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Merck
CN

10940

N-Octanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Synonym(s):

N-Capryloyl-DL-homoserine lactone

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About This Item

Empirical Formula (Hill Notation):
C12H21NO3
CAS Number:
Molecular Weight:
227.30
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
Beilstein/REAXYS Number:
1642628
MDL number:
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Product Name

N-Octanoyl-DL-homoserine lactone, ≥97.0% (HPLC)

Quality Segment

assay

≥97.0% (HPLC)

form

powder with small lumps

color

white to faintly beige

application(s)

detection

storage temp.

2-8°C

SMILES string

CCCCCCCC(=O)NC1CCOC1=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)

InChI key

JKEJEOJPJVRHMQ-UHFFFAOYSA-N

Application

Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.

Biochem/physiol Actions

N-Octanoyl-DL-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 are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.
N-octanoyl-homoserine lactone (N-C8-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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