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SMB00311

Sigma-Aldrich

Shogaol

≥90% (HPLC)

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C17H24O3
Číslo CAS:
555-66-8
Molekulová hmotnost:
276.37
Beilstein/REAXYS Number:
2056098
MDL number:
MFCD01736094
UNSPSC Code:
12352205
PubChem Substance ID:
329824943
NACRES:
NA.25

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

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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Zákazníci si také prohlíželi

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1 of 8

[6]-Gingerol, Zingiber officinale An antitumor, apoptosis-inducing compound of the ginger family that blocks EGF-induced cell transformation by inhibiting the activation of Activator Protein-1 (AP-1).

Sigma-Aldrich

345868

[6]-Gingerol, Zingiber officinale

Zingerone analytical standard

Supelco

88787

Zingerone

6-Gingerol phyproof® Reference Substance

PHL89201

6-Gingerol

10-Shogaol phyproof® Reference Substance

PHL83911

10-Shogaol

USP

USP

1291504

Powdered ginger

Zerumbone ≥98% (HPLC)

Sigma-Aldrich

Z3902

Zerumbone

Sigma-Aldrich

Sigma-Aldrich

W252204

Ginger oil

(E)-Guggulsterone ≥95% (HPLC), powder

Sigma-Aldrich

G4923

(E)-Guggulsterone

Assessment of Toxicological Effect of Shogaol in Albino Mice
Hassan S M and Hassan A H
Pakistan Veterinary Journal, 38(4), 377-383 (2018)
Qinghe Han et al.
Oncotarget, 8(26), 42001-42006 (2017-04-15)
6-Shogaol, a pungent agent isolated from Zingiber officinale Roscoe, has been known to have anti-tumor and anti-inflammatory effects. However, the anti-inflammatory effects and biological mechanism of 6-Shogaol in LPS-activated BV2 microglia remains largely unknown. In this study, we evaluated the
6-Shogaol ameliorates injury to the intestinal mucosa and increases survival after high-dose abdominal irradiation
Wang J, et al.,
Journal of functional foods, 36, 63-71 (2017)
H-R Kim et al.
Journal of applied microbiology, 130(4), 1142-1153 (2020-09-28)
This study aimed to assess the antifungal and anti-biofilm effects of 6-shogaol against Candida auris using in vitro phenotypic and genotypic analyses. Our results showed that 6-shogaol exhibited antifungal as well as anti-biofilm activity by inhibiting biofilm formation and eradicating
Ali Ghasemzadeh et al.
Molecules (Basel, Switzerland), 23(7) (2018-07-07)
Gingerols and shogaols are compounds found in ginger (Zingiber officinale Roscoe); shogaols are found in lower concentration than gingerols but exhibit higher biological activities. This work studied the effects of different drying methods including open sun drying (OSD) solar tunnel
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