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Merck
CN

804223

3-oxo-C12-aniline

Synonym(s):

3-oxo-N-phenyl-Dodecanamide, LasR inhibitor, non-hydrolysable head group

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About This Item

Empirical Formula (Hill Notation):
C18H27NO2
CAS Number:
1186509-19-2
Molecular Weight:
289.41
UNSPSC Code:
12352200
PubChem Substance ID:
329768853
NACRES:
NA.22

Key Documents

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SMILES string

CCCCCCCCCC(CC(NC1=CC=CC=C1)=O)=O

InChI

1S/C18H27NO2/c1-2-3-4-5-6-7-11-14-17(20)15-18(21)19-16-12-9-8-10-13-16/h8-10,12-13H,2-7,11,14-15H2,1H3,(H,19,21)

InChI key

GYOZLHQAMICVMN-UHFFFAOYSA-N

form

solid

storage temp.

−20°C

Application

This analog mimics the native 3-oxo-C12 AHL signal utilized by Pseudomonas aeruginosa for quorum sensing, yet contains a non-hydrolysable aniline head group. 3-oxo-C12-aniline is a strong inhibitor of the LasR receptor in P. aeruginosa.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT6791

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Design, synthesis and biological evaluation of abiotic, non-lactone modulators of LuxR-type quorum sensing
McInnis CE, and Blackwell HE
Bioorganic & Medicinal Chemistry, 19, 4812-4819 (2011)
Mutational Analysis of the Quorum-Sensing Receptor LasR Reveals Interactions that Govern Activation and Inhibition by Nonlactone Ligands.
Gerdt JP, et al.
Chemistry & Biology, 21, 1361-1369 (2014)
Grant D Geske et al.
Journal of the American Chemical Society, 129(44), 13613-13625 (2007-10-12)
Bacteria use a language of low molecular weight ligands to assess their population densities in a process called quorum sensing. This chemical signaling process plays a pivotal role both in the pathogenesis of infectious disease and in beneficial symbioses. There

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