N-(3-Oxododecanoyl)homoserine lactone

Base Information

• Chemical Name: N-(3-Oxododecanoyl)homoserine lactone
• CAS No.: 152833-54-0
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.395
• DSSTox Substance ID: DTXSID00934614
• Nikkaji Number: J1.006.258F
• Wikidata: Q27110197
• Metabolomics Workbench ID: 138182
• ChEMBL ID: CHEMBL482476
• Mol file: 152833-54-0.mol

Synonyms:3-oxo-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide;3O-C12 autoinducer;N-(3-oxodecanoyl)homoserine lactone;N-3-oxodecanoyl homoserine lactone;PA autoinducer;Pseudomonas aeruginosa autoinducer

Chemical Property of N-(3-Oxododecanoyl)homoserine lactone

Chemical Property:

• Vapor Pressure: 6.85E-11mmHg at 25°C
• Boiling Point: 519.4°Cat760mmHg
• Flash Point: 267.9°C
• PSA: 75.96000
• Density: 1.06g/cm³
• LogP: 3.35830
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 297.19400834
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)CC(=O)NC1CCOC1=O

Technology Process of N-(3-Oxododecanoyl)homoserine lactone

There total 23 articles about N-(3-Oxododecanoyl)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: 90.0%

(S)-2-(2-nonyl-1,3-dioxolan-2-yl)-N-(2-oxotetrahydrofuran-3-yl)acetamide (182359-61-1) → N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0)

Guidance literature:

With perchloric acid; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/ejoc.201300084

Reference yield: 21.0%

3-oxo-dodecanoic acid (61058-75-1) + 3-deoxy-L-glycero-tetronolactone (19444-84-9,52079-23-9,56881-90-4,112709-14-5) → N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm500215s

Reference yield:

L-homoserine lactone hydrochloride (2185-03-7) + 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione (182359-65-5) → N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; Reflux;

DOI:10.1016/j.ejmech.2015.02.026

upstream raw materials:

3-oxo-dodecanoic acid

L-homoserine lactone

L-homoserine lactone hydrochloride

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

Downstream raw materials:

N-(3-hydroxy-dodecanoyl)-L-homoserine lactone

Refernces

• 1、 Yu, Bin,Liu, Haoyue,Kong, Xiaoyan,Chen, Xinli,Wu, Chunli. "Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation". . p. 500 - 511. Retrieved 2019/01/03.
• 2、 Ren, Jing-Li,Zhang, Xu-Yao,Yu, Bin,Wang, Xi-Xin,Shao, Kun-Peng,Zhu, Xiao-Ge,Liu, Hong-Min. "Discovery of novel AHLs as potent antiproliferative agents". . p. 321 - 329. Retrieved 2015/03/04.