Unusual wax esters and glycolipids: Biocatalytical formation and physico‐chemical characterization

Lang, Siegmund; Multzsch, R.; Passeri, A.; Schmeichel, A.; Steffen, Beate; Wagner, Fritz; Hamann, D. D.; Cammenga, Heiko K.

doi:10.1002/abio.370110416

Cited by 19 publications

(13 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The catalytic activity of lipases toward hydroxy fatty acid esters was well studied by Hayes [20–23]. In the esterification of several hydroxyl fatty acids Rhizomucor miehei lipase was also adopted [24–27]. Steffen et al .…”

Section: Introductionmentioning

confidence: 99%

“…The catalytic activity of lipases toward hydroxy fatty acid esters was well studied by Hayes [20][21][22][23]. In the esterification of several hydroxyl fatty acids Rhizomucor miehei lipase was also adopted [24][25][26][27]. Steffen et al used R. miehei and Candida antarctica lipases as biocatalyst for the synthesis of monoglycerides of 17-hydroxy-and 12-hydroxystearic acids with high yield [27].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

Nowicki

Woch

Mościpan

et al. 2017

J Surfact & Detergents

View full text Add to dashboard Cite

The synthesis of selected polyoxyethylene–polyoxypropylene block copolymer (poloxamer) fatty acid monoesters is presented. Organotin homogeneous catalyst Sn bis(2-ethylhexanoate) effectively catalyzed the esterification reaction of (EO)–(PO)–(EO) block copolymer (poloxamer) with fatty acids. The reaction proceeded in high yield and high selectivity to monoesters. Content of diesters in final products was below 1 wt%. The new protocol opened up a high yield and high selective method for the synthesis of poloxamer fatty acid monoesters. These products are potentially interesting for industrial applications, e.g. in lubricants, cosmetics and, in particular, as potential emulsifying agents compatible with hydrocarbon bases, such as paraffin.Electronic supplementary materialThe online version of this article (doi:10.1007/s11743-017-2020-2) contains supplementary material, which is available to authorized users.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

Nowicki

Woch

Mościpan

et al. 2017

J Surfact & Detergents

View full text Add to dashboard Cite

show abstract

“…Application of enzymes in various biochemical modifications of fats and oils is well established, and the catalytic activity of lipases toward hydroxy fatty acids is also well studied by various workers (3)(4)(5)(6)(7)(8)(9)(10)(11). According to this information, 1,2-specific lipases cannot act upon the hydroxyl group of HFA; this property has been taken advantage of in the esterification of HFA and alcohol so that estolide or lactone formation is avoided.…”

mentioning

confidence: 95%

Lipase‐catalyzed synthesis of hydroxy stearates and their properties

Ghosh

Bhattacharyya

1998

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Hydroxy fatty acid (HFA) esters of long-chain alcohols, such as hydroxy stearates, have potential applications from lubricants to cosmetics. These esters were synthesized enzymatically to overcome the problems associated with chemical processes. An immobilized lipase, Rhizomucor miehei, was employed as catalyst in the esterification reaction between hydroxy-stearic acid as a source of HFA and monohydric fatty alcohols (C 8 -C 18 ). The yields of esters were in the range of 82-90% by conducting the reactions at 65 ± 2°C, 2-5 mm Hg pressure, and 10% lipase concentration. The products were analyzed by infrared spectroscopy, and some of their analytical characteristics were determined. JAOCS 75, 1057-1059 (1998).KEY WORDS: Enzymatic esterification, hydroxy fatty acid, hydroxy stearates, lipase, Rhizomucor miehei, wax esters.Hydroxy fatty acids (HFA), derived from several natural and synthetic sources, have many applications. HFA and their derivatives are used in cosmetics, in paints and coatings, in lubricants, and in the food industry. They are useful intermediates in the synthesis of fine chemicals and pharmaceuticals (1).HFA are found in many natural sources. For example, castor oil contains 12-hydroxy oleic acid, or ricinoleic acid, which incorporates a hydroxyl group at the C 12 -atom. When subjected to hydrogenation, this castor oil fatty acid gives 12-hydroxy stearic acid. Hydroxy stearates are usually known in the form of wax esters. These wax esters form gelatinous crystalline matrixes; by contrast, with the nonhydroxy derivatives, either no crystals at all are formed, or the crystals are not held in suspension. The hydroxy derivatives have wide application in leather coatings, for oil resistance and water imperviousness, and in roll leaf foils, because of their alcohol solubility and excellent wetting and adhesion to metallic particles (2). These wax esters can be produced either by hydrogenation of castor oil fatty acid esters or directly by reacting the fatty acid and an alcohol at high temperature in the presence of tin, titanium, or sulfuric acid catalyst for up to 20 h. This high-temperature process can lead to degradation of the ester and undesired side reactions; additionally, the resulting energy costs are high. Recently, the possibility of carrying out reactions with microbial lipases has been explored because of regio-and stereospecificity of the enzymes and because of the greater degree of purity that can be obtained for the desired reaction products.Application of enzymes in various biochemical modifications of fats and oils is well established, and the catalytic activity of lipases toward hydroxy fatty acids is also well studied by various workers (3-11). According to this information, 1,2-specific lipases cannot act upon the hydroxyl group of HFA; this property has been taken advantage of in the esterification of HFA and alcohol so that estolide or lactone formation is avoided. For example, Rhizomucor miehei lipase has been employed in the esterification of several different HFA (3,5,11) and ...

show abstract

“…Application of enzymes in various biochemical modifications of fats and oils with nonoxygenated fatty acids is well studied, but there is very few literature information regarding the use of enzymes in the modification of oils, which contain fatty acid with hydroxyl groups. Catalytic activity of lipases toward hydroxy fatty acids was studied by Hayes in his different publications [3][4][5] and also by Lang et al [6], Wagner et al [7], Steffen et al [8], and Bhattacharyya et al [9]. They all showed that lipases did not catalyze the esterification of the hydroxyl group of the fatty acid with alcohol so that estolide or lactone formation can be avoided.…”

mentioning

confidence: 99%

Enzymatic interesterification of blends of castor oil and some oils rich in saturated fatty acids

Ghosh¹,

Bhattacharyya²

1999

Fett/Lipid

View full text Add to dashboard Cite

Unusual wax esters and glycolipids: Biocatalytical formation and physico‐chemical characterization

Cited by 19 publications

References 7 publications

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

Lipase‐catalyzed synthesis of hydroxy stearates and their properties

Enzymatic interesterification of blends of castor oil and some oils rich in saturated fatty acids

Contact Info

Product

Resources

About