Low-molecular-weight contact allergens in p-tert-butylphenol-formaldehyde resin.
BACKGROUND
p-tert-Butylphenol-formaldehyde resin (PTBPFR) is a contact allergen that is included in most standard patch test series. This resin consists of a large number of substances most of which are unknown.


OBJECTIVE
The aim of this study was to investigate if allergens in PTBPFR are molecules mainly of low (MW < 250), medium, or high molecular weight (MW > 1,000); to isolate and identify some of the low molecular weight components of the resin; and for new substances to determine if these were allergens.


METHODS
Gel permeation chromatography, patch testing, high-pressure liquid chromatography, mass spectrometry, and nuclear magnetic resonance spectrometry were used.


RESULTS
Patch test reactions indicated allergens in low-, medium-, and high-molecular-weights fractions. The strongest patch test reactivity was seen to a medium molecular weight fraction constituting only 6% wt/wt of the resin for 4 of the patients. Two patients reacted positively to low molecular weight fractions, and one of these patients reacted only to these fractions. The following substances were isolated: 4-tert-butyl-[1,2]benzoquinone, 4-tert-butyl-2,6-bis-hydroxymethyl-phenol, 4-tert-butylbenzene-1,2-diol, 4-tert-butyl-2-hydroxymethyl-phenol, 5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzaldehyde, 4-tert-butyl-2-hydroxymethyl-6-methoxymethyl-phenol, and p-tert-butylphenol. Patients reacted positively to 5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzaldehyde and 4-tert-butyl-2-hydroxymethyl-6-methoxymethyl-phenol but not to 4-tert-butyl-[1,2]benzoquinone.


CONCLUSIONS
Two new allergens in PTBPFR were found: 5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzaldehyde and 4-tert-butyl-2-hydroxymethyl-6-methoxymethyl-phenol.
Zimerson
Erik
E
Department of Occupational and Environmental Dermatology, Malmö University Hospital, Malmö, Sweden.
Bruze
Magnus
M
D000485:Allergens / Q000009:adverse effects* / Q000737:chemistry; D016022:Case-Control Studies; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D017449:Dermatitis, Allergic Contact / Q000175:diagnosis / Q000209:etiology*; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D008970:Molecular Weight; D010328:Patch Tests; D012117:Resins, Synthetic / Q000009:adverse effects* / Q000737:chemistry*; D012680:Sensitivity and Specificity
D000485:Allergens; D012117:Resins, Synthetic; C014273:p-tert-butylphenolformaldehyde resin