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53727

Sigma-Aldrich

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

≥97% (HPLC)

Synonyme(s) :

3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide

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About This Item

Formule empirique (notation de Hill):
C16H29NO4
Numéro CAS:
182359-60-0
Poids moléculaire :
299.41
Numéro MDL:
MFCD16875424
Code UNSPSC :
41116134
ID de substance PubChem :
329757976
Nomenclature NACRES :
NA.25

Pureté

≥97% (HPLC)

Composition

carbon, 63.5-64.9%
nitrogen, 4.4-4.9%

Température de stockage

−20°C

Chaîne SMILES 

CCCCCCCCCC(O)CC(=O)NC1CCOC1=O

InChI

1S/C16H29NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h13-14,18H,2-12H2,1H3,(H,17,19)

Clé InChI

RGTXFFYJJNWEPV-UHFFFAOYSA-N

Actions biochimiques/physiologiques

N-(3-Hydroxydodecanoyl)-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.
Quorum-sensing signal generation

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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B M Davis et al.
Biophysical journal, 101(1), 245-254 (2011-07-05)
A practical label-free method for the rapid determination of small-molecule critical micelle concentration (CMC) using a fixed-angle light-scattering technique is described. Change in 90° light scattering at a fixed wavelength of incident radiation with increasing bacterial quorum molecule concentration and
Tommaso R I Cataldi et al.
Journal of mass spectrometry : JMS, 43(1), 82-96 (2007-08-22)
A method for the comprehensive profiling of the N-acyl-homoserine lactone (AHL) family of bacterial quorum-sensing molecules is presented using liquid chromatography (LC) coupled to a hybrid quadrupole linear ion trap (LTQ) and Fourier-transform ion-cyclotron-resonance mass spectrometer (FTICR). We demonstrate an
L Passador et al.
Journal of bacteriology, 178(20), 5995-6000 (1996-10-01)
A series of structural analogs of the Pseudomonas aeruginosa autoinducer [PAI, N-3-oxo-dodecanoyl homoserine lactone] were obtained and tested for their ability to act as autoinducers in stimulating the expression of the gene for elastase (lasB) by measuring beta-galactosidase production from
Meng Gui et al.
Frontiers in microbiology, 9, 1712-1712 (2018-08-16)
Sturgeon is an important fresh water-culture fish in China. A problem with sturgeon is its high susceptibility to spoilage. Food spoilage is reported to be regulated by quorum sensing (QS). To identify the QS signals acetylated homoserine lactones (AHLs) in
Kaoru Yamabe et al.
Biomedical research (Tokyo, Japan), 41(6), 259-268 (2020-12-04)
Recently, opportunistic nosocomial infections caused by Acinetobacter baumannii have become increasingly prevalent worldwide. The pathogen often establishes biofilms that adhere to medical devices, causing chronic infections refractory to antimicrobial therapy. Clinical reports have indicated that some macrolide antibiotics are effective
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