G1046

Sigma-Aldrich

[6]-Gingerol

≥98% (HPLC)

Synonym(s):
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-, 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone, 6-Gingerol
Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
Molecular Weight:
294.39
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98% (HPLC)

storage condition

protect from light
under inert gas

solubility

methanol: 1 mg/mL, clear, colorless

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC[C@H](O)CC(=O)CCc1ccc(O)c(OC)c1

InChI

1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1

InChI key

NLDDIKRKFXEWBK-AWEZNQCLSA-N

Looking for similar products? Visit Product Comparison Guide

General description

[6]-Gingerol is implicated in apoptosis, cell cycle regulation, cytotoxic activity and inhibition of angiogenesis. It prevents serotonin release and platelet aggregation. Gingerol has immunomodulatory, antiapoptotic, antihyperglycemic, antilipidemic and antiemetic properties.

Application

[6]-Gingerol has been used:
  • to study its effects on transient receptor potential (TRP) channels
  • to study its effects on experimental models of non-alcoholic steatohepatitis
  • to determine its effects on microsomal prostaglandine E2 synthase 1 (mPGES-1), glycogen synthase kinase 3β (GSK-3β) and β-catenin pathway in A549 cell line
  • to analyse the effects of 6-Shogaol (6-SG) on diabetic nephropathy (DN) in db/db mice

Biochem/physiol Actions

Bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. [6]-Gingerol down regulates proinflammatory cytokine release by macrophages. It has been shown to inhibit COX-2 expression by blocking the activation of p38 MAP kinase and NF-κB in phorbol ester-stimulated mouse skin.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G1046.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Poovvathingal Haris et al.
International journal of biological macromolecules, 113, 124-131 (2018-02-20)
6-Gingerol [5-hydroxy-1-(4-hydroxy-3-methoxyphenyl) decan-3-one], the bio-active ingredient of the popular Indian spice ginger (Zingiber officinale Roscoe), is well-known for its pharmacological and physiological actions. The potent antioxidant, antiemetic, antiulcer, antimicrobial, analgesic, hypoglycemic, antihypertensive, antihyperlipidemic, immunostimulant, anti-inflammatory, cardiotonic, and cancer prevention activities...
Effects of ginger and its pungent constituents on transient receptor potential channels
Kim YS, et al.
International Journal of Molecular Medicine, 38(6), 1905-1914 (2016)
Khairunnisa' Md Yusof et al.
Molecules (Basel, Switzerland), 20(6), 10280-10297 (2015-06-06)
Numerous bioactive compounds have cytotoxic properties towards cancer cells. However, most studies have used single compounds when bioactives may target different pathways and exert greater cytotoxic effects when used in combination. Therefore, the objective of this study was to determine...
Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3beta and beta-catenin pathway in A549 cell line
Eren D and Betul YM
Chemico-Biological Interactions, 258, 257-265 (2016)
Effect of Herbal Supplement-Drug Interactions on Therapeutic Drug Monitoring
Chin AC and Baskin LB
Therapeutic Drug Monitoring, 417-445 (2012)
Articles
Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.
Read More

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