5556-84-3

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-Trimethoxybenzaldehyde is used as a starting reagent for the preparation of imine derivatives, which might exhibit glycosidase inhibitory properties. These inhibitors are essential in the development of drugs targeting various diseases, including diabetes and obesity, by modulating the activity of glycosidase enzymes.
2,3,5-Trimethoxybenzaldehyde is also used as a starting reagent for the preparation of phenylalkylamine analogs with psychoactive properties. These analogs have potential applications in the development of medications for the treatment of neurological and psychiatric disorders, such as depression, anxiety, and schizophrenia.
Used in Chemical Synthesis:
2,3,5-Trimethoxybenzaldehyde serves as a starting reagent for the preparation of flavonoids, a class of natural compounds with diverse biological activities. Flavonoids are found in many plants and have been extensively studied for their antioxidant, anti-inflammatory, and anticancer properties. The synthesis of flavonoids using 2,3,5-trimethoxybenzaldehyde can contribute to the development of novel therapeutic agents and nutraceuticals.

InChI:InChI=1/C10H12O4/c1-12-8-4-7(6-11)10(14-3)9(5-8)13-2/h4-6H,1-3H3

Upstream product

• 2179-22-8 2,5-dihydroxy-3-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 62648-55-9 5-hydroxy-2,3-dimethoxybenzaldehyde 
• 36873-96-8 2,3,5-trimethoxybenzoic acid 
• 23030-39-9 1-bromo-2,3,5-trimethoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 100460-33-1 7,7-dimethoxy-2,5-cycloheptadiene-1,4-dione 
• 149-73-5 trimethyl orthoformate 
• 100460-34-2 5,5,6-trimethoxy-2-cycloheptene-1,4-dione 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 6324-49-8 2,3-dimethoxy-5-nitrobenzaldehyde 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 13330-65-9 2,4-dimethoxyphenol 

Downstream Products

• 91134-67-7 (E)-2,3,5-trimethoxy-β-nitro-styrene 
• 36873-96-8 2,3,5-trimethoxybenzoic acid 
• 107301-77-9 2,3,5-trimethoxy-benzyl alcohol 
• 6010-78-2 2-nitro-1-(2,3,5-trimethoxyphenyl)propene 
• 88775-44-4 2,3,5-trimethoxy-3',4'-methylenedioxychalcone 
• 93092-17-2 2'-hydroxy-2,3,4',5,5',6'-hexamethoxychalcone 
• 94272-89-6 2,3,5-trimethoxybenzylaminoacetaldehyde diethyl acetal 
• 171526-69-5 1-(2,3,5-Trimethoxy-phenyl)-undecan-1-ol 
• 93092-19-4 5-hydroxy-2',3',5',6,7-pentamethoxyflavone 
• 93746-14-6 5,6,7-Trimethoxy-2-(2,3,5-trimethoxy-phenyl)-chroman-4-one 
• 93092-18-3 5,6,7-Trimethoxy-2-(2,3,5-trimethoxy-phenyl)-chromen-4-one 
• 110361-77-8 methyl 2,3,5-trimethoxybenzoate 
• 146202-78-0 2,3,5-trimethoxyphenylacetonitrile 
• 5273-81-4 cis-2,3,5-Trimethoxy-1-propenyl-benzol 

Relevant academic research and scientific papers

An Improved Preparation of the p-Tropoquinone Mono- and Diacetals by Thallium(III) Nitrate Oxidation of 2-Alkoxy-5-hydroxytropones

The thallium(III) nitrate-oxidation of 2-alkoxy-5-hydroxytropones gave, in good yields, the mono- and diacetals of tropoquinones, which can be used for the introduction of oxygen functions to the seven-membered nucleus and preparation of the substituted t

Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives

In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.

Attempt to synthesize 2,3,5,4′-tetrahydroxystilbene derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG)

An attempt to synthesize aglycone 1 derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG) via the Wittig reaction and Mizoroki-Heck reaction is described. In the Wittig protocol, 2,3,5,4′-tetramethoxystilbene 2 was obtained. Additionally, a palladium-catalyzed Mizoroki-Heck reaction strategy yielded 2-aryl-2,3-dihydrobenzofuran 13 instead of derivative 12 in good yield.

DNA cleavage by Di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu(II), and alkali

Several 5-alkyl-1,3-dihydroxybenzene (5-alkylresorcinol, 1) and 6-alkyl-1,2,4-trihydroxybenzene (2) derivatives were prepared and used to study the mechanism by which such compounds effect Cu(II)-dependent DNA strand scission. Comparison of the methyl, n-pentyl, n-undecyl, and n-hexadecyl derivatives in each structural series indicated that the efficiency of DNA cleavage increased with increasing length of the alkyl substituent. DNA cleavage by the 5-alkylresorcinols appears to involve initial oxygenation of the benzene nucleus, a process that occurs readily at alkaline pH in the presence of Cu2+ and O2. The resulting trihydroxylated benzenes mediate DNA cleavage in a reaction dependent on the presence of both Cu2+ and O2. The mechanism appears to involve reduction of Cu2+ by the trihydroxybenzene moiety in 2, with subsequent formation of reactive oxygen species. The ability of catalase and dimethyl sulfoxide to suppress DNA strand scission is consistent with the intermediacy of H2O2 and ?OH in the DNA strand scission process.

Synthesis of 2-Methoxystypandrone: Comments on the Structure of Ventilaginone

The structure of 2-methoxystypandrone a naphthoquinone isolated from Polygonum cuspidatum, Rhamnus fallax, and Ventilago calyculata is confirmed by synthesis as 6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione (1).The structure proposed for ventilaginone, an unusual naphthalene isolated from Ventilago maderaspatana, 8,9-dimethoxy-5-methylnaphtho-1,3-dioxin-4-yl methyl ketone (17), is shown by synthesis to be erroneous.Alternative structures are considered.

Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo[c]phenanthridine alkaloids. (1). Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides

For the sake of establishment of a versatile synthetic method for benzo[c]phenanthridine alkaloids, improvement of the Robinson synthetic method was examined. Thirteen chalcones (7a-m) were prepared by condensation of two acetophenone derivatives (15 and 16) with eleven benzaldehyde derivatives (19a-k) as fundamental starting materials. Hydrocyanation of these chalcones (7a-1) except one (7m) gave the corresponding 2,4-bisaryl-4-oxobutyronitriles (8a-1). Eleven 2,4-bisaryl-4-oxobutyramides (9a-k) were also prepared.