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(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-).
In the Vinony graph
Within Vinony's link graph, (E)-ajoene is referenced by 5 other articles, and connects out to Spanish, medicine and blood.
Vinony files it under Chembox image size set and Organic disulfides.
Its subject is documented across 14 Wikipedia language editions.
Chemical data
- Formula
- C9H14OS3
- Molecular weight
- 234.4 g/mol
- IUPAC name
- (E)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
- SMILES
- C=CCSS/C=C/CS(=O)CC=C
- InChIKey
- IXELFRRANAOWSF-FNORWQNLSA-N
- XLogP
- 1.7
- Polar surface area
- 86.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 234.021
Show 5 more facts
- Commons category
- Ajoene
- chemical formula
- C₉H₁₄OS₃
- canonical SMILES
- C=CCSSC=CCS(=O)CC=C
- isomeric SMILES
- C=CCSS/C=C/CS(=O)CC=C
- found in taxon
- Allium
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- History and syntheses
- Medicinal properties
- References
- External links
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.
Excerpted from Wikipedia’s “(E)-ajoene” article, available under the CC BY-SA 4.0 licence.