(E)-ajoene
Sign in to saveAjoene is an organosulfur compound found in garlic (Allium sativum) extracts. It is a colorless liquid that contains sulfoxide and disulfide functional groups. The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four stereoisomers, which differ in terms of the stereochemistry of the central alkene (E- vs Z-) and the chirality of the sulfoxide sulfur (R- vs S-).
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4 sectionsContents
- History and syntheses
- Medicinal properties
- References
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Ajoene is an organosulfur compound found in garlic (Allium sativum) extracts. It is a colorless liquid that contains sulfoxide and disulfide functional groups. The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four stereoisomers, which differ in terms of the stereochemistry of the central alkene (E- vs Z-) and the chirality of the sulfoxide sulfur (R- vs S-).
==History and syntheses== The structure of ajoene was determined and it was synthesized based on biosynthetic considerations in 1984, correcting an incorrect structure published in 1983. A short, scalable total synthesis of ajoene was reported in 2018 by Wirth and coworkers while a biosynthetically modeled synthesis of trifluoroajoene from difluoroallicin was published in 2017. Syntheses of various ajoene analogues have also been reported. The chemistry of ajoene has been extensively investigated.