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51481

Sigma-Aldrich

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

≥96% (HPLC), carbon 64.7-67.3 %

Sinonimo/i:

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

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139,00 €

About This Item

Formula empirica (notazione di Hill):
C18H33NO4
Numero CAS:
Peso molecolare:
327.46
Numero MDL:
Codice UNSPSC:
41116134
ID PubChem:
NACRES:
NA.25

139,00 €


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Saggio

≥96% (HPLC)

Composizione

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

Temperatura di conservazione

−20°C

Stringa SMILE

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)
IKQUESGRCDRZTI-UHFFFAOYSA-N

Azioni biochim/fisiol

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[1][2][3][4][5]. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs[3], and a research focus for the prevention of biofilm formation[6][7][8].
Quorum-sensing signal generation

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Pittogrammi

Skull and crossbones

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 3 Oral

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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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
Jonghyeon Shin et al.
Molecular systems biology, 16(3), e9401-e9401 (2020-03-07)
Synthetic genetic circuits offer the potential to wield computational control over biology, but their complexity is limited by the accuracy of mathematical models. Here, we present advances that enable the complete encoding of an electronic chip in the DNA carried

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