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Molecules 2017, 22(5), 770;

An Optimized Facile Procedure to Synthesize and Purify Allicin

Department of Plant Physiology, RWTH Aachen University, D-52056 Aachen, Germany
Division of Bioorganic Chemistry, School of Pharmacy, Campus B2 1, University of Saarland, D-66123 Saarbruecken, Saarland, Germany
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Academic Editors: Thomas J. Schmidt and Derek J. McPhee
Received: 1 March 2017 / Revised: 28 April 2017 / Accepted: 5 May 2017 / Published: 10 May 2017
(This article belongs to the Special Issue The Chemistry of Alliums)
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Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by H2O2 using acetic acid as a catalyst was published in 2001 by Lawson and Wang. Here we report on improvements to this basic method, clarify the mechanism of the reaction and show that it is zero-order with respect to DADS and first-order with respect to the concentration of H2O2. The progress of allicin synthesis and the reaction mechanism were analyzsd by high-performance liquid chromatography (HPLC) and the identity and purity of the products was verified with LC-MS and 1H-NMR. We were able to obtain allicin of high purity (>98%) and >91% yield, with standard equipment available in any reasonable biological laboratory. This protocol will enable researchers to prepare and work with easily and cheaply prepared allicin of high quality. View Full-Text
Keywords: allicin; Allium sativum; diallyl-disulfide; catalytic oxidation; reactive sulfur species; dipropyl-disulfide; thiosulfinate allicin; Allium sativum; diallyl-disulfide; catalytic oxidation; reactive sulfur species; dipropyl-disulfide; thiosulfinate

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Albrecht, F.; Leontiev, R.; Jacob, C.; Slusarenko, A.J. An Optimized Facile Procedure to Synthesize and Purify Allicin. Molecules 2017, 22, 770.

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