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1.
Hiroaki Kubouchi Hideto Kai Kazuo Miyashita Koji Matsuda 《Journal of the American Oil Chemists' Society》2002,79(6):567-570
The effects of two types of commercial emulsifiers, sucrose FA esters and polyglycerol FA esters, on the oxidation of soybean
oil TAG-in-water emulsions were studied. Both emulsifiers influenced the oxidative stability of soybean oil TAG in the emulsion,
but they had little effect on the oxidation of TAG in bulk phase. When the TAG were dispersed with sucrose esters having the
same FA composition, the oxidative stability increased as their hydrophilic-lipophilic balance (HLB) increased. On the other
hand, when the HLB was the same, the oxidative stability increased with increasing acyl chain length of the FA esterified
on sucrose ester. However, the effect of the polyglycerol ester could not be explained by the relationship with HLB or the
acyl composition. When the stability of TAG in emulsion was compared under the same concentrations of TAG, emulsifier, and
oxidation inducer, the TAG dispersed with sucrose esters were oxidatively less stable than with polyglycerol esters. Analysis
of the emulsion droplet size suggested that the lower oxidative stability of TAG dispersed with sucrose esters was partly
due to their relatively smaller droplet sizes. 相似文献
2.
Marina Cerdeira Valentina Pastore Liliana V. Vera Silvana Martini Roberto J. Candal María L. Herrera 《European Journal of Lipid Science and Technology》2005,107(12):877-885
The effect of highly hydrophobic emulsifiers, the palmitic sucrose ester P‐170 (hydrophilic/lipophilic balance (HLB) = 1.0), the stearic sucrose ester S‐170 (HLB = 1.0), the polyglycerol ester decaglycerol decastearate DAS 7S (HLB = 3.7) and the polyglycerol ester decaglycerol dodecabehenate DDB 750 (HLB = 2.6), on the nucleation of a high melting point milk fat fraction (HMF) and its blends with sunflower oil (SFO) was investigated by polarized laser light turbidimetry, X‐ray diffractometry and polarized light microscopy (PLM). Addition of polyglycerol esters accelerated nucleation, giving shorter induction times for the same supercooling. On the contrary, sucrose esters inhibited nucleation since induction times were elongated in all conditions selected. Addition of emulsifiers modified the polymorphic behavior in the blends with SFO. The β' form was promoted especially with the addition of S‐170. DAS 7S and DDB 750 promoted crystallization. PLM images showed many small crystals that did not appear in HMF images. Addition of P‐170 and S‐170 delayed nucleation and inhibited crystal growth. Crystals were notoriously smaller than the ones that appeared in HMF images. The Fisher–Turnbull model was used to calculate activation free energies of nucleation. In all cases, sucrose esters elevated the energy barrier for nucleation. Polyglycerol esters, however, if they had an effect on the energy barrier, lowered the values. 相似文献
3.
Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1992,69(1):9-13
A number of carbohydrate fatty acid polyesters, potential fat substitutes, were screened for their ability to reduce surface
and interfacial tensions alone or as blends with commercial emulsifiers. Commercial sucrose ester emulsifiers (Ryoto, Mitsubishi-Kasei
Food Corporation, Tokyo, Japan) were evaluated alone or blended with other sucrose esters or with other carbohydrate fatty
acid polyesters, and their surfactant properties were examined in terms of their ability to reduce surface and interfacial
tensions at different concentrations and to stabilize oil-in-water (o/w) and water-in-oil (w/o) food emulsions at room and
refrigeration temperatures, respectively.
In general, when used alone the carbohydrate polyesters were excellent stabilizers of w/o emulsions and poor stabilizers of
o/w emulsions. Blending lipophilic carbohydrate polyesters with hydrophilic commercial emulsifiers, such as S-1670, produced
stable o/w emulsions and unstable w/o emulsions. Our results suggest that emulsifier blends of potential fat substitutes with
FDA-approved commercial sugar ester emulsifiers can be prepared for possible use in low-calorie foods, cosmetics and pharmaceuticals
as o/w and w/o emulsifiers. 相似文献
4.
