Allixin
From Wikipedia, the free encyclopedia
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| Preferred IUPAC name
3-Hydroxy-5-methoxy-6-methyl-2-pentyl-4H-pyran-4-one | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C12H18O4 | |
| Molar mass | 226.272 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Allixin is a phytoalexin found in garlic (Allium sativum) bulbs. It was first isolated and characterized in 1989.[1] When garlic is stored for long periods of time, it can form visible accumulations of crystalline allixin on its surface, particularly in areas where tissue has become necrotic.[2] After 2 years of storage, the amount of allixin accumulated can approach 1% of the dry weight of the cloves. Since allixin has weak antimicrobial activity,[1] these high concentrations are thought to be produced by the garlic bulb to protect itself from further damage from microorganisms.
Since allixin is found in high concentrations in garlic, there has been scientific interest in determining if it is responsible for any of the known health benefits of garlic. As a result of ongoing research, a variety of biological activities have been attributed to allixin. Pharmaceutical drug discovery research based on derivatives of allixin has followed.[3]
Two laboratory syntheses of allixin have been developed. In the first method, reported in 1997, allixin was synthesized in 22 steps starting from D-mannose.[4] A shorter synthesis was developed in 1998 which involved only 5 steps, starting from 5-methylfurfural.[5]
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