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N-Tetradecanoyl-DL-homoserine lactone

Product Code:
 
CDX-T0147
Product Group:
 
Other Biochemicals
Supplier:
 
Chemodex
Regulatory Status:
 
RUO
Shipping:
 
AMBIENT
Storage:
 
+4°C
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Chemical Structure
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Chemical Structure

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CDX-T0147-M01010 mg£84.00
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CDX-T0147-M05050 mg£267.00
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Further Information

Alternate Names/Synonyms:
C14-HSL; tDHL; N-(2-Oxotetrahydrofuran-3-yl)tetradecanamide; N-Myristoyl-DL-homoserine lactone
Appearance:
White solid.
CAS:
98206-80-5
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)19-15-16-22-18(19)21/h2-16H2,1H3
InChiKey:
RSNWXHNBZSWFLG-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 98206-80-5. Formula: C18H33NO3. MW: 311.5. Synthetic. N-Tetradecanoyl-DL-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.
MDL:
MFCD01862913
Molecular Formula:
C18H33NO3
Molecular Weight:
311.5
Package Type:
Vial
Product Description:
N-Tetradecanoyl-DL-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.
Purity:
>97% (GC)
SMILES:
CCCCCCCCCCCCCCC(=O)N1CCOC1=O
Solubility Chemicals:
Soluble in chloroform.
Source / Host:
Synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.

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)