W. L. Kubie J. L. O'Donnell H. M. Teeter J. C. Cowan 《Journal of the American Oil Chemists' Society》1963,40(3):105-107
In the development of a stable linseed oil emulsion paint, a series of emulsifiers were prepared from linseed, oil and its
fatty acids and alcohols: (a) linseed monoglycerides, (b) mono-and dilinseed fatty sorbitan esters and a mixed ester obtained
by the transesterification of linseed oil with sorbitol, (c) polyoxyethylene ether adducts formed by reacting, ethylene oxide
with these sorbitan esters, and (d) linseed polyoxyethylene ether made by ethoxylation of linseed alcohols. Another series
of surfactants was prepared by esterifying a polyoxyethylene ether of sorbitol with various amounts of linseed fatty acids.
Conditions of preparation and pertinent physical, and chemical properties of the emulsifiers are given.
Some of these emulsifiers demonstrated filmforming properties. Combinations were formulated into linseed oil emulsion paints
with and without zinc oxide. Paints containing zinc oxide have been relatively stable in viscosity for about 2 yr. 相似文献
5.
Preparation of sucrose esters by interesterification 总被引:7,自引:0,他引:7
Feuge R. O. Zeringue H. J. Weiss T. J. Brown Mona 《Journal of the American Oil Chemists' Society》1970,47(2):56-60
Reactions between sucrose and esters of long chain fatty acids customarily have been conducted in a mutual solvent, such as
dimethylformamide. The solvent-free interesterification of molten sucrose and fatty acid esters at temperatures between 170–187
C has now been performed with the aid of lithium, sodium and potassium soaps as catalysts and solubilizers. When the reactants
were heated rapidly and then subjected to reduced pressure, the interesterifications could be brought to equilibrium in 12
min or less, including the time necessary to melt the sucrose. The several soaps and combinations of soaps employed differed
markedly in their performance. No sucrose esters were obtained with lithium palmitate, while the yield with lithium oleate
was among the best, but consisted of over 90% tetra- and higher esters of sucrose. Lower esters were best produced with combinations
of lithium oleate with sodium or potassium oleate employed at a level of about 25% total soaps, based on the weight of sucrose.
The type of fatty acid ester employed also markedly affected the yield of sucrose esters. Among the esters tested, methyl
carbitol palmitate (which could be formed in situ), monopalmitin, distearin and technical grade diglycerides (48% diglycerides)
prepared from completely hydrogenated cottonseed oil, interesterified readily.
Presented at the AOCS Meeting, Minneapolis, October 1969.
So. Utiliz. Res. Dev. Div., ARS, USDA. 相似文献
6.
S. Thiebaud J. Aburto I. Alric E. Borredon D. Bikiaris J. Prinos C. Panayiotou 《应用聚合物科学杂志》1997,65(4):705-721
In the present study, starch octanoates OCST1.8 and OCST2.7 with degrees of substitution (d.s.) of 1.8 and 2.7, respectively, and dodecanoate DODST2.7 (d.s. = 2.7), were prepared by esterification of native starch with fatty acid chlorides. Our analyses, including elemental analysis, FTIR, contact angle, DSC, and TGA measurements confirmed the esterification reaction of starch and the degree of substitution. The ester group was found to act like an internal plasticizer, with an increase in the number and the size of fatty acyl chains grafted onto starch. These starch esters were mixed with low density polyethylene (LDPE) at various proportions in a Haake Rheomixer. Water and moisture absorption, thermal and mechanical properties, and biodegradation were investigated as a function of blend composition. The DODST2.7/LDPE blends showed, in general, better thermal stability and higher elongation, but lower tensile strength and water absorption, than did corresponding OCST/LDPE blends. The addition of starch esters to LDPE led to a very slow rate of biodegradation of these blends. © 1997 John Wiley & Sons, Inc. J Appl Polym 65: 705–721, 1997 相似文献
7.
