Shogaol

[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
  1. ^ a b Compton, Richard G.; Batchelor-McAuley, Christopher; Ngamchuea, Kamonwad; Chaisiwamongkhol, Korbua (2016-10-31). "Electrochemical detection and quantification of gingerol species in ginger (Zingiber officinale) using multiwalled carbon nanotube modified electrodes". Analyst. 141 (22): 6321–6328. Bibcode:2016Ana...141.6321C. doi:10.1039/C6AN02254E. ISSN 1364-5528. PMID 27774555. 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. ^ Govindarajan, Sathyanarayana (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. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID 2039598.