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Merck
모든 사진(1)

주요 문서

10939

Sigma-Aldrich

N-Heptanoyl-DL-homoserine lactone

≥97.0% (HPLC)

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About This Item

실험식(Hill 표기법):
C11H19NO3
CAS Number:
Molecular Weight:
213.27
MDL number:
UNSPSC 코드:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

제품명

N-Heptanoyl-DL-homoserine lactone, ≥97.0% (HPLC)

Quality Level

분석

≥97.0% (HPLC)

양식

powder with small lumps

색상

white to faintly brown

저장 온도

−20°C

SMILES string

CCCCCCC(=O)NC1CCOC1=O

InChI

1S/C11H19NO3/c1-2-3-4-5-6-10(13)12-9-7-8-15-11(9)14/h9H,2-8H2,1H3,(H,12,13)

InChI key

FTMZLSDESAOPSZ-UHFFFAOYSA-N

애플리케이션

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

생화학적/생리학적 작용

N-Heptanoyl-DL-homoserine lactone (C7HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
N-Heptanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such asEcherichia 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.

포장

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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문서 라이브러리 방문

Armando M Pomini et al.
Journal of natural products, 71(6), 1032-1036 (2008-05-10)
(S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano
Detection of acyl-homoserine lactones by Escherichia and Salmonella.
Soares JA, Ahmer BM.
Current Opinion in Microbiology, 12, 188-193 (2011)
Frank Wilco Bartels et al.
Biophysical journal, 92(12), 4391-4400 (2007-03-27)
Intercellular communication by means of small signal molecules coordinates gene expression among bacteria. This population density-dependent regulation is known as quorum sensing. The symbiotic nitrogen-fixing bacterium Sinorhizobium meliloti Rm1021 possesses the Sin quorum sensing system based on N-acyl homoserine lactones
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
Leo Eberl
International journal of medical microbiology : IJMM, 296(2-3), 103-110 (2006-02-24)
The genus Burkholderia contains over 30 species, many of which are important human pathogens. In addition to the primary pathogens Burkholderia pseudomallei and Burkholderia mallei, several species have emerged as opportunistic pathogens in persons suffering from cystic fibrosis (CF) and

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