N-3-oxo-dodecanoyl-L-Homoserine lactone

Cayman Chemical Item Number 10007895

3-oxo-C12-HSL (CAS 168982-69-2)

See more

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules.1 N-3-oxo-dodecanoyl-L-homoserine lactone (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.2 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.3

1. Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

2. Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett 244 297-304 (2005).

3. Smith, R.S., Fedyk, E.R., Springer, T.A., et al. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-κB and activator protein-2. J Immunol 167 366-374 (2001).

Synonyms
  • 3-oxo-C12-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​dodecanamide
CAS Number 168982-69-2
Molecular Formula C16H27NO4
Formula Weight 297.4
Formulation A crystalline solid
Purity ≥98%
λmax 202, 250 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCCC(=O)​CC(=O)​N[C@H]​1CCOC1=O
InCHI Code
Copy InCHI code to clipboard
​1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)​12-15(19)​17-14-10-11-21-16(14)​20/h14H,2-12H2,1H3,(H,17,19)​/t14-/m0/s1
InCHI Key
Copy InCHI key to clipboard
PHSRRHGYXQCRPU-AWEZNQCLSA-N

Download free InCHI Key generation software

N-3-oxo-dodecanoyl-L-Homoserine lactone is available in the following screening library:

Size Price Quantity Subtotal
1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
50 mg $805.00 $0.00
Bulk Contact
Cart Total $0.00

Bulk Inquiry Form:

Thank you for requesting a bulk size for this product.










X

Enter number, size, and select unit. Example: 2 x 500 mg




Please indicate any analytical testing requirements, special handling, packaging, or delivery requirements.

Pricing updated 2015-04-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

N-3-hydroxydecanoyl-L-Homoserine lactone
N-3-hydroxyoctanoyl-L-Homoserine lactone
N-butyryl-L-Homoserine lactone
N-butyryl-L-Homoserine lactone-d5
N-dodecanoyl-L-Homoserine lactone-3-hydrazone-biotin
N-hexanoyl-L-Homoserine lactone
N-hexanoyl-L-Homoserine lactone-d3
N-(β-ketocaproyl)-L-Homoserine lactone
Show all 8 Hide all but first 3

Downloads

Batch-specific Information

Get batch-specific data and documents by batch number


Separate multiple batch numbers with commas

Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

JOIN OUR SOCIAL NETWORK!

Please wait...

Lost password?