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

Base Information

• Chemical Name: N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide
• CAS No.: 67605-85-0
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.195
• DSSTox Substance ID: DTXSID30435962
• Nikkaji Number: J533.613I
• Wikidata: Q27461123
• Metabolomics Workbench ID: 70788
• ChEMBL ID: CHEMBL207316
• Mol file: 67605-85-0.mol

Synonyms:BHL-serine;C(4)-HSL;C4-HSL;N-butanoyl-L-homoserine lactone;N-butyryl-L-homoserine lactone;N-butyrylhomoserine lactone

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120-123 °C
• Refractive Index: 1.476
• Boiling Point: 428.06 °C at 760 mmHg
• PKA: 14.78±0.20(Predicted)
• Flash Point: 212.683 °C
• PSA: 55.40000
• Density: 1.131g/cm³
• LogP: 0.60910
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.08954328
• Heavy Atom Count: 12
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

N-butyryl-L-Homoserine lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCC(=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. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. 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-butyryl-L-Homoserine lactone is a quorum-sensing signaling molecule produced by P. aeruginosa. It induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 μM. N-butyryl-L-Homoserine lactone (50 μM) induces rhamnolipid accumulation in P. aeruginosa growth media.
• Uses: Butyryl-L-homoserine lactone is a short acylhomoserine lactone isolated from Pseudomonas aeruginosa in 1995 and demonstrated to be a quorum sensing modulator in biofilms. 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 shorterchains displaying opposing actions to the longer chains. N-butyryl-L-Homoserine lactone is a diffusable quorum sensing lactone.

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

There total 2 articles about N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 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:

α-amino-γ-butyrolactone hydrobromide (6305-38-0) → N-butyryl-DL-homoserine lactone (67605-85-0,98426-48-3)

Guidance literature:

With water; sodium carbonate; anschliessend Behandeln mit Buttersaeure-anhydrid;

Reference yield:

→ N-butyryl-DL-homoserine lactone (67605-85-0,98426-48-3)

Guidance literature:

Reference yield: 48.2%

N-butyryl-DL-homoserine lactone (67605-85-0,98426-48-3) → N-(2-oxo-tetrahydro-furan-3-yl)-selenobutyramide (1268997-95-0)

Guidance literature:

With woollins’ reagent; In toluene; Inert atmosphere; Reflux;

upstream raw materials:

α-amino-γ-butyrolactone hydrobromide

Downstream raw materials:

N-(2-oxo-tetrahydro-furan-3-yl)-selenobutyramide

Refernces