Contents

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
CAS Number	23513-13-5 Y 555-66-8 (non-specific) Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL25948 N
ChemSpider	4445106 N
PubChem CID	5281794
UNII	83DNB5FIRF N
InChI 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
SMILES CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Chemical compound

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.

Shogaols group[edit]

[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

Synthesis[edit]

A possible synthesis starts with a Claisen condensationofvanillin and acetone, producing dehydrozingerone. Afterwards the product reacts in an aldol condensation with hexanalintetrahydrofurane 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]

References[edit]