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6-Gingerol

CAS No.23513-14-6
Chemical Name:6-Gingerol
CBNumber:CB4328683
Molecular Formula:C17H26O4
Formula Weight:294.39
MOL File:23513-14-6.mol

6-Gingerol Property

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
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)
FDA UNII 925QK2Z900
NIST Chemistry Reference Gingerol(23513-14-6)
UNSPSC Code 85151701
NACRES NA.77

Safety

Hazard Codes :Xn
Risk Statements :22-36/37/38
Safety Statements :26-36/37
RIDADR :UN 2811 6.1 / PGIII
WGK Germany :3
RTECS :HE0757000
HS Code :29145090

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

6-Gingerol Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: G1046
Product name : [6]-Gingerol
Purity: ≥98% (HPLC)
Packaging: 5MG
Price: ₹25741.85
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: G1046
Product name : [6]-Gingerol
Purity: ≥98% (HPLC)
Packaging: 10MG
Price: ₹47770.73
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 50866
Product name : [6]-Gingerol
Purity: analytical standard
Packaging: 10MG
Price: ₹45529.95
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 345868
Product name : [6]-Gingerol, Zingiber officinale - CAS 23513-14-6 - Calbiochem
Purity: An antitumor, apoptosis-inducing compound of the ginger family that blocks EGF-induced cell transformation by inhibiting the activation of Activator P
Packaging: 5MG
Price: ₹20510
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: G0413
Product name : [6]-Gingerol
Purity:
Packaging: 20MG
Price: ₹33400
Updated: 2022/05/26
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6-Gingerol Chemical Properties,Usage,Production

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:Gingerol is 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. It has a role as an antineoplastic agent and a plant metabolite. It is a beta-hydroxy ketone and a member of guaiacols.
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.
Mechanism of action 6-Gingerol suppressed UVB-induced translocation of NF-κB from cytosol to nucleus via prevention of IκBα phosphorylation and COX-2 expression and transactivation in HaCaT cells in vitro. [6]-Gingerol suppressed COX-2 expression at mRNA and protein levels and translocation of NF-κB in UVB-irradiated skin of hairless mice. It suppressed TPA-induced COX-2 gene expression in the skin of mice by inhibiting the p38 MAP kinase-NF-κB signalling pathway. These findings suggest the chemopreventive effect of 6-Gingerol on UVB-induced skin disorders, including cancer. Jeong et al. found that 6-Gingerol inhibited the growth of colon cancer by inhibiting LTA4 hydrolase. 6-Gingerol suppressed PGE2 levels in IL-1β-stimulated human oral keratinocytes. Overall, these studies demonstrated that [6]-gingerol exerts anti-cancer and cancer-preventive activities by targeting the AA pathway.
Anticancer Research 6-Gingerol is a plant polyphenol and an active constituent of Zingiber officinale, which shows antioxidant, anti-inflammation, and antitumor properties. It has been reported to possess anti-cancer and chemopreventive potentials against several cancers, including skin, colorectal, gastrointestinal and pancreatic. It can inhibit NOS, TNF-α, and COX-2 enzymes, which are regulated by NF-κB. It hinders the cell growth of prostate, gastric, and breast cancer cells and suppresses the lung metastasis of B16F10 melanoma. It exhibits an antitumorigenic effect in human colorectal cancer cells via upregulating NSAID-activated gene-1 (NAG-1). Italters ERK1/2/JNK/AP1 pathway and induces apoptosis in colon cancer cells in acaspase-dependent manner. ROS levels were significantly increased in K562 and MOLT4 cells treated with gingerol, and apoptosis was induced in leukaemia cells by the mitochondrial pathway.