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Shogaol

FieldValue
heatVery hot (chemical)
scoville160,000

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. 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.

The name shogaol is derived from the Japanese name for ginger (生姜、shōga).

Shogaol is rated 160,000 SHU on the Scoville scale. When compared to other pungent compounds, shogaol is moderately more pungent than piperine, but 100 times less than capsaicin.

CompoundScoville Heat Units
(SHU)
Capsaicinvauthors = Govindarajan, Sathyanarayanadate = 1991title = Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequencesjournal = Critical Reviews in Food Science and Nutritionvolume = 29issue = 6pages = 435–474doi = 10.1080/10408399109527536pmid = 2039598 }}
[6]-Shogaol160,000
Piperine100,000
[6]-Gingerol60,000

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.

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.

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.

References

References

  1. Harold McGee. (2004). "On Food and Cooking: The Science and Lore of the Kitchen". Scribner.
  2. (2016-10-31). "Electrochemical detection and quantification of gingerol species in ginger (Zingiber officinale) using multiwalled carbon nanotube modified electrodes". Analyst.
  3. (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition.
  4. (2015). "Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1". BioMed Research International.
  5. [[NSF International]] ''Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography'' {{full citation needed. (February 2015)
  6. Hung-Cheng Shih. (March 2014). "Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects.". [[International Journal of Molecular Sciences]].
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

pungent-flavors o-methylated-natural-phenols ginger
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