Homoserine lactone

Base Information

• Chemical Name: Homoserine lactone
• CAS No.: 1192-20-7
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID00862589
• Nikkaji Number: J38.532H
• Wikidata: Q105222809
• Metabolomics Workbench ID: 78602
• Mol file: 1192-20-7.mol

Synonyms:homoserine lactone;homoserine lactone hydrobromide;homoserine lactone hydrochloride, (S)-isomer;homoserine lactone, (S)-isomer

Chemical Property of Homoserine lactone

Chemical Property:

• Vapor Pressure: 0.0148mmHg at 25°C
• Melting Point: 194 °C
• Boiling Point: 257.1oC at 760 mmHg
• PKA: 7.89±0.20(Predicted)
• Flash Point: 120.1oC
• PSA: 55.40000
• Density: 1.206g/cm3
• LogP: 5.06630
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 91.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Aminooxolan-2-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(=O)C1N

Technology Process of Homoserine lactone

There total 16 articles about 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: 78.6%

DL-methionine (59-51-8,26062-47-5,58576-49-1) → 2-aminobutyrolactone (1192-20-7)

Guidance literature:

With tetra-n-propylammonium bromide; 4-nitro-benzoyl chloride; In ethanol; water; at 90 ℃; for 7h; Reagent/catalyst;

Reference yield:

(±)-N-(3-oxooctanoyl)homoserine lactone (106983-27-1) → 4-butanolide (96-48-0) + n-pentyl methyl ketone (110-43-0) + 3-oxo-octanal (3223-40-3) + 3-oxooctanamide (768402-48-8) + 2-aminobutyrolactone (1192-20-7)

Guidance literature:

With Calibrin Z; at 25 ℃; for 0.5h; Reagent/catalyst; Temperature; Catalytic behavior;

DOI:10.1021/acs.jafc.7b03918

Reference yield:

2-(hydroxyimino)-γ-butyrolactone (5400-68-0) → 2-aminobutyrolactone (1192-20-7)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; water; Hydrogenation;

upstream raw materials:

α-bromo-γ-butyrolactone

(S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one

N-acetyl-(R,S)-2-amino-4-butyrolactone

2-(hydroxyimino)-γ-butyrolactone

Downstream raw materials:

2-Oxobutyric acid

(d)selenomethionine

(l)selenomethionine

2-Amino-4-bromo-butyric acid

Refernces

• 1、 Naik, Sajo P.,Scholin, Jonathon,Ching, San,Chi, Fang,Herpfer, Marc. "Quorum Sensing Disruption in Vibrio harveyi Bacteria by Clay Materials". . p. 40 - 44. Retrieved 2018/01/17.
• 2、 Shiraiwa, Tadashi,Miyazaki, Hideya,Ohta, Atsushi,Waki, Yukitaka,Yasuda, Masahiro,Morishita, Toshimitsu,Kurokawa, Hidemoto. "Optical resolution by preferential crystallization of (RS)-α-amino-γ-butyrolactone hydrochloride". . p. 2322 - 2325. Retrieved 2007/10/03.