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51481

Sigma-Aldrich

N-(3-Hydroxy-tetradecanoyl)-DL-homoserin-lacton

≥96% (HPLC), carbon 64.7-67.3 %

Synonym(e):

3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)-tetradecanamid

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About This Item

Empirische Formel (Hill-System):
C18H33NO4
CAS-Nummer:
172670-99-4
Molekulargewicht:
327.46
MDL-Nummer:
MFCD16875425
UNSPSC-Code:
41116134
PubChem Substanz-ID:
329757696
NACRES:
NA.25

Qualitätsniveau

100

Assay

≥96% (HPLC)

Zusammensetzung

carbon, 64.7-67.3%
nitrogen, 4.0-4.5%

Lagertemp.

−20°C

SMILES String

CCCCCCCCCCCC(O)CC(=O)NC1CCOC1=O

InChI

1S/C18H33NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h15-16,20H,2-14H2,1H3,(H,19,21)

InChIKey

IKQUESGRCDRZTI-UHFFFAOYSA-N

Biochem./physiol. Wirkung

N-(3-Hydroxytetradecanoyl)-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; 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

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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
Chiara Cavaliere et al.
Toxins, 11(9) (2019-08-30)
Zearalenone (ZEN) is a nonsteroidal estrogenic mycotoxin produced by various Fusarium species and commonly occurring in corn and other cereals. Even though its acute toxicity is low, still the estrogenic activity of ZEN and metabolites is a matter of concern.
Tommaso R I Cataldi et al.
Journal of mass spectrometry : JMS, 43(1), 82-96 (2007-08-22)
A method for the comprehensive profiling of the N-acyl-homoserine lactone (AHL) family of bacterial quorum-sensing molecules is presented using liquid chromatography (LC) coupled to a hybrid quadrupole linear ion trap (LTQ) and Fourier-transform ion-cyclotron-resonance mass spectrometer (FTICR). We demonstrate an
Nicolas Kylilis et al.
Nature communications, 9(1), 2677-2677 (2018-07-12)
Advancing synthetic biology to the multicellular level requires the development of multiple cell-to-cell communication channels that propagate information with minimal signal interference. The development of quorum-sensing devices, the cornerstone technology for building microbial communities with coordinated system behaviour, has largely
M R Parsek et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(8), 4360-4365 (1999-04-14)
Acyl homoserine lactones (acyl-HSLs) are important intercellular signaling molecules used by many bacteria to monitor their population density in quorum-sensing control of gene expression. These signals are synthesized by members of the LuxI family of proteins. To understand the mechanism
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