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N-Dodecanoyl-DL-homoserine lactone

SIGMA/17247 - ≥97.0% (HPLC)

Synonym: N-Lauroyl-DL-homoserine lactone

CAS Number: 18627-38-8
Empirical Formula (Hill Notation): C16H29NO3
Molecular Weight: 283.41
MDL Number: MFCD03100412
Linear Formula: C16H29NO3
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-17247-25MG 25 mg
 $298.00
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assay ≥97.0% (HPLC)
color white to faint beige
form powder
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
mp 114-117 °C
Quality Level 100 
SMILES string CCCCCCCCCCCC(=O)NC1CCOC1=O
storage temp. 2-8°C
technique(s) ligand binding assay: suitable
Application: Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
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.
Biochem/physiol Actions: 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.
Biochem/physiol Actions: Quorum-sensing signal generation.
Packaging: Bottomless glass bottle. Contents are inside inserted fused cone.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥97.0% (HPLC)
mp 114-117 °C
Storage Temp. 2-8°C
UNSPSC 12352209

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