Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

SMB00311

Sigma-Aldrich

Shogaol

≥90% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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

Looking for similar products? Visit Product Comparison Guide

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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SMB00311-VAR:
SMB00311-BULK:
SMB00311-50MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
Assessment of Toxicological Effect of Shogaol in Albino Mice
Hassan S M and Hassan A H
Pakistan Veterinary Journal, 38(4), 377-383 (2018)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service