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Chemodex
N-(3-Oxododecanoyl)-L-homoserine lactone
Product Details | |
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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 |
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.
(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)