N-Dodecanoyl-L-homoserine lactone

CHF 64.00
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CDX-D0335-M0055 mgCHF 64.00
CDX-D0335-M05050 mgCHF 383.00
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Product Details
Synonyms N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide; dDHL; C12-HSL
Product Type Chemical
Properties
Formula C16H29NO3
MW 283.4
CAS 137173-46-7
Source/Host Chemicals Synthetic.
Purity Chemicals ≥98% (NMR)
Appearance White powder.
Solubility Soluble in DMSO and dimethylformamide (approx. 30mg/ml).
Identity Determined by 1H-NMR.
Declaration Manufactured by Chemodex.
Other Product Data

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Our product description may differ slightly from the original manufacturers product datasheet.

InChi Key WILLZMOKUUPJSL-AWEZNQCLSA-N
Smiles CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Keep cool and dry.
Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
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Product Specification Sheet
Datasheet Download PDF

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-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β) 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.

Product 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)

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