5708-85-0Relevant articles and documents
Conversion of a cyclic α,β-unsaturated ketone into a tertiary dienyl hydroperoxide: Application to the first hemisynthesis of 15-hydroperoxyabietic acid
Haberkorn,Mutterer,Giménez Arnau,Lepoittevin
, p. 1723 - 1726 (2001)
The first hemisynthesis of 15-hydroperoxyabietic acid, a major contact allergen among the oxidation products of colophony, is reported. The key step includes a new approach to easily obtain a dienyl tertiary hydroperoxide from a cyclic α,β-unsaturated ketone. The procedure is based on the formation of a bromodiene using a Vilsmeier's reagent, followed by a halogen/metal exchange and alkylation with acetone, to afford the dienyl alcohol precursor of the hydroperoxide.
Investigation of the Allergenic Principles from Colophony: Autoxidation, Synthesis, and Sensitization
Krohn, Karsten,Budianto, Emil,Floerke, Ulrich,Hausen, Bjoern M.
, p. 911 - 920 (2007/10/02)
The autoxidation of abietic acid (1a), levopimaric acid (2a), and dehydroabietic acid (3a) was studied and the compounds 3a as well as (after esterification) 8b, 9b, 10b, 11b (from 1a); 6b (from 2a); and 4b, 5b (from 3a) were isolated for the first time.Some derivatives (6a, 6b, 13b/14b, and 7b) were semi-synthezised.The isolated autoxidation products, the synthetic compounds and some polar fractions of natural colophony were tested for their sensitizing capacity.Compounds 4a, 10b, 16, and 18 as well as the combined polar fraction A-D of colophony show enhanced sensitizing capacity.Methylation of the acids to the ester significantly reduces their activity.Key Words: Resin acids, autoxidation of / Colophony, allergy of / Sensitizing potency