Related Experiment Video
Updated: Sep 27, 2026

Extraction of Ramie Fiber in Alkali Hydrogen Peroxide System Supported by Controlled-release Alkali Source
Published on: February 6, 2018
Mechanism of simmondsin decomposition during sodium hydroxide treatment
M Van Boven1, M Laga, S Leonard
1Laboratory of Toxicology and Food Chemistry, Katholieke Universiteit Leuven, Van Evenstraat 4, Belgium. maurits.vanboven@pharm.kuleuven.ac.be
Abstract:
Jojoba seed meal shows appetite-suppressing activity due to the presence of simmondsin. This pharmacological activity disappears with treatment of the meal with sodium hydroxide. To elucidate this mechanism of inactivation, the reaction of simmondsin in 1 N NaOH at 20 degrees C was monitored as a function of time. The end products of the reaction as well as intermediates were isolated and identified. The half-life of simmondsin was approximately 60 min with d-glucose and 2-hydroxy-3-methoxyphenylacetonitrile as reaction end products. The reaction mechanism could be elucidated by the isolation of isosimmondsin and a simmondsin lactone derivative. Those compounds were isolated and purified by a combination of column chromatography and HPLC and identified mainly by HRMS and NMR spectroscopy.
Related Concept Videos
Synthesis and Decomposition Reactions
Esters to Carboxylic Acids: Saponification
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
Acids, Bases and Neutralization Reactions
Acids, Bases and Neutralization Reactions
Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

