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Sigma-Aldrich

N-Hexanoyl-L-homoserine lactone

≥96% (HPLC)

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Synonym(s):
N-Caproyl-L-homoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]hexanamide, C6-HSL, HHL
Empirical Formula (Hill Notation):
C10H17NO3
CAS Number:
147852-83-3
Molecular Weight:
199.25
Beilstein:
8143287
MDL number:
MFCD12912260
PubChem Substance ID:
329758205

Assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -32±3°, c = 0.2 in methanol

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

storage temp.

−20°C

SMILES string

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

InChI

1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)/t8-/m0/s1

InChI key

ZJFKKPDLNLCPNP-QMMMGPOBSA-N

Related Categories

Biochem/physiol Actions

N-Hexanoyl-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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Orrapun Selamassakul et al.
Journal of food science, 85(3), 707-717 (2020-02-12)
This study evaluated the biological properties of peptides from brown rice protein hydrolyzed by bromelain (eb-RPH) in relation to flavor characteristic. The fractionation into peptides < 1 kDa was observed to improve the DPPH, ABTS, and hydroxyl radical-scavenging activities (0.19, 2.28, and
Xue Yang et al.
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E S W Jones et al.
South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde, 107(10), 887-891 (2017-10-13)
Non-adherence to antihypertensives is a cause of 'pseudo-treatment-resistant' hypertension. To determine whether monitoring plasma amlodipine concentrations and inhibition of angiotensin-converting enzyme (ACE) can be adjunct adherence tools. Patients with hypertension who were prescribed enalapril and amlodipine were enrolled. Blood pressures
S Torabi Delshad et al.
Journal of applied microbiology, 125(2), 356-369 (2018-04-26)
A variety of pathogens use quorum sensing (QS) to control the expression of their virulence factors. QS interference has hence been proposed as a promising antivirulence strategy. The specific aim of this study was to isolate bacteria from trout tissue
Jeng Yeong Chow et al.
Biochemistry, 48(20), 4344-4353 (2009-04-21)
The PLL(PTE-like lactonase)-group of enzymes within the amidohydrolase superfamily hydrolyze N-acyl-homoserine lactones (AHLs) that are involved in bacterial quorum-sensing pathways. These enzymes possess the (beta/alpha)(8)-barrel fold and serve as attractive templates for in vitro evolution and engineering of quorum-quenching biological
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