Dounia Arcens Etienne Grau Stphane Grelier Henri Cramail Frdric Peruch 《European Journal of Lipid Science and Technology》2020,122(4)
Enzymatic synthesis of fatty acid glucose esters from different fatty acyl donors are performed via enzymatic catalysis in the presence of Candida antarctica lipase B (CALB), using acetonitrile as the solvent. The acyl donor nature (fatty acid or fatty acid vinyl ester) and structure are varied. Lower reaction rates and lower conversions are obtained with fatty acids in comparison to their corresponding vinyl esters. Moreover, the acyl donor with the longest chain length gives the highest conversions. The presence of unsaturation on the acyl donor chain is also shown to be detrimental to the conversion. Practical Applications: The practical applications of the present work are related to the production of gluco‐esters that could be used as nonionic surfactants as detergents, cosmetics and food emulsifiers, emollients or conservatives, respectively. In this study, it is shown that in order to get high production yields, each reaction parameter has to be tuned properly. 相似文献
8.
Autoxidation rates of five types of safflower oil esters increased in the following order: monoacylglycerol (MG), methyl ester
(ME), diacylglycerol (DG), triacylglycerol (TG) and sucrose ester (SE). The differences in autoxidation rate were confirmed
by measuring autoxidation of similar esters of linoleic acid. The order of the oxidation rates corresponded to the number
of acyl groups per molecule. This relationship was explainable by the idea that intramolecular free radical chain reaction
between actyl groups of esters occurs more rapidly than intermolecular chain reaction.
The position of acyl groups also affected the oxidation rates of esters in that 1,3-dilinolein autoxidized more rapidly than
1,2-dilinolein. This difference in oxidation rate may result from a closer arrangement of acyl groups in 1,3-dilinolein than
those in the 1,2-isomer. 相似文献
9.
Chwen-Jen Shieh Casimir C. Akoh Philip E. Koehler 《Journal of the American Oil Chemists' Society》1996,73(4):455-460
The physical properties of sucrose polyester (SPE), prepared from different composite blends of fatty acid methyl esters (FAME)
of safflower oil, palm oil, and peanut oil, were evaluated by mixture response surface methodology. Optimum combinations of
fatty, acids to achieve specific physical properties of SPE were determined. The SPE most similar in physical properties to
peanut oil was obtained with a 55:45 molar ratio of mixed FAME from safflower oil and peanut oil. The physical properties
of SPE were significantly affected by the degree of saturation and the average chainlength of their composite fatty acids. 相似文献
10.
Pin-Der Duh Wen Jye Yen Gow-Chin Yen 《Journal of the American Oil Chemists' Society》1999,76(2):201-204
The oxidative stability of polyunsaturated fatty acids (PUFA) and soybean oil homogenized with emulsifiers was investigated.
Model emulsions were prepared from PUFA, including linoleic acid (LA), arachidonic acid (AA), eicosapentaenoic acid (EPA),
and docosahexaenoic acid (DHA), and from soybean oil emulsified with different emulsifiers: three Tween emulsifiers (Tween
20, Tween 60, Tween 80) and two sucrose esters (S-1170 and S-1570) were used. The results showed that the emulsions prepared
from LA and the various emulsifiers, oxidized at 40°C, were unstable. However, the corresponding AA, EPA, and DHA emulsions
were stable, indicating that PUFA with a higher degree of unsaturation were more stable with emulsifiers than without the
emulsifiers. In the soybean oil-in-water model system, the oxidation of soybean oil with various emulsifiers was less than
without the emulsifiers. 相似文献
11.
It has been confirmed, from observations with an electron microscope after staining negatively with aqueous uranyl acetate
solutions and using a flourescent microscope, that sucrose fatty acid esters form closed vesicles. The range of particle size
of the vesicle, consisting of chromatographically fractionated sucrose dilaurate, was apparently 70–700 nm in the longer diameter
of individual vesicles based on the transmission electron microscopic (TEM) observation. The weight-average particle size
was 424 nm as shown by means of the photon-correlation method. The amounts of 6-carboxyfluorescein trapped in the vesicles
of sucrose fatty acid esters were determined, and it was ascertained that the volumes of the central water phase depended
upon the acyl chain lengths of fatty acid residues. Further, the effect of the additives [cholesterol and dicetyl phosphate
(DCP) was examined. As an example, the vesicle of sucrose stearate had a central water phase of 1.7 one water/mol ester, and
showed a slow release of 6-carboxyfluorescein from the central water phase after preparation of the vesicle. 相似文献
12.
