51086
N-Heptanoyl-L-homoserine lactone
≥96% (HPLC)
Synonym(s):
N-[(3S)-Tetrahydro-2-oxo-3-furanyl]heptanamide, C7-HSL
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About This Item
Empirical Formula (Hill Notation):
C11H19NO3
CAS Number:
Molecular Weight:
213.27
NACRES:
NA.85
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
10258594
Product Name
N-Heptanoyl-L-homoserine lactone, ≥96% (HPLC)
Quality Level
assay
≥96% (HPLC)
form
powder or crystals
optical activity
[α]/D -29±3°, c = 0.2 in methanol
color
white
suitability
conforms to structure for Proton NMR spectrum
storage temp.
−20°C
SMILES string
O=C1OCC[C@@H]1NC(CCCCCC)=O
InChI
1S/C11H19NO3/c1-2-3-4-5-6-10(13)12-9-7-8-15-11(9)14/h9H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
InChI key
FTMZLSDESAOPSZ-VIFPVBQESA-N
Biochem/physiol Actions
N-Heptanoyl-L-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
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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J K Lithgow et al.
Molecular microbiology, 37(1), 81-97 (2000-08-10)
N-(3-hydroxy-7-cis-tetradecenoyl)-L-homoserine lactone (3OH, C14:1-HSL) is a quorum-sensing signalling molecule produced by Rhizobium leguminosarum. It is unusual in that it inhibits the growth of several strains of R. leguminosarum and was previously known as 'small bacteriocin'. The cinRI locus responsible for
Megan E Pomianek et al.
ACS chemical biology, 2(5), 293-295 (2007-05-24)
Small-molecule agonists and antagonists of bacterial quorum sensing can enhance our understanding of this form of cell-cell communication. A recent effort has discovered effective modulators of the autoinducer-1 circuit for bacterial quorum sensing by the synthesis and evaluation of a
F Wisniewski-Dyé et al.
Journal of bacteriology, 184(6), 1597-1606 (2002-03-02)
Analysis of N-acyl-L-homoserine lactones (AHLs) produced by Rhizobium leguminosarum bv. viciae indicated that there may be a network of quorum-sensing regulatory systems producing multiple AHLs in this species. Using a strain lacking a symbiosis plasmid, which carries some of the
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 51086-10MG | 04061832463698 |
| 51086-50MG | 04061832463704 |