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51086

Sigma-Aldrich

N-Heptanoyl-L-homoserine lactone

≥96% (HPLC)

Synonyme(s) :

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]heptanamide, C7-HSL

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About This Item

Formule empirique (notation de Hill):
C11H19NO3
Numéro CAS:
177158-20-2
Poids moléculaire :
213.27
Numéro Beilstein :
10258594
Numéro MDL:
MFCD11113138
Code UNSPSC :
12352211
ID de substance PubChem :
329757669
Nomenclature NACRES :
NA.85

product name

N-Heptanoyl-L-homoserine lactone, ≥96% (HPLC)

Niveau de qualité

100

Pureté

≥96% (HPLC)

Forme

powder or crystals

Activité optique

[α]/D -29±3°, c = 0.2 in methanol

Couleur

white

Adéquation

conforms to structure for Proton NMR spectrum

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

FTMZLSDESAOPSZ-VIFPVBQESA-N

Actions biochimiques/physiologiques

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

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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
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
Kaimin Niu et al.
Indian journal of microbiology, 57(3), 329-338 (2017-09-15)
An increasing concern on resistance to multiple-antibiotics has led to the discovery of novel agents and the establishment of new precaution strategy. Numerous plant sources have been widely studied to reduce virulence of pathogenic bacteria by interfering cell-to-cell based communication
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