2150-45-0

Usage

Uses

Used in Chemical Synthesis:
METHYL 3,5-DIHYDROXYBENZOATE is used as a key intermediate in the synthesis of various compounds, such as methyl 2-hydroxy-6-methoxybenzoate and oxamyl propionic acid. Its unique chemical structure and properties make it a valuable building block for the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
METHYL 3,5-DIHYDROXYBENZOATE can be utilized as a starting material for the development of new drugs or drug candidates. Its hydrogen-bonding capabilities and fluorescence properties may contribute to the design of novel therapeutic agents with improved efficacy and selectivity.
Used in Research and Development:
Due to its unique fluorescence properties, METHYL 3,5-DIHYDROXYBENZOATE can be employed in research and development for various applications, such as the study of molecular interactions, the development of new analytical methods, and the investigation of biological processes.
Used in Material Science:
The compound's fluorescence characteristics may also find applications in material science, where it could be used in the development of new materials with specific optical or electronic properties, such as sensors or optoelectronic devices.

InChI:InChI=1/C8H8O4/c1-12-8(11)7-5(9)3-2-4-6(7)10/h2-4,9-10H,1H3

Upstream product

• 67-56-1 methanol 
• 303-07-1 2,6-Dihydroxybenzoic acid 
• 124479-80-7 2‐(methoxycarbonyl)‐1,3‐phenylene diacetate 
• 74-88-4 methyl iodide 
• 25983-51-1 2,6-bis(benzyloxy)benzoic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 108-46-3 recorcinol 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 79205-25-7 4-methylpyoluteorin O,O-diacetate 
• 186581-53-3 diazomethane 

Downstream Products

• 90151-18-1 2,6-dihydroxy benzohydrazide 
• 3147-50-0 2,6-dihydroxy benzamid 
• 60237-95-8 2,6-dihydroxy-benzoic acid dimethylamide 
• 116865-53-3 2,6-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid methyl ester 
• 529-61-3 euxanthone 
• 74292-72-1 methyl 2-hydroxy-6-isopropoxybenzoate 
• 74292-74-3 methyl 2-hydroxy-6-(benzyloxy)benzoate 
• 51798-17-5 3-Butyryl-2,6-dihydroxy-benzoic acid methyl ester 
• 259684-89-4 methyl 2,6-bis(3,5-dibenzyloxy-benzyloxy)benzoate 
• 219954-41-3 Methyl 2,6-di(3-bromopropoxy)benzoate 
• 253680-65-8 2-hydroxy-6-octyloxy-benzoic acid methyl ester 
• 253680-67-0 2-hydroxy-6-undecyloxy-benzoic acid methyl ester 
• 253680-69-2 2-eicosyloxy-6-hydroxy-benzoic acid methyl ester 
• 130442-13-6 2-(methoxycarbonyl)-3-(tetradecyloxy)phenol 

Relevant academic research and scientific papers

Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer

Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.

Convergent Protein Phosphatase Inhibitor Design for PTP1B and TCPTP: Exchangeable Vanadium Coordination Complexes on Graphene Quantum Dots

Development of potent and specific inhibitors of protein tyrosine phosphatase 1B (PTP1B) with desired drug-like properties is still a challenge. Based on the crystal structures of PTP1B transition state analog consisting of a vanadate peptide, a novel approach is proposed to design PTP1B inhibitors, in which the tyrosyl vanadate ester of a PTP1B peptide mimic (PL1) is stably integrated on the membrane permeable graphene quantum dots (GQDs). The vanadate complexes (GQD-PL1-VV) prepared exhibit high potency (Ki?= 6?± 1?× 10?9 m) and selectivity (selectivity index SI >200?for PTP1B versus the T-cell protein tyrosine phosphatase, TCPTP) in solution and in HepG2 cells. Oral administration of GQD-PL1-VV in db/db model mice shows selective PTP1B inhibition in liver and fat tissues and exhibits improved anti-diabetic activity compared to bis(maltolato)oxovanadium(IV). Moreover, exchange of PL1 to a TCPTP-specific ligand (PL2) results in potent TCPTP inhibition (Ki?= 59?± 12?× 10?9 m) as expected with SI ≈23 versus PTP1B. Overall, the present results provide a paradigm shift and a general design of phosphatase inhibitors consisting of GQDs, a complexing targeting ligand and vanadium (V) for selective regulation of PTP1B both in vitro and vivo.

Synthesis, photochemical isomerization and photophysical properties of hydrazide-hydrazone derivatives

Hydrazide-hydrazone derivatives have been utilized in molecular switches, sensing, metallo assemblies, drugs and other applications. The hydrazide-hydrazone functional group contains the -CO-NH-NCH- moiety that yields the hydrazide-hydrazone group its physical, chemical and biochemical properties; however, the application in security protection has not been explored before. Herein, the 2-(ortho-), 3-(meta-), 4-(para-) substituted pyridine conjugated to 2,6-dihydroxybenzoic acid, which containing hydrazide-hydrazone as photoswitch linker were designed and synthesized (3a-3c). Interestingly, when irradiating the ortho-substituted pyridine of molecule 3a with a light of 365 nm, obvious emission intensity enhancements were detected. However, 3a-3c before irradiation and 3b-3c after irradiation show no fluorescence. UV-vis, fluorescence, 1H NMR and Fourier transform infrared spectra and density functional theory calculations were carried out, which revealed that the hydrazide-hydrazone derivative of 3a could undergo a characteristic E to Z photoisomerization after light irradiation for 365 nm. The Z isomer of 3a may have additional intramolecular hydrogen bonds to restrict the motions of the molecule, thus increasing the fluorescence intensity of 3a. The experimental and molecular calculation results agreed and thus demonstrated the first example of invisible ink based on the hydrazide-hydrazone motif.

Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities

Natural products have always been an important source of new hits and leads in drug discovery, with the marine environment being regarded as a significant source of novel and exquisite bioactive compounds. Yicathins B and C are two marine-derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol/water system and a biomimetic model-based system. As the xanthonic nucleus is a “privileged structure”, other biological activities were evaluated, namely antitumor and anti-inflammatory activities. An interesting anti-inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti-infective and anti-inflammatory) marine-inspired xanthone derivatives.

Pyrimidine salicylic acid derivative as well as preparation method and application thereof

The invention provides a pyrimidine salicylic acid derivative as well as a preparation method and application thereof. The chemical structural formula of the pyrimidine salicylic acid derivative is represented by a formula (I) (shown in the description). The preparation method comprises the step of reacting by virtue of acid of bispyribac-sodium and trifluoroethanol or 4-butenol in an organic solvent in the presence of triethylamine and 1-hydroxybenzotriazole, so as to obtain the compound of the formula (I). The preparation method is simple in operation and relatively high in yield, the prepared pyrimidine salicylic acid derivative is low in dose and high in activity, has herbicidal activities to agricultural weeds such as dicotyledon weeds and monocotyledon weeds at 15g/hm, particularly has relatively prevention effects to the after-treatment of seedlings of goosefoots and crab grass and can be taken as a candidate compound of herbicides, a new choice is provided for the new species of the herbicides, and the pyrimidine salicylic acid derivative has potential industrial application prospects.

Bispyribac derivative, and preparation method and application of bispyribac derivative

The invention discloses a bispyribac derivative, and a preparation method and an application of the bispyribac derivative. The bispyribac derivative has the following structure as shown in the specification. The preparation method particularly comprises the following steps of: taking 2,6-dihydroxy-benzoic acid as a raw material for multi-step reactions to synthesize bispyribac (acid), then preparing bispyribac acyl chloride, further performing esterification reaction with 2-pyridyl ethanol to synthesize the bispyribac derivative, namely 2-(pyridine-2-yl) ethyl-2,6-bi((4,6-dimethoxy pyridine-2-yl) oxy) benzoate. The compound has better weeding activity and especially has better removal activity on a dicotyledonous weed, namely sisymbrium sophia, and the preparation method is simple to operate and higher in yield.

Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV

Using hydroxy-/dihydroxybenzoic acids as leads, a series of methyl, ethyl and iso-propyl esters of 4-hydroxy-benzoic acid, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids and of coumaric acid, were obtained and investigated for the inhibition of six mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, the cytosolic CA I, II and VII, and the transmembrane CA IX, XII and XIV, many of which are established drug targets. Other compounds incorporating phenol/catechol moieties were obtained from dopamine by reaction with fluorescein isothiocyanate or with 2,4,6-trisubstituted pyrylium salts. Some aminophenols were also derivatized in a similar manner, by using pyrylium salts. Many of these compounds showed increased inhibitory action compared to the lead compounds from which they were obtained, with efficacy in the submicromolar range against most investigated CA isoforms. As phenols are a class of less investigated CA inhibitors (CAIs) compared to the sulfonamides, and their mechanism of inhibition is less well understood, compounds of the type designed here may be helpful in gaining more insights into these phenomena.

Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene interactions

Quinolinium salt 3 is an effective additive that acts as a conformation control element (CCE) to promote macrocyclization to form rigid cyclophanes via olefin metathesis or Glaser-Hay coupling, which do not cyclize in the absence of the additive. The additives are easily synthesized and highly modifiable and have solubility profiles which allow for simple recovery via filtration.

Bone selective effect of an estradiol conjugate with a novel tetracycline-derived bone-targeting agent

In this study a novel bone-targeting agent containing elements of the tricarbonylmethane system of ring A of tetracycline was developed and was shown to bind to the mineral constituent of bone, hydroxyapatite. Conjugation of this bone-targeting agent to estradiol resulted in a bone-targeted estrogen (BTE2-A1) with an enhanced ability to bind to hydroxyapatite. In an ovariectomized rat model of osteoporosis a partial separation of the skeletal effects of estradiol from the uterine effects was observed following subcutaneous administration of BTE2-A1. This novel bone-targeting estradiol delivery system has the potential to improve the safety profile of estradiol in the treatment of osteoporosis.

Compounds for diagnosis, treatment and prevention of bone injury and metabolic disorders

The present invention relates to compounds of the formula or pharmaceutically acceptable salts thereof useful for the prophylaxis and treatment of degenerative bone disorders and for the acceleration of bone healing.