Highly Efficient Preparation of Lipophilic Hydroxycinnamates by Solvent-free Lipase-Catalyzed Transesterification was written by Weitkamp, Petra;Vosmann, Klaus;Weber, Nikolaus. And the article was included in Journal of Agricultural and Food Chemistry in 2006.Name: 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:
Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alc. such as lauryl, palmityl, and oleyl alc. under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium- and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4-hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate â?4-methoxycinnamate â?3-hydroxycinnamate > hydrocaffeate â?4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate â?sinapate. With respect to the position of the hydroxy substituents at the Ph moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, resp. Compounds with inverse chem. structure, i.e., 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl)propyl oleate and 3-(3,4-dimethoxyphenyl)propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid Me esters with the corresponding 3-phenylpropan-1-ols in high yield, as well. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Name: 3-(3,4-Dimethoxyphenyl)propan-1-ol).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Name: 3-(3,4-Dimethoxyphenyl)propan-1-ol
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem