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44558

Sigma-Aldrich

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

Synonym(s):

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide, C8-HSL

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About This Item

Empirical Formula (Hill Notation):
C12H21NO3
CAS Number:
147852-84-4
Molecular Weight:
227.30
Beilstein/REAXYS Number:
8148282
MDL number:
MFCD11113139
UNSPSC Code:
12352211
PubChem Substance ID:
329756519
NACRES:
NA.85

product name

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

Quality Level

100

assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -28±3°, c = 0.2 in methanol

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

application(s)

detection

storage temp.

−20°C

SMILES string

O=C1OCC[C@@H]1NC(CCCCCCC)=O

InChI

1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1

InChI key

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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Biochem/physiol Actions

N-Octanoyl-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, colonization, chemical defense and cell to cell communication among bacteria; for reviews see. AHLs are released as oligopeptides in Gram positive bacteria and as quorum signal in Gram negative bacteria. 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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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José Gomes et al.
Chemical communications (Cambridge, England), 49(2), 155-157 (2012-11-22)
We demonstrate the synthesis and immobilization of natural product hybrids featuring an acyl-homoserine lactone and a nitrodopamine onto biocompatible TiO(2) surfaces through an operationally simple dip-and-rinse procedure. The resulting immobilized hybrids were shown to be powerful quorum sensing (QS) activators
Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
Mattia Marenda et al.
Scientific reports, 6, 39142-39142 (2016-12-15)
Bacterial communities undergo collective behavioural switches upon producing and sensing diffusible signal molecules; a mechanism referred to as Quorum Sensing (QS). Exemplarily, biofilm organic matrices are built concertedly by bacteria in several environments. QS scope in bacterial ecology has been
J B Andersen et al.
Applied and environmental microbiology, 67(2), 575-585 (2001-02-07)
In order to perform single-cell analysis and online studies of N-acyl homoserine lactone (AHL)-mediated communication among bacteria, components of the Vibrio fischeri quorum sensor encoded by luxR-P(luxI) have been fused to modified versions of gfpmut3* genes encoding unstable green fluorescent
Meng Gui et al.
Frontiers in microbiology, 9, 1712-1712 (2018-08-16)
Sturgeon is an important fresh water-culture fish in China. A problem with sturgeon is its high susceptibility to spoilage. Food spoilage is reported to be regulated by quorum sensing (QS). To identify the QS signals acetylated homoserine lactones (AHLs) in
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