Shogaol

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Shogaol
Shogaol.png
Names
IUPAC name
(E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one
Other names
(6)-Shogaol
Identifiers
555-66-8 YesY
ChEMBL ChEMBL25948 N
ChemSpider 4445106 N
Jmol-3D images Image
PubChem 5281794
UNII 83DNB5FIRF N
Properties
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 verify (what isYesY/N?)
Infobox references
Shogaol
Heat (SR: 160,000)

Shogaol, also known as (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.[1]

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.[2]

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.

Compound Scoville Heat Units
(SHU)
Capsaicin 15,000,000[3]
(6)-Shogaol 160,000
Piperine 100,000
(6)-Gingerol 60,000

Pharmacology[edit]

Among ginger constituents, it has a very strong antitussive (anti-cough) effect.[medical citation needed]  Both shogaol and gingerols reduced blood pressure and gastric contraction.[4]  Shogaol has been shown to induce apoptosis (kill) in human colorectal carcinoma cells via reactive oxygen species.[5]  It is broken down into 16 metabolites via the mercapturic acid pathway.[4]  Acetylcysteine was found to reduce effectiveness of shogaol's apoptotic properties.[5]

References[edit]

  1. ^ Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426. 
  2. ^ NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography[full citation needed]
  3. ^ Ula (1996). The HPLC measures the capsaicinoid(s) in ppm, which can then be converted to Scoville units using a conversion factor of 15, 20 or 30 depending on the capsaicinoid.  Missing or empty |title= (help)[full citation needed] This would make capsaicin 15,000,000 SHU.
  4. ^ a b Suekawa, M; Ishige, A; Yuasa, K; Sudo, K; Aburada, M; Hosoya, E (1984). "Pharmacological studies on ginger. I. Pharmacological actions of pungent constitutents, (6)-gingerol and (6)-shogaol". Journal of pharmacobio-dynamics 7 (11): 836–48. PMID 6335723. 
  5. ^ a b Pan, Min-Hsiung; Hsieh, Min-Chi; Kuo, Jen-Min; Lai, Ching-Shu; Wu, Hou; Sang, Shengmin; Ho, Chi-Tang (2008). "6-Shogaol induces apoptosis in human colorectal carcinoma cellsviaROS production, caspase activation, and GADD 153 expression". Molecular Nutrition & Food Research 52 (5): 527. doi:10.1002/mnfr.200700157.