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3,4-Dimethoxybenzyl alcohol is an organic compound characterized by a benzyl alcohol structure with two methoxy groups attached at the 3rd and 4th positions on the benzene ring. It is known for its versatile chemical properties and potential applications in various fields.

93-03-8

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93-03-8 Usage

Uses

Used in Chemical Synthesis:
3,4-Dimethoxybenzyl alcohol is used as a key intermediate in the synthesis of various cyclotriveratrylenes (CTVs), which are cyclic molecular hosts with a cavity to accommodate guest molecules. This makes it valuable in the development of host-guest chemistry and molecular recognition.
Used in Total Synthesis:
3,4-Dimethoxybenzyl alcohol serves as a precursor in the total synthesis of salvianolic acid N, a bioactive compound with potential therapeutic applications.
Used in Microbial Fuel Cells (MFCs):
3,4-Dimethoxybenzyl alcohol is utilized as the fuel in microbial fuel cells (MFCs) to generate power. Its ability to be metabolized by certain fungi and bacteria makes it a promising candidate for sustainable energy production from lignocellulosic biomass.
Used in Lignin Degradation:
3,4-Dimethoxybenzyl alcohol is a secondary metabolite of some lignin-degrading fungi. Recent studies have explored its potential use as a fuel source for microbial fuel cells, highlighting its role in the biodegradation of lignocellulosic materials and its contribution to the development of renewable energy sources.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 4109, 1986 DOI: 10.1248/cpb.34.4109The Journal of Organic Chemistry, 59, p. 7138, 1994 DOI: 10.1021/jo00102a048

Check Digit Verification of cas no

The CAS Registry Mumber 93-03-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 93-03:
(4*9)+(3*3)+(2*0)+(1*3)=48
48 % 10 = 8
So 93-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5,10H,6H2,1-2H3

93-03-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A13396)  3,4-Dimethoxybenzyl alcohol, 97%   

  • 93-03-8

  • 25g

  • 395.0CNY

  • Detail
  • Alfa Aesar

  • (A13396)  3,4-Dimethoxybenzyl alcohol, 97%   

  • 93-03-8

  • 100g

  • 1002.0CNY

  • Detail
  • Alfa Aesar

  • (A13396)  3,4-Dimethoxybenzyl alcohol, 97%   

  • 93-03-8

  • 500g

  • 4421.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1193)  3,4-Dimethoxybenzylalcohol(VerapamilRelatedCompoundF-USP)  pharmaceutical secondary standard; traceable to USP

  • 93-03-8

  • PHR1193-500MG

  • 952.15CNY

  • Detail
  • USP

  • (1711440)  VerapamilRelatedCompoundF  United States Pharmacopeia (USP) Reference Standard

  • 93-03-8

  • 1711440-150MG

  • 13,501.80CNY

  • Detail

93-03-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (3,4-dimethoxyphenyl)methanol

1.2 Other means of identification

Product number -
Other names 3,4-Dimethoxybenzyl Alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:93-03-8 SDS

93-03-8Relevant articles and documents

Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)

Fayos,Barbero,Savirón,Orduna,Durán,Palma,Molinillo,Macías,Barroso,Mallor,Garcés-Claver

, p. 87 - 94 (2018)

Capsinoids exhibit health-promoting properties and are therefore compounds of interest for medical and food sciences. They are minor compounds present in relatively high concentrations in only a few number of pepper cultivars. It is desirable to quantify capsinoids to provide selected cultivars with high capsinoid contents, which can then be employed as health food product. Quantifying low concentrations of capsinoids from pepper fruit requires a precise and selective analytical technique such as HPLC coupled to electrospray ionization - mass spectrometry, with development of an internal standard essential. In this work, the synthesis method of a novel compound analogue of capsinoids, the (±)-3,4-dimethoxybenzyl-4-methyloctanoate, which could be a suitable internal standard for capsinoid determination by electrospray ionization - mass spectrometry is described. (±)-3,4-dimethoxybenzyl-4-methyloctanoate was stable under the analysis conditions and exerted chemical and physical properties similar to those of capsinoids. This internal standard will provide an accurate capsinoid determination by electrospray ionization - mass spectrometry, thus facilitating the pepper breeding programs, screening pepper cultivars and a better understanding of capsinoid biosynthetic pathway.

