N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide

Base Information

• Chemical Name: N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide
• CAS No.: 147852-83-3
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• DSSTox Substance ID: DTXSID101346642
• Nikkaji Number: J533.611B
• Wikidata: Q27461124
• Metabolomics Workbench ID: 119478
• Mol file: 147852-83-3.mol

Synonyms:C6-AHL;HHL-serine;N-hexanoyl-L-homoserine lactone

Chemical Property of N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132-134 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 434.039oC at 760 mmHg
• PKA: 15.03±0.20(Predicted)
• Flash Point: 216.299oC
• PSA: 55.40000
• Density: 1.082g/cm3
• LogP: 1.38930
• Storage Temp.: ?20°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 199.12084340
• Heavy Atom Count: 14
• Complexity: 215

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Hexanoyl-L-homoserine lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCC(=O)N[C@H]1CCOC1=O
• Description: Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-hexanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism. The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.
• Uses: Hexanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Rhizobium leguminosarum. Hexanoyl-L-homoserine lactone and other acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains.

Technology Process of N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide

There total 3 articles about N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

α-amino-γ-butyrolactone hydrobromide (6305-38-0) + Hexanoyl chloride (142-61-0) → (+/-)-N-hexanoyl-homoserine lactone (18627-35-5,147852-83-3,106983-28-2)

Guidance literature:

With pyridine; In chloroform; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.06.007

Reference yield: 54.0%

α-amino-γ-butyrolactone hydrobromide (6305-38-0) + hexanoic acid (142-62-1) → (+/-)-N-hexanoyl-homoserine lactone (18627-35-5,147852-83-3,106983-28-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In water; at 20 ℃; for 24h;

DOI:10.1021/jf050586e

Reference yield:

→ (+/-)-N-hexanoyl-homoserine lactone (18627-35-5,147852-83-3,106983-28-2)

Guidance literature:

2-Amino-4-butyrolacton*HBr, Hexanoylchlorid;

upstream raw materials:

α-amino-γ-butyrolactone hydrobromide

hexanoic acid

Hexanoyl chloride

Downstream raw materials:

N-hexanoyl-methionine

Refernces

• 1、 -. "ACYL HOMOSERINE LACTONES FOR INHIBITION OF CELL GROWTH". Page/Page column 9-10. . Retrieved 2008/06/13.