Shogaol

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[6]-Shogaol
Names
Preferred IUPAC name
(4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
Other names
  • [6]-Shogaol
  • (E)-[6]-Shogaol
  • Enexasogaol
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ ☒N
    Key: OQWKEEOHDMUXEO-BQYQJAHWSA-N ☒N
  • InChI=1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
    Key: OQWKEEOHDMUXEO-BQYQJAHWBO
  • CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
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
HeatVery hot (chemical)
Scoville scale160,000[1] SHU

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.

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 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]

[8]-shogaol
[10]-shogaol

Synthesis

A possible synthesis starts with a

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]

Possible synthesis of [6]-shogaol starting from vanillin

References

  1. ^
    S2CID 40241982
    .
  2. ^ Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426.
  3. PMID 2039598
    .
  4. ^ "Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1". Retrieved 3 December 2016.
  5. ^ NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography [full citation needed]
  6. PMID 24599082
    .
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