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SMB00311

Sigma-Aldrich

Shogaol

≥90% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C17H24O3
Numéro CAS:
555-66-8
Poids moléculaire :
276.37
Numéro Beilstein :
2056098
Numéro MDL:
MFCD01736094
Code UNSPSC :
12352205
ID de substance PubChem :
329824943
Nomenclature NACRES :
NA.25

Pureté

≥90% (HPLC)

Forme

liquid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

OQWKEEOHDMUXEO-BQYQJAHWSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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[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

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
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
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
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)
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
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