Benzoxonium chloride

A 37-year-old woman developed intense burning and pruritic eczema where she had applied a cream containing benzoxonium for seborrheic dermatitis for 5 months (3). The reaction disappeared on withdrawal of the cream. Patch tests were positive to benzoxonium chloride 0.1% aqueous on days 2 and 4. Patch tests with benzalkonium chloride and benzoxonium chloride in 20 controls were negative. 

Bruynzeel DP, de Groot AC, Weyland JW. Contact dermatitis to lauryl pyridinium chloride and benzoxonium chloride. Contact Dermatitis 1987 17(l) 41-2. 

Diaz-Ramon L, Aguirre A, Raton-Nieto JA, de Miguel M. Contact dermatitis from benzoxonium chloride. Contact Dermatitis 1999 41(l) 53-4. 

Benzoxonium chloride (D-301, ZY 15021, Absonal V, Bialcol, Bradophen, Orofar, CAS no. 19379-90-9). The patch-test concentration is 0.05% aqua. Allergic reactions are rare. 

Extension of the C-glycosylation reaction to the D-ribo series was at first disappointing. The sole product, obtained in high yield, from the reaction of 2,3,5-tri-0-benzoyl-/3-D-ribofuranosyl chloride (154), or the corresponding bromide (81), with diethyl sodiomalonate in 1,2-dimethoxyethane was the acetal 155, resulting102 from an attack on the dioxolenium carbon atom in the intermediate benzoxonium ion (156). 

Penta-0-benzoyl-/3-D-glucopyranose or, better, tetra-O-benzoyl-a-D-glucopyranosyl chloride in carbon tetrachloride can be converted at 75° with antimony pentachloride into a mixture of benzoxonium salts that contains 38% of the D-gluco, 25% of the D-manno, 10% of the D-altro, and 20% of the D-ido derivatives these results indicate... 

Treatment of methyl 2-0-benzoyl-3,4-0-benzylidene-P-D-arabinopyranoside with triphenylmethylium tetrafluoroborate in acetonitrile gave an equilibrium mixture of the benzoxonium ions (96) and (97), which reacted with chloride or iodide ions to give(98) and (99) in the ratio of 6 1 (X = Cl) or 1 2 (X = I), signifying differences in the reactivities of (96) and (97) towards different halide ions. The... 

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