|Jmol 3D model||Interactive image|
|Molar mass||276.38 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Shogaol, more accurately (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. Moreover, shogaol (and gingerol) are converted to other constituents when heat is applied over time, which is why ginger as its cooked loses its spicyness over time.
The name 'shogaol' is derived from the Japanese name for ginger (生姜、shōga).
Compound Scoville Heat Units
Capsaicin 15,000,000 (6)-Shogaol 160,000 Piperine 100,000 (6)-Gingerol 60,000
4-shogaol, 8-shogaol, 10-shogaol, and 12-shogal (all found in ginger) together comprise the group Shogaols. There also exist in ginger cultivars methylated shogaols: Methyl 6-shogaol and methyl 8-shogaol, respectively.
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.
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. Shogaol has been shown to induce apoptosis (kill) in human colorectal carcinoma cells via reactive oxygen species. It is broken down into 16 metabolites[which?] via the mercapturic acid pathway. Acetylcysteine was found to reduce effectiveness of shogaol's apoptotic properties.
Shogaol has one property the other ginger consituents, zingerone and gingerol have not been found to exhibit, namely memory and cognitive enhancing properties. Therefore, the exact method of preparation of ginger changes its biological effects.
- Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426.
- Ula (1996).
The HPLC measures the capsaicinoid(s) in ppm, which can then be converted to Scoville units using a conversion factor of 15, 20 or 30 depending on the capsaicinoid.Missing or empty
|title=(help)[full citation needed] This would make capsaicin 15,000,000 SHU.
- NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography[full citation needed]
- Suekawa, M; Ishige, A; Yuasa, K; Sudo, K; Aburada, M; Hosoya, E (1984). "Pharmacological studies on ginger. I. Pharmacological actions of pungent constitutents, (6)-gingerol and (6)-shogaol". Journal of pharmacobio-dynamics 7 (11): 836–48. PMID 6335723.
- Pan, Min-Hsiung; Hsieh, Min-Chi; Kuo, Jen-Min; Lai, Ching-Shu; Wu, Hou; Sang, Shengmin; Ho, Chi-Tang (2008). "6-Shogaol induces apoptosis in human colorectal carcinoma cellsviaROS production, caspase activation, and GADD 153 expression". Molecular Nutrition & Food Research 52 (5): 527. doi:10.1002/mnfr.200700157.
- Moon M, et al. 6-Shogaol, an active constituent of ginger, attenuates neuroinflammation and cognitive deficits in animal models of dementia. Biochemical and Biophysical Research Communications. June 2014; 449(1):8-13.