3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide

Base Information

• Chemical Name: 3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide
• CAS No.: 177158-19-9
• Molecular Formula: C18H31NO4
• Molecular Weight: 325.44300
• European Community (EC) Number: 631-498-3
• DSSTox Substance ID: DTXSID101346604
• Nikkaji Number: J767.323J
• Wikidata: Q27157780
• Metabolomics Workbench ID: 78431
• ChEMBL ID: CHEMBL8463
• Mol file: 177158-19-9.mol

Synonyms:177158-19-9;N-(3-Oxotetradecanoyl)-L-homoserine lactone;3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide;N-3-oxo-tetradecanoyl-L-Homoserine lactone;3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide;CHEMBL8463;CHEBI:84459;Tetradecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-;N-(3-oxo-tetradecanoyl)-homoserine lactone;N-(3-OXOTETRADECANOYL)-L-HOMOSERINE LACT;3-oxo-C14-HSL;3OC14-HSL;3O-C14-HSL;SCHEMBL3145030;YQFJJDSGBAAUPW-INIZCTEOSA-N;DTXSID101346604;HMS3648C04;BDBM50351510;LMFA08030015;MFCD12912433;AKOS040755768;N-3-Oxomyristoyl-L-homoserine lactone;N-3-oxo-Myristoyl-L-Homoserine lactone;N-3-Oxotetradecanoyl-L-homoserine lactone;PD021251;HY-116536;CS-0065798;N-(1,3-Dioxotetradecyl)-L-homoserine lactone;SR-01000946348;SR-01000946348-1;Q27157780;3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]tetradecanamide;K4G

Chemical Property of 3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide

Chemical Property:

• PSA: 72.47000
• LogP: 3.68910
• Storage Temp.: −20°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 325.22530847
• Heavy Atom Count: 23
• Complexity: 381

Purity/Quality:

98.5% ^*data from raw suppliers

N-3-Oxo-tetradecanoyl-L-homoserine lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(=O)CC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• Uses: 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 the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn, inhibits biofilm formation. N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-Oxo-C14-HSL), a member of a family of acyl homoserine lactones, may be used to determine its mechanisms and specificity of action as a signaling molecule involved in the regulation of bacterial quorum sensing.

Technology Process of 3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide

There total 17 articles about 3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide 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: 87.0%

(S)-N-(2-oxotetrahydrofuran-3-yl)-2-(2-undecyl-1,3-dioxolan-2-yl)acetamide (182359-63-3) → N-(3-oxotetradecanoyl)-L-homoserine lactone (177158-19-9)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.04.059

Reference yield: 62.0%

→ N-(3-oxotetradecanoyl)-L-homoserine lactone (177158-19-9)

Guidance literature:

Reference yield:

methyl 2-(2-undecyl-1,3-dioxolan-2-yl)acetate → N-(3-oxotetradecanoyl)-L-homoserine lactone (177158-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol / 6 h

With sodium hydroxide; In methanol;

DOI:10.1021/ja0530321

upstream raw materials:

L-homoserine lactone hydrochloride

5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

2-(2-undecyl-1,3-dioxolan-2-yl)acetic acid

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Refernces

• 1、 Hodgkinson, James T.,Galloway, Warren R.J.D.,Casoli, Mariangela,Keane, Harriet,Su, Xianbin,Salmond, George P.C.,Welch, Martin,Spring, David R.. "Robust routes for the synthesis of N-acylated-l-homoserine lactone (AHL) quorum sensing molecules with high levels of enantiomeric purity". . p. 3291 - 3294. Retrieved 2011/06/28.
• 2、 Pomini, Armando M.,Marsaioli, Anita J.. "Absolute configuration and antimicrobial activity of acylhomoserine lactones". experimental part. p. 1032 - 1036. Retrieved 2009/04/06.