39994-75-7

Basic information

• Product Name: Methyl L-threoninate hydrochloride
• Synonyms: L-threonineamide;H-Thr-OMe·HCl(oil);L-Threonine methyl ester hydrochloride, 98+%;L-Threonine methyl e;(2S,3R)-Methyl 2-aMino-3-hydroxybutanoate hydrochloride;H-Thr-OMe.Hcl (L-Threonine methyl ester hcl);H-Thr-OMe·HCl (yellowish oil);L-Threonine methyl ester hydrochloride≥ 98% (HPLC)
• CAS NO: 39994-75-7
• Molecular Formula: C₅H₁₁NO₃*ClH
• Molecular Weight: 169.61
• EINECS: 254-738-5
• Product Categories: Aromatic Esters;Amino Acids;Threonine [Thr, T];Amino Acids and Derivatives;Amino hydrochloride;Peptide Synthesis;Amino Acid Derivatives;Amino Acids;I - ZPeptide Synthesis;Modified Amino Acids;Threonine
• Mol File: 39994-75-7.mol

Chemical Properties

• Melting Point: 64 °C
• Boiling Point: 238.6 °C at 760 mmHg
• Flash Point: 98.1 °C
• Appearance: White/Powder
• Vapor Pressure: 0.000687mmHg at 25°C
• Storage Temp.: −20°C
• Water Solubility: Soluble in water.
• Sensitive: Moisture Sensitive & Hygroscopic
• BRN: 3562717
• CAS DataBase Reference: Methyl L-threoninate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-threoninate hydrochloride(39994-75-7)
• EPA Substance Registry System: Methyl L-threoninate hydrochloride(39994-75-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 39994-75-7(Hazardous Substances Data)

Usage

Uses

Used in Feed and Food Industry:
Methyl L-threoninate hydrochloride is used as a feed and food additive for [application reason] to enhance the nutritional value of animal feed and human food products. It helps in the growth and development of livestock and contributes to the overall health and well-being of animals.
Used in Pharmaceutical and Biotechnology Applications:
Methyl L-threoninate hydrochloride is used as an essential component in the synthesis of various pharmaceuticals and biotechnological products for [application reason] its role in the formation of important proteins in the human body, such as hemoglobin and insulin.
Used in Research and Development:
Methyl L-threoninate hydrochloride is used as a research compound for [application reason] to study its properties and potential applications in various fields, including pharmaceuticals, biotechnology, and nutrition.
Used in Nutritional Supplements:
Methyl L-threoninate hydrochloride is used as an ingredient in nutritional supplements for [application reason] to provide the body with the essential amino acid L-Threonine, which is vital for various physiological processes and overall health.

InChI:InChI=1/C5H11NO3.ClH/c1-3(7)4(6)5(8)9-2;/h3-4,7H,6H2,1-2H3;1H/t3?,4-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 24830-94-2 D-allo-threonine 
• 72-19-5 L-threonine 
• 60538-19-4 N-(tert-butoxycarbonyl)-l-threonine methyl ester 
• 1447695-69-3 cycloforskamide 
• 3373-59-9 L-threonine methyl ester 
• 75-36-5 acetyl chloride 
• 72-19-5 DL-threonine 
• 60143-52-4 DL-threonine hydrochloride 
• 72-19-5 rac-allo-threonine 
• 60143-52-4 DL-aThr*HCl 
• 28954-12-3 (2S,3S)-2-amino-3-hydroxybutanoic acid 
• 1487-49-6 3-hydroxybutyric acid methyl ester 
• 72-19-5 D-threonine 

Downstream Products

• 69568-63-4 tert.-Butyloxycarbonyl-L-threoninhydrazid 
• 49705-91-1 Z-Ile-Thr-OMe 
• 17896-55-8 Z(OMe)-Leu-Thr-OMe 
• 17462-42-9 N^ε-Benzyloxycarbonyl-N^α-pelargonoyl-L-lysin-L-threonin-methylester 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 130740-27-1 N-diphenylmethylene-L-threonine methyl ester 
• 60538-19-4 N-(tert-butoxycarbonyl)-l-threonine methyl ester 
• 22325-27-5 4,6-dimethyl-2-meraptopyrimidine 
• 74481-55-3 methyl (2S,3R)-3-hydroxy-2-triphenylmethylaminobutanoate 
• 132776-34-2 O-tert-Butyl-L-threonine Methyl Ester p-Toluenesulfonate 
• 102410-47-9 Pic(3-OBzl)-Thr-OMe 
• 73116-15-1 N-Z-O-tert-butyl-L-tyrosyl-L-threonine methyl ester 
• 83791-43-9 methyl (4S,5R)-5-methyl-2-carbonyloxazolidine-4-carboxylate 
• 196862-32-5 methyl (2S,3R)-2-(benzylamino)-3-hydroxybutanoate 

Relevant articles and documents

Stereoselective cycloaddition of monosubstituted ketene to a methyl glyoxylate- and threonine-derived imine: Synthesis of optically pure β-lactamic α-amino ester with high functionality

The reaction of chloroacetyl chloride and triethylamine with a chiral imine derived from the combination of methyl glyoxylate and protected L-threonine gave two optically active α-amino acid derivatives with a cis-substituted β-lactam skeleton in a 72:28 ratio. The major product is obtained in 59% yield by simple crystallisation.

(2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative as well as preparation method and application thereof

The invention discloses a (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative shown as a formula (I) or an optical isomer, a diastereomer and racemate mixture and pharmaceutically acceptable salt thereof as well as a preparation method and application of the (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative. It is shown by comparison of results of a positive control group and a model group on lymphedema prevention experiments that the compound disclosed in the invention shows obvious anti-edema activity.

