Shogaol
Chemical compound
From Wikipedia, the free encyclopedia
Shogaols are pungent constituents of ginger similar in chemical structure to gingerol. The most common of the group is [6]-shogaol. Like zingerone, it is produced when ginger is dried or cooked.[2] Moreover, shogaol (and gingerol) are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.
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| 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 their standard state (at 25 °C [77 °F], 100 kPa).
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| Shogaol | |
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| Heat | Very hot (chemical) |
| Scoville scale | 160,000[1] SHU |
The name shogaol is derived from the Japanese name for ginger (生姜、shōga).
Shogaol is rated 160,000 SHU on the Scoville scale.[1] When compared to other pungent compounds, shogaol is moderately more pungent than piperine, but 100 times less than capsaicin.
| Compound | Scoville Heat Units (SHU) |
|---|---|
| Capsaicin | 16,000,000[3] |
| [6]-Shogaol | 160,000 |
| Piperine | 100,000 |
| [6]-Gingerol | 60,000 |
Shogaols group
[4]-Shogaol, [8]-shogaol, [10]-shogaol, and [12]-shogaol (all found in ginger) together constitute the group shogaols. 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 a dehydration reaction of the gingerols. The ratio of shogaols to gingerols sometimes is taken as an indication of product quality.[5]
Synthesis
A possible synthesis starts with a Claisen condensation of vanillin and acetone, producing dehydrozingerone. Afterwards the product reacts in an aldol condensation with hexanal in tetrahydrofurane to 6-dehydroshogaol and 6-dehydrogingerol. Latter can be hydrogenated to [6]-gingerol by a catalyst. In the last step hydrochloric acid is added to get the desired [6]-shogaol.[6]
