13057-65-3

Basic information

• Product Name: beta-(2-methoxyphenoxy)lactic acid
• Synonyms: beta-(2-methoxyphenoxy)lactic acid;2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid
• CAS NO: 13057-65-3
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.2
• Mol File: 13057-65-3.mol

Chemical Properties

• Boiling Point: 355.8°Cat760mmHg
• Flash Point: 139.8°C
• Appearance: /
• Density: 1.302 g/cm³
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: beta-(2-methoxyphenoxy)lactic acid(CAS DataBase Reference)
• NIST Chemistry Reference: beta-(2-methoxyphenoxy)lactic acid(13057-65-3)
• EPA Substance Registry System: beta-(2-methoxyphenoxy)lactic acid(13057-65-3)

Safety Data

• Hazardous Substances Data: 13057-65-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Beta-(2-methoxyphenoxy)lactic acid is used as an intermediate compound for the synthesis of various pharmaceutical products. Its role in the metabolism of Guaifenesin, a muscle relaxant and expectorant, makes it a valuable component in the development of medications targeting muscle relaxation and respiratory health.
Used in Metabolic Research:
As a metabolite of Guaifenesin, beta-(2-methoxyphenoxy)lactic acid is utilized in metabolic research to study the biotransformation processes of the parent compound. This research can provide insights into the metabolic pathways and potential therapeutic applications of Guaifenesin and its derivatives.
Used in Drug Development:
The unique chemical structure of beta-(2-methoxyphenoxy)lactic acid makes it a potential candidate for the development of new drugs with muscle relaxant and expectorant properties. Researchers can explore its potential in creating novel therapeutic agents that may offer improved efficacy and reduced side effects compared to existing treatments.

InChI:InChI=1/C10H12O5/c1-14-8-4-2-3-5-9(8)15-6-7(11)10(12)13/h2-5,7,11H,6H2,1H3,(H,12,13)

Synthetic route

sodium 2-methoxyphenolate (13052-77-2) + 3-chloro-2-hydroxypropanoic acid (1713-85-5) → CVT-4786 (13057-65-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Reflux;	74%

guaifenesin (93-14-1) → CVT-4786 (13057-65-3)

Conditions	Yield
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; for 0.0833333h; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; water; toluene at 50℃; for 24h; pH=6.8;	73%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In water; acetonitrile at 35℃; aq. phosphate buffer; chemoselective reaction;	37.4%

guaifenesin (93-14-1) → (2-methoxyphenoxy)acetic acid (1878-85-9) + CVT-4786 (13057-65-3)

Conditions	Yield
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; toluene at 50℃; for 24h; chemoselective reaction;	A 10 %Spectr. B 73%

2-methoxy-phenol (90-05-1) → CVT-4786 (13057-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil 2: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Reflux View Scheme

diazomethane (186581-53-3, 908094-01-9) + CVT-4786 (13057-65-3) → C11H14O5

Conditions	Yield
In methanol; diethyl ether	n/a

Upstream product

• 93-14-1 guaifenesin 
• 90-05-1 2-methoxy-phenol 
• 13052-77-2 sodium 2-methoxyphenolate 
• 1713-85-5 3-chloro-2-hydroxypropanoic acid 

Relevant articles and documents

PRODUCTION METHOD OF α-HYDROXYCARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide an efficient production method of an α-hydroxycarboxylic acid in a mild condition, and to provide a production method of a biodegradable plastic from a raw material containing the α-hydroxycarboxylic acid. SOLUTION: In a synthesis method of an α-hydroxycarboxylic acid, which is a production method of the α-hydroxycarboxylic acid by oxidizing a 1,2-diol compound in a reaction system using a nitroxy radical including a skeleton represented by formula(1), water, and an organic solvent, the organic solvent is a compound unmixable with water (R1-R4 are respectively and independently 1-6C hydrocarbon groups). In the synthesis method of the α-hydroxycarboxylic acid, the reaction system has a pH value of 1.0-8.0, and includes a phosphate buffer solution or an acetate buffer solution, and at least one selected from a hypohalite and a halite is added to the reaction system, and further at least one selected from a tetraalkylammonium salt and a fatty acid is added thereto. COPYRIGHT: (C)2016,JPOandINPIT

Chemoselective catalytic oxidation of 1,2-diols to α-hydroxy acids controlled by TEMPO-ClO2 charge-transfer complex

Chemoselective catalytic oxidation from 1,2-diols to α-hydroxy acids in a cat. TEMPO/cat. NaOCl/NaClO2 system has been achieved. The use of a two-phase condition consisting of hydrophobic toluene and water suppresses the concomitant oxidative cleavage. A study of the mechanism suggests that the observed selectivity is derived from the precise solubility control of diols and hydroxy acids as well as the active species of TEMPO. Although the oxoammonium species TEMPO+Cl- is hydrophilic, the active species dissolves into the organic layer by the formation of the charge-transfer (CT) complex TEMPO-ClO2 under the reaction conditions.

Synthesis of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acids, intermediate products in the synthesis of cis-4-Aminochroman-3-ols

Oxidation of accessible (R)-3-chloropropane-1,2-diol to (R)-3-chloro-2-hydroxypropanoic acid and subsequent reaction of the latter with ortho-substituted sodium phenoxide gave a number of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acid which are intermediate products in the synthesis of nonracemic 4-aminochroman-3-ols.

Synthesis of ranolazine metabolites and their anti-myocardial ischemia activities

The anti-anginal drug Ranolazine, a partial fatty acid oxidation (pFOX) inhibitor, is thought to modulate the metabolism during myocardial ischemia by activating pyruvate dehydrogenase activity to promote glucose oxidation. Ranolazine and its five principal metabolites: CVT-2512, CVT-2513, CVT-2514, CVT-2738 and CVT-4786, were synthesized. The effect of Ranolazine and its metabolites on the ECG (electrocardiogram) of mice with myocardial ischemia induced by isoprenaline and their effect on alleviating the symptom of myocardial ischemia were tested and compared. The results showed that CVT-2738 and CVT-2513 could be protective against mice myocardial ischemia induced by isoprenaline. Within all the metabolites tested in this study, CVT-2738 exhibited the best potency, however, it was still less potent than Ranolazine.