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

CHF 64.00
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CDX-O0031-M01010 mgCHF 64.00
CDX-O0031-M02020 mgCHF 115.00
CDX-O0031-M100100 mgCHF 293.00
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Product Details
Synonyms 3-oxo-C12-HSL; 3OC12HSL; 3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]dodecanamide; N-(3-Oxododecanoyl) homoserine lactone; n-(3-Oxododecanoyl) L-homoserine lactone
Product Type Chemical
Properties
Formula

C16H27NO4

MW 297.39
CAS 168982-69-2
Source/Host Chemicals Synthetic.
Purity Chemicals ≥98% (NMR)
Appearance White powder.
Solubility Soluble in DMSO (20mg/ml), DMF (20mg/ml) or chloroform.
Identity Determined by 1H-NMR.
Declaration Manufactured by Chemodex.
Other Product Data

Click here for Original Manufacturer Product Datasheet
Our product description may differ slightly from the original manufacturers product datasheet.

InChi Key PHSRRHGYXQCRPU-AWEZNQCLSA-N
Smiles CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
Shipping and Handling
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.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF

Quorum sensing agent. N-(3-Oxododecanoyl)-L-homoserine lactone (3-oxo-C12-HSL) 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. 3-oxo-C12-HSL is one of the AHLs frequently identified in extracts of respiratory secretions from cystic fibrosis patients infected with P. aeruginosa and/or strains of the B. cepacia complex. 3-oxo-C12-HSL activates the transcription factors NF-κB and AP-2 to induce interleukin-8 production in human lung fibroblasts and epithelial cells, possibly contributing to the neutrophil infiltration and inflammation found in P. aeruginosa infections.

Product References

(1) R.S. Smith, et al.; J. Immunol. 167, 366 (2001) | (2) E.A. Yates, et al.; Infect. Immun. 70, 5635 (2002) |(3) C.E. Chambers, et al.; FEMS Microbiol. Lett. 244, 297 (2005) | (4) G. Nakagami, et al.; FEMS Immunol. Med. Microbiol. 62, 157 (2011) | (5) V.K. Yadav, et al.; Int. J. Med. Microbiol. 308, 858 (2018)

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