23513-14-6

Basic information

• Product Name: 6-Gingerol
• Synonyms: 1-(4'-HYDROXY-3'-METHOXYPHENYL)-5-HYDROXY-3-DECANONE;5-HYDROXY-1-(4'-HYDROXY-3'-METHOXYPHENYL)-3-DECANONE;6-GINGEROL;[6]-GINGEROL, ZINGIBER OFFICINALE;(5s)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one;GINGEROL;GINGEROL [6];(S)-5-HYDROXY-1-(4-HYDROXY-3-METHOXY-PHENYL-3-DECANONE
• CAS NO: 23513-14-6
• Molecular Formula: C17H26O4
• Molecular Weight: 294.39
• EINECS: 607-241-6
• Product Categories: Aromatic Phenols;Natural Plant Extract;The group of Ginerols;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 23513-14-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 31℃
• Boiling Point: 453 °C at 760 mmHg
• Flash Point: 159 °C
• Appearance: light yellow oiliness
• Density: 1.083 g/cm³
• Vapor Pressure: 5.39E-09mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: ?20°C
• Solubility: methanol: soluble1mg/mL, clear, colorless
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 6-Gingerol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Gingerol(23513-14-6)
• EPA Substance Registry System: 6-Gingerol(23513-14-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: HE0757000
• Hazardous Substances Data: 23513-14-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow ceraceous solid

Uses

[6]-Gingerol has been used:to study its effects on transient receptor potential (TRP) channelsto study its effects on experimental models of non-alcoholic steatohepatitisto determine its effects on microsomal prostaglandine E2 synthase 1 (mPGES-1), glycogen synthase kinase 3β (GSK-3β) and β-catenin pathway in A549 cell lineto 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.

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

6-Gingerol 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).

InChI:InChI=1/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

Upstream product

• 127766-49-8 (R)-3-[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-5-((1E,3E)-penta-1,3-dienyl)-4,5-dihydro-isoxazole 
• 56024-44-3 methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 23513-14-6 (+/-)-[6]-gingerol 
• 39886-80-1 1-(4-benzyloxy-3-methoxyphenyl)-5-hydroxydecan-3-one 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 66-25-1 hexanal 
• 60101-00-0 2-Methoxy-1-trimethylsilanyloxy-4-(3-trimethylsilanyloxy-but-3-enyl)-benzene 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 107487-01-4 (5-Pentyl-4,5-dihydro-isoxazol-3-ylmethyl)-phosphonic acid diethyl ester 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 61871-72-5 (E)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-1-decen-3-one 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 
• 69172-20-9 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde 

Downstream Products

• 1360109-90-5 (4R,6S)-4-(4-(benzyloxy)-3-methoxyphenethyl)-2,2-dimethyl-6-pentyl-1,3-dioxane 
• 1360109-92-7 (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol 
• 1360109-93-8 (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diyl diacetate 
• 863780-90-9 (3R,5S)-1-(3,4-dimethoxyphenyl)decane-3,5-diyl diacetate 
• 39886-85-6 (3S,5S)-3,5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)decane 
• 154905-69-8 (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol 
• 53254-51-6 (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diyl diacetate 
• 555-66-8 [6]-shogaol 
• 39886-76-5 [6]-gingerol 
• 72749-01-0 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 
• 2380-78-1 homovanillyl alcohol 
• 61871-71-4 1-(4-hydroxy-3-methoxyphenyl)decane-3,5-dione 
• 39886-85-6 1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 

Relevant articles and documents

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

METHOD FOR PREPARING HIGHLY ENANTIO-ENRICHED GINGEROLS

Disclosed is a method for preparing a chiral Gingerol compound. To prepare the chiral Gingerol compound, a racemic Gingerol compound is treated with kinetic resolution in the presence of a chiral catalyst compound and an alkali metal fluoride so a chiral Gingerol compound with high optical purity can be prepared. An oligo ethylene glycol-derived compound including an oligo ethylene glycol functional group, a basic part, and a hydroxy functional group of a binol derivative, an acidic part, can be used as a chiral catalyst compound.COPYRIGHT KIPO 2020