Synthesis of eugenol derivative by the ring opening of epoxide eugenol and its analysis through chemical reactivity: a DFT approach

• Published in: Natural product research Vol. 38; no. 7; pp. 1099 - 1107
• Main Authors: Abdou, Achraf, Maaghloud, Fatima Ezzahra, Elmakssoudi, Abdelhakim, Aboulmouhajir, Aziz, Jamal Eddine, Jamal, Dakir, Mohamed
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 02-04-2024; Taylor & Francis Ltd
• Subjects: Aluminum; Aluminum Chloride; Chemical reactions; chemical reactivity and thermochemistry; Chlorides; Density functional theory; DFT; Essential oils; Ethanol - analysis; Eugenol; Eugenol - analysis; Gas chromatography; Gas Chromatography-Mass Spectrometry; Herbal medicine; Mass spectrometry; Mass spectroscopy; Medicinal plants; Natural product; Oils, Volatile - chemistry; Reactivity; Ring opening; Synthesis; Syzygium - chemistry; Natural product; eugenol; DFT; chemical reactivity and thermochemistry
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2022.2132242

Eugenol, a plant bioactive component, is frequently found in a variety of medicinal plants with well-defined functional attributes. Essential oils containing eugenol were extracted from buds of Eugenia caryophyllata commonly named clove using hydrodistillation. Afterwards, the analysis of the essential oils using gas chromatography/mass spectrometry (GC/MS) shows that eugenol is the major constituent with 70.14% of it. The alkene group in eugenol was epoxidised using m-chloroperbenzoic acid leading to the synthesis of epoxide eugenol. The epoxide ring was cleaved to vanillyl glycol by mixed the epoxide eugenol with aluminum chloride hydrate in an ethanolic medium. A Density Functional Theory (DFT) study was investigated to understand the reactivity of the epoxide eugenol with the aluminum chloride hydrate. The results obtained from DFT based reactivity descriptors were in good agreement with the experiment results.