Specifications
- Purity
- ≥97% (GC)
- Appearance
- White solid
- Identity
- 1H-NMR
Properties
- Solvents
- chloroform
Category: Quorum Sensing
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
N-(3-Oxotetradecanoyl)-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 3-oxo-AHLs, stimulates the production of putisolvin, which in turn inhibits biofilm formation.
Synonyms | 3-oxo-C14-HSL, 3OC14-HSL, N-3-oxo-Myristoyl-L-Homoserine lactone |
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Purity | ≥97% (GC) |
Appearance | White solid |
CAS-Number | 177158-19-9 |
Molecular Formula | C18H31NO4 |
Molecular Weight | 325.4 |
Identity | 1H-NMR |
Solvents | chloroform |
Smiles | [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCC |
InChi Key | YQFJJDSGBAAUPW-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) A.L. Schaefer, et al.: J. Bacteriol. 178, 2897 (1996), (3) K.H. McClean, et. al.: Microbiol. 143, 3703 (1997), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) S.R. Chhabra, et al.: J. Med. Chem. 46, 97 (2003), (6) G.D. Geske: JACS 127, 12762 (2005), (7) J.F. Dubern, et al.: J. Bacteriol. 188, 2898 (2006), (8) F.W. Bartels, et al.: Biophys. J. 92, 4391 (2007), (9) A.M. Pomini & A.J. Marsaioli: J. Nat. Prod. 71, 1032 (2008), (10) M. Wahjudi, et al.: Microbiol 157, 2042 (2011), (11) B.M. Davis, et al.: Biophy. J. 101, 245 (2011), (12) C.H. Tan, et al.: ISME J. 8, 1186 (2014), (13) K.-G. Chan, et al.: Sci. World J. 2014, ID891041 (2014) |
InChi | InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1 |
Quantity | 10 mg, 50 mg, Bulk |