One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA

Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.

, (2022/01/13)

Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.

Direct use of the solid waste from oxytetracycline fermentation broth to construct Hf-containing catalysts for Meerwein-Ponndorf-Verley reactions

Chen, Yuxin,Yao, Xuefeng,Wang, Xiaolu,Zhang, Xuefeng,Zhou, Huacong,He, Runxia,Liu, Quansheng

, p. 13970 - 13979 (2021/04/22)

The oxytetracycline fermentation broth residue (OFR) is an abundant solid waste in the fermentation industry, which is hazardous but tricky to treat. The resource utilization of the waste OFR is still challenging. In this study, a novel route of using OFR was proposed that OFR was used as the organic ligands to construct a new hafnium based catalyst (Hf-OFR) for Meerwein-Ponndorf-Verley (MPV) reactions of biomass-derived platforms. The acidic groups in OFR were used to coordinate with Hf4+, and the carbon skeleton structures in OFR were used to form the spatial network structures of the Hf-OFR catalyst. The results showed that the synthesized Hf-OFR catalyst could catalyze the MPV reduction of various carbonyl compounds under relatively mild reaction conditions, with high conversions and yields. Besides, the Hf-OFR catalyst could be recycled at least 5 times with excellent stability in activity and structures. The prepared Hf-OFR catalyst possesses the advantages of high efficiency, a simple preparation process, and low cost in ligands. The proposed strategy of constructing catalysts using OFR may provide new routes for both valuable utilization of the OFR solid waste in the fermentation industry and the construction of efficient catalysts for biomass conversion.

Laccase-catalyzed oxidation of allylbenzene derivatives: Towards a green equivalent of ozonolysis

Antoniotti, Sylvain,Blerot, Bernard,Chietera, Giorgiana,Lecourt, Mathilde

supporting information, (2021/10/19)

Laccase-based biocatalytic reactions have been tested with and without mediators and optimized in the oxidation of allylbenzene derivatives, such as methyl eugenol taken as a model substrate. The reaction primarily consisted in the hydroxylation of the propenyl side chain, either upon isomerization of the double bond or not. Two pathways were then observed; oxidation of both allylic alcohol intermediates could either lead to the corresponding α,β-unsaturated carbonyl com-pound, or the corresponding benzaldehyde derivative by oxidative cleavage. Such a process consti-tutes a green equivalent of ozonolysis or other dangerous or waste-generating oxidation reactions. The conversion rate was sensitive to the substitution patterns of the benzenic ring and subsequent electronic effects.

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

Cao, Dawei,Xia, Shumei,Pan, Pan,Zeng, Huiying,Li, Chao-Jun,Peng, Yong

supporting information, p. 7539 - 7543 (2021/10/12)

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.

Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi

Zhuk, Tatyana S.,Skorobohatko, Oleksandra S.,Albuquerque, Wendell,Zorn, Holger

supporting information, (2021/02/02)

The reductive activity of various basidiomycetous fungi towards carbonyl compounds was screened on an analytical level. Some strains displayed high reductive activities toward aromatic carbonyls and aliphatic ketones. Utilizing growing whole-cell cultures of Dichomitus albidofuscus, the reactions were up-scaled to a preparative level in an aqueous system. The reactions showed excellent selectivities and gave the respective alcohols in high yields. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions. In particular, benzoic, vanillic, ferulic, and p-coumaric acid were reduced to benzyl alcohol, vanillin, dihydroconiferyl alcohol and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.

