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Stability of the mercaptobenzothiazole compounds

Hansson, Christer LU and Agrup, Gun LU (1993) In Contact Dermatitis 28(1). p.29-34
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
mercaptobenzothiazole, rubber, glutathione, cross-sensitivity, patch testing technique, mercapto mix, contact allergy
in
Contact Dermatitis
volume
28
issue
1
pages
29 - 34
publisher
Federation of European Neuroscience Societies and Blackwell Publishing Ltd
external identifiers
  • pmid:8428441
  • scopus:0027533346
ISSN
0105-1873
DOI
10.1111/j.1600-0536.1993.tb03320.x
language
English
LU publication?
yes
id
c987b4b7-ce3b-44b9-b2e1-5d094f8550b0 (old id 1107445)
date added to LUP
2008-07-31 09:12:52
date last changed
2017-07-30 03:55:18
@article{c987b4b7-ce3b-44b9-b2e1-5d094f8550b0,
  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.},
  author       = {Hansson, Christer and Agrup, Gun},
  issn         = {0105-1873},
  keyword      = {mercaptobenzothiazole,rubber,glutathione,cross-sensitivity,patch testing technique,mercapto mix,contact allergy},
  language     = {eng},
  number       = {1},
  pages        = {29--34},
  publisher    = {Federation of European Neuroscience Societies and Blackwell Publishing Ltd},
  series       = {Contact Dermatitis},
  title        = {Stability of the mercaptobenzothiazole compounds},
  url          = {http://dx.doi.org/10.1111/j.1600-0536.1993.tb03320.x},
  volume       = {28},
  year         = {1993},
}