Pentadiplandra brazzeana Baillon (Pentadiplandraceae) is known to contain benzyl-, 3-methoxybenzyl-, 4-methoxybenzyl-, 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. 2-Methoxybenzyl, 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, 3-methoxybenzyl, and 4-chlorobenzyl isothiocyanates were converted into the corresponding benzylamines. © 2012 American Chemical Society.
De Nicola, G.R., Montaut, S., Rollin, P., Nyegue, M., Menut, C., Iori, R., et al. (2013). Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 61(1), 137-142 [10.1021/jf3041534].
Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions
De Nicola, Gina R.;
2013
Abstract
Pentadiplandra brazzeana Baillon (Pentadiplandraceae) is known to contain benzyl-, 3-methoxybenzyl-, 4-methoxybenzyl-, 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. 2-Methoxybenzyl, 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, 3-methoxybenzyl, and 4-chlorobenzyl isothiocyanates were converted into the corresponding benzylamines. © 2012 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
