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

• 124-13-0 Octanal 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 91815-21-3 4-{2-[2-(2-Hydroxy-nonyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 91827-17-7 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetaldehyde 
• 91827-15-5 5-(4-Hydroxy-3-methoxy-phenyl)-3-oxo-pentanenitrile 
• 91827-16-6 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 
• 91827-14-4 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 121-33-5 vanillin 
• 97-53-0 4-allylguaiacol 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 

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

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

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.