[6]-Shogaol

• CAT Number: R056625
• CAS Number: 555-66-8
• Molecular Formula: C17H24O3
• Molecular Weight: 276.37
• Purity: ≥95%
• Synonyms: 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one; Shogaol
• Target: Autophagy
• Storage: -20°C
• IUPAC Name: (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
• 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+
• InChIKey: OQWKEEOHDMUXEO-BQYQJAHWSA-N
• SMILES: CCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC

Shogaol, also known as (6)-shogaol(R056625), is a pungent constituent of ginger similar in chemical structure to gingerol. Like zingerone, it is produced when ginger is dried or cooked. 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 (kill) 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.