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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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
Wai-Fong Yin et al.
Sensors (Basel, Switzerland), 12(3), 3472-3483 (2012-06-28)
Bacteria communicate by producing quorum sensing molecules called autoinducers, which include autoinducer-1, an N-hexanoyl homoserine lactone (AHL), and autoinducer-2. Bacteria present in the human oral cavity have been shown to produce autoinducer-2, but not AHL. Here, we report the isolation
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 51086-50MG | 04061832463704 |
| 51086-10MG | 04061832463698 |