NOVEL COMPOUNDS AND THEIR USE

The present invention provides compounds of the general formula (I) or a pharmaceutically acceptable prodrugs, salts and/or solvates thereof, wherein LHS is selected from the group consisting of LHSa and LHSb And wherein, the asterisk (*) marks the point of attachment; These compounds exhibit antibacterial activity against Gram-negative and Gram-positive bacteria, especially S. aureus, E. coli, K. pneumoniae and A. baumannii. Pharmaceutical compositions containing these compounds, therapeutic uses thereof and methods for manufacturing the same are also provided.

Bicyclic Lactams Derived from Serine or Cysteine and 2-Methylpropanal

Bicyclic lactams may be prepared from serine or cysteine and 2-methylpropanal; the resulting S, N -heterocycles are more stable than the corresponding O, N -heterocycles but both are synthetic intermediates capable of further elaboration.

A Novel N-Substituted Valine Derivative with Unique Peroxisome Proliferator-Activated Receptor γbinding Properties and Biological Activities

A proprietary library of novel N-Aryl-substituted amino acid derivatives bearing a hydroxamate head group allowed the identification of compound 3a that possesses weak proadipogenic and peroxisome proliferator-Activated receptor γ(PPARI) activating properties. The systematic optimization of 3a, in order to improve its PPARγagonist activity, led to the synthesis of compound 7j (N-Aryl-substituted valine derivative) that possesses dual PPARI/PPARα agonistic activity. Structural and kinetic analyses reveal that 7j occupies the typical ligand binding domain of the PPARγagonists with, however, a unique high-Affinity binding mode. Furthermore, 7j is highly effective in preventing cyclin-dependent kinase 5-mediated phosphorylation of PPARγserine 273. Although less proadipogenic than rosiglitazone, 7j significantly increases adipocyte insulin-stimulated glucose uptake and efficiently promotes white-To-brown adipocyte conversion. In addition, 7j prevents oleic acid-induced lipid accumulation in hepatoma cells. The unique biochemical properties and biological activities of compound 7j suggest that it would be a promising candidate for the development of compounds to reduce insulin resistance, obesity, and nonalcoholic fatty liver disease.

Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile

Benzimidazole is an important pharmacophore for clinically active drugs against inflammation and treatment of pain, however, it is associated with gastrointestinal side effects. Here we synthesized benzimidazole based agents with significant analgesic/anti-inflammatory potential but with less gastrointestinal adverse effects. In this study, we synthesized novel, orally bioavailable 2-mercaptobenzimidazole amino acid conjugates (4a–4o) and screened them for analgesic, anti-inflammatory and gastro-protective effects. The synthesized 2-mercaptbenzimidazole derivatives were characterized for their structure using FTIR, 1H NMR and 13C NMR spectroscopic techniques. The 2-mercaptobenzimidazole amino acid conjugates have found to possess potent analgesic, anti-inflammatory and gastroprotective activities, particularly with compound 4j and 4k. Most of the compounds exhibited remarkable anti-ulcer and antisecretory effects. Molecular docking studies were carried out to study the binding affinities and interactions of the synthesized compounds with target proteins COX-2 (PDB ID: 3LN1) and H+/K+-ATPase (PDB ID: 5Y0B). Our results support the clinical promise of these newly synthesized 2-mercaptobezimidazol conjugates as a component of therapeutic strategies for inflammation and analgesia, for which the gastric side effects are always a major limitation.

Synthetic Access to 3-Substituted Pyroglutamic Acids from Tetramate Derivatives of Serine, Threonine, allo-Threonine, and Cysteine

A general route which provides direct access to pyroglutamates from tetramates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is reported. This work permits direct scaffold hopping from tetramate to substituted pyroglutamates. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria.

Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective.

L-threonine-linked dihydroartemisinin-fluoroquinolone conjugates, intermediates thereof, and preparation methods and uses of conjugates and intermediates

The invention discloses L-threonine-linked dihydroartemisinin-fluoroquinolone conjugates represented by formula I, intermediates represented by formula II, preparation methods of the compounds of formula I and formula II, and uses of the compounds of the formula I in the preparation of drugs for resisting mycobacterium tuberculosis or/and drugs for lowering blood lipids.

Polypeptide raw material N-fluorenylmethoxycarbonyl-O-tert-butyl threonine preparation method

The invention discloses a polypeptide raw material N-fluorenylmethoxycarbonyl-O-tert-butyl threonine preparation method, and mainly solves the technical problems of complexity, long cycle, more wastegas, waste water and industrial residues, high cost, high dangerousness and the like in an original process. The preparation method includes the steps: first, suspending threonine in methanol, reducing temperature, dropping thionyl chloride and then removing solvents by concentration after temperature reaction to obtain threonine methyl ester hydrochloride; second, dissolving the threonine methylester hydrochloride in methylene dichloride, leading in isobutene, concentrating sulfuric acid and performing sealed reaction treatment to obtain oily O-tert-butyl threonine methyl ester; third, dissolving the O-tert-butyl threonine methyl ester in water and acetone, adding sodium hydroxide, enabling pH (potential of hydrogen) to be 11-12, performing reaction to obtain O-tert-butyl threonine solution, adding 9-fluorenylmethyl-N-succinimidyl carbonate, maintaining the pH of 8-9 of a system by the aid of alkali liquor, performing washing acidification extraction after reaction and performing treatment to obtain N-fluorenylmethoxycarbonyl-O-tert-butyl threonine serving as a final product.