44558

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

• Synonym(s): N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide, C8-HSL
• Empirical Formula (Hill Notation): C₁₂H₂₁NO₃
• CAS Number: 147852-84-4
• Molecular Weight: 227.30
• NACRES: NA.85
• PubChem Substance ID: 329756519
• UNSPSC Code: 12352211
• MDL number: MFCD11113139
• Beilstein/REAXYS Number: 8148282

Properties

• Product Name: N-Octanoyl-L-homoserine lactone, ≥96% (HPLC)
• Quality Segment: 100
• assay: ≥96% (HPLC)
• form: powder or crystals
• optical activity: [α]/D -28±3°, c = 0.2 in methanol
• color: white to off-white
• suitability: conforms to structure for Proton NMR spectrum
• application(s): detection
• storage temp.: −20°C
• SMILES string: O=C1OCC[C@@H]1NC(CCCCCCC)=O
• InChI: 1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1
• InChI key: JKEJEOJPJVRHMQ-JTQLQIEISA-N

Description

Biochem/physiol Actions

N-Octanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, colonization, chemical defense and cell to cell communication among bacteria; for reviews see. AHLs are released as oligopeptides in Gram positive bacteria and as quorum signal in Gram negative bacteria. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.

Quorum-sensing signal generation

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable