216596-71-3

216596-71-3 structure
216596-71-3 structure
  • Name: N-[(3S)-2-Oxotetrahydro-3-furanyl]undecanamide
  • Chemical Name: N-undecanoyl-L-Homoserine lactone
  • CAS Number: 216596-71-3
  • Molecular Formula: C15H27NO3
  • Molecular Weight: 269.380
  • Catalog: Research Areas Others
  • Create Date: 2017-11-28 20:45:51
  • Modify Date: 2024-04-15 17:00:15
  • Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.

Name N-undecanoyl-L-Homoserine lactone
Synonyms N-[(3S)-2-Oxotetrahydro-3-furanyl]undecanamide
Undecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
Description Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.
Related Catalog
Density 1.0±0.1 g/cm3
Boiling Point 475.8±34.0 °C at 760 mmHg
Molecular Formula C15H27NO3
Molecular Weight 269.380
Flash Point 241.5±25.7 °C
Exact Mass 269.199097
PSA 55.40000
LogP 2.62
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.477