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    N-(3-Oxohexanoyl)-L-homoserine lactone

    Available from stock

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      N-(3-Oxohexanoyl)-L-homoserine lactone

      SKU
      O0057

      Category: Quorum Sensing

      Synonyms
      3-oxo-C6-HSL , N-(β-Ketocaproyl)-L-homoserine lactone
      143537-62-6
      CAS-Number
      C10H15NO4
      Molecular Formula
      213.2
      Molecular Weight

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

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

      Properties

      Solvents
      chloroform

      Downloads

      Safety Data Sheet
      CDX O0057 MSDS.pdf
      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-(3-Oxohexanoyl)-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. At increased populations of bacteria, localized higher concentrations of 3OC6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ 3OC6-HSL in cell-to-cell communication. An autoinducer of P. fischeri luciferase and a specfic genetic regulator that is unrelated to at least one of the enzyme systems that it induces. It acts after excretion and accumulation in the extracellular medium.
      InChi
      InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
      References
      (1) A. Eberhard, et al.: Arch. Microbiol. 146, 35 (1986) , (2) N.J. Bainton, et al.: Biochem. J. 288, 997 (1992) , (3) P. Williams, et al.: FEMS Microbiol. Lett. 100, 161 (1992) , (4) R.H. Gomer: Curr. Biol. 4, 734 (1994) , (5) A. Chatterjee, et al.: Appl. Environ.Microbiol. 61, 1959 (1995) , (6) Y.H. Dong, et al.: Nature 411, 813 (2001) , (7) G.D. Geske, et al.: Bioorg. Med. Chem. Lett. 18, 5978 (2008) , (8) R.L. Frey, et al.: Environ. Sci. Tech. 44, 7465 (2010)
      InChi Key
      YRYOXRMDHALAFL-QMMMGPOBSA-N
      Smiles
      [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCC

      N-(3-Oxohexanoyl)-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. At increased populations of bacteria, localized higher concentrations of 3OC6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ 3OC6-HSL in cell-to-cell communication. An autoinducer of P. fischeri luciferase and a specfic genetic regulator that is unrelated to at least one of the enzyme systems that it induces. It acts after excretion and accumulation in the extracellular medium.

      SKU: O0057 Category: Quorum Sensing
      • Additional information

      Additional information

      Synonyms

      3-oxo-C6-HSL, N-(β-Ketocaproyl)-L-homoserine lactone

      Purity

      ≥97% (GC)

      Appearance

      White solid

      CAS-Number

      143537-62-6

      Molecular Formula

      C10H15NO4

      Molecular Weight

      213.2

      Identity

      1H-NMR

      Solvents

      chloroform

      Smiles

      [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCC

      InChi Key

      YRYOXRMDHALAFL-QMMMGPOBSA-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. Eberhard, et al.: Arch. Microbiol. 146, 35 (1986), (2) N.J. Bainton, et al.: Biochem. J. 288, 997 (1992), (3) P. Williams, et al.: FEMS Microbiol. Lett. 100, 161 (1992), (4) R.H. Gomer: Curr. Biol. 4, 734 (1994), (5) A. Chatterjee, et al.: Appl. Environ.Microbiol. 61, 1959 (1995), (6) Y.H. Dong, et al.: Nature 411, 813 (2001), (7) G.D. Geske, et al.: Bioorg. Med. Chem. Lett. 18, 5978 (2008), (8) R.L. Frey, et al.: Environ. Sci. Tech. 44, 7465 (2010)

      InChi

      InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1

      Quantity

      10 mg, 50 mg, Bulk

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