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    N-Dodecanoyl-DL-homoserine lactone

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    N-Dodecanoyl-DL-homoserine lactone

    SKU
    D0339

    Category: Quorum Sensing

    Synonyms
    C12-HSL , N-(2-Oxotetrahydro-3-furanyl)dodecanamide , N-Lauroyl-DL-homoserine lactone
    18627-38-8
    CAS-Number
    C16H29NO3
    Molecular Formula
    283.4
    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 +4°C.
    Handling Advice
    Protect from light and moisture.
    Long Term Storage
    +4°C
    Shipping
    AMBIENT
    Transportation
    Not dangerous goods
    Description
    N-Dodecanoyl-DL-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 also was shown to induce cell death by apoptosis.
    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)
    References
    (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994) , (2) K.H. McClean, et al.: Microbiol. 143, 3703 (1997) , (3) M.K. Parsek, et al.: PNAS 143, 3703 (1997) , (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000) , (5) G.D. Geske: JACS 127, 12762 (2005) , (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) , (9) L.R. Swem, et al.: Molecul. Cell 35, 143 (2009) , (10) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011) , (11) D.G. Deryabina, et al.: Microbiol 82, 133 (2013)
    InChi Key
    WILLZMOKUUPJSL-UHFFFAOYSA-N
    Smiles
    CCCCCCCCCCCC(=O)NC1CCOC1=O

    N-Dodecanoyl-DL-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 also was shown to induce cell death by apoptosis.

    SKU: D0339 Category: Quorum Sensing
    • Additional information

    Additional information

    Synonyms

    C12-HSL, N-(2-Oxotetrahydro-3-furanyl)dodecanamide, N-Lauroyl-DL-homoserine lactone

    Purity

    ≥97% (GC)

    Appearance

    White solid

    CAS-Number

    18627-38-8

    Molecular Formula

    C16H29NO3

    Molecular Weight

    283.4

    Identity

    1H-NMR

    Solvents

    chloroform

    Smiles

    CCCCCCCCCCCC(=O)NC1CCOC1=O

    InChi Key

    WILLZMOKUUPJSL-UHFFFAOYSA-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.

    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) M.K. Parsek, et al.: PNAS 143, 3703 (1997), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) G.D. Geske: JACS 127, 12762 (2005), (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), (9) L.R. Swem, et al.: Molecul. Cell 35, 143 (2009), (10) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011), (11) D.G. Deryabina, et al.: Microbiol 82, 133 (2013)

    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)

    Quantity

    10 mg, 50 mg, Bulk

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