Lauryldimethylamine oxide

Lauryldimethylamine oxide
Names
	IUPAC name N,N-Dimethyldodecan-1-amine oxide
	Other names Lauramine oxide; Dodecyldimethylamine oxide; Dimethyldodecylamine-N-oxide
Identifiers
CAS Number	1643-20-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	14688 ;
ECHA InfoCard	100.015.183
EC Number	216-700-6;
PubChem CID	15433;
UNII	4F6FC4MI8W ;
CompTox Dashboard (EPA)	DTXSID1020514 ;
	InChI InChI=1S/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3 Key: SYELZBGXAIXKHU-UHFFFAOYSA-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;
	SMILES CCCCCCCCCCCC[N+](C)(C)[O-];
Properties
Chemical formula	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:
CMC	1.70 mM[1][2]
Hazards
Safety data sheet	[3]
GHS pictograms	[3]
GHS Signal word	Danger[3]
GHS hazard statements	H314[3]
GHS precautionary statements	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).
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	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, 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 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]

References

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.
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. 83. pp. 16–28. doi:10.1007/BFb0116238. ISBN 978-3-7985-0840-8.
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 978-0-8247-0491-9.
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. PMID 16821893.CS1 maint: multiple names: authors list (link)
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.

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[birnie-1] 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.

[Hoffmann1990-2] 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. 83. pp. 16–28. doi:10.1007/BFb0116238. ISBN 978-3-7985-0840-8.

[sigma-3] 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. PMID 16821893.CS1 maint: multiple names: authors list (link)

[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.

Lauryldimethylamine oxide

See also

References