N-octadecanoyl-L-Homoserine lactone

N-octadecanoyl-L-Homoserine lactone
Item number Size Datasheet Manual SDS Delivery time Quantity Price
Cay13209-5 5 mg -

3 - 10 business days*

38.00€
Cay13209-10 10 mg -

3 - 10 business days*

72.00€
Cay13209-25 25 mg -

3 - 10 business days*

169.00€
Cay13209-50 50 mg -

3 - 10 business days*

300.00€
 
Quorum sensing is a regulatory system used by bacteria for controlling gene expression in... more
Product information "N-octadecanoyl-L-Homoserine lactone"
Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C18-HSL is one of four lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum sensing signaling in strains of S. meliloti, a nitrogen-fixing bacterial symbiont of the legume M. sativa. C18-HSL and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles. Formal Name: N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide. CAS Number: 479050-96-9. Synonyms: C18-HSL. Molecular Formula: C22H41NO3. Formula Weight: 367.6. Purity: >98%. Formulation: A crystalline solid. Solubility: Chloroform: 0.5 mg/ml. SMILES: O=C1[C@@H](NC(CCCCCCCCCCCCCCCCC)=O)CCO1. InChi Code: InChI=1S/C22H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)23-20-18-19-26-22(20)25/h20H,2-19H2,1H3,(H,23,24)/t20-/m0/s1. InChi Key: HGMDJDYXARRSKB-FQEVSTJZSA-N.
Keywords: C18-HSL, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide
Supplier: Cayman Chemical
Supplier-Nr: 13209

Properties

Application: Bioactive lipid assays
MW: 367.6 D
Formula: C22H41NO3
Purity: >98%
Format: Crystalline Solid

Database Information

CAS : 479050-96-9| Find alternatives

Handling & Safety

Storage: -20°C
Shipping: -20°C (International: -20°C)
Caution
Our products are for laboratory research use only: Not for administration to humans!
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