[6]-Shogaol

• CAT Number: R056625
• CAS Number: 555-66-8
• Molecular Formula: C17H24O3
• Molecular Weight: 276.4
• Purity: ≥95%
• Synonyms: 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one; Shogaol
• Target: Autophagy
• Storage: -20°C
• InChIKey: OQWKEEOHDMUXEO-BQYQJAHWSA-N

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. 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.

Reference

1:Glucuronidation and its impact on the bioactivity of [6]-shogaol. Wang P, Zhao Y, Zhu Y, Sang S.Mol Nutr Food Res. 2017 May 14. doi: 10.1002/mnfr.201700023. [Epub ahead of print] PMID: 28503853 2:6-Shogaol attenuates LPS-induced inflammation in BV2 microglia cells by activating PPAR-γ. Han Q, Yuan Q, Meng X, Huo J, Bao Y, Xie G.Oncotarget. 2017 Mar 30. doi: 10.18632/oncotarget.16719. [Epub ahead of print] PMID: 28410218 Free Article3:Sortilin-related receptor 1 interacts with amyloid precursor protein and is activated by 6-shogaol, leading to inhibition of the amyloidogenic pathway. Na JY, Song K, Lee JW, Kim S, Kwon J.Biochem Biophys Res Commun. 2017 Mar 18;484(4):890-895. doi: 10.1016/j.bbrc.2017.02.029. Epub 2017 Feb 8. PMID: 28188785 4:6-Paradol and 6-Shogaol, the Pungent Compounds of Ginger, Promote Glucose Utilization in Adipocytes and Myotubes, and 6-Paradol Reduces Blood Glucose in High-Fat Diet-Fed Mice. Wei CK, Tsai YH, Korinek M, Hung PH, El-Shazly M, Cheng YB, Wu YC, Hsieh TJ, Chang FR.Int J Mol Sci. 2017 Jan 17;18(1). pii: E168. doi: 10.3390/ijms18010168. PMID: 28106738 Free PMC Article5:[6]-gingerol and [6]-shogaol, active ingredients of the traditional Japanese medicine hangeshashinto, relief oral ulcerative mucositis-induced pain via action on Na+ channels. Hitomi S, Ono K, Terawaki K, Matsumoto C, Mizuno K, Yamaguchi K, Imai R, Omiya Y, Hattori T, Kase Y, Inenaga K.Pharmacol Res. 2017 Mar;117:288-302. doi: 10.1016/j.phrs.2016.12.026. Epub 2016 Dec 30. PMID: 28043879 6:Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3β and β-catenin pathway in A549 cell line. Eren D, Betul YM.Chem Biol Interact. 2016 Oct 25;258:257-65. doi: 10.1016/j.cbi.2016.09.012. Epub 2016 Sep 16. PMID: 27645308 7:6-Shogaol, an active compound of ginger, alleviates allergic dermatitis-like skin lesions via cytokine inhibition by activating the Nrf2 pathway. Park G, Oh DS, Lee MG, Lee CE, Kim YU.Toxicol Appl Pharmacol. 2016 Nov 1;310:51-59. doi: 10.1016/j.taap.2016.08.019. Epub 2016 Aug 22. PMID: 27562088 8:Efficient dehydration of 6-gingerol to 6-shogaol catalyzed by an acidic ionic liquid under ultrasound irradiation. Kou X, Li X, Rahman MR, Yan M, Huang H, Wang H, Su Y.Food Chem. 2017 Jan 15;215:193-9. doi: 10.1016/j.foodchem.2016.07.106. Epub 2016 Jul 19. PMID: 27542467 9:The ginger component 6-shogaol prevents TNF-α-induced barrier loss via inhibition of PI3K/Akt and NF-κB signaling. Luettig J, Rosenthal R, Lee IM, Krug SM, Schulzke JD.Mol Nutr Food Res. 2016 Dec;60(12):2576-2586. doi: 10.1002/mnfr.201600274. Epub 2016 Sep 16. PMID: 27487982 10:[6]-Shogaol, a dietary phenolic compound, induces oxidative stress mediated mitochondrial dependant apoptosis through activation of proapoptotic factors in Hep-2 cells. Annamalai G, Kathiresan S, Kannappan N.Biomed Pharmacother. 2016 Aug;82:226-36. doi: 10.1016/j.biopha.2016.04.044. Epub 2016 May 13. PMID: 27470359