596104-55-1

Basic information

• Product Name: 3-Oxo-dodecan-(2-aMinocyclohexanone)
• Synonyms: 3-Oxo-dodecan-(2-aMinocyclohexanone);3-Oxo-N-(2-oxocyclohexyl)dodecanamide
• CAS NO: 596104-55-1
• Molecular Formula: C18H31NO3
• Molecular Weight: 309.44364
• Mol File: 596104-55-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 496.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.01±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 11.21±0.46(Predicted)
• BRN: 10025937
• CAS DataBase Reference: 3-Oxo-dodecan-(2-aMinocyclohexanone)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxo-dodecan-(2-aMinocyclohexanone)(596104-55-1)
• EPA Substance Registry System: 3-Oxo-dodecan-(2-aMinocyclohexanone)(596104-55-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 596104-55-1(Hazardous Substances Data)

Upstream product

• 429675-23-0 5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 112-13-0 n-decanoyl chloride 
• 76835-64-8 methyl 3-oxododecanoate 
• 109873-29-2 (2-nonyl-[1,3]dioxolan-2-yl)-acetic acid methyl ester 
• 596104-60-8 (2-nonyl-[1,3]dioxolan-2-yl)-acetic acid 
• 1026983-94-7 (2-nonyl-[1,3]dioxolan-2-yl)-acetyl chloride 
• 862587-60-8 2-(2-nonyl-[1,3]dioxolan-2-yl)-N-(2-oxo-cyclohexyl)-acetamide 

Relevant articles and documents

Synthesis and stability of small molecule probes for Pseudomonas aeruginosa quorum sensing modulation

The human pathogen Pseudomonas aeruginosa uses N-butyryl-L-homoserine lactone (BHL) and N-(3-oxododecanyl)-L-homoserine lactone (OdDHL) as small molecule intercellular signals in a phenomenon known as quorum sensing (QS). QS modulators are effective at attenuating P. aeruginosa virulence; therefore, they are a potential new class of antibacterial agent. The lactone in BHL and OdDHL is hydrolysed under physiological conditions. The hydrolysis proceeds at a rate faster than racemisation of the α-chiral centre. Non-hydrolysable, non-racemic analogues (small molecule probes) were designed and synthesised, replacing the lactone with a ketone. OdDHL analogues were found to be relatively unstable to decomposition unless they were difluorinated between the β-keto amide. Stability studies on a non-hydrolysable, cyclohexanone analogue indicated that racemisation of the α-chiral centre was relatively slow. This analogue was assayed to show that the L-isomer is likely to be responsible for the QS autoinducing activity in P. aeruginosa and Serratia strain ATCC39006.