Ghanwa Afach Yasuhiro Kawanami Nopparat Cheetangdee Kazuhiro Fukada Ken Izumori 《Journal of the American Oil Chemists' Society》2008,85(8):755-760
The diesterification of d-psicose (the C-3 epimer of d-fructose) with fatty acid vinyl esters of selected acyl chain lengths (C8, C10, and C12) was successfully carried out using Candida antarctica lipase (Novozym 435) at 45 °C for 24 h to give the 1,6-diacyl-d-psicofuranoses with a high regioselectivity in good yields (83–90%). These diesters of d-psicose have hydrophilic-lipophilic balance (HLB) values (6.5–8.2) similar to HLB values of monoglyceride compounds which
constitute the largest single type of emulsifiers employed by the food industry. Ability of the d-psicose diesters to stabilize oil-in-water emulsions and the weight-averaged oil-droplet diameter in the emulsions was evaluated
in this study. Emulsion stability of oil droplets stabilized by d-psicose dicaprylate (0.3%, w/v in oil phase) was comparable to d-fructose dicaprylate (0.2%, w/v). It was further confirmed that the d-psicose diesters exhibited an emulsification activity depending on the chain length of fatty acid; d-psicose dicaprate showed better emulsion stability than the other diesters. 相似文献
13.
Novel products produced from seed oil materials (TAG, phospholipids, and minor components such as tocopherols, sterols, stanols,
and fatty acyl esters of the latter two) by enzyme-mediated purification or chemical modification are reviewed. The primary
focus is on “value-added products” of current and potential use (particularly in the food, cosmetics, and pharmaceutical industries)
that require the selectivity of enzymes and mild operating conditions, the latter being beneficial for polyunsaturated and
oxygenated acyl groups. The paper briefly reviews the biochemistry of enzymes in lipid modification (lipases, phospholipases,
and lipoxygenases) and discusses and assesses the current and future applications, current state of the art, and areas for
future research for the following enzyme-mediated processes: isolation of polyunsaturated and oxygenated FFA; formation of
structured TAG as nutraceuticals; formation of MAG, saccharide-FA esters, and other polyhydric alcohol ester as emulsifiers
and surfactants; isolation and/or modification of tocopherols and sterols as antioxidants; formation of hydroperoxides as
chemical intermediates; and modification of phospholipids for use in liposomes. 相似文献
14.
Isao Kobayashi Mitsutoshi Nakajima 《European Journal of Lipid Science and Technology》2002,104(11):720-727
This paper describes the preparation characteristics of food‐grade soybean oil‐in‐water (O/W) emulsions using a novel straight‐through extrusion filter, named a silicon straight‐through microchannel (MC). Polyglycerol fatty acid ester (PGFE), polyoxyethelene sorbitan monolaurate (Tween 20), and sucrose fatty acid ester were tested as emulsifiers. Optical observations of the emulsification process exhibited that monodisperse oil droplets were stably formed from an oblong straight‐through MC for PGFE and Tween 20. The effect of the emulsifier on the straight‐through MC emulsification behavior is discussed. The selected PGFE‐ and Tween 20‐containing systems enabled us to prepare monodisperse O/W emulsions with droplet diameters of 38—39 μm and coefficients of variation below 3% using an oblong straight‐through MC with a 16 μm‐equivalent channel diameter. 相似文献
15.
16.
W. W. Abramitis 《Journal of the American Oil Chemists' Society》1977,54(11):A853-A857
Fats, oils, and their derivatives are reviewed, in their roles as emulsifiers and surfactants and as pesticide derivatives, and in their activity per se. As emulsifiers and surfactants they offer a wide range of hydrophile-lipophile balance (HLB) values to assist formulators in developing saleable products. Their lipoid solubilities aid in evaporation retardation, plant penetration, and absorption. Often they greatly improve the performance of the active ingredients. Nitrogen derivatives such as amines and quaternaries, fatty alcohols, acid esters, and other agricultural chemicals are reviewed. Examples are cited on the effect of the length of the carbon chain and their number in such herbicides as 2,4-D and dalapon, as well as the biological properties of various aliphatic groups in insect larvicides, plant growth regulators, and fungicides. The role vegetable oils can play in the looming energy shortages as petroleum oil substitutes is discussed. They offer a challenging future in agricultural applications. 相似文献
17.
