Synthesis of some glucose-fatty acid esters by lipase from Candida antarctica and their emulsion functions

Abstract

The synthesis of glucose esters with palmitic acid, lauric acid and hexanoic acid using lipase enzyme was studied and their emulsion functionality in oil-in-water system were compared. Reactions at 3:1M ratio of fatty acids-to-glucose had the highest conversion percentages (over 90% for each of the fatty acid). Initial conversion rate increased as substrate solubility increased. Ester bond formation was confirmed by nuclear magnetic resonance technique that the chemical shifts of glucose H-6 and α-carbon protons of fatty acids in the ester molecules shifted to the higher fields. Contact angle of water on esters' pelleted surface increased as the hydrophobicity increased. Glucose esters' and commercial sucrose esters' functionality as emulsifiers were compared. Glucose esters delayed, but did not prevent coalescence, because the oil droplets diameter doubled during 7days. Sucrose esters prevented coalescence during 7days since the droplets diameter did not have significant change.

Construction of Synthetic Microbiota for Reproducible Flavor Compound Metabolism in Chinese Light-Aroma-Type Liquor Produced by Solid-State Fermentation

“…were widely used in food fermentation due to their production of various lipases (Antarctica lipase A, rugosa lipases, glucose ester synthesis lipase, etc.) (61)(62)(63). When Candida and Saccharomyces spp.…”

Acylation of unprotected lactose with 1,18‐octadec‐9‐enedioyl chloride for the synthesis of monocatenary and bolaform agro‐based surfactants

“…The presence of very weak signals at 2.4 and 2.45 ppm is observed and attributed possibly to monocatenary agro‐based surfactant product and acyl chloride reagent, respectively. This observation suggests the low efficiency of the preparative HPLC purification method . In the lactose moiety, one H‐1 proton was observed as a doublet (d) in δ 4.406 ppm; one H‐2 proton was observed as a doublet (d) in δ 4.071 ppm; two H‐3 protons were observed as a doublet (d) in δ 3.674 ppm; two H‐4 protons were observed as a doublet (d) in δ 3.413 ppm; three H‐5 protons were observed as a doublet ( m ) in δ 3.316 ppm; two H‐6 protons were observed as a doublet ( m ) in δ 3.0–3.1 ppm; and three H‐7 protons were observed as a doublet ( m ) in δ 2.8 ppm and a weak doublet at 2.78 ppm attributed to lactose isomers (Figure ) …”

“…The main differences between monocatenary and bolaform 1 H NMR spectra are the number of protons assigned to the lactose moiety and also the chemical shift of the triplet associated to the methylene group in α position of ester functional group C H 2 COOR ( δ 2.35 ppm), or associated to the methylene group in α position of acid functional group C H 2 COOH ( δ 2.40 ppm) . Also, very weak signals were observed and attributed either to a low purity or to the presence of geometric isomers of monocatenary agro‐based surfactant product …”

“…This observation suggests the low efficiency of the preparative HPLC purification method. [32] In the lactose moiety, one H-1 proton was observed as a doublet (Figure 3). [33] Moreover, the purity of bolaform cannot be evaluated solely using its NMR spectrum.…”

“…[34] Also, very weak signals were observed and attributed either to a low purity or to the presence of geometric isomers of monocatenary agro-based surfactant product. [18,32] Infrared spectroscopy (FTIR) is a fast, inexpensive and sensitive technique used for the analysis of functional groups, and it identified chemical bonds in molecules. FTIR spectra include different peaks as a function of wavenumber (400-4000 cm À1 ) producing a sample profile as a distinctive and molecular fingerprint.…”