title: Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions.
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.
authors.affiliation: Consiglio per la Ricerca e la Sperimentazione in Agricoltura, Centro di Ricerca per le Colture Industriali (CRA-CIN), Bologna, Italy.
authors.forename: Gina R
authors.initials: GR
authors.lastname: De Nicola
authors.forename: Sabine
authors.initials: S
authors.lastname: Montaut
authors.forename: Patrick
authors.initials: P
authors.lastname: Rollin
authors.forename: Maximilienne
authors.initials: M
authors.lastname: Nyegue
authors.forename: Chantal
authors.initials: C
authors.lastname: Menut
authors.forename: Renato
authors.initials: R
authors.lastname: Iori
authors.forename: Arnaud
authors.initials: A
authors.lastname: Tatibouët
mesh_terms: D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D017879:Isothiocyanates / Q000737:chemistry*; D059625:Liquid-Liquid Extraction; D013057:Spectrum Analysis
chemical_list: D017879:Isothiocyanates; C031403:benzyl isothiocyanate