G1046

[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: 23513-14-6
• Molecular Weight: 294.39
• NACRES: NA.25
• PubChem Substance ID: 329799719
• UNSPSC Code: 12352205
• MDL number: MFCD00210507

Properties

• Quality Segment: 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

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves