Quaternary Ammonium Salts as Germicides. I. Non-acylated Quaternary Ammonium Salts Derived from Aliphatic Amines¹

Abstract

Non-acylated Quaternary Ammonium Salts from Aliphatic Amines 753 XIII did not readily add bromine. The methyl alcoholic filtrate of this experiment yielded 18.5% of IV when diluted with water, melting point and mixed melting point with a sample of this compound described in another experiment, 57°. This product also turned pink upon exposure to light.Acknowledgment.-We wish to express our appreciation to Mrs. M. S. Sherman for carrying out the recorded microanalyses. Summary The molecular rearrangement of fluorylidene dimethyl sulfide to fluorene-1 -dimethyl sulfide was effected in an alkaline medium. By graded oxidation the rearrangement product was converted into fluorene-1 -dimethyl sulfone, fluorenone-1-dimethyl sulfone and fluorenone-1-carboxylic acid. The above-named acid and its ethyl ester were characterized by comparison with authentic specimens. The -SCH3 group of fluorene-1 -dimethy 1 sulfide was substituted by -OCH3, -Br, -OH and -H. Fluorene-1methyl bromide in an alcoholic solution of sodium methylate yielded sym.-difluorene-1,1 '-ethylene and fluorene-1 -dimethyl oxide.

Effectiveness of Disinfectants in Killing Enterobacter sakazakii in Suspension, Dried on the Surface of Stainless Steel, and in a Biofilm

“…Benzalkonium chloride is known to have different bactericidal activities depending on the length of its hydrophobic chain (24). The general order of antibacterial activity, which depends on the length of the alkyl chain, has been reported to be C 14 Ͼ C 16 Ͼ C 12 Ն C 18 Ͼ C 10 Ͼ C 8 (24,29,46). Merianos (35) reported that C 12 , C 14 , and C 16 homologues are most effective in inactivating yeasts and molds, gram-positive bacteria, and gram-negative bacteria, respectively.…”

The Mode of Action of N-(n-Dodecyl)diethanolamine with Particular Reference to the Effect of Protonation on Uptake by Escherichia coli

“…As in other homologous series such as the n-alkylamines (Fuller, 1942;Cummings et al, 1g53), and the alkyltrimethylammonium bromides (Shelton et al, 1946), the more potent homologues bear more than six but fewer than 18 carbon atoms in the alkyl chain, maximum potency within the series being displayed by those members bearing between 12 and 16 carbon atoms.…”

Synthesis, Spectroscopic and Semiempirical Studies of New Quaternary Alkylammonium Conjugates of Sterols

“…Then the appropriate amine (0.24 mmol) was added and the mixture heated under reflux for 2 h. The precipitate formed was filtered off and crystallized from CH 3 CN-EtOH (90:1), to give white solids. 930, 2,868, 1,740, 1,623, 1,489, 1,467, 1,404, 1,371, 1,227, 1,205, 1,138, 1,014 957, 2,852, 1,743, 1,635, 1,467, 1,371, 1,247, 1,205, 1 956, 2,934, 2,868, 1,741, 1,671, 1,488, 1,467, 1,378, 1,228, 1,211, 1,014 ( 928, 2,851, 1,740, 1,488, 1,468, 1,405, 1,378, 1,228, 1,209, 1,001 (17): white solid (92%), m.p. 210-212 °C.…”

“…Some of them are used as antiseptics and preservation agents [15]. It is proved that the derivatives which contain from 8 to 14 carbon atoms in the alkyl chain group show the greatest biocidal activity [16][17][18]. The mechanism of biocidal activity of quaternary alkylammonium salts is based on adsorption of the alkylammonium cation on the bacterial cell surface, diffusion through the cell wall and then binding and disruption of the cytoplasmatic membrane.…”

“…This work reports the synthesis and physicochemical properties of new quaternary alkylammonium conjugates of ergosteryl 3β-bromoacetate (4), cholesteryl 3β-bromoacetate (5) and dihydrocholesteryl 3β-bromoacetate (6) with N,N-dimethyl-N-octylamine (7,11,15), N,N-dimethyl-N-decylamine (8,12,16), N,N-dimethyl-N-dodecylamine (9,13,17), N,N-dimethyl-N-tetradecylamine (10, 14, 18) in acetonitrile. The potential pharmacological activities of the synthesized compounds have been studied using a computer-aided drug discovery approach with the in silico Prediction of Activity Spectra for Substances (PASSs) program.…”