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Key Documents

17248

Sigma-Aldrich

N-Decanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Synonym(s):

N-(tetrahydro-2-oxo-3-furanyl)-Decanamide

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About This Item

Empirical Formula (Hill Notation):
C14H25NO3
CAS Number:
Molecular Weight:
255.35
Beilstein:
1644700
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

product name

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

Assay

≥97.0% (HPLC)

form

powder

color

white

mp

111-114 °C

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

CCCCCCCCCC(=O)NC1CCOC1=O

InChI

1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)

InChI key

TZWZKDULKILUPV-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

N-Decanoyl-DL-homoserine lactone (N-C10-HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-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-Decanoyl-DL-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 are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

Packaging

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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