54845-40-8

Usage

Uses

Used in Medical Diagnostics:
α-Hydroxy-3-methoxybenzeneacetic acid methyl ester is used as a biomarker for the diagnosis and monitoring of neuroendocrine tumors, such as pheochromocytoma and neuroblastoma. The measurement of its levels in urine provides valuable information about the presence and activity of these tumors, aiding in their diagnosis and management.
Used in Research and Clinical Settings:
α-Hydroxy-3-methoxybenzeneacetic acid methyl ester is used as a research tool to study the effects of catecholamine metabolism and its implications in various physiological and pathological conditions. This helps in understanding the underlying mechanisms and potential treatments for related health issues.

InChI:InChI=1/C10H12O4/c1-13-8-5-3-4-7(6-8)9(11)10(12)14-2/h3-6,9,11H,1-2H3

Upstream product

• 67-56-1 methanol 
• 32174-39-3 3-methoxymandelic acid 
• 151-50-8 potassium cyanide 
• 591-31-1 3-methoxy-benzaldehyde 
• 53313-94-3 m-methoxymandelonitrile 
• 83585-22-2 methyl 2-(3-methoxyphenyl)-2-oxoacetate 
• 93554-98-4 3-methoxy-α-[(trimethylsilyl)oxy]benzeneacetonitrile 
• 557-20-0 diethylzinc 

Downstream Products

• 134432-62-5 Methyl 2-(3-methoxyphenyl)-2-(4,6-dimethoxy-2-pyrimidinyloxy)acetate 
• 83585-22-2 methyl 2-(3-methoxyphenyl)-2-oxoacetate 
• 86215-57-8 bromo-(3-methoxy-phenyl)-acetic acid methyl ester 
• 66560-13-2 (1R,2S)-1-(3-Methoxy-phenyl)-cyclopropane-1,2-dicarboxylic acid dimethyl ester 
• 77053-82-8 (1R,2S)-1-(3-Methoxy-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 66505-06-4 1-(m-methoxyphenyl)-1,2-cyclopropanedicarboximide 
• 86215-42-1 1-(m-methoxyphenyl)-3-methyl-3-azabicyclo[3.1.0]hexane 
• 83177-57-5 1-(3-methoxyphenyl)-3-azabicyclo[3.1.0]hexane 
• 21150-12-9 (R)-m-Methoxymandelic acid 
• 32345-57-6 hydroxy-(3-methoxy-phenyl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Multinuclear zinc bisamidinate catalyzed asymmetric alkylation of α-ketoesters and its unique chemoselectivity

The multinuclear Zn-bisamidinate catalyzed enantioselective addition of Et2Zn to α-ketoesters has been developed. The steric tuning of two amidinate units as well as multiple coordination on the Zn atoms play a key role in achieving high enantioselectivity (up to 98% ee) and unique chemoselectivity. The present catalyst exhibited the preferential alkylation of α-ketoesters even in the presence of aldehydes.

Ru-MACHO-Catalyzed Highly Chemoselective Hydrogenation of α-Keto Esters to 1,2-Diols or α-Hydroxy Esters

A ruthenium pincer catalyst has been shown to be highly effective for the hydrogenation of a wide range of α-keto esters, affording either diols or hydroxy esters depending on the choice of reaction conditions. Strong base, high temperature, and pressure favor the formation of diols whilst the opposite is true for the hydroxy esters.

PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS

The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.

Enantioselectivity of carbonic anhydrase catalyzed hydrolysis of mandelic methyl esters

We report the first enantioselective hydrolysis of esters catalyzed by caebonic anhydrase.We found that mandelic methyl esters are good substrates for carbonic anhydrase.The R enantiomers are better substrates and enantiomeric excess values are moderate (40-51percent).

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.