Enzymatic alcoholysis reaction of soy phospholipids

Abstract

Lipase-catalyzed alcoholysis of soy phospholipids was investigated to simultaneously make lysophospholipids and fatty acid esters of individual alcohols. Alcoholysis was carried out by stirring a mixture of soy phospholipids and individual alcohols in equimolar proportions with 10% (by weight of reactants) Mucor miehei lipase at 55°C for 24 h. The products were isolated by column chromatography after removal of the lipase. Lysophospholipids (in 69-78% molar yield) were obtained from soy phospholipids, and the yield of esters of various alcohols also conformed nearly with theoretical yields. JAOCS 74, 597-599 (1997).KEY WORDS: Alcoholysis, column chromatography, longchain alcohol esters, lysophospholipid, Mucor miehei lipase, short-and long-chain alcohols, soy phospholipid.In recent years, lipase-catalyzed transformation reactions of lipids have become important for making ester derivatives from fats and oils for various specific applications (1,2). Phospholipids, which constitute a class of industrially important surfactants, are also receiving attention for various lipase-catalyzed transformations. The conversion of phospholipids to lysophospholipids and fatty acids is usually performed by the action of phospholipases A 1 and A 2 (3-5). There are also some triacylglycerol lipases that can cleave fatty acids from the sn-1 and/or sn-2 positions of diacylglycerophospholipids to yield lysophospholipids with useful functional properties (6-9).Conversion of phospholipid to lysophospholipid by reptilian phospholipases suffers from two distinct disadvantages. Considerable difficulties are faced in deactivation of the enzymes after completion of the reaction. Also, the phospholipases show poor activity in primary alcohols or in organic solvents (10,11). On the contrary, fungal lipases function perfectly well in nearly anhydrous alcohols, and some of them have been shown to accept phospholipid as substrate (12-15).We are aware of only two literature reports concerning synthesis of lysophospholipids from soy phospholipids by lipase-catalyzed alcoholysis. One communication, published by Samey et al. (16), shows the possibilities of modifying phospholipids by alcoholysis reaction with alcohols such as ethanol, isopropanol and n-butanol, catalyzed by lipase from Rhizomucor miehei, to produce lysophospholipids. In the other publication (17), lysophospholipids were produced by glycerolysis of soy phospholipids with an immobilized form of this same lipase as a catalyst.Production of long-chain alcohol esters of C 16 -C 18 fatty acids is industrially important because these quite hydrophobic compounds are widely used as lubricants, plasticizers, and in cosmetics. Depending on the chainlength of the fatty acids and alcohols, products vary in consistency from liquid to solid waxes (18). The production of long-chain alcohol esters of fatty acids by alcoholysis involving chemical catalysts is well established. However, there are certain disadvantages of the chemical catalyst route. It is nonspecific and leads to total conversion of f...

Lysophosphatidylcholine Synthesis by Lipase-catalyzed Ethanolysis

“…1 TLC-FID Because there existed the reaction of lyso-phospholipid and alcohols, the lyso-phospholipid conversion was not higher than phospholipid conversion. The values in our study were higher greatly than the values reported by Ghosh and Bhattacharyya 16 .…”

“…In general, the reaction rate could be significantly enhanced by the addition of small amounts of water to the reaction mixture 14 . The immobilized lipase of Mucor miehei Lipozyme IM-20 could catatlyze the alcoholysis of soy PLs to produce Lyso-PLs, the alcohols were glycerol, butanol, octanol, and so on 15,16 …”

Lipase-catalyzed production of lysophospholipids

“…Moreover the authors highlighted some advantages of alcoholysis vs. hydrolysis of phospholipids such as the homogeneous reaction mixture thus simplifying the overall process control and allowing continuous operation. Lipase-catalyzed alcoholysis of natural phospholipids from soybean was also investigated (Ghosh and Bhattacharyya, 1997) using Lipozyme IM-20 ® (immobilized lipase from M. miehei, Novozymes, Denmark) and various short-and long-chain alcohols (C 4 to C 18 ). The aim of the authors was to simultaneously produce LPLs and fatty acid esters of individual alcohols, the latter having also important industrial applications.…”

Production of Surface Active Compounds by Biocatalyst Technology

“…Enzymatic alcoholysis of PLs also produce lyso-PLs and along with fatty acid esters. 19,20 The starting alcohol can be glycerol, methanol, or ethanol for example. In general, the reaction rate could be significantly enhanced by the addition of small amounts of water to the reaction mixture.…”