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Safety Information

10940

Sigma-Aldrich

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:
106983-30-6
Molecular Weight:
227.30
Beilstein:
1642628
MDL number:
MFCD01862915
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57646862
NACRES:
NA.26

product name

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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

10940-VAR:
10940-BULK:
10940-25MG:

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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Hebert F Culler et al.
Genes, 9(5) (2018-05-16)
Atypical enteropathogenic Escherichia coli are capable to form biofilm on biotic and abiotic surfaces, regardless of the adherence pattern displayed. Several E. coli mechanisms are regulated by Quorum sensing (QS), including virulence factors and biofilm formation. Quorum sensing is a
Hongsup Kim et al.
Journal of bacteriology, 194(5), 982-992 (2011-12-20)
Burkholderia glumae possesses a quorum-sensing (QS) system mediated by N-octanoyl-homoserine lactone (C(8)-HSL) and its cognate receptor TofR. TofR/C(8)-HSL regulates the expression of a transcriptional regulator, qsmR. We identified one of the universal stress proteins (Usps), Usp2, from a genome-wide analysis
Francisco Pérez-Montaño et al.
Research in microbiology, 162(7), 715-723 (2011-05-24)
Legume-nodulating rhizobia use N-acyl homoserine lactones (AHLs) to regulate several physiological traits related to the symbiotic plant-microbe interaction. In this work, we show that Sinorhizobium fredii SMH12, Rhizobium etli ISP42 and Rhizobium sullae IS123, three rhizobial strains with different nodulation
Xinqi Huang et al.
Current microbiology, 74(1), 68-76 (2016-11-04)
Marine algae provide a unique niche termed the phycosphere for microorganism inhabitation. The phycosphere environment is an important niche for mutualistic and competitive interactions between algae and bacteria. Quorum sensing (QS) serves as a gene regulatory system in the microbial
Ali E McClean et al.
Phytopathology, 102(2), 195-203 (2012-01-13)
Several members of the bacterial genus Brenneria are pathogenic on different tree species. Cell-free extracts from the bacterial phytopathogens Brenneria rubrifaciens, B. salicis, and B. nigrifluens induced production of the red pigment rubrifacine in the B. rubrifaciens bruI insertional mutant
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