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Merck

Activation and cross-reactivity pattern of a new allergen in adhesive plaster.

Contact dermatitis (2000-01-22)
O Bergendorff, C Hansson
RÉSUMÉ

N,N'-disalicylidene-1,2-diaminopropane is a copper inhibitor present in some adhesive plasters, rubber products and gasoline. Upon contact with water it is hydrolyzed to salicylaldehyde and 1,2-diaminopropane. All patients in this study showed positive patch-test reactions to N,N'-disalicylidene-1,2-diaminopropane, and also to 1,2-diaminopropane and ethylenediamine. None reacted to salicylaldehyde. Patch testing with different N,N'-disalicylidene-derivatives showed localization of the amino groups in positions 1 and 2 to be a prerequisite of cross-reactivity to 1,2-diaminopropane and ethylenediamine. An extraction procedure and a high-performance liquid chromatography (HPLC) method for the analysis of adhesive plasters is described. Studies of the hydrolysis of the copper inhibitor at physiological pH showed rapid formation of 1,2-diaminopropane under biomimetic conditions.

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Sigma-Aldrich
1,2-Diaminopropane, 99%
Sigma-Aldrich
N,N′-Bis(salicylidene)-1,3-propanediamine, 99%
Sigma-Aldrich
(S)-(−)-1,2-Diaminopropane dihydrochloride, 99%
Sigma-Aldrich
(R)-(+)-1,2-Diaminopropane dihydrochloride, 99%