Specifications
- Purity
- ≥97% (HPLC)
- Appearance
- White to off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- ethanol, methanol, DMF, DMSO, water (insoluble)
Available from stock
N-Octadecanoyl-L-homoserine lactone
- SKU
- O0137
Category: Quorum Sensing
- Synonyms
- C18-L-HSL , N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide
- 479050-96-9
- CAS-Number
- C22H41NO3
- Molecular Formula
- 367.6
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- 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
- 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.
- Smiles
- O=C(N[C@@H]1C(OCC1)=O)CCCCCCCCCCCCCCCCC
- InChi Key
- HGMDJDYXARRSKB-FQEVSTJZSA-N
- 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)
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.
Additional information
| Synonyms | C18-L-HSL, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide |
|---|---|
| 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 |
