All Photos(1)
Synonym(s):
(S)-N-(2-Oxotetrahydrofuran-3-yl)butyramide, BHL, N-Butanoyl-L-homoserine lactone, N-Butyrylhomoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]butanamide
Empirical Formula (Hill Notation):
C8H13NO3
Recommended Products
Quality Level
Assay
≥95% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
CCCC(N[C@@H]1C(OCC1)=O)=O
InChI
1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1
InChI key
VFFNZZXXTGXBOG-LURJTMIESA-N
Biochem/physiol Actions
C4-HSL (N-butyryl-L-Homoserine lactone) is a quorum-sensing signaling molecule produced by Pseudomonas aeruginosa. C4-HSL induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 µM. C4-HSL exhibits antibacterial activity against MDR S. aureus isolates but had no effect on A. baumannii.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Y Jiang et al.
Molecular microbiology, 28(1), 193-203 (1998-05-21)
In Pseudomonas aeruginosa, synthesis of the quorum-sensing signal molecules N-butanoyl-L-homoserine lactone (BHL) and N-hexanoyl-L-homoserine lactone (HHL) requires the Luxl homologue Rhll(Vsml). By using thin-layer chromatography in conjunction with high-performance liquid chromatography (HPLC) and mass spectrometry, we show that purified Rhll
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