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    N-Dodecanoyl-L-homoserine lactone

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      N-Dodecanoyl-L-homoserine lactone

      SKU
      D0335

      Category: Quorum Sensing

      Synonyms
      N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide , dDHL , C12-HSL
      137173-46-7
      CAS-Number
      C16H29NO3
      Molecular Formula
      283.4
      Molecular Weight

      For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥98% (NMR)
      Appearance
      White powder
      Identity
      1H-NMR

      Properties

      Solvents
      DMSO, dimethylformamide (approx. 30 mg/ml)
      Optical Activity
      [α]/D -25±5°, c = 0.2 in methanol
      Shipping
      AMBIENT
      Short Term Storage
      +4°C
      Long Term Storage
      +4°C
      Handling Advice
      Protect from light and moisture.
      Use / Stability
      Stable for at least 2 years after receipt when stored at +4°C.
      Hazard statements
      H413
      Transportation
      Not dangerous goods
      Description
      N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.
      Smiles
      CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
      InChi Key
      WILLZMOKUUPJSL-AWEZNQCLSA-N
      References
      (1) G.D. Geske: JACS 127, 12762 (2005) , (2) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011) , (3) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994) , (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000) , (5) K.H. McClean, et al.: Microbiol. 143, 3703 (1997) , (6) K. Gomi, et al.: Infect. Immun. 74, 7029 (2006) , (7) S. Kristiansen, et al.: APMIS 116, 361 (2008) , (8) Y. Huang, et al.: ISME 1, (2008)
      InChi
      InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

      N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.

      SKU: D0335 Category: Quorum Sensing
      • Additional information

      Additional information

      Synonyms

      N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide, dDHL, C12-HSL

      Purity

      ≥98% (NMR)

      Appearance

      White powder

      CAS-Number

      137173-46-7

      Molecular Formula

      C16H29NO3

      Molecular Weight

      283.4

      Identity

      1H-NMR

      Solvents

      DMSO, dimethylformamide (approx. 30 mg/ml)

      Optical Activity

      [α]/D -25±5°, c = 0.2 in methanol

      Smiles

      CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O

      InChi Key

      WILLZMOKUUPJSL-AWEZNQCLSA-N

      Shipping

      AMBIENT

      Short Term Storage

      +4°C

      Long Term Storage

      +4°C

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      Stable for at least 2 years after receipt when stored at +4°C.

      Hazard statements

      H413

      Transportation

      Not dangerous goods

      References

      (1) G.D. Geske: JACS 127, 12762 (2005), (2) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011), (3) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) K.H. McClean, et al.: Microbiol. 143, 3703 (1997), (6) K. Gomi, et al.: Infect. Immun. 74, 7029 (2006), (7) S. Kristiansen, et al.: APMIS 116, 361 (2008), (8) Y. Huang, et al.: ISME 1, (2008)

      InChi

      InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

      Quantity

      5 mg, 50 mg, Bulk

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