39886-76-5

Basic information

• Product Name: 6-GINGEROL,(+/-)
• Synonyms: rac-[6]-Gingerol
• CAS NO: 39886-76-5
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.388
• Product Categories: Aromatics, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 39886-76-5.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 453.0±35.0 °C(Predicted)
• Appearance: /
• Density: 1.083±0.06 g/cm3(Predicted)
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 6-GINGEROL,(+/-)(CAS DataBase Reference)
• NIST Chemistry Reference: 6-GINGEROL,(+/-)(39886-76-5)
• EPA Substance Registry System: 6-GINGEROL,(+/-)(39886-76-5)

Safety Data

• Hazardous Substances Data: 39886-76-5(Hazardous Substances Data)

Usage

Description

6-GINGEROL,(+/-), also known as rac-[6]-Gingerol, is the racemic mixture of [6]-Gingerol, which is the active constituent of fresh ginger, and its enantiomer. It possesses antihepatotoxic effects and can suppress spontaneous Ca2+ spikes and isometric contraction.

Uses

Used in Pharmaceutical Industry:
6-GINGEROL,(+/-) is used as a pharmaceutical agent for its antihepatotoxic effects, helping to protect the liver from damage and toxicity.
Used in Muscle Relaxation:
6-GINGEROL,(+/-) is used as a muscle relaxant for its ability to suppress spontaneous Ca2+ spikes and isometric contraction, providing relief from muscle tension and cramps.
Used in Nutraceutical Industry:
6-GINGEROL,(+/-) can be used as a nutraceutical ingredient for its potential health benefits, such as its anti-inflammatory and antioxidant properties, which may contribute to overall well-being and support a healthy immune system.

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 
• 69172-20-9 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde 
• 39886-80-1 1-(4-benzyloxy-3-methoxyphenyl)-5-hydroxydecan-3-one 
• 4547-43-7 methyl 6-hydroxycaproate 
• 1186501-32-5 (S,E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-1-en-3-one 
• 1360109-86-9 (S)-1-(4-(benzyloxy)-3-methoxyphenyl)-5-(tert-butyldimethylsilyloxy)dec-1-yn-3-one 
• 1360109-85-8 C₃₀H₄₄O₄Si 
• 1360109-87-0 (5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 
• 23513-14-6 (+/-)-[6]-gingerol 

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 
• 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 

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.

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.

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