Lauryldimethylamine oxide
 | |
| Names | |
|---|---|
| IUPAC name
N,N-Dimethyldodecan-1-amine oxide | |
| Other names
Lauramine oxide; Dodecyldimethylamine oxide; Dimethyldodecylamine-N-oxide | |
| Identifiers | |
| 3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.015.183 |
| EC Number | 216-700-6 |
| PubChem CID |
|
| |
| |
| Properties | |
| C14H31NO | |
| Molar mass | 229.41 g·mol−1 |
| Appearance | White solid |
| Density | 0.996 g/ml |
| Boiling point | 132–133 °C (270–271 °F; 405–406 K) |
| Surface tension: | |
| 1.70 mM[1][2] | |
| Hazards | |
| Safety data sheet | [3] |
| GHS pictograms |  [3] |
| GHS signal word | Danger[3] |
| H314[3] | |
| P280, P305+351+338, P310[3] | |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is  ?) | |
| Infobox references | |
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 may be used to solubilize proteins.
At high concentrations, DDAO 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 hydrophilic surfactant: it forms normal micelles and normal liquid crystalline phases. High hydrophilicity of this surfactant can be explained by the fact that it forms very strong hydrogen bonds with water: the energy of DDAO – water hydrogen bond is about 50 kJ/mol.[6]
See also
- Myristamine oxide – An analogous compound with a C14 tail
References
- 1 2 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.
- ↑ Hoffmann, H. (1990). "Correlation between surface and interfacial tensions with micellar structures and properties of surfactant solutions". 83: 16–28. doi:10.1007/BFb0116238.
- 1 2 3 4 5 Sigma-Aldrich Co., N,N-Dimethyldodecylamine N-oxide. Retrieved on 2017-01-04.
- ↑ Friedli, Floyd E (2001). Detergency of Specialty Surfactants. New York, NY: Dekker. ISBN 0-8247-0491-6.
- ↑ Kocherbitov, V., Söderman, O. (2006). "Hydration of Dimethyldodecylamine-N-Oxide: Enthalpy and Entropy Driven Processes". J.Phys.Chem.B. 110 (27): 13649–13655. PMID 16821893. doi:10.1021/jp060934v.
- ↑ 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: 111–118. doi:10.1016/j.theochem.2006.12.043.