| Identification | Back Directory | [Name]
N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone | [CAS]
929222-14-0 | [Synonyms]
3-hydroxy-N-(2-oxooxolan-3-yl)decanamide
N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone
N-(3-Hydroxydecanoyl)-DL-homoserine lactone
N-[(RS)-3-Hydroxydecanoyl]-DL-homoserine lactone
3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)decanamide
Decanamide, 3-hydroxy-N-(tetrahydro-2-oxo-3-furanyl)- | [Molecular Formula]
C14H23NO4 | [MDL Number]
MFCD28016586 | [MOL File]
929222-14-0.mol | [Molecular Weight]
269.337 |
| Chemical Properties | Back Directory | [Boiling point ]
516.8±50.0 °C(Predicted) | [density ]
1.09±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Acetonitrile: soluble,DMF: soluble | [form ]
A solid | [pka]
14.25±0.20(Predicted) | [InChI]
1S/C14H25NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h11-12,16H,2-10H2,1H3,(H,15,17) | [InChIKey]
DOICJCCMIBBSOO-UHFFFAOYSA-N | [SMILES]
O=C(CC(O)CCCCCCC)NC1C(OCC1)=O |
| Hazard Information | Back Directory | [Uses]
N-3-Hydroxydecanoyl-DL-Homoserine lactone is a bacterial quorum-sensing molecule. N-3-Hydroxydecanoyl-DL-Homoserine lactone activates the transcription factor SdiA (EC50 = 0.6 μM), which detects N-acyl homoserine lactones (AHLs), and exerts its effect in Salmonella enterica (S. enterica)12. | [Biological Activity]
N-(3-Hydroxydecanoyl)-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteriasuch as Echerichia and Salmonellaand are involved in quorum sensingcell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugsand a research focus for the prevention of biofilm formation.''Quorum-sensing signal generation | [References]
[1] Fekete A, et al. Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors. Anal Bioanal Chem. 2007 Jan;387(2):455-67. DOI:10.1007/s00216-006-0970-8
[2] Janssens JC, et al. Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue. Appl Environ Microbiol. 2007 Jan;73(2):535-44. DOI:10.1128/AEM.01451-06 |
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| Company Name: |
Merck KGaA
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21-20338288 |
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www.sigmaaldrich.cn |
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