20491-91-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4,5-Trimethoxyphenol is used as an antioxidant and antimicrobial agent for its potential to combat various diseases and infections.
Used in Food Science:
2,4,5-Trimethoxyphenol is used as a natural preservative to extend the shelf life of food products and maintain their quality.
Used in Cosmetics Industry:
2,4,5-Trimethoxyphenol is used as an ingredient in cosmetic products for its anti-inflammatory and neuroprotective properties, as well as its potential as a natural preservative.

Upstream product

• 14227-16-8 2,4,5-trimethoxyacetoxybenzene 
• 60-29-7 diethyl ether 
• 67-66-3 chloroform 
• 4460-86-0 asaraldehyde 
• 7722-84-1 dihydrogen peroxide 
• 10028-15-6 ozone 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 13239-13-9 2,5-dimethoxyhydroquinone 
• 74-88-4 methyl iodide 
• 73490-49-0 (E)-3-(2,4,5-trimethoxyphenyl)prop-2-enoic acid 
• 30225-87-7 2,4,5-trimethoxyphenyl formate 
• 80749-75-3 (E)-3-(2,4,5-trimethoxy-phenyl)-acrylic acid methyl ester 

Downstream Products

• 67271-97-0 2,4,4,5-tetramethoxycyclohexa-2,5-dienone 
• 3117-03-1 2,5-dimethoxyquinone 
• 2441-46-5 1,2,4,5-tetramethoxybenzene 
• 426834-30-2 1-cyclopropanecarbonyloxy-2,4,5-trimethoxybenzene 
• 1600526-71-3 C₃₁H₅₃NO₅ 
• 1600526-72-4 C₃₈H₆₆N₂O₆ 
• 1600526-73-5 C₃₃H₅₇NO₅ 
• 1600526-74-6 C₄₂H₇₄N₂O₆ 
• 1600526-75-7 2-hexadecyl-3,6-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione 
• 1600526-83-7 1-hexadecyl-2,3,5,6-tetramethoxy-4-methylbenzene 
• 1600526-77-9 C₃₉H₆₈N₂O₆ 
• 1600526-78-0 C₃₂H₅₅NO₅ 
• 1600526-79-1 C₃₉H₆₈N₂O₆ 
• 1600526-80-4 C₃₄H₅₉NO₅ 

Relevant academic research and scientific papers

Influence of Remote intramolecular hydrogen bonds on the stabilities of phenoxyl radicals and benzyl cations

(Figure presented) Remote intramolecular hydrogen bonds (HBs) in phenols and benzylammonium cations influence the dissociation enthalpies of their O-H and C-N bonds, respectively. The direction of these intramolecular HBs, para → meta or meta → para, dete

Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives

A set of new dihydro-1H-pyrazolo[1,3-b]pyridine and pyrazolo[1,3-b]pyridine embelin derivatives was synthesized through a multicomponent reaction from natural embelin, 3-substituted-5-aminopyrazoles and aldehydes. The synthesized compounds were evaluated against three hematologic tumor cell lines, HEL (acute erythroid leukemia), K-562 (chronic myeloid leukemia) and HL-60 (acute myeloid leukemia), and five breast cancer cell lines (SKBR3, MCF-7, MDA-MB-231, BT-549, HS-578T). The primate non-malignant kidney Vero cell line was used as the control of cytotoxicity. From the obtained results, some structure–activity relationships were out-lined. Furthermore, in silico prediction of physicochemical properties and ADME parameters were determined for the derivatives with the best antiproliferative values.

A new family of densely functionalized fused-benzoquinones as potent human protein kinase CK2 inhibitors

A new series of 2-amino-4-phenyl-6-hydroxy-7-alkyl-pyranobenzoquinones was synthesized as ATP-competitive CK2 inhibitors. They were readily synthesized through a three-component Knoevenagel condensation-Michael addition-heterocyclization reaction from ald

MULTIFUNCTIONAL RADICAL QUENCHERS

The invention provides a compound of formula (I): [insert formula (I)] wherein X, Y, and R1-R4 have any of the values defined in the specification, and salts thereof, as well as compositions comprising the compounds or salts. The compounds are useful for treating diseases associated with impaired mitochondrial function in an animal.

ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF

Disclosed are methods, compounds, and compositions useful for increasing autophagy and promoting longevity. The methods, compounds, and compositions relate to urolithins and urolithin precursors and use thereof. Certain urolithins are represented by Formula I, while certain urolithin precursors are represented by Formula IV. The urolithin may be urolithin A, urolithin B, urolithin C, or urolithin D. The urolithin precursor may be ellagic acid or an ellagitannin. The methods include in vivo, ex vivo, and in vitro uses of the compounds and compositions.

Discovery and biological evaluation of novel 1,4-benzoquinone and related resorcinol derivatives that inhibit 5-lipoxygenase

5-Lipoxygenase (5-LO), an enzyme that catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes, is an attractive drug target for the pharmacotherapy of inflammatory and allergic diseases. Here, we present the discovery and biological evaluation of novel series of 1,4-benzoquinones and respective resorcinol derivatives that efficiently inhibit human 5-LO, with little effects on other human lipoxygenases. SAR analysis revealed that the potency of the compounds strongly depends on structural features of the lipophilic residues, where bulky naphthyl or dibenzofuran moieties favor 5-LO inhibition. Among the 1,4-benzoquinones, compound Ig 5-[(2-naphthyl)methyl]-2- hydroxy-2,5-cyclohexadiene-1,4-dione potently blocked 5-LO activity in cell-free assays with IC50 = 0.78 μM, and suppressed 5-LO product synthesis in polymorphonuclear leukocytes with IC50 = 2.3 mM. Molecular docking studies suggest a concrete binding site for Ig in 5-LO where select π-π interactions along with hydrogen bond interactions accomplish binding to the active site of the enzyme. Together, our study reveals novel valuable 5-LO inhibitors with potential for further preclinical assessment as anti-inflammatory compounds.

Synthesis and cytotoxic activity of geranylmethoxyhydroquinone derivatives

The new synthetic geranyl-2,4-methoxyhydroquinone 1 and the known geranyl-4,5-methoxyhydroquinone 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,3,5-trimethoxyphenol using BF3·Et2O as a catalyst. Furthermore,

Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants

Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy-and tetramethoxybenzoic acids accessed by lithiation-carboxylation reactions. Direct enolate acylation was preferred over Baker-Venkataraman rearrangement when there were methoxy groups at both the 2-and the 6-position of the benzoic acid derivatives.

Synthesis and biological evaluation of hydrophilic embelin derivatives

In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogue

Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophage-like RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E2 (PGE2). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for hsPLA2, surface plasmon resonance (SPR) experiments were performed.