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SMB00311

Shogaol

≥90% (HPLC)

Synonym(s):

[6]-Shogaol, (6)-Shogaol, 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one

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About This Item

Empirical Formula (Hill Notation):
C17H24O3
CAS Number:
555-66-8
Molecular Weight:
276.37
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
329824943
MDL number:
MFCD01736094
Beilstein/REAXYS Number:
2056098
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Quality Segment

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Codes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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