SMB00311

Shogaol

≥90% (HPLC)

• Synonym(s): [6]-Shogaol, (6)-Shogaol, 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one
• Empirical Formula (Hill Notation): C₁₇H₂₄O₃
• CAS Number: 555-66-8
• Molecular Weight: 276.37
• Beilstein: 2056098
• MDL number: MFCD01736094
• UNSPSC Code: 12352205
• PubChem Substance ID: 329824943
• NACRES: NA.25

Properties

• Quality Level: 200
• Assay: ≥90% (HPLC)
• form: liquid
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: CCCCC\C=C\C(=O)CCc1ccc(O)c(OC)c1
• 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+
• InChI key: OQWKEEOHDMUXEO-BQYQJAHWSA-N

Description

General description

Shogaol or 6-shogaol, the pungent metabolite of dried ginger, is one of the main bioactive compounds extracted from the natural dietary rhizome, Zingiber officinale Roscoe (ginger). It is the dehydrated successor of 6-gingerol with an α,β-unsaturated ketone skeleton.

Application

Shogaol has been used to determine its safe dose to evaluate potential toxicity in higher concentrations in mice models. It has also been used to investigate its antioxidant effects on the modulation of TRPC5 (ITRPC5) and TRPA1 (ITRPA1) currents.

Biochem/physiol Actions

Shogaols exhibits higher potency, efficacy, and biological activities than gingerols. It is an excellent antioxidant agent, that protects human primary epidermal melanocytes against oxidative stress by activating nuclear factor E2-related factor (Nrf2)-antioxidant response. Shogaol also displays antimicrobial, antifungal, and anti-biofilm activities against Candida albicans, and Candida auris. It exerts anti-inflammatory properties and protects against abdomen irradiation (ABI)-induced intestinal side effects. 6-shogaol also inhibits lipopolysaccharide (LPS)-induced inflammation via peroxisome proliferator-activated receptor gamma (PPAR-γ) activation.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable