| Identification | More | [Name]
6-Gingerol | [CAS]
23513-14-6 | [Synonyms]
1-(4'-HYDROXY-3'-METHOXYPHENYL)-5-HYDROXY-3-DECANONE
5-HYDROXY-1-(4'-HYDROXY-3'-METHOXYPHENYL)-3-DECANONE
(5s)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one
6-GINGEROL
[6]-GINGEROL, ZINGIBER OFFICINALE
GINGEROL
GINGEROL [6]
(S)-5-HYDROXY-1-(4-HYDROXY-3-METHOXY-PHENYL-3-DECANONE
(s)-(+)-(6)gingerol
(s)-(+)-3-decanon
(s)-(6)-gingerol
(s)-3-decanon
Gingerols
6-Gingerol std.
6-GINGEROL, 98% HPLC
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)
rac-(R*)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
(S)-8-Oxo-10-(3-methoxy-4-hydroxyphenyl)decane-6-ol | [EINECS(EC#)]
607-241-6 | [Molecular Formula]
C17H26O4 | [MDL Number]
MFCD00210507 | [Molecular Weight]
294.39 | [MOL File]
23513-14-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
31℃ | [Boiling point ]
453.0±35.0 °C(Predicted) | [density ]
1.083±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
methanol: soluble1mg/mL, clear, colorless | [form ]
Pale yellow oil | [pka]
10.02±0.20(Predicted) | [color ]
White to Light yellow | [Detection Methods]
NMR,HPLC | [InChI]
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 | [InChIKey]
NLDDIKRKFXEWBK-AWEZNQCLSA-N | [SMILES]
C(C1=CC=C(O)C(OC)=C1)CC(=O)C[C@@H](O)CCCCC | [LogP]
2.485 (est) | [CAS DataBase Reference]
23513-14-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Gingerol(23513-14-6) |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow ceraceous solid | [Uses]
[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
| [Definition]
ChEBI: A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger. | [General Description]
[6]-Gingerol is a naturally occurring plant phenoland an active pungent constituent found in the rhizome of ginger, which is known to possess anti-inflammatory, anti-tumor and antioxidant properties and can hence, serve as a potential candidate in the treatment of cancer. | [Biological Activity]
6-Gingerol is the major pharmacologically-active component of ginger. It is known to exhibit a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. 6-Gingerol has been found to possess anticancer activities via its effect on a variety of biological pathways involved in apoptosis, cell cycle regulation, cytotoxic activity, and inhibition of angiogenesis.
| [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. | [Anticancer Research]
It is a plant polyphenol and an active constituent of Zingiber officinale, whichshowed antioxidant, anti-inflammation, and antitumor properties. It has the capacityto inhibit NOS, TNF-α, and COX-2 enzymes which are regulated by NF-κB(Aggarwal and Shishodia 2004; Wang et al. 2012). It hinders the cell growth ofprostate, gastric, and breast cancer cells and suppresses the lung metastasis ofB16F10 melanoma. It exhibits antitumorigenic effect in human colorectal cancercells via upregulating NSAID-activated gene-1 (NAG-1) (Aggarwal et al. 2008). Italters ERK1/2/JNK/AP1 pathway and induces apoptosis in colon cancer cells in acaspase-dependent manner (Singh et al. 2016b). ROS levels were significantlyincreased in K562 and MOLT4 cells treated with gingerol, and apoptosis wasinduced in leukemia cells by mitochondrial pathway (Wang et al. 2012). |
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