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| Names | |
|---|---|
| Preferred IUPAC name (4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one | |
Other names
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| Properties | |
| C17H24O3 | |
| Molar mass | 276.376 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
| Shogaol | |
|---|---|
| Heat | Very hot (chemical) |
| Scoville scale | 160,000[1] SHU |
Shogaols arepungent constituents ofginger similar in chemical structure togingerol. The most common of the group is[6]-shogaol. Likezingerone, it is produced when ginger is dried or cooked.[2] Moreover, shogaol (andgingerol) are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.
The nameshogaol is derived from theJapanese name for ginger (生姜、shōga).
Shogaol is rated 160,000 SHU on theScoville scale.[1] When compared to other pungent compounds, shogaol is moderately more pungent thanpiperine, but less thancapsaicin.
| Compound | Scoville Heat Units (SHU) |
|---|---|
| Capsaicin | 16,000,000[3] |
| [6]-Shogaol | 160,000 |
| Piperine | 100,000 |
| [6]-Gingerol | 60,000 |
[4]-Shogaol, [8]-shogaol, [10]-shogaol, and [12]-shogaol (all found in ginger) together constitute the groupshogaols. There also exist in ginger cultivars methylated shogaols: methyl [6]-shogaol and methyl [8]-shogaol, respectively.[4]
Shogaols are artifacts formed during storage or through excess heat, probably created by adehydration reaction of the gingerols. The ratio of shogaols to gingerols sometimes is taken as an indication of product quality.[5]
A possible synthesis starts with aClaisen condensation ofvanillin andacetone, producing dehydrozingerone. Afterwards the product reacts in analdol condensation withhexanal intetrahydrofurane to 6-dehydroshogaol and 6-dehydrogingerol. Latter can behydrogenated to [6]-gingerol by a catalyst. In the last stephydrochloric acid is added to get the desired [6]-shogaol.[6]
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