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Key Documents

09945

Sigma-Aldrich

N-Butyryl-DL-homoserine lactone

≥96.0% (HPLC)

Synonym(s):

N-(tetrahydro-2-oxo-3-furanyl)-Butanamide

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About This Item

Empirical Formula (Hill Notation):
C8H13NO3
CAS Number:
Molecular Weight:
171.19
Beilstein:
6375
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

Assay

≥96.0% (HPLC)

form

powder or crystals

color

white to faint beige

SMILES string

CCCC(=O)NC1CCOC1=O

InChI

1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)

InChI key

VFFNZZXXTGXBOG-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

N-Butyryl-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.

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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Longyi Lv et al.
Journal of hazardous materials, 354, 72-80 (2018-05-08)
Quorum sensing (QS) signalling has been extensively studied in single species populations, activated sludge, biofilm and aerobic granular sludge. However, ecological roles of QS in anaerobic granular sludge, particularly in the content of the relationship between QS signalling and microbial
Tomohiro Morohoshi et al.
FEMS microbiology letters, 279(1), 124-130 (2008-01-08)
In tests, Chromobacterium violaceum ATCC 12472 produced several N-acyl-L-homoserine lactones (AHLs). Of these, N-(3-hydroxydecanoyl)-L-homoserine lactone was dominant, and controlled violacein production by quorum sensing. Strain VIR07, an AHL-deficient mutant, did not produce violacein. Violacein production in VIR07 was induced by
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.
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
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

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