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68224

N-Dodecanoyl-L-homoserine lactone

Name: <I>N</I>-Dodecanoyl-<SC>L</SC>-homoserine lactone
Brand: SIGMA

≥96% (HPLC), suitable for mass spectrometry (MS)

Synonym(s):

N-Lauroyl-L-homoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide, C12-HSL

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₉NO₃

CAS Number:

137173-46-7

Molecular Weight:

283.41

NACRES:

NA.28

PubChem Substance ID:

329760775

UNSPSC Code:

12352211

MDL number:

MFCD11976890

Beilstein/REAXYS Number:

9281984

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Product Name

N-Dodecanoyl-L-homoserine lactone, ≥96% (HPLC)

Quality Level

100

assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -25±5°, c = 0.2 in methanol

technique(s)

mass spectrometry (MS): suitable

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

storage temp.

−20°C

SMILES string

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

InChI

1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

InChI key

WILLZMOKUUPJSL-AWEZNQCLSA-N

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Related Categories

Chemistry & Biochemicals

Biochemicals

Cell Culture Supplements & Reagents

Amino Acids – Building Blocks of Life Science

Biochem/physiol Actions

N-Dodecanoyl-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

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Identification of extracellular N-acylhomoserine lactone acylase from a Streptomyces sp. and its application to quorum quenching.

Sun-Yang Park et al.

Applied and environmental microbiology, 71(5), 2632-2641 (2005-05-05)

N-acylhomoserine lactones (AHLs) play an important role in regulating virulence factors in pathogenic bacteria. Recently, the enzymatic inactivation of AHLs, which can be used as antibacterial targets, has been identified in several soil bacteria. In this study, strain M664, identified

Detection, purification and characterisation of quorum-sensing signal molecules in plant-associated bacteria.

G Brelles-Mariño et al.

Journal of biotechnology, 91(2-3), 197-209 (2001-09-22)

Quorum sensing (also called autoinduction) is a term that describes an environmental sensing system that allows bacteria to monitor their own population density. Autoinduction relies upon the interaction of a small diffusible signal molecule (the autoinducer) with a transcriptional activator

Identification of Unanticipated and Novel N-Acyl L-Homoserine Lactones (AHLs) Using a Sensitive Non-Targeted LC-MS/MS Method.

Nishaben M Patel et al.

PloS one, 11(10), e0163469-e0163469 (2016-10-06)

N-acyl L-homoserine lactones (AHLs) constitute a predominant class of quorum-sensing signaling molecules used by Gram-negative bacteria. Here, we report a sensitive and non-targeted HPLC-MS/MS method based on parallel reaction monitoring (PRM) to identify and quantitate known, unanticipated, and novel AHLs

Role of RpoS in stress resistance, quorum sensing and spoilage potential of Pseudomonas fluorescens.

Xiaoxiang Liu et al.

International journal of food microbiology, 270, 31-38 (2018-02-23)

Microorganism activities are considered the main cause of most food spoilage, leading to great economic losses. Pseudomonas fluorescens is a Gram-negative bacterium that is widely found in food and has high spoilage activity. RpoS is considered an important global regulator

Cytotoxicity of N-dodecanoyl-Lhomoserine lactone and 5-N-dodecyl resorcinol to human granulocytes and monocytes: a comparative study.

Sviridova, T. et al.

Central European Journal of Immunology, 38, 310-316 (2013)

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Global Trade Item Number

SKU	GTIN
BP266	04061835269457
PHR1714-1G	04061834801948
N4128-250MG	04061834116455
N4128-50MG	04061832851006
1469005-200MG	04061838737182
Y0000522	04061833803936
46525-250MG	04061834245537
N1200000	04061834107019
N4128-5G	04061834116462
N4128-1G	04061834116448
68224-50MG	04061832464015
68224-10MG	04061832754949

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