5533-00-6

Basic information

• Product Name: 3-methoxy-4-(methoxymethoxy)benzaldehyde
• Synonyms: 3-methoxy-4-(methoxymethoxy)benzaldehyde;4-(Methoxymethoxy)-3-methoxybenzaldehyde
• CAS NO: 5533-00-6
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.19988
• EINECS: 226-881-3
• Mol File: 5533-00-6.mol
• Article Data: 40

Chemical Properties

• Melting Point: 40 °C
• Boiling Point: 316.5°Cat760mmHg
• Flash Point: 139.5°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.000409mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 3-methoxy-4-(methoxymethoxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-4-(methoxymethoxy)benzaldehyde(5533-00-6)
• EPA Substance Registry System: 3-methoxy-4-(methoxymethoxy)benzaldehyde(5533-00-6)

Safety Data

• Hazardous Substances Data: 5533-00-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3-methoxy-4-(methoxymethoxy)benzaldehyde is used as a building block for the development of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and functional groups make it a versatile compound in the synthesis of various drug candidates.
Used in Organic Synthesis:
3-methoxy-4-(methoxymethoxy)benzaldehyde is used as a key intermediate in the synthesis of complex organic molecules. Its presence of multiple functional groups allows for a wide range of chemical reactions, making it a valuable component in the creation of new compounds.
Used in Fragrance and Flavoring Industries:
Due to its aromatic properties, 3-methoxy-4-(methoxymethoxy)benzaldehyde is used in the fragrance and flavoring industries. Its pleasant scent and flavor profile make it a desirable ingredient in the development of various consumer products, such as perfumes, colognes, and food additives.
Overall, 3-methoxy-4-(methoxymethoxy)benzaldehyde has many potential applications in various industries and is a versatile compound in organic chemistry.

InChI:InChI=1/C10H12O4/c1-12-7-14-9-4-3-8(6-11)5-10(9)13-2/h3-6H,7H2,1-2H3

Upstream product

• 121-33-5 vanillin 
• 107-30-2 chloromethyl methyl ether 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 65299-00-5 3-hydroxy-4-(methoxymethoxy)benzaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 13057-17-5 bromethyl methyl ether 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 

Downstream Products

• 110048-27-6 2'-hydroxy-3,5'-dimethoxy-4-methoxymethoxy-trans-chalcone 
• 62427-71-8 (E)-3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylaldehyde 
• 119100-24-2 2'-Hydroxy-3-methoxy-4,4'-bis(methoxymethoxy)chalcone 
• 52328-99-1 1-(3-methoxy-4-methoxymethyloxyphenyl)-(1E)-1-buten-3-one 
• 148625-89-2 (1E,4E)-1,5-Bis-(3-methoxy-4-methoxymethoxy-phenyl)-penta-1,4-dien-3-one 
• 220300-07-2 methyl (E)-4-methoxymethyl-3-methoxycinnamate 
• 110049-01-9 6-methoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-chroman-4-one 
• 112742-16-2 5,7,8-trimethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-chroman-4-one 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 121-33-5 vanillin 
• 263887-27-0 4-ethynyl-2-methoxy-1-(methoxymethoxy)benzene 
• 5533-01-7 [3-methoxy-4-(methoxymethoxy)phenyl]methanol 
• 3391-75-1 2-methoxy-4-((E)-phenylethenyl)phenol 

Relevant articles and documents

Synthesis and Photoswitching Properties of Bioinspired Dissymmetric I-Pyrone, an Analogue of Cyclocurcumin

Cyclocurcumin (CC), a turmeric curcuminoid with potential therapeutic properties, is also a natural photoswitch that may undergo E/Z photoisomerization under UV light. To be further exploited in relevant biological applications, photoactivation under near-infrared (NIR) irradiation is required. Such requirement can be met through opportune chemical modifications, by favoring two-photon absorption (TPA) probability. Herein, a general and efficient synthesis of a biomimetic 2,6-disubstituted-δ-pyrone analogue of CC is described, motivated by the fact that molecular modeling previews an order of magnitude increase of its NIR TPA compared to CC. Three retrosynthetic pathways have been identified (i) via an aryl-oxazole intermediate or via aryl-diynone through (ii) a bottom-up or (iii) a top-down approach. While avoiding the passage through unstable synthons or low-yield intermediate reactions, only the latest approach could conveniently afford the 2,6-disubstituted-I-pyrone analogue of CC, in ten steps and with an overall yield of 18%. The photophysical properties of our biomimetic analogue have also been characterized showing an improved photoisomerization yield over the parent natural compound. The potentially improved nonlinear optical properties, as well as enhanced stability, may be correlated to the enforcement of the planarity of the pyrone moiety leading to a quadrupolar D-π-A-π-D system.

