17247

N-Dodecanoyl-DL-homoserine lactone

≥97.0% (HPLC), suitable for ligand binding assays

• Synonym(s): N-Lauroyl-DL-homoserine lactone
• Empirical Formula (Hill Notation): C₁₆H₂₉NO₃
• CAS Number: 18627-38-8
• Molecular Weight: 283.41
• UNSPSC Code: 12352209
• eCl@ss: 32160406
• PubChem Substance ID: 57647620
• NACRES: NA.26
• MDL number: MFCD03100412

Properties

• Product Name: N-Dodecanoyl-DL-homoserine lactone, ≥97.0% (HPLC)
• Quality Segment: 100
• assay: ≥97.0% (HPLC)
• form: powder
• technique(s): ligand binding assay: suitable
• color: white to faint beige
• mp: 114-117 °C
• storage temp.: 2-8°C
• SMILES string: CCCCCCCCCCCC(=O)NC1CCOC1=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)
• InChI key: WILLZMOKUUPJSL-UHFFFAOYSA-N

Description

Application

Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones[1].

Biochem/physiol Actions

N-Dodecanoyl-DL-homoserine lactone (C12-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 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 involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.

N-Lauroyl- DL-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 are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

Quorum-sensing signal generation.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)