Cetylalkonium chloride

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Structural formula
Structural formula of 16-BAC
General
Surname Cetylalkonium chloride
other names
  • 16-BAC
  • Benzylhexadecyldimethylammonium chloride
  • Cetalkonium Chloride ( INN )
  • Cetyldimethylbenzylammonium chloride
Molecular formula C 25 H 46 ClN
External identifiers / databases
CAS number 122-18-9
EC number 204-526-3
ECHA InfoCard 100.004.116
PubChem 31202
Wikidata Q18345315
properties
Molar mass 396.09 g mol −1
Physical state

firmly

Melting point

55-65 ° C

safety instructions
GHS labeling of hazardous substances
05 - Corrosive 07 - Warning 09 - Dangerous for the environment

danger

H and P phrases H: 302-312-314-400
P: 273-280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cetylalkonium chloride (synonymous 16-benzyldimethylhexadecylammonium chloride , 16-BAC) is a cationic surfactant that was patented by IG Farben in 1934 .

properties

Cetylalkonium chloride is used in biochemistry in the course of BAC-PAGE for the separation of strongly positively charged proteins and glycosylated membrane proteins and for 2D gel electrophoresis of membrane proteins, including the separation of mitochondrial membrane proteins.

In ophthalmology , cetylalkonium chloride is used to provide emulsions with positive charges, which causes the micelles to repel one another.

As a quaternary ammonium compound, cetylalkonium chloride has antibacterial properties. The effective antibacterial concentration is between 0.01 and 0.1% (m / V).

In the USA and Great Britain, among other things, it is used in mouthwashes . It has been listed as an OTC drug ingredient in the US since 2010 . In Great Britain, cetylalkonium chloride has been on the "Consolidated list of substances which are present in authorized medicines for general sale" since 2012 , with a maximum concentration of 0.1% (m / V) on the skin or oral mucosa.

synthesis

To synthesize cetyalkonium chloride, hexadecylamine is first stirred with benzyl chloride in a mass ratio of 185 to 126.5 for 8 hours at 100.degree. After cooling, the crystalline product is reacted with methyl chloride.

Individual evidence

  1. ↑ a b c Datasheet Benzyldimethylhexadecylammonium chloride from Sigma-Aldrich , accessed on December 27, 2015 ( PDF ).
  2. ↑ a b Entry on cetalkonium chloride in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  3. ↑ Entry on cetalkonium chloride. In: Römpp Online . Georg Thieme Verlag, accessed on December 27, 2015.
  4. ↑ DE Macfarlane: Use of benzyldimethyl-n-hexadecylammonium chloride ("16-BAC"), a cationic detergent, in an acidic polyacrylamide gel electrophoresis system to detect base labile protein methylation in intact cells. In: Analytical biochemistry. Volume 132, Number 2, July 1983, pp. 231-235, PMID 6625164 .
  5. ↑ Joachim Hartinger, Katinka Stenius, Dagmar Högemann, Reinhard Jahn : 16-BAC / SDS-PAGE: a two-dimensional gel electrophoresis system suitable for the separation of integral membrane proteins. In: Analytical Biochemistry. Vol. 240, No. 1, 1996, pp. 126-133, PMID 8811889 , doi : 10.1006 / abio.1996.0339 .
  6. ^ RP Zahedi, J. Moebius, A. Sickmann: Two-dimensional BAC / SDS-PAGE for membrane proteomics. In: Sub-cellular biochemistry. Volume 43, 2007, pp. 13-20, PMID 17953388 .
  7. ↑ RJ Brown, N. Kinkl, M. Beer, M. Ueffing: Two-dimensional electrophoresis of membrane proteins. In: Analytical and bioanalytical chemistry. Volume 389, Number 4, October 2007, pp. 1033-1045, doi : 10.1007 / s00216-007-1514-6 , PMID 17680235 .
  8. ↑ HG Nothwang, J. Schindler: Two-dimensional separation of membrane proteins by 16-BAC-SDS-PAGE. In: Methods in molecular biology (Clifton, NJ). Volume 528, 2009, pp. 269-277, doi : 10.1007 / 978-1-60327-310-7_19 , PMID 19153699 .
  9. ↑ B. Wenge, H. Bönisch, J. Grabitzki, G. Lochnit, B. Schmitz, MH Ahrend: Separation of membrane proteins by two-dimensional electrophoresis using cationic rehydrated strips. In: Electrophoresis. Volume 29, Number 7, April 2008, pp. 1511-1517, doi : 10.1002 / elps.200700546 , PMID 18318447 .
  10. ↑ RJ Brown, N. Kinkl, H. Zischka, M. Ueffing: 16-BAC / SDS-PAGE analysis of membrane proteins of yeast mitochondria purified by free flow electrophoresis. In: Methods in molecular biology (Clifton, NJ). Volume 528, 2009, pp. 83-107, doi : 10.1007 / 978-1-60327-310-7_6 , PMID 19153686 .
  11. ↑ F. Lallemand, P. Daull, S. Benita, R. Buggage, JS Garrigue: Successfully improving ocular drug delivery using the cationic nanoemulsion, novasorb. In: Journal of drug delivery. Volume 2012, 2012, p. 604204, doi : 10.1155 / 2012/604204 , PMID 22506123 , PMC 3313063 (free full text).
  12. ↑ P. Daull, F. Lallemand, JS Garrigue: Benefits of cetalkonium chloride cationic oil-in-water nanoemulsions for topical ophthalmic drug delivery. In: The Journal of pharmacy and pharmacology. Volume 66, number 4, April 2014, pp. 531-541, doi : 10.1111 / jphp.12075 , PMID 24001405 , PMC 4283994 (free full text).
  13. ^ JJ Harrison, RJ Turner, DA Joo, MA Stan, CS Chan, ND Allan, HA Vrionis, ME Olson, H. Ceri: Copper and quaternary ammonium cations exert synergistic bactericidal and antibiofilm activity against Pseudomonas aeruginosa. In: Antimicrobial agents and chemotherapy. Volume 52, number 8, August 2008, pp. 2870-2881, doi : 10.1128 / AAC.00203-08 , PMID 18519726 , PMC 2493123 (free full text).
  14. ↑ FDA: OTC Active Ingredients . Retrieved December 27, 2015.
  15. ↑ MHRA . Retrieved December 27, 2015.
  16. ^ William Andrew Publishing: Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier, 2013, ISBN 978-0-815-51856-3 , p. 932.