121-98-2

Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl anisate is used as a flavoring agent for its sweet, creamy, anisic vanilla-like, slightly spicy, woody, and powdery heliotropine-like aroma characteristics at 10.0% concentration. It is also used as a fragrance ingredient for its spicy, sweet, anisic-like taste with woody vanilla, licorice, and methyl salicylate nuances, along with a lingering sweet coumarin vanilla aftertaste at 10 ppm concentration.
Used in Analytical Chemistry:
Methyl p-anisate has been used as a standard for the quantification of odorant compounds in French mimosa absolute oil by GC-Sniffing, a technique that combines gas chromatography with olfactory detection to identify and quantify odor-active compounds in complex samples.
Used in Medical Research:
Methyl anisate is a potential biomarker for mycobacteria, as it is released from Mycobacterium tuberculosis and can be detected in the breath of tuberculosis patients. This property can be utilized in the development of diagnostic tools and methods for the early detection and monitoring of tuberculosis infections.

Preparation

By esterification of anisic acid with methanol or from sodium anisate, dimethyl sulfate and small amounts of methanol.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 1959, 1992 DOI: 10.1016/0040-4039(92)88113-J

Biochem/physiol Actions

Taste at 10 ppm

Purification Methods

Distil the ester and/or crystallise it from EtOH. [Beilstein 10 H 159, 10 III 297, 10 IV 360.]

InChI:InChI=1/C9H10O3/c1-6-5-7(12-2)3-4-8(6)9(10)11/h3-5H,1-2H3,(H,10,11)/p-1

Upstream product

• 100444-35-7 4-methoxy-benzoic acid ; calcium compound 
• 67-56-1 methanol 
• 100-09-4 4-methoxybenzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 151-50-8 potassium cyanide 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 74-88-4 methyl iodide 
• 99-96-7 4-hydroxy-benzoic acid 
• 186581-53-3 diazomethane 
• 4456-36-4 di(p-methoxyphenyl)tellurium dichloride 
• 201230-82-2 carbon monoxide 
• 36309-68-9 p-methoxyphenyltellurium trichloride 
• 874-90-8 4-methoxybenzonitrile 
• 104-93-8 p-methylanizole 

Downstream Products

• 40061-46-9 1-(4-methoxy-phenyl)-2-pyrazin-2-yl-ethanone 
• 6316-54-7 4-methoxy-benzoic acid benzyl ester 
• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 95936-03-1 2,4-bis-(4-methoxy-phenyl)-4-methyl-pent-2-ene 
• 41070-23-9 1-(4-methoxyphenyl)-2,4,4-trimethylpentane-1,3-dione 
• 105401-95-4 3-isopropyl-4-methoxy-benzoic acid methyl ester 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 859076-89-4 1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione 
• 847-83-6 p-methoxytrityl alcohol 
• 80202-77-3 2,2',4,4'-tetramethoxy-4''-methoxytrityl alcohol 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 40757-20-8 methyl 4-methoxy-3-nitrobenzoate 
• 35450-37-4 methyl 3-bromo-4-methoxybenzoate 
• 137058-17-4 Methyl cis/trans-4-methoxycyclohexanecarboxylate 

Relevant academic research and scientific papers

Evaluation of nanostructured vanadium(v) oxide in catalytic oxidations

Nanostructured V2O5 was prepared by electrochemical anodization in the presence of complex fluoride electrolytes. The reactivity of nanostructured V2O5 was compared to a commercially available V2O5 sample in several oxidation reactions. Catalyst nanostructuring offers improvements in yields as well as rate enhancement in oxidations.

Preparation and condensation reactions of a new light-fluorous Mukaiyama reagent: reliable purification with fluorous solid phase extraction for esters and amides

A modified light-fluorous Mukaiyama reagent bearing a C8F17 tag was prepared and examined in ester and amide forming condensation reactions. Following the reactions, the desired product was effectively separated from the fluorous pyridone by-product using a simple fluorous solid phase extraction.

Alkoxycarbonylation reactions using aryl fluorosulfonates

Aryl fluorosulfonates are shown to undergo palladium catalysed alkoxycarbonylation with a variety of alcohols under mild basic conditions at ambient CO pressure.

Improved carbonylation of heterocyclic chlorides and electronically challenging aryl bromides

Optimized conditions are described that effect the carbonylation of diverse heterocyclic chlorides to yield the desired alkyl esters. In addition, bromoanilines and bromoanisoles, which normally are poor substrates under standard carbonylation protocols, were efficiently converted to the desired products under these new conditions. The nature of the metal bidentate ligand complex was found to be critical. Specifically, a correlation between ligand bite angle and catalytic efficiency is documented.

Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents

Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+[rad] bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.

Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters

An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.

Oxidation of acetals by dimethyldioxirane

Kinetic data (k2's, LFER and activation parameters) for the oxidation of a series of acetals by dimethyldioxirane to the corresponding esters in dried acetone are reported; the results are consistent with either a H-atom abstraction or direct insertion mechanism.

Total synthesis of aristogin C in aqueous systems

Aristogin C (4), a new diaryl either isolated from the leaves of Aristolochia elegans, was synthesized through a three-step procedure with readily available materials. All of the three reactions were carried out in aqueous systems. Copyright Taylor & Francis Group, LLC.

Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions

Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.

Photoelectrochemistry on TiO2/Ti anodes as a tool to increase the knowledge about some photo-oxidation mechanisms in CH3CN

Through current efficiency measurements, obtained from the photoelectrochemical oxidation at TiO2 (rutile)/Ti anodes, further mechanistic information has been obtained regarding the TiO2 photosensitized oxidation of benzylic alcohols, ethers and 1,2-diols in CH 3CN. In deaerated medium, two electrons are captured by the semiconductor from all the considered substrates (one from the substrate, the second from the intermediate benzylic radical). In contrast, in aerated CH 3CN, the number of TiO2-captured electrons can be reduced to one because, depending on its oxidizability, the benzylic radical can be competitively captured by oxygen. Copyright