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51086

Sigma-Aldrich

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:
177158-20-2
Molecular Weight:
213.27
Beilstein:
10258594
MDL number:
MFCD11113138
UNSPSC Code:
12352211
PubChem Substance ID:
329757669
NACRES:
NA.85

product name

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

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (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
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
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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