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

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

Uses

Used in Pharmaceutical Industry:
6-Gingerol is used as a pharmaceutical agent for its anti-inflammatory, anti-tumor, and antioxidant properties, which can contribute to the treatment of cancer.
Used in Research:
6-Gingerol is used as a research compound to study its effects on various biological processes and conditions, such as:
1. Studying its effects on transient receptor potential (TRP) channels.
2. Investigating its effects on experimental models of non-alcoholic steatohepatitis.
3. Determining its effects on microsomal prostaglandin E2 synthase 1 (mPGES-1), glycogen synthase kinase 3β (GSK-3β), and β-catenin pathway in A549 cell line.
4. Analyzing 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.

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

• 39886-80-1 1-(4-benzyloxy-3-methoxyphenyl)-5-hydroxydecan-3-one 
• 127766-49-8 (R)-3-[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-5-((1E,3E)-penta-1,3-dienyl)-4,5-dihydro-isoxazole 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 92511-73-4 (S)-5-Pentyl-3-((R)-toluene-4-sulfinylmethyl)-4,5-dihydro-isoxazole 
• 146830-56-0 (-)(2S)-1,2-Epoxy-7-<(tert-butyldiphenylsilyl)oxy>heptane 
• 146830-55-9 (+)<(S)R,2S>-1-(p-Tolylsulfinyl)-7-<(tert-butyldiphenylsilyl)oxy>-2-heptanol 
• 1186501-32-5 (S,E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-1-en-3-one 
• 91815-20-2 4-{2-[2-(2-Hydroxy-heptyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1080-12-2 Dehydrozingerone 
• 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 

Downstream Products

• 23513-13-5 [6]-shogaol 
• 36700-42-2 <6>-diacetylgingerol 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 555-66-8 [6]-shogaol 
• 39886-76-5 [6]-gingerol 
• 72749-01-0 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 
• 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 
• 1360109-90-5 (4R,6S)-4-(4-(benzyloxy)-3-methoxyphenethyl)-2,2-dimethyl-6-pentyl-1,3-dioxane 

Relevant articles and documents

GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM

The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.

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.

6-gingerol derivative and its preparation and application

A 6-gingerol derivative and its preparation and application are provided. That derivative has the following structure. The derivative of the present invention has antitumor activity and inhibit effect on tumor cells. In addition, the chemical properties o

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

Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols

A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents

Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.

An Efficient Enantioselective Synthesis of Natural Gingerols, the Active Principles of Ginger

A straightforward synthesis of (S)-gingerols 1-3 has been described. The requisite stereogenic center in the target molecules was introduced by Sharpless asymmetric dihydroxylation using a chiral complex, AD-mix β. This route is simple and efficient to prepare the products in very good yields.

Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds

[6]-Gingerol and [6]-shogaol are the major pungent components in ginger with a variety of biological activities including antioxidant activity. To explore their structure determinants for antioxidant activity, we synthesized eight compounds differentiated by their side chains which are characteristic of the C1-C2 double bond, the C4-C5 double bond or the 5-OH, and the six- or twelve-carbon unbranched alkyl chain. Our results show that their antioxidant activity depends significantly on the side chain structure, the reaction mediums and substrates. Noticeably, existence of the 5-OH decreases their formal hydrogen-transfer and electron-donating abilities, but increases their DNA damage- and lipid peroxidation-protecting abilities. Additionally, despite significantly reducing their DNA strand breakage-inhibiting activity, extension of the chain length from six to twelve carbons enhances their anti-haemolysis activity.