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857521P

Avanti

N-Octanoyl-L-homoserine lactone

(S)-N-(2-Oxotetrahydrofuran-3-yl)octanamide, powder

Synonym(s):

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide, C8-HSL

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About This Item

Empirical Formula (Hill Notation):
C12H21NO3
CAS Number:
147852-84-4
Molecular Weight:
227.30
Beilstein/REAXYS Number:
8148282
MDL number:
MFCD11113139
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (857521P-10MG)
pkg of 1 × 50 mg (857521P-50MG)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

bacterial lipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1

InChI key

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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General description

N-Octanoyl-L-homoserine lactone (C8-HSL) is a N-acyl homoserine lactone (N-acyl-HSL). It is highly nonpolar.

Biochem/physiol Actions

N-Octanoyl-L-homoserine lactone (C8-HSL) is produced by many gram-negative bacteria like Pseudomonas fluorescens, Ralstonia solanacearum, Vibrio fischeri, and Yersinia pseudotuberculosis. In Escherichia coli, C8-HSL is encoded by the gene Ytb1. Generally, these homoserine lactones (HSLs) are quorum sensing signaling molecules. HSLs play a key role in biofilm formation. They function as an autoinducer molecule and involved in cell to cell communication depending on cell density population.
Quorum-sensing signal generation

Packaging

5 mL Amber Glass Screw Cap Vial (857521P-10MG and 857521P-50MG)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A hierarchical quorum-sensing system in Yersinia pseudotuberculosis is involved in the regulation of motility and clumping.
Atkinson S, et al.
Molecular Microbiology, 33(6), 1267-1277 (1999)
Characterization of N-acylhomoserine lactones produced by bacteria isolated from industrial cooling water systems.
Okutsu N, et al.
Sensors, 16(1), 44-44 (2016)
P D Shaw et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(12), 6036-6041 (1997-06-10)
Many Gram-negative bacteria regulate gene expression in response to their population size by sensing the level of acyl-homoserine lactone signal molecules which they produce and liberate to the environment. We have developed an assay for these signals that couples separation

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