23028-17-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid is used as a pharmaceutical agent for its potential health benefits, leveraging its antioxidant properties to contribute to anti-inflammatory and neuroprotective effects. Its presence in natural dietary sources underscores its potential as a therapeutic compound.
Used in Nutritional Supplements:
In the nutritional supplement industry, 3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid is utilized as an ingredient to enhance the antioxidant capacity of supplements, aiming to support overall health and well-being by providing additional anti-inflammatory and neuroprotective benefits.
Used in Functional Foods:
3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid is employed as an additive in functional foods to capitalize on its health-promoting properties. Its incorporation into food products can offer consumers the benefits of its antioxidant, anti-inflammatory, and neuroprotective effects, contributing to a more health-conscious diet.
Used in Cosmetics:
In the cosmetics industry, 3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid is used as an active ingredient for its antioxidant and potentially anti-aging properties. It may be incorporated into skincare products to protect the skin from oxidative stress and support skin health.
Used in Agricultural Products:
3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid may also find use in agricultural applications, potentially serving as a natural antioxidant to extend the shelf life of fruits and vegetables, thereby reducing spoilage and waste.

InChI:InChI=1/C9H10O5/c1-9(14,8(12)13)5-2-3-6(10)7(11)4-5/h2-4,10-11,14H,1H3,(H,12,13)

Upstream product

• 4228-66-4 L-586462 
• 215872-63-2 8-O-4'-dehydrodiferulic acid 
• 1081-71-6 3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid 
• 65329-03-5 2-(acetylamino)-3-[3,4-bis(acetyloxy)phenyl]-(2Z)-2-propenoic acid 
• 68307-79-9 2-hydroxy-3-(3,4-dihydroxyphenyl)acrylic acid 
• 20283-92-5 (R)-(+)-rosmarinic acid 
• 68307-79-9 (Z)-3-(3,4-dihydroxyphenyl)-2-hydroxyacrylic acid 
• 1174920-56-9 clinopodic acid C 
• 1331784-38-3 lycopic acid A 
• 1331784-39-4 lycopic acid B 

Downstream Products

• 179128-86-0 3-(3,4-Bis-benzyloxy-phenyl)-2-hydroxy-propionic acid 
• 179128-87-1 3-(3,4-diallyloxyphenyl)lactic acid 
• 68595-72-2 3-(3',4'-Dihydroxyphenyl)-2-hydroxypropansaeure(TMS)4 
• 54814-41-4 (+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 
• 20283-92-5 (R)-(+)-rosmarinic acid 
• 1174681-30-1 (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (S)-PGME amide 
• 1174681-32-3 (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide 

Relevant academic research and scientific papers

Salvianolic acids T and U: A pair of atropisomeric trimeric caffeic acids derivatives from root of Salvia miltiorrhiza

Two new trimeric caffeic acids, named salvianolic acids T and U (1 and 2), were isolated from the underground part of Salvia miltiorrhiza. Their structures, consisting of three caffeic acid units, were determined based on extensive 1D- and 2D-spectroscopic analyses and electronic circular dichroism (ECD) calculations.

Oxidative metabolism of typical phenolic compounds of Danshen by electrochemistry coupled to quadrupole time-of-flight tandem mass spectrometry

An electrochemistry coupled to online quadrupole time-of-flight tandem mass spectrometry (EC/Q-TOF/MS) was applied to investigate the oxidative transformation and metabolic pathway of five phenolic acids in Danshen sample. Simulation of the phase I oxidative metabolism was carried out in an electrochemical reactor equipped with a glassy carbon working electrode. The phase II reactivity of the generated oxidative products towards biomolecules (such as glutathione) was investigated by ways of covalent adduct formation experiments. The results obtained by EC/MS were compared with well-known in vitro studies by conducting rat liver microsome incubations. Structures of the electrochemically produced metabolites were identified by accurate mass measurement and previously results in vivo metabolites. It was indicated that the electrochemical oxidation was in good accordance with similar products found in vivo experiments. In conclusion, this work confirmed that EC/Q-TOF/MS was a promising analytical tool in the prediction of metabolic transformations of functional foods.

Hydrolysis of Rosmarinic Acid from Rosemary Extract with Esterases and Lactobacillus johnsonii in Vitro and in a Gastrointestinal Model

Rosmarinic acid (RA) was identified as one of the main components of rosemary extracts and has been ascribed to a number of health benefits. Several studies suggested that after ingestion, RA is metabolized by gut microflora into caffeic acid and derivati

Unveiling the interaction profile of rosmarinic acid and its bioactive substructures with serum albumin

Rosmarinic acid, a phytochemical compound, bears diverse pharmaceutical profile. It is composed by two building blocks: caffeic acid and a salvianic acid unit. The interaction profile, responsible for the delivery of rosmarinic acid and its two substructure components by serum albumin remains unexplored. To unveil this, we established a novel low-cost and efficient method to produce salvianic acid from the parent compound. To probe the interaction profile of rosmarinic acid and its two substructure constituents with the different serum albumin binding sites we utilised fluorescence spectroscopy and competitive saturation transfer difference NMR experiments. These studies were complemented with transfer NOESY NMR experiments. The thermodynamics of the binding profile of rosmarinic acid and its substructures were addressed using isothermal titration calorimetry. In silico docking studies, driven by the experimental data, have been used to deliver further atomic details on the binding mode of rosmarinic acid and its structural components.

