Specifications
- Purity
- ≥97% (GC)
- Identity
- 1H-NMR
- Appearance
- White solid
Properties
- Solvents
- chloroform
Available from stock
N-Tetradecanoyl-L-homoserine lactone
- SKU
- T0144
Category: Quorum Sensing
- Synonyms
- C14-HSL , tDHL , N-[(3S)-2-Oxotetrahydro-3-furanyl]tetradecanamide , N-Myristoyl-L-homoserine lactone
- 202284-87-5
- CAS-Number
- C18H33NO3
- Molecular Formula
- 311.5
- Molecular Weight
- Short Term Storage
- +4°C
- Use / Stability
- Stable for at least 2 years after receipt when stored at -20°C.
- Handling Advice
- Protect from light and moisture.
- Long Term Storage
- -20°C
- Shipping
- AMBIENT
- Transportation
- Not dangerous goods
- Description
- N-Tetradecanoyl-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. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain AHLs, stimulates bacterial growth. C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis. Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
- InChi
- InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1
- References
- (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994) , (2) K.H. McClean, et al.: Microbiol. 143, 3703 (1997) , (3) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000) , (4) J.J. Huang, et al.: Appl. Environ. Microbiol. 69, 5941 (2003) , (5) G.D. Geske: JACS 127, 12762 (2005) , (6) A. Komiya-Ito, et al.: Res. J. Microbiol. 1, 353 (2006) , (7) D. Stankowska, et al.: Microbiol. Immunol. Infect. 41, 243 (2008) , (8) T. Karlsson, et al.: J. Leuk. Biol. 91, 15 (2012)
- InChi Key
- ZQAYHOXXVBVXPZ-INIZCTEOSA-N
- Smiles
- CCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
N-Tetradecanoyl-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. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain AHLs, stimulates bacterial growth. C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis. Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
Additional information
| Synonyms | C14-HSL, tDHL, N-[(3S)-2-Oxotetrahydro-3-furanyl]tetradecanamide, N-Myristoyl-L-homoserine lactone |
|---|---|
| Purity | ≥97% (GC) |
| Appearance | White solid |
| CAS-Number | 202284-87-5 |
| Molecular Formula | C18H33NO3 |
| Molecular Weight | 311.5 |
| Identity | 1H-NMR |
| Solvents | chloroform |
| Smiles | CCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O |
| InChi Key | ZQAYHOXXVBVXPZ-INIZCTEOSA-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. |
| Transportation | Not dangerous goods |
| References | (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994), (2) K.H. McClean, et al.: Microbiol. 143, 3703 (1997), (3) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (4) J.J. Huang, et al.: Appl. Environ. Microbiol. 69, 5941 (2003), (5) G.D. Geske: JACS 127, 12762 (2005), (6) A. Komiya-Ito, et al.: Res. J. Microbiol. 1, 353 (2006), (7) D. Stankowska, et al.: Microbiol. Immunol. Infect. 41, 243 (2008), (8) T. Karlsson, et al.: J. Leuk. Biol. 91, 15 (2012) |
| InChi | InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1 |
| Quantity | 10 mg, 50 mg, Bulk |
