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Molecules 2017, 22(5), 770; doi:10.3390/molecules22050770

An Optimized Facile Procedure to Synthesize and Purify Allicin

1
Department of Plant Physiology, RWTH Aachen University, D-52056 Aachen, Germany
2
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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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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