Salvianolic acid L, a potent phenolic antioxidant from Salvia officinalis

Salvianolic acid L, a rosmarinic acid dimer, was isolated from Salvia officinalis and identified as 7,8-dihydroxy-2-(3,4-dihydroxyphenyl)-1,2-dihydronaphthalene-1,3-dicarboxylic acid di(1-carboxy-2-(3,4-dihydroxyphenyl))ethyl ester. Two novel hydrolytic products 7,8-dihydroxy-2-(3,4-dihydroxyphenyl)-1,2-dihydronaphthalene-1,3-dicarboxylic acid and the corresponding 3-monoester were also isolated and characterized. Salvianolic acid L showed strong free radical scavenging activities for DPPH and superoxide anion radicals.

New Benzofuran Lignans from Nepeta multifida

The new benzofuran lignans nepetamultin A (1) and B (2) were isolated from flowers of Nepeta multifida L. [Schizonepeta multifida (L.) Briq.; Lamiaceae]. UV and NMR spectroscopic and mass spectrometric data indicated 1 was the 9′9′′′-di-O-methyl ester of schizotenuin A; 2, the 9′-O-methyl ester of schizotenuin C1. Biological studies revealed that 1 and 2 possessed antioxidant and antihyaluronidase activity.

New phenolic glycosides from Anemone chinensis Bunge and their antioxidant activity

ABATRACT: Nine compounds, five phenolic glycosides (1, 2, 4–6), three phenylpropanoids (7–9), and a furanone glycoside (3), were isolated from aqueous soluble extract of the dried roots of Anemone chinensis Bunge. The structures of new compounds (1–4) were elucidated by comprehensive spectroscopic data analysis as well as chemical evidence. Pulsatillanin A (1) demonstrated significant antioxidant effects through scavenging free radical in DPPH assay, and relieved the oxidative stress in LPS-induced RAW 264.7 cells by reducing ROS production, enhancing antioxidant enzyme SOD activity, replenishing depleted GSH in a dose-dependent manner. Western blot analysis revealed that 1 showed antioxidant activity via activating Nrf2 signaling pathway.

Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof

The synthesis and molecular structure details of R- 3,4-dihydroxyphenyl lactic acid (danshensu) and related compounds, i.e. S isomer and the key intermediates have been described. Danshensu is an important water soluble phenolic acid of Salvia miltiorrhiza herb (danshen or red sag) with numerous applications in traditional Chinese medicine (TCM). Our synthetic approach was based on the Knoevenagel condensation of the protected 3,4-dihydroxybenzaldehyd and Meldrum acid derivative, followed by asymmetric Sharples dihydroxylation, reductive mono dehydroxylation and final deprotection. All compounds were characterized by various spectroscopic techniques: 1H-, 13C- magnetic resonance (NMR); Fourier-transformed infrared (FTIR); Raman, HR mass spectroscopy. For the determination of compound optical purities original HPLC methods were developed which allowed for the efficient resolution of danshensu R and S enantiomers as well as its intermediate enantiomers, using commercially available chiral stationary phases. Furthermore, in order to better understand danshensu specificity as a potential API in drug formulation, the physicochemical properties of the compounds were studied by thermal analysis, including differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Method for preparing salvianolic acid A

The invention discloses a method for preparing salvianolic acid A. The method includes the following steps that firstly, salvianolic acid B is prepared into a solution with the concentration of 35-45 mg/mL by means of NaOH or NaHCO3 with the pH value of 3.5-4.5, the solution is placed in a subcritical water reaction kettle, after the temperature of a heating furnace reaches 170-190 DEG C and is stabilized, the reaction kettle is placed into the heating furnace, the reaction kettle is taken out after 50-70 min and placed in ice water bath or cold water to be cooled, the liquid is taken out and subjected to freeze-drying, and a crude product rich in salvianolic acid A is obtained; secondly, salvianolic acid A is separated and purified by means of high-speed countercurrent chromatography, wherein a solvent system is prepared from petroleum ether, ethyl acetate, n-butyl alcohol and water according to the ratio of 2:3:1:9, 10 mM of trifluoroacetic acid is added to an upper phase to form a stationary phase, 10 mM ammonia water is a lower phase and serves as a mobile phase, the volume of a high-speed countercurrent chromatography column is 200-400 mL, the sample loading amount is 1.0-1.2 g, the rotation speed is 600-1000 rpm, the flow speed is 1-4 mL/min, and the detection wavelength is 280 nm. The method is low in cost, easy to operate and high in efficiency, salvianolic acid crude extracts can be converted on a large scale, and a salvianolic acid A monomeric compound with the purity higher than 98% is separated and prepared.

Method converting danshinolic acid B into tanshinol

The invention discloses a method converting danshinolic acid B into tanshinol, comprising regulating the pH of a solution of the root of red-rooted salvia extract to 7.0-12.0 by a pH modifier, then heating and refluxing to obtain an extract converting solution of the root of red-rooted salvia with a converting temperature of 80-120 DEG C and the converting time of 0.5-4h, and finally regulating the pH of the extract converting solution of the root of red-rooted salvia to 2.0-6.0 by the pH modifier. The danshinolic acid B is more thoroughly converted into the tanshinol, content of the danshinolic acid B is lower than 1.0mg/ml, no organic solvents such as ethyl alcohol, acetone and ethylene acetate are needed in a converting process; content is stable in storage after converting; the operation is simple and no equipment is needed.