Shogaol
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| Names | |
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| IUPAC name
(E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one
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| Other names
(6)-Shogaol
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| Identifiers | |
555-66-8  |
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| ChEMBL | ChEMBL25948  |
| ChemSpider | 4445106 |
| Jmol 3D model | Interactive image |
| PubChem | 5281794 |
| UNII | 83DNB5FIRF |
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| Properties | |
| C17H24O3 | |
| Molar mass | 276.38 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
| Shogaol | |
|---|---|
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| Heat | (SR: 160,000) |
Shogaol, also known as (6)-shogaol, is a pungent constituent of ginger similar in chemical structure to gingerol. Like zingerone, it is produced when ginger is dried or cooked.[1]
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.[2]
The name 'shogaol' is derived from the Japanese name for ginger (生姜、shōga).
Shogaol is rated 160,000 SHU on Scoville scale. When compared to other pungent compounds, shogaol is moderately more pungent than piperine, but less than capsaicin.
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Compound Scoville Heat Units
(SHU)Capsaicin 15,000,000[3] (6)-Shogaol 160,000 Piperine 100,000 (6)-Gingerol 60,000
Pharmacology
Among ginger constituents, it has a very strong antitussive (anti-cough) effect.[medical citation needed] Both shogaol and gingerols reduced blood pressure and gastric contraction.[4] Shogaol has been shown to induce apoptosis (kill) in human colorectal carcinoma cells via reactive oxygen species.[5] It is broken down into 16 metabolites via the mercapturic acid pathway.[4] Acetylcysteine was found to reduce effectiveness of shogaol's apoptotic properties.[5]
References
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- ↑ NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography[full citation needed]
- ↑ Lua error in package.lua at line 80: module 'strict' not found.[full citation needed] This would make capsaicin 15,000,000 SHU.
- ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
