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07028

Sigma-Aldrich

N-Decanoyl-L-homoserine lactone

≥96% (HPLC)

Synonym(s):

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]decanamide, C10-HSL

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About This Item

Empirical Formula (Hill Notation):
C14H25NO3
CAS Number:
177315-87-6
Molecular Weight:
255.35
MDL number:
MFCD11113140
UNSPSC Code:
12352211
PubChem Substance ID:
329748327
NACRES:
NA.85

assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -24±3°, c = 0.2 in methanol

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

application(s)

cell analysis

storage temp.

−20°C

SMILES string

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

InChI

1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)/t12-/m0/s1

InChI key

TZWZKDULKILUPV-LBPRGKRZSA-N

Biochem/physiol Actions

N-Decanoyl-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, cell to cell communication among bacteria; for reviews see. 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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Jian Woon Chen et al.
Sensors (Basel, Switzerland), 13(10), 13217-13227 (2013-10-03)
In the bacteria kingdom, quorum sensing (QS) is a cell-to-cell communication that relies on the production of and response to specific signaling molecules. In proteobacteria, N-acylhomoserine lactones (AHLs) are the well-studied signaling molecules. The present study aimed to characterize the
M R Parsek et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(16), 8789-8793 (2000-08-02)
Recent advances in studies of bacterial gene expression have brought the realization that cell-to-cell communication and community behavior are critical for successful interactions with higher organisms. Species-specific cell-to-cell communication is involved in successful pathogenic or symbiotic interactions of a variety
Wen-Zhao Wang et al.
Applied and environmental microbiology, 78(22), 7985-7992 (2012-09-04)
N-acylhomoserine lactones (AHLs) are used as quorum-sensing (QS) signal molecules by many gram-negative bacteria. We have reported that Chryseobacterium sp. strain StRB126, which was isolated from the root surface of potato, has AHL-degrading activity. In this study, we cloned and
Yanan Cao et al.
Applied and environmental microbiology, 78(6), 1899-1908 (2012-01-17)
N-Acylated homoserine lactone (AHL) lactonases are capable of degrading signal molecules involved in bacterial quorum sensing and therefore represent a new approach to control bacterial infection. Here a gene responsible for the AHL lactonase activity of Bacillus sp. strain AI96
P D Shaw et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(12), 6036-6041 (1997-06-10)
Many Gram-negative bacteria regulate gene expression in response to their population size by sensing the level of acyl-homoserine lactone signal molecules which they produce and liberate to the environment. We have developed an assay for these signals that couples separation
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