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    N-Tetradecanoyl-L-homoserine lactone

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      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

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥97% (GC)
      Identity
      1H-NMR
      Appearance
      White solid

      Properties

      Solvents
      chloroform
      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.

      SKU: T0144 Category: Quorum Sensing
      • Additional information

      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

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