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51481

Sigma-Aldrich

N-(3-Hydroxytetradecanoyl)-DL-homoserine lactone

≥96% (HPLC), carbon 64.7-67.3 %

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H33NO4
CAS Number:
172670-99-4
Molecular Weight:
327.46
MDL number:
MFCD16875425
UNSPSC Code:
41116134
PubChem Substance ID:
329757696
NACRES:
NA.25

Assay

≥96% (HPLC)

composition

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

storage temp.

−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)

InChI key

IKQUESGRCDRZTI-UHFFFAOYSA-N

Biochem/physiol Actions

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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.
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
Zhao Peng et al.
Archives of toxicology, 94(2), 573-588 (2019-12-19)
Deoxynivalenol (DON) cannot be totally removed due to its stable chemical characteristics and chronic exposure to low doses of DON causes significant toxic effects in humans and animals. However, the potential hazard of such low-dose exposure in target organs still
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