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Spectroscopic studies of cutaneous photo sensitizing agents 6. identification of the free radicals generated during the photolysis of musk ambrette musk xylene and musk ketone



Spectroscopic studies of cutaneous photo sensitizing agents 6. identification of the free radicals generated during the photolysis of musk ambrette musk xylene and musk ketone



Photochemistry and Photobiology 38(6): 671-678



Musk ambrette (4-tert-butyl-3-methoxy-2,5-dinitrotoluene), a common component of perfumes, soaps and some food flavorings, can cause cutaneous photosensitization reactions including photoallergy [in humans]. These may be mediated through free radicals formed during photolysis. When musk ambrette was photolyzed under N in basic methanol, 2 distinct nitro anion radicals were identified by ESR. One radical was centered on a nitro group in the plane of the aromatic ring while the other was centered on a nitro group twisted out of the plane of the ring due to steric hindrance by bulky substituents on either side of the group; the 2 radicals appeared to interconvert and maintain an equilibrium concentration ratio. Two closely related compounds which are also used in perfumes, but have not been reported to cause photosensitizing reactions, also produced free radicals during photolysis. Musk xylene (2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene) generated 2 nitro anion radicals, both of which were centered on twisted nitro groups, while musk ketone (3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone) produced only 1 nitro anion radical, which is also twisted. Although these nitro anion radicals are probably the 1st step in the photolysis of these nitroaromatic molecules, it seems likely that in vivo they will undergo further reduction to produce more reactive species including the corresponding nitroso and hydroxylamine derivatives. Autoxidation of the nitro anion radical intermediate forms superoxide.

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