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09926

Sigma-Aldrich

N-Hexanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Synonym(s):

N-Caproyl-DL-homoserine lactone

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About This Item

Empirical Formula (Hill Notation):
C10H17NO3
CAS Number:
Molecular Weight:
199.25
Beilstein:
1640340
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

Assay

≥97.0% (HPLC)

form

powder or crystals

technique(s)

LC/MS: suitable

color

white to faint beige

mp

101-106 °C

storage temp.

2-8°C

SMILES string

CCCCCC(=O)NC1CCOC1=O

InChI

1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)

InChI key

ZJFKKPDLNLCPNP-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

N-Hexanoyl-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 and are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.
Quorum-sensing signal generation

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

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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Albert Soler et al.
International journal of environmental research and public health, 15(5) (2018-05-23)
Quorum sensing (QS) is a mechanism dependent on bacterial density. This coordinated process is mediated by the synthesis and the secretion of signal molecules, called autoinducers (AIs). N-acyl-homoserine lactones (AHLs) are the most common AIs that are used by Gram-negative
Daniel Wynn et al.
The Analyst, 143(19), 4774-4782 (2018-09-15)
There are an estimated 48 million cases of foodborne illness in the United States every year. In general, these illnesses are the result of unintentional contamination and improper food handling. Because bacterial contamination plays a major role in food spoilage
Joanne Hothersall et al.
Applied microbiology and biotechnology, 90(3), 1017-1026 (2011-02-15)
Transcription of the 74 kb Pseudomonas fluorescens mupirocin [pseudomonic acid (PA)] biosynthesis cluster depends on quorum sensing-dependent regulation via the LuxI/LuxR homologues MupI/MupR. To facilitate analysis of novel PAs from pathway mutants, we investigated factors that affect mup gene expression.
L Eberl
Systematic and applied microbiology, 22(4), 493-506 (2000-05-04)
The view of bacteria as unicellular organisms has strong roots in the tradition of culturing bacteria in liquid media. However, in nature microbial activity is mainly associated with surfaces where bacteria form highly structured and cooperative consortia which are commonly
Robert Czajkowski et al.
Acta biochimica Polonica, 56(1), 1-16 (2009-03-17)
Many Gram-positive and Gram-negative bacteria communicate using small diffusible signal molecules called autoinducers. This process, known as quorum sensing (QS), links cell density to the expression of genes as diverse as those associated with virulence factors production of plant and

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