Lauryldimethylamine oxide: Difference between revisions

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|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=14 | H=31 | N=1 | O=1
| C=14 | H=31 | N=1 | O=1
| Appearance =
| Appearance = White solid
| Density =
| Density = 0.996 g/ml
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPtC = 132 - 133
| Solubility = }}
| Solubility =
| CMC = 1.70 mM<ref name=birnie>{{cite journal|last1=Birnie|first1=C. R.|last2=Malamud|first2=D.|last3=Schnaare|first3=R. L.|title=Antimicrobial Evaluation of N-Alkyl Betaines and N-Alkyl-N,N-Dimethylamine Oxides with Variations in Chain Length|journal=Antimicrobial Agents and Chemotherapy|date=1 September 2000|volume=44|issue=9|pages=2514–2517|doi=10.1128/AAC.44.9.2514-2517.2000}}</ref>}}<ref name="Hoffmann1990">{{cite journal|last1=Hoffmann|first1=H.|title=Correlation between surface and interfacial tensions with micellar structures and properties of surfactant solutions|volume=83|year=1990|pages=16–28|doi=10.1007/BFb0116238}}</ref>
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| ExternalSDS =<ref name="sigma">{{Sigma-Aldrich|id=40234|name=N,N-Dimethyldodecylamine N-oxide|accessdate=2017-01-04}}</ref>
| MainHazards =
| GHSSignalWord = Danger<ref name="sigma" />
| GHSPictograms ={{GHSp|GHS05}}<ref name="sigma" />
| HPhrases = {{H-phrases|314}}<ref name="sigma" />
| PPhrases = {{P-phrases|280|305+351+338|310}}<ref name="sigma" />
| FlashPt =
| FlashPt =
| AutoignitionPt = }}
| AutoignitionPt = }}
}}
}}


⚫
'''Lauryldimethylamine oxide''' (LDAO), also known as dodecyldimethylamine oxide (DDAO), is an [[amine oxide]] based [[zwitterionic]] [[surfactant]], with a C<sub>12</sub> (dodecyl) alkyl tail. It is one of the most frequently-used surfactants of this type.<ref>{{cite book | title = Detergency of Specialty Surfactants | first = Floyd E | last = Friedli | isbn = 0-8247-0491-6 | year = 2001 | publisher = Dekker | location = New York, NY }}</ref> Like other amine oxide based surfactants it is [[antimicrobial]], being against the common bacteria ''S. aureus'' and ''E. coli'',<ref name=birnie /> however it is also non-denaturing and may be used to solubilize proteins.
'''Lauryldimethylamine oxide''', also known as dodecyldimethylamine oxide or DDAO, (also
⚫
N,N-Dimethyldodecylamine N-oxide), is an [[amine oxide]] [[surfactant]]. It is one of the most frequently-used surfactants of this type.<ref>{{cite book | title = Detergency of Specialty Surfactants | first = Floyd E | last = Friedli | isbn = 0-8247-0491-6 | year = 2001 | publisher = Dekker | location = New York, NY }}</ref>


At high concentrations, DDAO forms [[liquid crystal]]line phases.<ref>{{cite journal | author = Kocherbitov, V., Söderman, O. | title = Hydration of Dimethyldodecylamine-N-Oxide: Enthalpy and Entropy Driven Processes| journal = J.Phys.Chem.B. | year = 2006| volume = 110 | pages = 13649–13655 | doi = 10.1021/jp060934v | pmid = 16821893 | issue = 27}}</ref> Despite having only one polar atom that is able to interact with water - the oxygen atom (the [[quaternary ammonium cation|quaternary]] nitrogen atom is hidden from intermolecular interactions), DDAO is a strongly hydrophilic surfactant: it forms normal [[micelle]]s 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.<ref>{{cite journal |author1=Kocherbitov, V. |author2=Veryazov, V. |author3=Söderman, O. | title = Hydration of Trimethylamine-N-oxide and of Dimethyldodecylamine-N-oxide: An Ab Initio study | journal = J. Molec. Struct.: Theochem. | year = 2007 | volume = 808 | pages = 111–118 | doi = 10.1016/j.theochem.2006.12.043}}</ref>
At high concentrations, DDAO forms [[liquid crystal]]line phases.<ref>{{cite journal | author = Kocherbitov, V., Söderman, O. | title = Hydration of Dimethyldodecylamine-N-Oxide: Enthalpy and Entropy Driven Processes| journal = J.Phys.Chem.B. | year = 2006| volume = 110 | pages = 13649–13655 | doi = 10.1021/jp060934v | pmid = 16821893 | issue = 27}}</ref> Despite having only one polar atom that is able to interact with water - the oxygen atom (the [[quaternary ammonium cation|quaternary]] nitrogen atom is hidden from intermolecular interactions), DDAO is a strongly hydrophilic surfactant: it forms normal [[micelle]]s 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.<ref>{{cite journal |author1=Kocherbitov, V. |author2=Veryazov, V. |author3=Söderman, O. | title = Hydration of Trimethylamine-N-oxide and of Dimethyldodecylamine-N-oxide: An Ab Initio study | journal = J. Molec. Struct.: Theochem. | year = 2007 | volume = 808 | pages = 111–118 | doi = 10.1016/j.theochem.2006.12.043}}</ref>


==See Also==
==See Also==
*[[Myristamine oxide]] - C16 analogue
*[[Myristamine oxide]] - An analogous compound with a C<sub>14</sub> tail


==References==
==References==

Revision as of 16:19, 4 January 2017

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 Edit this at Wikidata
EC Number
  • 216-700-6
  • 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
Boiling point 132–133 °C (270–271 °F; 405–406 K)
Surface tension:
1.70 mM[1]
Hazards
GHS labelling:
class="wikitable collapsible" style="min-width: 50em;"
GHS hazard pictograms[4]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

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| Danger[3]

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| H314[3]

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| P280, P305+P351+P338, P310[3]

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| Safety data sheet (SDS) | [3] |-





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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.[5] Like other amine oxide based surfactants it is antimicrobial, being against the common bacteria 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.[6] 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.[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.
  2. ^ Hoffmann, H. (1990). "Correlation between surface and interfacial tensions with micellar structures and properties of surfactant solutions". 83: 16–28. doi:10.1007/BFb0116238. {{cite journal}}: Cite journal requires |journal= (help)
  3. ^ a b c d e Sigma-Aldrich Co., N,N-Dimethyldodecylamine N-oxide. Retrieved on 2017-01-04.
  4. ^ "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).
  5. ^ Friedli, Floyd E (2001). Detergency of Specialty Surfactants. New York, NY: Dekker. ISBN 0-8247-0491-6.
  6. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ 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.
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