Shogaol

Shogaol
Names
IUPAC name
(E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one
Other names
(6)-Shogaol
Identifiers
555-66-8 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL25948 N
ChemSpider 4445106 N
ECHA InfoCard 100.190.262
PubChem 5281794
UNII 83DNB5FIRF N
Properties
C17H24O3
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).
N verify (what is YesYN ?)
Infobox references
Shogaol
Heat (SR: 160,000)

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.[1] 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).

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.

Compound Scoville Heat Units
(SHU)
Capsaicin 15,000,000[2]
(6)-Shogaol 160,000
Piperine 100,000
(6)-Gingerol 60,000

Shogaols group

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.[3]

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.[4]

Pharmacology

Among ginger constituents, it has a very strong antitussive (anti-cough) effect. Both shogaol and gingerols reduced blood pressure and gastric contraction.[5] Shogaol has been shown to induce apoptosis in human colorectal carcinoma cells via reactive oxygen species.[6] It is broken down into 16 metabolites via the mercapturic acid pathway.[5] Acetylcysteine was found to reduce effectiveness of shogaol's apoptotic properties.[6]

Shogaol has one property the other ginger constituents, zingerone and gingerol have not been found to exhibit, namely memory and cognitive enhancing properties.[7] Therefore, the exact method of preparation of ginger changes its biological effects.

References

  1. ↑ Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426.
  2. ↑ 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) This would make capsaicin 15,000,000 SHU.
  3. ↑ "Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1". Retrieved 3 December 2016.
  4. ↑ NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography
  5. 1 2 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.
  6. 1 2 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.
  7. ↑ 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.
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