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G1046 Sigma-Aldrich

[6]-Gingerol

≥98% (HPLC)

Synonym: 3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-, 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone, 6-Gingerol

  • CAS Number 23513-14-6

  • Empirical Formula (Hill Notation) C17H26O4

  • Molecular Weight 294.39

  •  MDL number MFCD00210507

  •  PubChem Substance ID 329799719

  •  NACRES NA.25

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Properties

Related Categories Antioxidant, Cell Biology, Functional Foods, Nutrition Research, Oils and Resin-derived,
Quality Level   200
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
HE0757000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

NF-κB and Inflammation

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. Oxidative cellular ...
BioFiles 2007, 2.4, 14.
Keywords: Acetylations, Adhesion, Angiogenesis, Apoptosis, Cancer, Carcinogens, Catalysis, Cell culture, Cell proliferation, Cell signaling, Cellular processes, Degradations, Diabetes, Diseases, Environmental, Gene expression, Glycosylations, High performance liquid chromatography, Inflammation, PAGE, Phosphorylations, Thin layer chromatography, Transcription, transformation

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Peer-Reviewed Papers
15

References

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