77398-92-6

Basic information

• Product Name: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone
• Synonyms: 3-Dodecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-
• CAS NO: 77398-92-6
• Molecular Formula: C₁₉H₃₀O₄
• Molecular Weight: 322
• Mol File: 77398-92-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 476℃
• Flash Point: 162℃
• Appearance: /
• Density: 1.058
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone(77398-92-6)
• EPA Substance Registry System: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone(77398-92-6)

Safety Data

• Hazardous Substances Data: 77398-92-6(Hazardous Substances Data)

Usage

Source

Rhizome of Curcuma longa (turmeric)

Chemical structure

Diketone derivative with a dodecanoyl chain attached to a phenolic ring with a methoxy and hydroxy group

Biological activities

Anti-inflammatory, antioxidant, antifungal, antimicrobial

Therapeutic applications

Treatment of cancer, diabetes, neurological disorders
Potential as a natural food preservative
Diverse pharmacological effects and potential applications in medicine and food industry

Upstream product

• 97-53-0 4-allylguaiacol 
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• 1186501-40-5 [8]-dehydrogingerol 
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• 91827-15-5 5-(4-Hydroxy-3-methoxy-phenyl)-3-oxo-pentanenitrile 
• 91827-17-7 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetaldehyde 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 124-13-0 Octanal 
• 91815-21-3 4-{2-[2-(2-Hydroxy-nonyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
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• 1619234-12-6 (S)-3-((tert-butyldimethylsilyl)oxy)decanoic acid 

Downstream Products

• 36700-45-5 [8]-shogaol 
• 36700-45-5 [8]-shogaol 
• 23513-08-8 [8]-gingerol 
• 135272-33-2 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-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.

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

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.