Several food emulsifiers have been found to serve as crystal structure modifiers for stearic acid crystallized from various
organic solvents. Stearic acid that usually precipitates under appropriate crystallization conditions as the B- form is converted
into the C- form when 1- 5% of sorbitan esters or ethoxylated sorbitan esters of fatty acids are present in the solution.
Other emulsifiers such as polyglycerol esters, bdsubstituted monoglycerides and sucrose esters of fatty acids consisting of
bulky hydrophilic groups are also effective emulsifiers in preserving the C- form of the crystallized stearic acid. The active
emulsifiers modify the external crystal habit of stearic acid. Mass spectrograph analysis indicates that sorbitan monostearate
(Span 60) is precipitated with the stearic acid. 相似文献
18.
A. Yaghmur A. Aserin Y. Mizrahi A. Nerd N. Garti 《Journal of the American Oil Chemists' Society》1999,76(1):15-18
We prepared stable oil-in-water emulsions of argan oil with two different types of mixtures of nonionic emulsifiers. Three
different types of oil (Israeli argan oil, Moroccan argan oil, and soybean oil) were emulsified with mixtures of Span 80 and
Tween 80. The optimum HLB value for argon oil was 11.0 (±1.0). The argan oil-in-water emulsions were stable for more than
5 mon at 25°C. Synergistic effects were found in enhancing stability of emulsions prepared with sucrose monostearate. The
origin of the oil and the internal content of natural emulsifiers, such as monoglycerides and phospholipids, have a profound
influence on its interfacial properties and on the stability of the argan oil-in-water emulsions. 相似文献
19.
Monoglycerol and polyglycerol esters of fatty acids have been prepared in an emulsion medium of polyglycerol in esters of
fatty acids. Transesterification between glycerol or polyglycerols and methyl esters of fatty acids is made at relatively
low temperatures (95–150 C) in the presence of alkaline catalyst and anionic or nonionic emulsifiers. The reaction system
consists of two immiscible phases transformed into a “milky” (macro) or transparent (micro) emulsion throughout the heating
process. The product obtained using this technology is not a highly substituted ester since the transesterification reaction
is selective. The type and the amount of emulsifier have to be carefully selected. Unsuitable emulsifiers which will not stabilize
the emulsion are ineffective in enlarging the contact between the reactants; therefore, the conversion of the reactants is
very poor. With suitable emulsifiers, the conversions and the yields improved due to a better contact between reactants. 相似文献
20.
Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1994,71(3):319-323
Two immobilized lipases fromCandida antarctica (SP 382) andC. cylindraceae, nowrugosa (2001), catalyzed the synthesis of novel acetylated glucose fatty acid esters with glucose pentaacetate (GP) and Trisun 80
(80% oleic) vegetable oil or methyl oleate as substrates in organic solvents. The relative yield was between 6.4–52%, and
the incorporation of oleic acid onto the glucose was between 31–100%. In addition, these enzymes were able to catalyze the
synthesis of glucose fatty acid esters with free glucose as the sugar substrate. The highest oleic acid incorporation (100%)
was obtained in benzene with SP 382 lipase and Trisun 80 as the acyl donor. With methyl oleate as the acyl donor, greater
incorporation was obtained in benzene (90.5%) compared to 75% in isooctane. The 2001 lipase was better in benzene/pyridine
(2∶1 vol/vol) 74%) and chloroform (61%) compared to benzene and isooctane. However, with free glucose and Trisun 80 as substrates,
both enzymes gave acceptable levels of oleic acid incorporation (82–100%) in benzene, benzene/pyridine and pyridine. The best
conditions for the ester interchange reaction reported are: lipase (10% by weight of substrate); incubation time 48 h; molar
ratio of Trisun/GP 1∶2; 3 mL solvent and 3% added water. These glucose esters have potential applications as emulsifiers in
food, cosmetics and pharmaceutical formulations. 相似文献