Cookie Policy: This site uses cookies to improve your experience. You can find out more about our use of cookies in our Privacy Policy. By continuing to browse this site you agree to our use of cookies.
Chemodex
N-(3-Oxododecanoyl)-DL-homoserine lactone
![Loading...](https://adipogen.com/pub/static/version1703841973/frontend/raffiniert/adipogen/de_CH/images/loader-1.gif)
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 |
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. |
Documents | |
MSDS | Inquire |
Product Specification Sheet | |
Datasheet |
![]() |
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.
(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)