495-78-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-Hydroxyphenyl)propionic acid is used as a growth substrate for various strains of E. coli, which is essential for the study and development of new pharmaceutical compounds and understanding the metabolic pathways of these bacteria.
Used in Biomedical Research:
3-(2-Hydroxyphenyl)propionic acid serves as a standard in the study of microbial metabolism of catechin stereoisomers, which is crucial for understanding the bioavailability and health benefits of these compounds in the human body.
Used in Microbiology:
As a growth substrate for E. coli strains, 3-(2-Hydroxyphenyl)propionic acid is used to support the growth and maintenance of these bacteria in laboratory settings, allowing researchers to study their metabolic processes and potential applications in various fields.
Used in Chemical Analysis:
The crystal structure of 3-(2-Hydroxyphenyl)propionic acid, with its monoclinic form and P21/c space group, provides valuable information for researchers in the field of chemical analysis, particularly in understanding the structural properties of similar compounds and their potential applications in various industries.

InChI:InChI=1/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)/p-1

Upstream product

• 614-60-8 o-Coumaric acid 
• 1643-28-3 3-(2-chlorophenyl)propanoic acid 
• 59577-13-8 3-(2-hydroxyphenyl)propanenitrile 
• 6342-77-4 2-methoxy-benzenepropanoic acid 
• 91-64-5 coumarin 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 95-13-6 1-indene 
• 7732-18-5 water 
• 288311-17-1 2-trifluoromethyl-chroman-2-ol 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 7417-18-7 2-methoxyphenethyl alcohol 
• 35144-25-3 1-(2-methoxyphenyl)-ethyl chloride 
• 36449-75-9 1-(2-bromoethyl)-2-methoxybenzene 

Downstream Products

• 20921-04-4 ethyl 3-(2-hydroxyphenyl)propanoate 
• 78027-95-9 3-(2-hydroxy-5-phenylazo-phenyl)-propionic acid 
• 2669-94-5 6-hydroxy-3,4-dihydrocoumarin 
• 749878-59-9 3-(5-bromo-2-hydroxy-phenyl)-propionic acid 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 220285-28-9 3-(2-ethoxyphenyl)propionic acid 
• 55001-09-7 methyl 3-(2-methoxyphenyl)propanoate 
• 20349-89-7 methyl 3-(2-hydroxyphenyl)propionate 
• 129967-35-7 phenylmethyl 3-[(4-phenylmethoxy)phenyl]propanoate 
• 59116-13-1 3-(2-Hydroxy-phenyl)-propionic acid propyl ester 
• 268544-18-9 N-succinimidyl 3-(2-hydroxyphenyl)propionate 
• 64-19-7 acetic acid 
• 69-72-7 salicylic acid 
• 20452-56-6 3-(3,6-dioxocyclohexa-1,4-dien-1-yl)propanoic acid 

Relevant academic research and scientific papers

Macroporous silica microcapsules immobilizing esterase with high hydrolysis reactivity

An esterase, 3,4-dihydrocoumarin hydrolase, was directly immobilized into silica microcapsules. The hydrolysis reaction of 3,4-dihydrocoumarin by a macroporous silica microcapsule immobilizing the esterase was faster than those by mesoporous ones. Using t

Industrial production method of 4-hydroxy-1-indanone

The invention discloses an industrial production method of 4-hydroxy-1-indanone, and relates to the technical field of organic chemistry, the industrial production method comprises the following steps: taking dihydrocoumarin as a raw material, carrying out hydrolysis reaction on the dihydrocoumarin under the catalysis of hydrochloric acid to obtain an intermediate 1, and carrying out cyclization reaction on the intermediate 1 and polyphosphoric acid under the catalysis of strongly acidic resin to obtain the 4-hydroxy-1-indanone. The preparation method disclosed by the invention is short in route, easily available in raw materials, high in yield, moderate in reaction condition, suitable for industrial production, less in three wastes, more environment-friendly, easier to operate and stable in process.

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.

Pd nanoparticles on reverse phase silica gel as recyclable catalyst for Suzuki-Miyaura cross coupling reaction and hydrogenation in water

Two catalytic systems, consisting of palladium nanoparticles supported by reverse phase amino functionalized silica are utilized as catalysts for Suzuki-Miyaura reaction and hydrogenation in water. The catalysts were developed by modifying silica into bidentate ligands, using either 2-pyridinecarboxaldehyde or 2,2′-bipyridine-4,4′-dicarboxylic acid. The synthesized catalysts showed quantitative reaction yields and recyclability with negligible leaching of Pd nanoparticles. Various characterization techniques including XPS, ICP-MS, SEM, BET, XRD, TEM, 1H- and 13C- NMR are used to verify the efficiency of the catalysts.

Catalytic hydrolysis of hydrophobic esters on/in water by high-silica large pore zeolites

Hydrolysis of water-insoluble esters is an industrially important but challenging reaction, because the esters are mostly present in oil droplets on water during the reaction. On the basis of the screening results for hydrolysis of a water-insoluble ester, 3-phenylpropionate, on/in water by 25 types of heterogeneous and homogenous catalysts, we have found that Hβ zeolite with a moderate Si/Al ratio (Si/Al = 75), Hβ-75, is an effective and reusable catalyst for hydrolysis of hydrophobic esters. The hydrolysis of esters with different sizes is studied by Hβ and HZSM5 zeolites with different Si/Al ratios, and the results show the hydrophobicity, pore size and number of Br?nsted acid sites are critical factors affecting the catalytic activity for this system. Kinetic and adsorption studies show that the high yields by Hβ-75 are due to preferential interaction of the hydrophobic zeolite pore with hydrophobic esters over polar molecules (carboxylic acids, water, alcohols) and transfer of the carboxylic acids to the oil droplets on water, both of which inhibit the reverse reaction (esterification of the carboxylic acids).

Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide

The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Raney nickel-catalyzed hydrogenation of unsaturated carboxylic acids with sodium borohydride in water

A mild, selective, and green method for the reduction of unsaturated carboxylic acids with sodium borohydride-Raney nickel (W6) system in water is reported. This method is practical and safe and avoids use of organic solvents. Taylor & Francis Group, LLC.

Microbial reduction of coumarin, psoralen, and xanthyletin by Glomerella cingulata

Microbial transformation of coumarin, psoralen, and xanthyletin was performed with the fungus Glomerella cingulata. The main reaction pathways involved reduction at α,β-unsaturated δ-lactone ring on coumarin analogue. Coumarin was metabolized by G. cingul