Ajoene

Ajoene

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Identifiers
CAS Number	92285-01-3 Y
ChEMBL	ChEMBL122890 Y
ChemSpider	4533332 Y
Jmol 3D model	Interactive image
PubChem	5386591
InChI InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+ Y Key: IXELFRRANAOWSF-FNORWQNLSA-N Y InChI=1/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+ Key: IXELFRRANAOWSF-FNORWQNLBE
SMILES O=S(C/C=C/SSC/C=C)C\C=C
Properties
Chemical formula	C9H14OS3
Molar mass	234.4 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ajoene /ˈɑːhoʊ.iːn/ is an organosulfur compound found in garlic (Allium sativum). 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 isomers, which differ in terms of the stereochemistry of central alkene (E- vs Z-) and the chirality of the sulfoxide.

History and biosynthesis

It was first isolated in 1983 by Rafael Apitz-Castro and Mahendra K. Jain (patent US4665088 [1][2]) Its basic organic chemistry has been extensively investigated.

Ajoene is formed from a chemical reaction involving two allicin molecules. The release of allicin occurs when a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil).

Allicin, the biosynthetic precursor to ajoene.

Medicinal properties

Ajoene has medicinal uses. It functions as an antioxidant by inhibiting the release of superoxide. Ajoene also has antithrombotic (anti-clotting) properties, which helps prevent platelets in the blood from forming blood clots, potentially reducing the risk of heart disease and stroke in humans. Ajoene has shown potential virucidal properties against a number of viruses including vesicular stomatitis, vaccinia, human rhinovirus parainfluenza, and herpes simplex. In the infected cell system of a human immunodeficiency virus (HIV), it is shown to block the integrin-dependent processes. Ajoene has broad-spectrum antimicrobial (antibacterial and antifungal) properties, Ajoene has been investigated as an anti-leukemia agent for acute myeloid leukemia therapy. Ajoene has been found to decrease basal-cell carcinoma tumor size by inducing apoptosis while it has also been shown effective in inhibiting tumor cell growth by targeting the microtubule cytoskeleton of such cells and by other mechanisms. Ajoene inhibits genes controlled by quorum sensing.