Process for preparing flavonoid derivatives and the intermediate thereof

The present invention provides: a method for manufacturing a flavonoid derivative using a reaction for synthesizing a chalcone derivative by a protection/deprotection reaction of a hydroxyl group and an aldol condensation reaction; and an intermediate thereof. By the method for manufacturing the flavonoid derivative of the present invention can manufacture the flavonoid derivative such as velutin and homoeriodictyol, the present invention can be usefully used in industrial fields such as cosmetics requiring mass production of flavonoid derivatives.

Method for synthesizing compound Paulownione C and Tomentodiplone O

The invention relates to a method for synthesizing natural products Tomentodiplacone O and Paulownione C. The method adopts 2, 4, 6-Trihydroxyacetophenone monohydrate compound, citral, clove aldehydeand vanillin as initial raw materials, general inorganic alkali as a catalyst, and methanol with low toxicity as a solvent; high-toxicity pyridine is avoided, and two natural products Tomentodiplone Oand Paulownione C are prepared through five steps. The method has the advantages of simple synthetic route, simple operation, green and high efficiency, thereby solving the problem of high toxicity and low yield of the prepared benzopyran compound, and the method has certain industrial economic value.

Drug compound for treating hepatopathy and application thereof

The invention discloses a drug compound for treating hepatopathy and application thereof. The drug compound specifically serves as a compound shown in general formula (I) or an optical isomer or a pharmaceutically-acceptable salt of the compound. The compound or the optical isomer or the pharmaceutically-acceptable salt of the compound has a good curative effect and low toxicity on hepatopathy, especially fatty liver. Experiments show that the compound has an obvious protective effect on zebrafish nonalcoholic fatty liver, so that the drug compound has a good application prospect in medicinesfor treatment or prevention of hepatopathy, especially fatty liver or liver fibrosis or liver cirrhosis.

STYRYLBENZOTHIAZOLE DERIVATIVES AND USES IN IMAGING

This disclosure relates to styrylbenzothiazole derivatives for use as in vivo imaging agents for the diagnosis of Parkinson's disease (PD) or other degenerative disorders or conditions of the central nervous system. Early diagnosis is particularly advantageous as neuroprotective treatment can be applied to healthy neural cells to delay or even prevent the onset of debilitating clinical symptoms.

General approach to neolignan-core of the boehmenan natural product family

Abstract: A novel approach to the neolignan-core skeletons of boehmenan natural products and to dehydrodiconiferyl alcohol glucosides based on the Fe(III)-promoted oxidative coupling has been achieved. Obtained common intermediates were further selectively modified to yield the basic molecular core possessing three orthogonally protected alkoxy functionalities available for further selective modifications. Graphical abstract: [Figure not available: see fulltext.].

Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization

The cyclohexene moiety of the tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene core of palodesangrens could be assembled in a biomimetic and step-economical fashion by the Diels-Alder reaction between the electron-rich (E)-1,3-butadienylarenes as the diene and the electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens could be prepared in three steps and up to 38% yield.

A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach

Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.

Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

A simple and efficient method for removal of phenolic methoxymethyl ethers in the presence of 30?mol% of bismuth trichloride in acetonitrile/water is described. Notable features of the cleavage protocol entail use of an ecofriendly bismuth reagent, ease of handling, low cost, operational simplicity, and good functional group compatibility. A number of structurally varied phenolic methoxymethyl ethers were cleaved in good to excellent yields.

Synthesis of Two Natural Furan-Cyclized Diarylheptanoids via 2-Furaldehyde

Two natural diarylheptanoids, 2-benzyl-5-(2-phenylethyl)furan (1) and 2-methoxy-4-{[5-(2-phenylethyl)furan-2-yl]methyl}phenol (2), were synthesized starting from 2-furaldehyde. A Wittig reaction of 2-furaldehyde with benzyltriphenylphosphonium bromide followed by reduction of the alkene C=C bond with Mg gave 2-(2-phenylethyl)furan (5). Lithiation of 5 with BuLi at -78 followed by alkylation with benzyl bromide gave natural product 1. In another approach, Friedel-Crafts acylation of compound 5 with benzoyl chloride followed by deoxygenation of the C=O group afforded 1. The natural product 2 was also synthesized by acylation of 5 with 4-acetoxy-3-methoxybenzoyl chloride (16) followed by deoxygenation and deacetylation.