106983-28-2

Basic information

• Product Name: N-CAPROYL-L-HOMOSERINE LACTONE
• Synonyms: N-CAPROYL-L-HOMOSERINE LACTONE;N-HEXANOYL-DL-HOMOSERINE LACTONE;n-caproyl-dl-homoserine lactone;N-(2-oxotetrahydrofuran-3-yl)hexanaMide;N-Hexanoyl-Dl-Homoserine Lactone(WXC03365)
• CAS NO: 106983-28-2
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• Mol File: 106983-28-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• BRN: 1640340
• CAS DataBase Reference: N-CAPROYL-L-HOMOSERINE LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CAPROYL-L-HOMOSERINE LACTONE(106983-28-2)
• EPA Substance Registry System: N-CAPROYL-L-HOMOSERINE LACTONE(106983-28-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 106983-28-2(Hazardous Substances Data)

Usage

Uses

Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.

Biochem/physiol Actions

N-Hexanoyl-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 and are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

Upstream product

• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 
• 142-61-0 Hexanoyl chloride 
• 142-62-1 hexanoic acid 

Downstream Products

• 21394-52-5 N-hexanoyl-methionine 

Relevant articles and documents

Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists.

Acyl-homoserine lactones from Erwinia psidii R. IBSBF 435T, a guava phytopathogen (Psidium guajava L.)

The phytopathogen Erwinia psidii R. IBSBF 435T causes rot in branches, flowers, and fruits of guava (Psidium guajava L.), being responsible for crop losses, and has no effective control. It was demonstrated that this strain produces two compounds [S-(-)-N-hexanoyl and N-heptanoyl-homoserine lactone], both belonging to the class of quorum-sensing signaling substances. A protocol using gas chromatography - flame ionization detection with chiral stationary phase is described for the absolute configuration determination of a natural acyl-homoserine lactone. Biological assays with specific reporter and synthesis of identified substances are also described. This is the first report on the N-heptanoyl-homoserine lactone occurrence in the Erwinia genus.