68224

N-Dodecanoyl-L-homoserine lactone

≥96% (HPLC), suitable for mass spectrometry (MS)

• Synonym(s): N-Lauroyl-L-homoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide, C12-HSL
• Empirical Formula (Hill Notation): C₁₆H₂₉NO₃
• CAS Number: 137173-46-7
• Molecular Weight: 283.41
• Beilstein: 9281984
• MDL number: MFCD11976890
• UNSPSC Code: 12352211
• PubChem Substance ID: 329760775
• NACRES: NA.28

Properties

• product name: N-Dodecanoyl-L-homoserine lactone, ≥96% (HPLC)
• Assay: ≥96% (HPLC)
• form: powder or crystals
• optical activity: [α]/D -25±5°, c = 0.2 in methanol
• technique(s): mass spectrometry (MS): suitable
• color: white to off-white
• suitability: conforms to structure for Proton NMR spectrum
• storage temp.: −20°C
• SMILES string: O=C1OCC[C@@H]1NC(CCCCCCCCCCC)=O
• InChI: 1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1
• InChI key: WILLZMOKUUPJSL-AWEZNQCLSA-N

Description

Biochem/physiol Actions

N-Dodecanoyl-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, cell to cell communication among bacteria; for reviews see. 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

• Hazard Statements: H413
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable