–2517. doi:10.1128/AAC.44.9.2514-2517.2000. PMC 90094. PMID 10952604.
  2. ^ Hoffmann, H. (1990). "Correlation between surface and interfacial tensions with micellar structures and properties of surfactant solutions". Interfaces in Condensed Systems. Progress in Colloid & Polymer Science. Vol. 83. pp. 16–28. doi:10.1007/BFb0116238. ISBN 978-3-7985-0840-8.
  3. ^ a b c d e Sigma-Aldrich Co., N,N-Dimethyldodecylamine N-oxide. Retrieved on 2017-01-04.
  4. ^ Friedli, Floyd E (2001). Detergency of Specialty Surfactants. New York, NY: Dekker. ISBN 978-0-8247-0491-9.
  5. ^ Kocherbitov, V.; Söderman, O. (2006). "Hydration of Dimethyldodecylamine-N-Oxide: Enthalpy and Entropy Driven Processes". J. Phys. Chem. B. 110 (27): 13649–13655. doi:10.1021/jp060934v. hdl:2043/3224. PMID 16821893.
  6. ^ Kocherbitov, V.; Veryazov, V.; Söderman, O. (2007). "Hydration of Trimethylamine-N-oxide and of Dimethyldodecylamine-N-oxide: An Ab Initio study". J. Molec. Struct. Theochem. 808 (1–3): 111–118. doi:10.1016/j.theochem.2006.12.043.
  7. ^ "Lauryldimethylamine oxide | C14H31NO | ChemSpider". Archived from the original on 2024-04-14. Retrieved 2024-12-27.