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
• MDL number: MFCD00210507
• UNSPSC Code: 12352205
• PubChem Substance ID: 329799719
• NACRES: NA.25

Properties

• 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

Description

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.

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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves