182359-60-0

Basic information

• Product Name: NULL
• Synonyms: N-(3-Hydroxydodecanoyl)-DL-hoMoserine lactone;3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide;3-hydroxy-N-(2-oxooxolan-3-yl)dodecanamide
• CAS NO: 182359-60-0
• Molecular Formula: C16H29NO4
• Molecular Weight: 299.40576
• Mol File: 182359-60-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 532.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 14.24±0.20(Predicted)
• CAS DataBase Reference: NULL(CAS DataBase Reference)
• NIST Chemistry Reference: NULL(182359-60-0)
• EPA Substance Registry System: NULL(182359-60-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 182359-60-0(Hazardous Substances Data)

Upstream product

• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 334-48-5 1-decanoic acid 
• 429675-23-0 5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 182359-65-5 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1883-13-2 3-hydroxydodecanoic acid 
• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 

Relevant articles and documents

Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase

Abstract: An enzymatic method to produce N-acyl homoserine lactones (AHLs) is described. This report represents the first example of the synthesis of bioactive AHLs using immobilized Candida antarctica lipase as the catalyst. The reaction yields, evaluate

Immunosuppressive but non-LasR-inducing analogues of the pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

Figure Presented. The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the β-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N1-(5-chloro-2-hydroxyphenyl)-N 3-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators

Comparative immune modulatory activity for a range of synthetic analogues of a Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone (30, C12-HSL), is described. Twenty-four single or combination systematic alteration