25379-88-8

Usage

InChI:InChI=1/C9H10O4/c1-13-9(12)5-6-2-3-7(10)8(11)4-6/h2-4,10-11H,5H2,1H3

Upstream product

• 67-56-1 methanol 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 1126-62-1 (3,4-dihydroxy-phenyl)-acetonitrile 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 156-38-7 4-hydroxyphenylacetate 
• 775-01-9 3,4-dihydroxymandelic acid 
• 29413-65-8 methyl 2-(3,4-dihydroxyphenyl)-2-hydroxyacetate 
• 7664-93-9 sulfuric acid 

Downstream Products

• 10597-60-1 hydroxytyrosol 
• 35400-16-9 (3,4-Diacetoxy-phenyl)-acetic acid methyl ester 
• 15964-79-1 methyl (3,4-dimethoxyphenyl)acetate 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 
• 15373-33-8 methyl 2-(3,4-bis(benzyloxy)phenyl)acetate 
• 38515-62-7 2-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetic acid methyl ester 
• 874111-06-5 [7-(4-nitro-benzoyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-acetic acid methyl ester 
• 874111-16-7 1-(4-aminophenyl)-3,5-dihydro-7,8-ethylenedioxy-4H-2,3-benzodiazepin-4-one 
• 874111-09-8 6-(4-nitro-phenyl)-2,3,8,10-tetrahydro-1,4-dioxa-7,8-diaza-cyclohepta[b]naphthalen-9-one 
• 874111-08-7 [7-(3-methyl-4-nitro-benzoyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-acetic acid methyl ester 
• 874111-10-1 6-(3-methyl-4-nitro-phenyl)-2,3,8,10-tetrahydro-1,4-dioxa-7,8-diaza-cyclohepta[b]naphthalen-9-one 
• 1290605-61-6 methyl 2-{3,4-bis[(4-methoxybenzyl)oxy]phenyl}acetate 
• 500573-80-8 methyl 2-[3,4-bis(octyloxy)phenyl]acetate 
• 129504-03-6 Methyl (4-hydroxy-3-allyloxyphenyl)acetate 

Relevant academic research and scientific papers

Antioxidant properties of two novel lipophilic derivatives of hydroxytyrosol

Two novel lipophilic derivatives of the natural olive oil phenol, hydroxytyrosol (HT), were synthesized using 3,4-dihydroxyphenylacetic acid as starting material. Their antioxidant activities and kinetics compared to HT and TBHQ were assessed by Rancimat,

Synthesis of Forsythenethoside A, a Neuroprotective Macrocyclic Phenylethanoid Glycoside, and NMR Analysis of Conformers

Forsythenethoside A (1) is a structurally unique macrocyclic phenylethanoid glycoside, which was isolated from Forsynthia suspensa and displayed considerable neuroprotective activities. Here, we report its first chemical synthesis via a longest linear sequence of 14 steps in 5% overall yield wherein intramolecular oxidative coupling was successfully employed to realize the pivotal macrocyclization. NMR analysis revealed the existence of an unexpected conformational interconversion of the congested macrocycles.

Flavonoids, flavonoid metabolites, and phenolic acids inhibit oxidative stress in the neuronal cell line HT-22 monitored by ECIS and MTT assay: A comparative study

A real-time and label-free in vitro assay based on electric cell-substrate impedance sensing (ECIS) was established, validated, and compared to an end-point MTT assay within an experimental trial addressing the cytoprotective effects of 19 different flavo

Bioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols

A bioorthogonal ligation and cleavage method via reactions of chloroquinoxalines (CQ) and ortho-dithiophenols (DT) is presented. Double nucleophilic substitutions of ortho-dithiophenols to chloroquinoxalines provide conjugates containing tetracyclic benzo[5,6][1,4]dithiino[2,3-b]quinoxaline with strong built-in fluorescence together with release of the other functional molecules. Three cleavable linkers were designed and successfully used in release of the molecules containing biotin from the protein conjugates. The CQ-DT bioorthogonal reactions can be applied for the bioorthogonal ligations, bioorthogonal cleavages, and trans-tagging of proteins, and show advantages of readily accessible unnatural orthogonal groups, appealing reaction kinetics (k2≈1.3 m?1 s?1), excellent biocompatibility of orthogonal groups, and high stability of conjugates. This complements previous bioorthogonal reactions and is a new route for protein-fishing applications and in-gel fluorescence analysis.

Regioselectivity of Cobalamin-Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate

Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4-substituted catechols was investigated employing the cobalamin-dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta- or para-position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta-selective with 4-substituted catechols bearing hydrophilic groups, it was para-selective for hydrophobic substituents. Furthermore, the presence of water miscible co-solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.

Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle

Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection “hot-spots,” medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure–activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.

Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin

Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.

Preparation method of hydroxytyrosol

The invention relates to the technical field of medicinal chemical synthesis, in particular to a preparation method of hydroxytyrosol. The preparation method of the hydroxytyrosol comprises the following step of taking an alcohol and/or an ether as a solvent to carry out a reaction on methyl 3,4-dihydroxyphenylacetate under the action of a reducing agent and Lewis acid to obtain the hydroxytyrosol. According to the preparation method of the hydroxytyrosol, the reducing agent and the Lewis acid are matched for carrying out catalytic reducing, so that reaction activity is improved, and the product yield and purity are high. In addition, the single solvent is used, so that post-treatment is convenient, the solvent is convenient to recycle, energy consumption and material loss are reduced, andproduction cost is greatly saved.

BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY

The present invention relates to novel bio-inspired hybrid compounds of formula I which act as proteasome activators and exhibit anti-ageing activity, as well as methods for their synthesis. These hybrid compounds combine the structural features of hydroxytyrosol and the natural antioxidant vitamin E or its bioisosteres in one molecular scaffold. The compounds of formula I, which include structural proteasome activators (activation by stereochemical interaction), can be used in the production of anti-ageing products, such as cosmetic preparations. Additionally, they can be used in conditions and diseases where the proteasome is down-regulated, as well as proteasome-activation control compounds.

NHC catalyzed enantioselective Coates-Claisen rearrangement: A rapid access to the dihydropyran core for oleuropein based secoiridoids

We present the short synthesis of the suitably functionalized enantioselective dihydropyran core of secoiridoids using an N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangement mechanism. The key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangement for the dihydropyran core, (ii) the assembly of the target dihydropyran core structure of oleuropein from a highly diastereoselective exocyclic trans alkene, and (iii) the highly stereoselective assembly of a monoterpene elenolide core structure.