29511-09-9

Usage

Uses

Used in Pharmaceutical and Medical Applications:
m-THPA is used as a potential therapeutic agent for neurological disorders, cardiovascular diseases, and cancer due to its antioxidant and anti-inflammatory properties. Its free radical scavenging activity may help protect cells from oxidative damage, and its role in regulating the immune response and reducing inflammation in the body makes it a valuable compound for pharmaceutical and medical applications.
Used in Antioxidant Applications:
m-THPA is used as an antioxidant to protect cells from oxidative damage by scavenging free radicals, which can help prevent or treat various diseases and conditions associated with oxidative stress.
Used in Anti-inflammatory Applications:
m-THPA is used as an anti-inflammatory agent to regulate the immune response and reduce inflammation in the body, which can be beneficial in treating various inflammatory conditions and diseases.

Upstream product

• 652-55-1 Curvulic acid 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 156-38-7 4-hydroxyphenylacetate 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 151562-59-3 1,8-dihydroxy-10-<2-(3,4,5-trihydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone 

Downstream Products

• 2989-06-2 methyl 2-(3,4,5-trimethoxyphenyl)acetate 
• 1569261-64-8 prop-2-yn-1yl 2-(3,4,5-trihydroxyphenyl)acetate 
• 106773-21-1 (3,4,5-triacetoxy-phenyl)-acetic acid 

Relevant academic research and scientific papers

Anticancer Activity of Phenolic Acids of Natural or Synthetic Origin: A Structure-Activity Study

Several phenolic acids-caffeic and gallic acid derivatives-were synthesized and screened for their potential antiproliferative and cytotoxic properties, in different human cancer cell lines: mammary gland and cervix adenocarcinomas and lymphoblastic leukemia. The selected phenols were structurally related, which allowed us to gather important information regarding the structure-activity relationships underlying the biological activity of such compounds. This is proposed to be due to a balance between the antioxidant and pro-oxidant properties of this kind of agent. Distinct effects were found for different cell lines, which points to a significant specificity of action of the drugs tested. It was verified, for the types of cancer investigated, that the trihydroxylated derivatives yielded better results than the dihydroxylated ones. Tests in noncancerous cells, human lung fibroblasts, were also undertaken, in view of determining the toxic side effects of the compounds studied.

Synthesis method of stable isotope labeled troquinol hydrochloride

The invention relates to a synthesis method of stable isotope labeled troquinol hydrochloride, and belongs to the field of organic synthesis. The synthesis method of stable isotope labeled troquinol hydrochloride comprises the following steps: by taking a compound (II) as a raw material, synthesizing to obtain a compound (III), further condensing the compound (III) with a compound (IV) to obtain acompound (V), reacting the compound (V) with isotope-labeled methyl iodide to obtain an isotope-labeled compound (VI), performing cyclization to generate an isotope-labeled compound (VII), and finally, carrying out catalytic debenzylation and salification to obtain the stable isotope-labeled troquinol hydrochloride (I). The synthetic raw materials and intermediates are simple and easy to obtain,the chemical purity and isotope abundance of the target product isotope-labeled tratroquinol hydrochloride are high, and the method can be used as an internal standard substance for drug quality inspection, athlete drug inspection and related metabolic mechanism research, and has important practical application values.

Structure-Based Design of High-Affinity Macrocyclic FKBP51 Inhibitors

The FK506-binding protein 51 (FKBP51) emerged as a key player in several diseases like stress-related disorders, chronic pain, and obesity. Linear analogues of FK506 called SAFit were shown to be highly selective for FKBP51 over its closest homologue FKBP52, allowing the proof-of-concept studies in animal models. Here, we designed and synthesized the first macrocyclic FKBP51-selective ligands to stabilize the active conformation. All macrocycles retained full FKBP51 affinity and selectivity over FKBP52 and the incorporation of polar functionalities further enhanced affinity. Six high-resolution crystal structures of macrocyclic inhibitors in complex with FKBP51 confirmed the desired selectivity-enabling binding mode. Our results show that macrocyclization is a viable strategy to target the shallow FKBP51 binding site selectively.

