N-Octadecanoyl-L-homoserine lactone [CAS 479050-96-9]
N-Octadecanoyl-L-homoserine lactone [CAS 479050-96-9]
SKU:QM-0105267
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Product Details
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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 research 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. C18-HSL, one of four lipophilic long acyl side chain AHLs produced by the LuxI AHL synthase homolog SinI, is involved in quorum-sensing signaling in strains of Rhizobium meliloti (a nitrogen-fixing bacterial symbiont of the legume M. sativa) . C18-HSL and other hydrophobic AHLs tend to localize in the relatively lipophilic environment of bacterial cells and cannot diffuse freely across the cell membrane. Long-chain N-acyl homoserine lactones can be exported from cells by efflux pumps, or can be transported between communicating cells by extracellular outer membrane vesicles.
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CAS Number
[479050-96-9]
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Molecular Formula
C22H41NO3
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Molecular Weight
367.57
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Smiles
CCCCCCCCCCCCCCCCCC(N[C@@H]1C(OCC1)=O)=O
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Target
Biochemical Assay Reagents
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Solubility
10 mM in DMSO
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Storage Conditions
Store at room temperature 3 years
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Shipping Conditions
Room Temperature
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Hazard Statement
H302, H315, H319, H335
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Precautions
H302, H315, H319, H335
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N-Octadecanoyl-L-homoserine lactone [CAS 479050-96-9]
N-Octadecanoyl-L-homoserine lactone is a premium-grade research compound supplied by Quantimol for laboratory and scientific applications.