107257-18-1

Basic information

• Product Name: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone
• Synonyms: CAS号:107257-18-1分子式:C21H34O4分子量:350EINECS号:相关类别:Mol文件:107257-18-1.mol 5-羟基-1-(4-羟基-3-甲氧基苯基)-3-十四酮 性质沸点500℃
• CAS NO: 107257-18-1
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350
• Mol File: 107257-18-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 500℃
• Flash Point: 166℃
• Appearance: /
• Density: 1.037
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone(107257-18-1)
• EPA Substance Registry System: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone(107257-18-1)

Safety Data

• Hazardous Substances Data: 107257-18-1(Hazardous Substances Data)

Usage

Group components

Contains a 1-(4-hydroxy-3-methoxyphenyl) group and a tetradecanone group

Source

Found in Paeonia lactiflora, a traditional Chinese herbal medicine

Pharmacological properties

Anti-inflammatory, antioxidant, neuroprotective, hepatoprotective

Therapeutic potential

Studied in experimental models of Alzheimer's, Parkinson's, and liver injury

Importance

Interesting compound for further research and potential therapeutic applications

Upstream product

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• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
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• 69172-20-9 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde 
• 57371-42-3 4-allyl-1-benzyloxy-2-methoxybenzene 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 
• 97-53-0 4-allylguaiacol 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 91827-14-4 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 91827-16-6 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 
• 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 

Downstream Products

• 1212158-11-6 (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one 
• 23513-15-7 10-gingerol 
• 104186-05-2 trans-10-shogaol 
• 36752-54-2 [10]-shogaol 

Relevant articles and documents

An Improved Route to the Preparation of 6-, 8-, 10-Gingerols

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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.

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.