147795-40-2

Basic information

• Product Name: N-(3-Oxodecanoyl)-L-homoserine lactone
• Synonyms: N-(3-Oxodecanoyl)-L-homoserine lactone;3OC10-HSL;3-oxo-C10-HSL;3-oxo-N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-decanamide
• CAS NO: 147795-40-2
• Molecular Formula: C14H23NO4
• Molecular Weight: 269.33672
• Product Categories: Amino Acids;Homoserine LactonesMicrobiology;Modified Amino Acids;Quorum Sensing / Signaling Compounds
• Mol File: 147795-40-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 90-92 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 503.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 11.25±0.46(Predicted)
• CAS DataBase Reference: N-(3-Oxodecanoyl)-L-homoserine lactone(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-Oxodecanoyl)-L-homoserine lactone(147795-40-2)
• EPA Substance Registry System: N-(3-Oxodecanoyl)-L-homoserine lactone(147795-40-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 147795-40-2(Hazardous Substances Data)

Usage

Uses

N-(3-Oxodecanoyl)-L-homoserine lactone (3-Oxo-C10-HSL) may be used to study the signaling involved in the regulation of bacterial quorum sensing.

General Description

N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL) is among belongs to the group of homoserine lactones that includes N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone.

Biochem/physiol Actions

Acyl homoserine lactone used as an autoinducer of quorum signaling by Pseudomonas putida, Yersinia enterocolitica, and other Gram-negative bacteria.

Upstream product

• 13283-92-6 β-ketodecanoic acid 
• 2185-02-6 L-homoserine lactone 
• 868054-76-6 2-(2-heptyl-1,3-dioxolan-2-yl)acetic acid 
• 182359-62-2 (S)-N-(2-oxotetrahydrofuran-3-yl)-2-(2-heptyl-1,3-dioxolan-2-yl)acetamide 
• 66696-81-9 5-(1-hydroxyoctylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 103576-44-9 2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 2185-03-7 L-homoserine lactone hydrochloride 
• 124-07-2 Octanoic acid 
• 111-64-8 n-octanoic acid chloride 
• 22348-96-5 methyl 3-oxodecanoate 
• 821-55-6 2-Nonanone 
• 71989-28-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine 

Downstream Products

• 192883-12-8 N-(3-hydroxy-decanoyl)-L-homoserine lactone 

Relevant articles and documents

Disruption of biofilm formation by the human pathogen Acinetobacter baumannii using engineered quorum-quenching lactonases

Acinetobacter baumannii is a major human pathogen associated with multidrug-resistant nosocomial infections; its virulence is attributed to quorum-sensing-mediated biofilm formation, and disruption of biofilm formation is an attractive antivirulence strategy. Here, we report the first successful demonstration of biofilm disruption in a clinical isolate of A. baumannii S1, using a quorum-quenching lactonase obtained by directed evolution; this engineered lactonase significantly reduced the biomass of A. baumannii-associated biofilms, demonstrating the utility of this antivirulence strategy. Copyright

Identification and Quantification of N-Acyl Homoserine Lactones Involved in Bacterial Communication by Small-Scale Synthesis of Internal Standards and Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry

N-acyl homoserine lactones (AHL) are small signal molecules involved in the quorum sensing of many gram-negative bacteria, and play an important role in biofilm formation and pathogenesis. Present analytical methods for identification and quantification of AHL require time-consuming sample preparation steps and are hampered by the lack of appropriate standards. By aiming at a fast and straightforward method for AHL analytics, we investigated the applicability of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Suitable MALDI matrices, including crystalline and ionic liquid matrices, were tested and the fragmentation of different AHL in collision-induced dissociation MS/MS was studied, providing information about characteristic marker fragments ions. Employing small-scale synthesis protocols, we established a versatile and cost-efficient procedure for fast generation of isotope-labeled AHL standards, which can be used without extensive purification and yielded accurate standard curves. Quantitative analysis was possible in the low pico-molar range, with lower limits of quantification reaching from 1 to 5 pmol for different AHL. The developed methodology was successfully applied in a quantitative MALDI MS analysis of low-volume culture supernatants of Pseudomonas aeruginosa. [Figure not available: see fulltext.].

MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS

The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a l