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Sigma-Aldrich® [6]-Gingerol≥98% (HPLC)

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Empirical Formula (Hill Notation):  C17H26O4

CAS Number:  23513-14-6

Molecular Weight:  294.39

MDL number:  MFCD00210507

UNSPSC Code:  12352205

PubChem Substance ID:  329799719

NACRES:  NA.25

Quality Level:  200

Assay:  ≥98% (HPLC)

storage condition:

protect from light

under inert gas


solubility:   methanol: 1 mg/mL, clear, colorless

application(s):

metabolomics

vitamins, nutraceuticals, and natural products

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

General description

[6]-Gingerol is implicated in apoptosis, cell cycle regulation, cytotoxic activity and inhibition of angiogenesis.[1] It prevents serotonin release and platelet aggregation.[2] Gingerol has immunomodulatory, antiapoptotic, antihyperglycemic, antilipidemic and antiemetic properties.[2]

Application

[6]-Gingerol has been used:


  • to study its effects on transient receptor potential (TRP) channels[3]
  • to study its effects on experimental models of non-alcoholic steatohepatitis[4]
  • 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[5]
  • to analyse the effects of 6-Shogaol (6-SG) on diabetic nephropathy (DN) in db/db mice[6]

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.