106983-27-1

Basic information

• Product Name: N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE
• Synonyms: N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE;3-oxo-N-(2-oxotetrahydrofuran-3-yl)octanaMide;3-Oxo-N-(tetrahydro-2-oxo-3-furanyl)-octanamide;N-(β-Ketooctanoyl)-DL-homoserine lactone;N-(3X-Oxooctanoyl)-DL-homoserine lactone
• CAS NO: 106983-27-1
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.28356
• Mol File: 106983-27-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• Solubility: chloroform: soluble50mg/mL, clear, very faintly yellow
• CAS DataBase Reference: N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE(106983-27-1)
• EPA Substance Registry System: N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE(106983-27-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 106983-27-1(Hazardous Substances Data)

Usage

General Description

N-(3-oxooctanoyl)-DL-homoserine lactone, also known as 3-oxo-C8-homoserine lactone, is a chemical compound belonging to the class of homoserine lactones, which are commonly found in bacteria. This chemical is a signaling molecule used in a process called quorum sensing, which allows bacteria to communicate and coordinate their behavior based on population density. In the case of N-(3-oxooctanoyl)-DL-homoserine lactone, it is involved in regulating the expression of genes related to virulence, biofilm formation, and other processes in various bacterial species. It has been studied for its potential role in bacterial pathogenesis and as a target for the development of antibacterial compounds.

Upstream product

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Downstream Products

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Relevant articles and documents

Absolute configuration and antimicrobial activity of acylhomoserine lactones

(S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano is reported herein. As with all other substances of this class, the lactone moiety possesses S configuration, corroborating the hypothesis that it shares the same biosynthetic pathway as the (S)-N-hexanoylhomoserine lactone and also that some LuxI homologues can accept both hexanoyl- and heptanoyl-ACP as precursors. Evaluation of the antimicrobial activity of enantiomeric acylhomoserine lactones against three Gram-positive bacteria (Bacillus cereus, B. subtilis, and Staphylococcus aureus) revealed important features between absolute configuration and antimicrobial activity. The N-heptanoylhomoserine lactone was considerably less active than the 3-oxo derivatives. Surprisingly, non-natural (R)-N-(3-oxo-octanoyl)homoserine lactone was as active as the S enantiomer against B. cereus, while the synthetic racemic product was less active than either enantiomer.