Specifications
- Purity
- ≥97% (HPLC)
- Appearance
- White to off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- ethanol, methanol, DMF, DMSO, water (insoluble)
Category: Quorum Sensing
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.
Synonyms | C18-L-HSL, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide |
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Purity | ≥97% (HPLC) |
Appearance | White to off-white powder |
CAS-Number | 479050-96-9 |
Molecular Formula | C22H41NO3 |
Molecular Weight | 367.6 |
Identity | 1H-NMR |
Solvents | ethanol, methanol, DMF, DMSO, water (insoluble) |
Smiles | O=C(N[C@@H]1C(OCC1)=O)CCCCCCCCCCCCCCCCC |
InChi Key | HGMDJDYXARRSKB-FQEVSTJZSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
Hazard statements | H302 |
GHS Symbol | GHS07 |
Signal word | Warning |
Transportation | Not dangerous goods |
References | (1) J.P. Pearson, et al., J. Bacteriol. 181, 1203 (1999), (2) M. Marketon, et al., J. Bacteriol. 184, 5686 (2002), (3) J.E. Gonzalez & N.D. Keshavan, Microbiol. Mol. Biol. Rev. 70, 859 (2006), (4) T.A. Gould, et al., J. Bacteriol. 188, 773 (2006), (5) C.G.N. Penalver, et al., FEBS Lett. 580, 561 (2006), (6) L. Mashburn-Warren & M. Whiteley, Mol. Microbiol. 61, 839 (2006), (7) L. Cegelski, et al., Nat. Rev. Microbiol. 6, 17 (2008) |
Quantity | 10 mg, 50 mg, Bulk |