72749-01-0

Basic information

• Product Name: (R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one
• Synonyms: (5R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one;(R)-[6]-Gingerol;(R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one
• CAS NO: 72749-01-0
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 0
• Mol File: 72749-01-0.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one(72749-01-0)
• EPA Substance Registry System: (R)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one(72749-01-0)

Safety Data

• Hazardous Substances Data: 72749-01-0(Hazardous Substances Data)

Upstream product

• 39886-80-1 1-(4-benzyloxy-3-methoxyphenyl)-5-hydroxydecan-3-one 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 66-25-1 hexanal 
• 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 
• 72724-06-2 (-)-(R)-1-(4-Benzyloxy-3-methoxyphenyl)-5-hydroxydecan-3-one 
• 56024-44-3 methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 127766-49-8 (R)-3-[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-5-((1E,3E)-penta-1,3-dienyl)-4,5-dihydro-isoxazole 
• 91815-20-2 4-{2-[2-(2-Hydroxy-heptyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-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 
• 555-66-8 [6]-shogaol 
• 39886-76-5 [6]-gingerol 
• 72749-01-0 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 
• 61871-71-4 1-(4-hydroxy-3-methoxyphenyl)decane-3,5-dione 
• 2380-78-1 homovanillyl alcohol 
• 39886-85-6 1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol 

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