2577-46-0

Basic information

• Product Name: Methyl L-isoleucinate
• Synonyms: methyl L-isoleucinate;(3S)-3-Methyl-L-norvaline methyl ester;(3S)-L-Isoleucine methyl ester;L-Isoleucine methyl;(2S,3S)-methyl 2-amino-3methylpentanoate;(2S,3S)-2-Amino-3-methylpentanoic acid methyl ester
• CAS NO: 2577-46-0
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.2
• EINECS: 219-931-0
• Mol File: 2577-46-0.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 169.203 °C at 760 mmHg
• Flash Point: 42.685 °C
• Appearance: /
• Density: 0.955 g/cm³
• Vapor Pressure: 1.56mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: 2-8°C
• PKA: 7.98±0.39(Predicted)
• CAS DataBase Reference: Methyl L-isoleucinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-isoleucinate(2577-46-0)
• EPA Substance Registry System: Methyl L-isoleucinate(2577-46-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2577-46-0(Hazardous Substances Data)

Usage

Description

Methyl L-isoleucinate, also known as (2S,3S)-Methyl 2-Amino-3-methylpentanoate, is an organic compound derived from the amino acid L-isoleucine. It is characterized by its unique chemical structure, which includes a methyl group and an amino group attached to a branched-chain carbon skeleton. Methyl L-isoleucinate is known for its potential applications in various industries due to its versatile properties.

Uses

Used in the Chemical Industry:
Methyl L-isoleucinate is used as a building block for the synthesis of various chemical compounds, such as polymers and pharmaceuticals. Its unique structure allows it to be a valuable component in the development of new materials with specific properties.
Used in the Polymer Industry:
Methyl L-isoleucinate is used as a monomer in the preparation method of polybutylene succinate. This application takes advantage of its ability to form polymers with desirable characteristics, such as biodegradability and mechanical strength, making it a promising candidate for sustainable and eco-friendly materials.

InChI:InChI=1/C7H15NO2/c1-4-5(2)6(8)7(9)10-3/h5-6H,4,8H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 319-78-8 D-Isoleucine 
• 1356449-88-1 calyxamide B 
• 73-32-5 L-isoleucine 
• 17901-01-8 N-(tert-butoxycarbonyl)isoleucine methyl ester 
• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 610800-47-0 (2S,3S)-methyl 3-methyl-2-(4-nitrophenylsulphonamido)pentanoate 
• 1169571-12-3 aspereline A 
• 1169571-13-4 aspereline B 
• 1169571-14-5 aspereline C 
• 1169571-16-7 aspereline E 
• 1169571-17-8 aspereline F 
• 1356449-87-0 calyxamide A 
• 1420846-00-9 metatacarboline G 

Downstream Products

• 78569-25-2 Z-L-Leu-D-Ileu-OH 
• 20807-11-8 ((benzyloxy)carbonyl)glycyl-L-isoleucine 
• 27482-73-1 ZTyrIleOMe 
• 5254-68-2 N-(N,O-bis-benzyloxycarbonyl-L-tyrosyl)-L-isoleucine methyl ester 
• 122242-36-8 S-benzyl-N-benzyloxycarbonyl-L-cysteinyl=>L-phenylalanyl=>L-isoleucine methyl ester 
• 86961-90-2 S-benzyl-N-benzyloxycarbonyl-cysteinyl=>tyrosyl=>isoleucine methyl ester 
• 102320-12-7 N-(O-acetyl-N-formyl-L-tyrosyl)-L-isoleucine methyl ester 
• 42537-96-2 N-(N-benzyloxycarbonyl-L-leucyl)-L-isoleucine 
• 121467-96-7 S-benzyl-N-(toluene-4-sulfonyl)-cysteinyl=>tyrosyl=>isoleucine methyl ester 
• 14445-54-6 L-isoleucinamide 
• 1948-78-3 DL-isoleucine hydroxyamide 
• 59189-00-3 N-carbobenzyloxy-L-tryptophanyl-L-isoleucine methyl ester 
• 4817-98-5 Z-Leu-Ile-OMe 
• 4474-95-7 N-(benzyloxycarbonyl)-L-phenylalanyl-L-isoleucine methyl ester 

Relevant articles and documents

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

Cleavable Amide Bond: Mechanistic Insight into Cleavable 4-Aminopyrazolyloxy Acetamide at Low pH

The cleavage of amide bonds under mild acidic conditions is a rare chemical event. N-Acetamide bond of peptides is extremely stable even under the strongest organic acid trifluoromethanesulfonic acid. This report mechanistically describes a new cleavable amide bond in 4-aminopyrazolyloxy acetamide peptide analogues under mild acidic conditions such as trifluoroacetic acid (10-20%) or HCl (0.1-4.0 N) at room temperature, and the formation of unusual lactam from 4-aminopyrazolyloxy acetic acid after evaporation of solvent. This is a rare chemical event in peptide bond, which could be explored as acid-sensitive protecting group of free amines.

Heterocyclic Compounds from the Mushroom Albatrellus confluens and Their Inhibitions against Lipopolysaccharides-Induced B Lymphocyte Cell Proliferation

Eight hetereocyclic compounds conflamides B-I with an unprecedented skeleton and their precursor conflamide A were isolated from the mushroom Albatrellus confluens. Their structures and absolute configurations were determined by use of NMR studies, total synthesis, and calculated ECD spectra. Conflamides D and E were found to exhibit potent inhibition against LPS-induced B lymphocyte cell proliferation with IC50 values 1.48 and 5.71 μM, respectively.