Chemodex

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

CHF 71.00
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CDX-O0032-M01010 mgCHF 71.00
CDX-O0032-M02020 mgCHF 122.00
CDX-O0032-M100100 mgCHF 316.00
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Product Details
Synonyms OdDHL; 3O-C12-DL-HSL; 3-oxo-C12-HSL; 3OC12HSL; n-(3-Oxododecanoyl) DL-homoserine lactone; 3-Oxo-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide; 3-Oxo-N-(2-oxooxolan-3-yl)dodecanamide
Product Type Chemical
Properties
Formula C16H27NO4
MW 297.39
CAS 152833-54-0
Source/Host Chemicals Synthetic
Purity Chemicals ≥97% (NMR)
Appearance White to off-white powder.
Solubility Soluble in DMSO 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-UHFFFAOYSA-N
Smiles O=C(CC(CCCCCCCCC)=O)NC1C(OCC1)=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.
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Product Specification Sheet
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Description

Quorum sensing agent. N-(3-Oxododecanoyl)-L-homoserine lactone (3-oxo-C12-HSL) is a small diffusible signaling molecule, also identified as P. aeruginosa autoinducer (PAI), 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. 3-oxo-C12-HSL activates the transcription factors NF-κB and AP-2 to induce interleukin-8, cyclooxygenase 2, and prostaglandin E2 production in human lung fibroblasts and epithelial cells, possibly contributing to the neutrophil infiltration and inflammation found in P. aeruginosa infections. 3-oxo-C12-HSL also suppresses human and murine leucocyte proliferation and inhibits LPS-induced secretion of TNF-R and IL-12. 3-oxo-C12-HSL accelerated apoptosis in mammalian macrophages and neutrophils and shown to inhibit the growth of human colorectal, breast and prostate cancer cells.

Product References

(1) J.P. Pearson, et al.; PNAS 91, 197 (1994) | (2) L. Passador, et al.; J. Bacteriol. 178, 5995 (1996) | (3) S.R. Chhabra, et al.; J. Med. Chem. 46, 97 (2003) | (4) K. Gomi, et al.; Host Resp. Inflamm. 74, 7029 (2006) | (5) S. Kristiansen, et al.; J. Path. Microbiol. Immunol. 116, 361 (2008) | (6) H.-B. Liu, et al.; Biotechnol. Bioeng. 106, 119 (2010) | (7) M.L. Mayer, et al.; PLoS One 6, e16246 (2011) | (8) H. Chai, et al.; Investig. Drugs 30, 157 (2012) | (9) S.Y. Eum, et al.; Am. J. Physiol. Gastrointest. Liver Physiol. 306, G992 (2014) | (10) S. Horke, et al.; Infect. Immun. 83, 3369 (2015) | (11) V.K. Yadav, et al.; Int. J. Med. Microbiol. 308, 858 (2018)

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