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SMB00311

Sigma-Aldrich

Shogaol

≥90% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C17H24O3
CAS-Nummer:
555-66-8
Molekulargewicht:
276.37
Beilstein:
2056098
MDL-Nummer:
MFCD01736094
UNSPSC-Code:
12352205
PubChem Substanz-ID:
329824943
NACRES:
NA.25

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Qualitätsniveau

200

Assay

≥90% (HPLC)

Form

liquid

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

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+

InChIKey

OQWKEEOHDMUXEO-BQYQJAHWSA-N

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Allgemeine Beschreibung

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).[1] It is the dehydrated successor of 6-gingerol with an α,β-unsaturated ketone skeleton.[1]

Anwendung

Shogaol has been used to determine its safe dose to evaluate potential toxicity in higher concentrations in mice models.[2] It has also been used to investigate its antioxidant effects on the modulation of TRPC5 (ITRPC5) and TRPA1 (ITRPA1) currents.[3]

Biochem./physiol. Wirkung

Shogaols exhibits higher potency, efficacy, and biological activities than gingerols.[1] It is an excellent antioxidant agent[4], that protects human primary epidermal melanocytes against oxidative stress by activating nuclear factor E2-related factor (Nrf2)-antioxidant response.[5] Shogaol also displays antimicrobial[4], antifungal, and anti-biofilm activities against Candida albicans[6], and Candida auris.[7] It exerts anti-inflammatory properties and protects against abdomen irradiation (ABI)-induced intestinal side effects.[8] 6-shogaol also inhibits lipopolysaccharide (LPS)-induced inflammation via peroxisome proliferator-activated receptor gamma (PPAR-γ) activation.[9]

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000385098
0000301790
0000301790
0000385098
SLCN0160

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Kunden haben sich ebenfalls angesehen

Slide 1 of 8

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

Zingeron analytical standard

Supelco

88787

Zingeron

6-Gingerol phyproof® Reference Substance

PHL89201

6-Gingerol

10-Shogaol phyproof® Reference Substance

PHL83911

10-Shogaol

USP

USP

1291504

Pulverförmiger Ingwer

Zerumbone ≥98% (HPLC)

Sigma-Aldrich

Z3902

Zerumbone

Sigma-Aldrich

Sigma-Aldrich

W252204

Ginger oil

(E)-Guggulsteron ≥95% (HPLC), powder

Sigma-Aldrich

G4923

(E)-Guggulsteron

Lingli Yang et al.
International journal of molecular sciences, 21(10) (2020-05-21)
Skin is a major target of oxidative stress. Increasing evidence suggests that oxidative stress is the cause of melanocyte disappearance in vitiligo, which is an acquired pigmentary skin disorder characterized by patches of skin that have lost pigmentation. New herbal
Jin-Hyung Lee et al.
Frontiers in cellular and infection microbiology, 8, 299-299 (2018-09-14)
Candida albicans is an opportunistic pathogen and responsible for candidiasis. C. albicans readily forms biofilms on various biotic and abiotic surfaces, and these biofilms can cause local and systemic infections. C. albicans biofilms are more resistant than its free yeast
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
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)
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