Bioactivity and structural properties of novel synthetic analogues of the protozoan toxin climacostol

Climacostol (5-[(2Z)-non-2-en-1-yl]benzene-1,3-diol) is a resorcinol produced by the protozoan Climacostomum virens for defence against predators. It exerts a potent antimicrobial activity against bacterial and fungal pathogens, inhibits the growth of sev

p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids

Trihydroxyphenolic acids such as 3,4,5-trihydroxycinnamic acid (3,4,5-THCA) 4c and 2-(3,4,5-trihydroxyphenyl)acetic acid (3,4,5-THPA) 2c are strong antioxidants that are potentially useful as medicinal agents. Our results show that p-hydroxyphenylacetate (HPA) 3-hydroxylase (HPAH) from Acinetobacter baumannii can catalyze the syntheses of 3,4,5-THPA 2c and 3,4,5-THCA 4c from 4-HPA 2a and p-coumaric acid 4a, respectively. The wild-type HPAH can convert 4-HPA 2a completely into 3,4,5-THPA 2c within 100 min (total turnover number (TTN) of 100). However, the wild-type enzyme cannot efficiently synthesize 3,4,5-THCA 4c. To improve the efficiency, the oxygenase component of HPAH (C2) was rationally engineered in order to maximize the conversion of p-coumaric acid 4a to 3,4,5-THCA 4c. Results from site-directed mutagenesis studies showed that Y398S is significantly more effective than the wild-type enzyme for the synthesis of 3,4,5-THCA 4c; it can catalyze the complete bioconversion of p-coumaric acid 4a to 3,4,5-THCA 4c within 180 min (TTN ～ 23 at 180 min). The yield and stability of 3,4,5-THPA 2c and 3,4,5-THCA 4c were significantly improved in the presence of ascorbic acid. Thermostability studies showed that the wild-type C2 was very stable and remained active after incubation at 30, 35, and 40 °C for 24 h. Y398S was moderately stable because its activity was retained for 24 h at 30 °C and for 15 h at 35 °C. Transient kinetic studies using stopped-flow spectrophotometry indicated that the key improvement in the reaction of Y398S with p-coumaric acid 4a lies within the protein-ligand interaction. Y398S binds to p-coumaric acid 4a with higher affinity than the wild-type enzyme, resulting in a shift in equilibrium toward favoring the productive coupling path instead of the path leading to wasteful flavin oxidation.

Conversion of oxiranes and CO2 to organic cyclic carbonates using a recyclable, bifunctional polystyrene-supported organocatalyst

The development of a heterogeneous one-component bifunctional catalyst system able to catalyse the conversion of carbon dioxide and oxiranes to organic cyclic carbonates at low temperature (45 °C) is reported. The bifunctional system can be easily recycled and reactivated when required. When compared with other heterogeneous organocatalysts for the same transformation, the reported catalyst is active at much milder temperatures, thus emphasising the optimal sustainability profile of the new catalyst system.

Acidity and stability of 10-substituted 1,8-dihydroxy-9(10H)-anthracenones

The decomposition of 10-substituted anthralin derivatives in dimethyl sulfoxide and ethanol was determined. While 10-ω-phenylalkylidene derivatives were thoroughly stable, 10-ω-phenylacyl-substituted compounds were slowly degraded to danthron and the corresponding carboxylic acids. However, the stability of these derivatives was markedly improved as compared to that of anthralin. Determination of the pK(a) values showed that the ω-phenylacyl derivatives were somewhat stronger acids than anthralin, while ω-phenylalkylidene-substitution generally leaves the acidity of the anthralin part unchanged.

Method of treating hemoglobinopathies

A therapeutic process for treating anemias in primates, including man, particularly those anemias of genetic origin including sickle-cell anemia, which comprises administering to an anemic primate an amount of a polyhydroxy benzoic, mandelic or phenylacetic acid derivative as specified at a dose level sufficient to increase fetal hemoglobin.