Shogaol

Shogaol

Names
IUPAC name (E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one
Other names (6)-Shogaol
Identifiers
CAS Number	555-66-8 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL25948 N
ChemSpider	4445106 N
ECHA InfoCard	100.190.262
PubChem	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	276.38 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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. 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.

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.

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.

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

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