N-undecanoyl-L-Homoserine lactone

Base Information

• Chemical Name: N-undecanoyl-L-Homoserine lactone
• CAS No.: 216596-71-3
• Molecular Formula: C15H27NO3
• Molecular Weight: 269.38000
• DSSTox Substance ID: DTXSID701025436
• Nikkaji Number: J1.358.126F
• ChEMBL ID: CHEMBL9031
• Mol file: 216596-71-3.mol

Synonyms:N-undecanoyl-L-Homoserine lactone;216596-71-3;N-[(3S)-2-Oxooxolan-3-yl]undecanamide;N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE;N-[(3S)-Tetrahydro-2-oxo-3-furanyl]undecanamide;CHEMBL9031;C11-HSL;SCHEMBL3985513;YAWJNUREPGJHSG-ZDUSSCGKSA-N;DTXSID701025436;MFCD11976916;AKOS040756095;HY-114773;CS-0064287;J-014215

Chemical Property of N-undecanoyl-L-Homoserine lactone

Chemical Property:

• PSA: 55.40000
• LogP: 3.33980
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 269.19909372
• Heavy Atom Count: 19
• Complexity: 279

Purity/Quality:

97% ^*data from raw suppliers

N-undecanoyl-L-Homoserine lactone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCCCCCCC(=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. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C11-HSL possesses a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in P. aeruginosa strains.

Technology Process of N-undecanoyl-L-Homoserine lactone

There total 1 articles about N-undecanoyl-L-Homoserine lactone 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:

undecanoyl chloride (17746-05-3) + L-homoserine lactone hydrochloride (2185-03-7) → N-undecanoyl-L-homoserine lactone (216596-71-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jm020909n

upstream raw materials:

undecanoyl chloride

L-homoserine lactone hydrochloride

Refernces