Highly efficient Meerwein-Ponndorf-Verley reductions over a robust zirconium-organoboronic acid hybrid

Song, Jinliang,Hua, Manli,Huang, Xin,Visa, Aurelia,Wu, Tianbin,Fan, Honglei,Hou, Minqiang,Zhang, Zhaofu,Han, Buxing

, p. 1259 - 1265 (2021/02/26)

The Meerwein-Ponndorf-Verley (MPV) reaction is an attractive approach to selectively reduce carbonyl groups, and the design of advanced catalysts is the key for these kinds of interesting reactions. Herein, we fabricated a novel zirconium organoborate using 1,4-benzenediboronic acid (BDB) as the precursor for MPV reduction. The prepared Zr-BDB had excellent catalytic performance for the MPV reduction of various biomass-derived carbonyl compounds (i.e., levulinate esters, aldehydes and ketones). More importantly, the number of borate groups on the ligands significantly affected the catalytic activity of the Zr-organic ligand hybrids, owing to the activation role of borate groups on hydroxyl groups in the hydrogen source. Detailed investigations revealed that the excellent performance of Zr-BDB was contributed by the synergetic effect of Zr4+and borate. Notably, this is the first work to enhance the activity of Zr-based catalysts in MPV reactions using borate groups.

Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

Dhokale, Bhausaheb,Susarrey-Arce, Arturo,Pekkari, Anna,Runemark, August,Moth-Poulsen, Kasper,Langhammer, Christoph,H?relind, Hanna,Busch, Michael,Vandichel, Matthias,Sundén, Henrik

, p. 6344 - 6355 (2020/10/28)

The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.

Triazole derivative as well as preparation method and application thereof

-

Paragraph 0081; 0088-0090, (2020/06/09)

The invention relates to a triazole derivative as well as a preparation method and application thereof, which belong to the technical field of organic synthetic drugs. The structure of the triazole derivative is shown as a formula I. In the formula I, R1 and R2 are H, Cl, Br,-CF3,-CH(CH3)2 or -OCH3, and R1 and R2 are not H at the same time. R3 is -CH2 or -COCH2; X and Y are N or C, X and Y are not C at the same time, and X and Y are not N at the same time. The triazole derivative disclosed by the invention has a certain inhibition effect on germs of various crop diseases. Small toxic andside effects on plants are achieved. The preparation method of the triazole derivative is simple.

CNN pincer ruthenium complexes for efficient transfer hydrogenation of biomass-derived carbonyl compounds

Figliolia, Rosario,Cavigli, Paolo,Comuzzi, Clara,Del Zotto, Alessandro,Lovison, Denise,Strazzolini, Paolo,Susmel, Sabina,Zuccaccia, Daniele,Ballico, Maurizio,Baratta, Walter

supporting information, p. 453 - 465 (2020/01/21)

The ligand HCNNOMe (6-(4-methoxyphenyl)-2-aminomethylpyridine) is easily prepared from the commercially available 6-(4-methoxyphenyl)pyridine-2-carbaldehyde by the reaction of hydroxylamine and hydrogenation (H2, 1 atm) with Pd/C. The pincer complexes cis-[RuCl(CNNOMe)(PPh3)2] (1) and [RuCl(CNNOMe)(PP)] (PP = dppb, 2; and dppf, 3) are synthesized from [RuCl2(PPh3)3], HCNNOMe and PP (for 2 and 3) in 2-propanol with NEt3 at reflux and are isolated in 85-93% yield. Carbonylation of 1 (CO, 1 atm) gives [RuCl(CNNOMe)(CO)(PPh3)] (4) (79% yield) which cleanly reacts with Na[BArf4] and PCy3, affording the cationic trans-[Ru(CNNOMe)(CO)(PCy3)(PPh3)][BArf4] (5) (92% yield). These robust pincer complexes display remarkably high catalytic activity in the transfer hydrogenation (TH) of lignocellulosic biomass carbonyl compounds, using 2-propanol at reflux in a basic medium (NaOiPr or K2CO3). Thus, furfural, 5-(hydroxymethyl)furfural and Cyrene are reduced to the corresponding alcohols with 2 and 3, at S/C in the range of 10 000-100 000, within minutes or hours (TOF up to 1 500 000 h-1). The monocarbonyl complex 5 was found to be extremely active in the TH of cinnamaldehyde, vanillin derivatives and ethyl levulinate at S/C in the range of 10 000-50 000. Vanillyl alcohol is also obtained by the TH of vanillin with 5 (S/C = 500) in 2-propanol in the presence of K2CO3.

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