bs-76663C

DATASHEET

Formulation Powder

Storage: Stable for 2 years after receipt when stored at -20°C.

Product Information:

CAS Number: 479050-96-9

Molecular formula: C22H41NO3

Molecular weight: 367.6

Purity: >97% (HPLC)

Appearance: White to off-white powder.

Solubility: Soluble in ethanol, methanol, DMF or DMSO. Insoluble in water.

InChiKey: HGMDJDYXARRSKB-FQEVSTJZSA-N

SMILES: O=C(N[C@@H]1C(OCC1)=O)CCCCCCCCCCCCCCCCC

SMILES: CCCCCCCCCCCCCCCCCC(=O)NC1CCOC1=O

Description:

N-Octadecanoyl-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. C18-HSL is a lipophilic, long acyl side-chain bearing AHL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes. It tends 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 extracellular outer membrane vesicles.