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857523P

Avanti

N-Tetradecanoyl-L-homoserine lactone

Avanti Research™ - A Croda Brand

Synonym(s):

(S)-N-(2-Oxotetrahydrofuran-3-yl)tetradecanamide

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About This Item

Empirical Formula (Hill Notation):
C18H33NO3
CAS Number:
202284-87-5
Molecular Weight:
311.46
UNSPSC Code:
12352211
NACRES:
NA.25

description

(S)-N-(2-Oxotetrahydrofuran-3-yl)tetradecanamide

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (857523P-10MG)
pkg of 1 × 50 mg (857523P-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(CCCCCCCCCCCCC)=O

General description

N-Tetradecanoyl-L-homoserine lactone/C14-HSL is a N-acylhomoserine lactone (HSL). C14-HSL is a non-polar compound. All HSLs possess a homoserine lactone moiety and a fatty acyl group with varying carbon length ranging from 4 to 14 carbons. They also have either 3-oxo, 3-hydroxyl, or fully reduced methylene groups at the C-3 position.

Biochem/physiol Actions

N-acylhomoserine lactones derivatives (HSLs) are produced and utilized by Gram negative bacteria as signaling molecules, to invade and colonize higher organisms. It is a quorum sensing signaling molecule commonly modulates cell density-dependent regulatory mechanisms.

Packaging

5 mL Amber Glass Screw Cap Vial (857523P-10MG and 857523P-50MG)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

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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Acyl homoserine lactone-based quorum sensing in a methanogenic archaeon.
Zhang G, et al.
The ISME Journal, 6(7), 1336-1336 (2012)
Occurrence of N-acyl-L-homoserine lactones in extracts of some Gram-negative bacteria evaluated by gas chromatography-mass spectrometry.
Cataldi TRI, et al.
Analytical biochemistry, 361(2), 226-235 (2007)
The hydrolysis of unsubstituted N-acylhomoserine lactones to their homoserine metabolites: Analytical approaches using ultra performance liquid chromatography.
Englmann M, et al.
Journal of Chromatography A, 1160(1-2), 184-193 (2007)

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