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Article Dans Une Revue Journal of Agricultural and Food Chemistry Année : 2013

Stability of Benzylic-Type Isothiocyanates in HydrodistillationMimicking Conditions

Résumé

Pentadiplandra brazzeana Baillon (Pentadiplandraceae) is known to contain benzyl-, 3-methoxybenzyl-, 4methoxybenzyl-, 3,4-dimethoxybenzyl-, and indole-type glucosinolates, and the essential oil obtained from its roots is mainly constituted of benzyl isothiocyanate and benzyl cyanide. In a previous study by the authors, it was surmised that partial hydrolytic degradation of 4-methoxybenzyl isothiocyanate, one major expected compound, occurred during the hydrodistillation process of essential oil preparation. To probe this hypothesis, a selection of diversely substituted benzylic-type isothiocyanates was submitted to standard hydrodistillation-mimicking conditions. After extraction with dichloromethane, the reaction mixtures were analyzed using GC-MS. The aqueous phases resulting from liquid−liquid extraction were analyzed by HPLC and GC-MS. 2Methoxybenzyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, and 3,4,5-trimethoxybenzyl isothiocyanates underwent conversion into 2-methoxybenzyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, and 3,4,5-trimethoxybenzyl alcohols, respectively, whereas benzyl, 3methoxybenzyl, and 4-chlorobenzyl isothiocyanates were converted into the corresponding benzylamines.
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Dates et versions

hal-00840999 , version 1 (03-07-2013)

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Citer

Gina R. de Nicola, Sabine Montaut, Patrick Rollin, Maximilienne Nyegue, Renato Iori, et al.. Stability of Benzylic-Type Isothiocyanates in HydrodistillationMimicking Conditions. Journal of Agricultural and Food Chemistry, 2013, 61, pp.137-142. ⟨10.1021/jf30415341⟩. ⟨hal-00840999⟩
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