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Mechanism for 6-methylcoumarin Photoallergenicity

Mechanism for 6-methylcoumarin Photoallergenicity

S Kato, T Seki, Y Katsumura, T Kobayashi, K Komatsu, S Fukushima

Toxicol Appl Pharmacol. 1985 Nov;81(2):295-301.

PMID: 4060155

Abstract:

6-Methylcoumarin (6-MC), a synthetic fragrance material, has been reported to be photoallergenic both in man and in guinea pigs. To elucidate the possible mechanism of photoallergenicity, 6-MC in ethanolic solution was exposed to 200 joules/cm2 of long-wavelength ultraviolet (UV) ranging from 320 to 400 nm for 16 hr, and was examined for its contact allergenicity by means of a modified guinea pig maximization test. Strong allergic responses were observed, indicating that UV plays a catalytic role in forming contact allergens during irradiation. The solution was fractionated to isolate and purify contact sensitizers by gel-permeation chromatography and high-performance liquid chromatography. By employing mass spectrometry and proton and carbon-13 nuclear magnetic resonance, mono- and diethyl esters of 6-MC dimer were compounds identified which showed allergic reactions in guinea pigs sensitized with UV-irradiated 6-MC.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP92488	6-Methylcoumarin		92-48-8	Price

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