N-Heptanoyl-DL-homoserine lactone

Base Information

• Chemical Name: N-Heptanoyl-DL-homoserine lactone
• CAS No.: 106983-26-0
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.277
• Hs Code.: 2932209090
• ChEMBL ID: CHEMBL488749
• DSSTox Substance ID: DTXSID30407866
• Metabolomics Workbench ID: 138693
• Nikkaji Number: J1.006.263B
• Mol file: 106983-26-0.mol

Synonyms:N-Heptanoyl-DL-homoserine lactone;106983-26-0;N-(2-oxooxolan-3-yl)heptanamide;N-(2-Oxotetrahydrofuran-3-yl)heptanamide;CHEMBL488749;SCHEMBL12341630;DTXSID30407866;Homoserine lactone, N-heptanoyl-;FTMZLSDESAOPSZ-UHFFFAOYSA-N;MFCD01862914;HY-115393;CS-0083194;Heptanamide, N-(tetrahydro-2-oxo-3-furanyl)-;N-Heptanoyl-DL-homoserine lactone, >=97.0% (HPLC);82FBC7F8-02FF-4811-BF33-57EA6A9E9A17

Chemical Property of N-Heptanoyl-DL-homoserine lactone

Chemical Property:

• PSA: 55.40000
• LogP: 1.77940
• Storage Temp.: −20°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 228

Purity/Quality:

98.5% ^*data from raw suppliers

N-Heptanoyl-DL-homoserine lactone ≥97.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(=O)NC1CCOC1=O

Technology Process of N-Heptanoyl-DL-homoserine lactone

There total 10 articles about N-Heptanoyl-DL-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%

α-amino-γ-butyrolactone hydrobromide (6305-38-0) + Heptanoic acid chloride (2528-61-2) → (+/-)-N-heptanoyl-homoserine lactone (106983-26-0,177158-20-2)

Guidance literature:

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

DOI:10.1016/j.bmc.2012.06.007

Reference yield: 81.0%

→ N-heptanoyl-L-homoserine lactone (106983-26-0,177158-20-2)

Guidance literature:

Reference yield: 64.0%

oenanthic acid (111-14-8) + α-amino-γ-butyrolactone hydrobromide (6305-38-0) → (+/-)-N-heptanoyl-homoserine lactone (106983-26-0,177158-20-2)

Guidance literature:

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

DOI:10.1021/jf050586e

upstream raw materials:

oenanthic acid

α-amino-γ-butyrolactone hydrobromide

Heptanoic acid chloride

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

Refernces

• 1、 Syrpas, Michail,Ruysbergh, Ewout,Stevens, Christian V.,De Kimpe, Norbert,Mangelinckx, Sven. "Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators". . p. 2539 - 2549. Retrieved 2014.
• 2、 Sabbah, Mohamad,Fontaine, Fanny,Grand, Lucie,Boukraa, Mohamed,Efrit, Mohamed L.,Doutheau, Alain,Soulere, Laurent,Queneau, Yves. "Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators". scheme or table. p. 4727 - 4736. Retrieved 2012/08/29.