7549-33-9

Usage

Uses

Used in Food Industry:
Anisyl Propionate is used as a flavor enhancer for intensifying vanilla, plum, and quince flavors in beverages, baked goods, and candy. It is used in small concentrations at 6-20 ppm to provide a pleasant and distinct taste to these products. It is typically stored in glass or tin containers to maintain its stability and quality.

Preparation

By esterification of anisic alcohol with propionic anhydride

Metabolism

In substituted anisoles with a carboxyl group or a potential carboxyl group attached to the aromatic ling, the ether link is relatively stable (Williams, 1959). In the fungicidin-producing soil organism Actinomyces aureus, anisyl alcohol is metabolized to anisic acid, followed by demethylation and hydroxylation to give protocatechuic acid, which is degraded to succinic acid （Tsai.Chu,Yank&Tsao,1965).

InChI:InChI=1/C11H14O3/c1-3-11(12)14-8-9-4-6-10(13-2)7-5-9/h4-7H,3,8H2,1-2H3

Upstream product

• 802294-64-0 propionic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-62-6 propionic acid anhydride 
• 1007229-67-5 4‐methoxybenzyl 2‐bromopropanoate 
• 1612216-62-2 (4-methoxyphenyl)methyl 2-iodopropanoate 

Downstream Products

• 934008-41-0 (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester 

Relevant academic research and scientific papers

Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

Oxidative activation of dihydropyridine amides to reactive acyl donors

Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields. This journal is

On the synthesis, characterization and reactivity of n-heteroaryl-boryl radicals, a new radical class based on five-membered ring ligands

The synthesis and physical characterization of a new class of N-heterocycle-boryl radicals is presented, based on five membered ring ligands with a N(sp2) complexation site. These pyrazole-boranes and pyrazaboles exhibit a low bond dissociation energy (BDE; B-H) and accordingly excellent hydrogen transfer properties. Most importantly, a high modulation of the BDE(B-H) by the fine tuning of the N-heterocyclic ligand was obtained in this series and could be correlated with the spin density on the boron atom of the corresponding radical. The reactivity of the latter for small molecule chemistry has been studied through the determination of several reaction rate constants corresponding to addition to alkenes and alkynes, addition to O 2, oxidation by iodonium salts and halogen abstraction from alkyl halides. Two selected applications of N-heterocycle-boryl radicals are also proposed herein, for radical polymerization and for radical dehalogenation reactions.

5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

5,5′-Dimethyl-3,3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated by filtration and recycled to its azoisoxazole by oxidation.

Microwave oven synthesis of esters promoted by imidazole

Using imidazole as promotion agent, primary, secondary and phenolic alcohol compounds were esterified with aliphatic and aromatic carboxylic acid anhydrides. Heating a ternary mixture of alcohol, anhydride and imidazole in an unmodified microwave oven produced esters in low to high yields, depending on the steric bulk of the alcohol.

Sodium Borohydride-Carboxylic Acid Systems - A new Method of Acylation of Alcohols, Phenols and Thiophenols

A new method of acylation of alcohols, phenols and thiophenols in sodium borohydride-carboxylic acid system is described.A plausible mechanism of this acylation through tetraacyloxyborate derivative has been postulated.