Stability of the mercaptobenzothiazole compounds

Research output: Contribution to journalArticle

Abstract

An analytical quantitative high-pressure liquid chromatography (HPLC) method was developed for simultaneous determination of all mercaptobenzothiazole derivatives in the mercapto mix patch testing standard. The stability of the mercaptobenzothiazoles constituting the mercapto mix was studied both in petrolatum and in buffer solution at pH 6.5, with and without glutathione. In petrolatum vehicle, dibenzothiazyl disulfide was the dominant compound found in stored mercapto mix. In buffer solution at pH 6.5, 2-mercaptobenzothiazole and the sulfenamide derivatives morpholinyl mercaptobenzothiazole and N-cyclohexyl-2-benzothiazyl sulfenamide were converted into dibenzothiazyl disulfide. In the presence of glutathione, both the sulfenamide derivatives and the dibenzothiazyl disulfide were rapidly converted into 2-mercaptobenzothiazole. The findings explain the "cross-sensitivities" reported for the mercaptobenzothiazole group as a result of chemical reactions resulting in one main hapten. The use of a single substance for patch testing for mercaptobenzothiazole hypersensitivity is proposed.

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Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Dermatology and Venereal Diseases

Keywords

  • mercaptobenzothiazole, rubber, glutathione, cross-sensitivity, patch testing technique, mercapto mix, contact allergy
Original languageEnglish
Pages (from-to)29-34
JournalContact Dermatitis
Volume28
Issue number1
Publication statusPublished - 1993
Publication categoryResearch
Peer-reviewedYes