Preparation of 2-Monoglycerides

Mazur, Adam; Hiler, George D.; El-Nokaly, Magda

doi:10.1021/bk-1991-0448.ch005

Cited by 11 publications

(7 citation statements)

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“…The relationship between k cat and K m can then be related to the partition coefficient of the substrate between the organic solvent and aqueous solution (19): [1] Thus, at a fixed value for the concentration of substrate B, the value of the ratio of K m /k cat could be related to the partition coefficients, P A , of the substrate A in a given solvent system.…”

Section: Resultsmentioning

confidence: 99%

“…More recently, enzyme-catalyzed production of monoacylglycerols or partial acylglycerols has proved promising due to the mild reaction conditions employed and high selectivity obtained. Synthesis of monoacylglycerols via enzymatic means has been carried out by hydrolysis (1,2) or glycerolysis (3,4) of fats and oils, or by direct synthesis from glycerol and fatty acids or transesterification from fatty-acid esters (5,6). A comprehensive summary of the recent progress of enzymatic production of monoacylglycerols has been made by Bornscheuer (7).…”

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confidence: 99%

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Kinetics of enzymatic synthesis of isopropylidene glycerol esters by goat pregastric lipase

Lai

Hattori

O’Connor

1999

J Americ Oil Chem Soc

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The goat pregastric lipase-catalyzed esterification of isopropylidene glycerol with caproic acid, to form isopropylidene glycerol caproate, followed a ping pong bi bi mechanism incorporating an acyl-enzyme intermediate. The maximum rate was estimated to be 96 µmol min -1 mg -1 in isooctane at 35°C, and the Michaelis-Menten constants for isopropylidene glycerol and caproic acid were 0.23 and 0.32 M, respectively. The catalyzed rate also correlated well with the partition coefficient of caproic acid between the organic and aqueous phases. The results suggest that the desolvation energy of the substrate from the bulk medium to the active site of the enzyme dominates the reaction rate for the enzyme-catalyzed reaction in organic media.Paper no. J9049 in JAOCS 76, 845-851 (July 1999).

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Kinetics of enzymatic synthesis of isopropylidene glycerol esters by goat pregastric lipase

Lai

Hattori

O’Connor

1999

J Americ Oil Chem Soc

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“…Lipases range from rigorously 1,3‐specific to completely non‐specific 38. Positionally specific lipases can be classified into three groups, non‐specific,39, 40 1,3‐specific18, 39–42 and 2‐specific 14, 30, 43. Previous results showed that the extracellular lipases produced by the growth of P roquefortii spores and emerging mycelia in suspension cultures using butter oil as the main substrate were obviously 2‐specific 14.…”

Section: Discussionmentioning

confidence: 99%

Fungal metabolism of butter and shea oils by Penicillium roquefortii in solid state cultures

Liu

2003

J Sci Food Agric

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Monoacylglycerols (monoglycerides, MAGs) were produced from butter oil and shea stearin fraction (shea oil) by two strains of Penicillium roquefortii, FRR 2456 (isolated from a spoilt melon) and Wisbey PJ (a commercial dairy strain), at pH 7.0 at 10 and 25 • C. The system was designed as a model of cheese using modified Czapek medium in solid state cultures. Shea oil with its unique fatty acid profile (stearic, oleic and palmitic acids) was used for comparison with butter oil. Yields of MAGs, which ranged from 3 to 14 g kg −1 oil, were higher with butter than with shea oil and higher when the spoilage strain FRR 2456 was used. Monoacylglycerols produced by mycelium-bound lipases from both fungal strains were mainly sn-1(3) or α isomers (60-70 mol%). Monopalmitin was the major MAG produced from both butter and shea oils. The production and use of MAGs alone or in combination with free fatty acids (FFAs) as food preservatives are discussed. It is implied that sn-1(3) MAGs together with free fatty acids may be part of a natural antimicrobial system in relatively high-pH foods such as blue mould-ripened cheese where growth of foodborne pathogens such as Listeria monocytogenes can be a problem.

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“…MAG se mogu efikasno dobijati i u dvofaznom sistemu koji sadrži model triglicerid (C 8:0 -C 14:0 ), n-heksan, alifatični alkohol (na primer 2-butanol) i vodeni rastvor pufera i 1,3-sn-specifične lipaze [26]. Navedeni dvofazni sistem voda/organski rastvarač omogućava biokatalizu lipofilnih supstrata jer obezbeđuje i polarnu fazu za rastvaranje enzima i nepolarnu fazu za rastvaranje supstrata.…”

Section: Hidrolizaunclassified

Synthesis of monoacylglycerols by enzymatic methods

Bradić¹,

Ognjanović²,

Bezbradica³

et al. 2010

Hem Ind

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Monoacylglycerols are non-ionic surfactants widely used in the food industry. They are also important in cosmetic and pharmaceutical industries as drug carriers and for the consistency improvements in creams and lotions. Current process for their production is based on the glycerolysis of natural fats and oils in the presence of inorganic catalysts at temperatures higher than 220 oC. The major drawbacks of this process include high-energy consumption, low yield, and poor product quality. The use of lipases for the monoacylglycerols production offers environmental advantages and a reduction in energy consumption. Besides, the same surfactants prepared by the enzymatic synthesis may be labeled as “natural”. Recent progress in the application of highly-stable lipases in the organic solvents offers the possibility of employing various methods to the enzyme-catalyzed synthesis of monoacylglycerols, such as selective hydrolysis of fats and oils using 1,3-regiospecific lipases, the esterification of glycerol with fatty acids and the glycerolysis of fats or oils. In this review, different reaction systems such as aqueous-organic two-phase systems, microemulsions and reverse micelles systems, anhydrous organic solvents, solvent-free systems with free or immobilized lipases, as well as the use of two-phase membrane reactor systems are presented. We discuss some of the key factors, such as the control of water content, removing of the products from reaction system, and the effects of solvent on the lipase activity and selectivity, that must be addressed in order to obtain an efficient reaction system with high yields of monoacylglycerols. Engineering of the enzymatic monoacylglycerols synthesis processes requires also optimization of other factors as: molar ratio of substrates, temperature, type of lipase immobilization and supports (if any), reactor design and operating regime

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Preparation of 2-Monoglycerides

Cited by 11 publications

References 0 publications

Kinetics of enzymatic synthesis of isopropylidene glycerol esters by goat pregastric lipase

Kinetics of enzymatic synthesis of isopropylidene glycerol esters by goat pregastric lipase

Fungal metabolism of butter and shea oils by Penicillium roquefortii in solid state cultures

Synthesis of monoacylglycerols by enzymatic methods

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