The objective of the work was to produce capric acid rich structured lipids starting from various Indian indigenous vegetable oils, such as rice bran, ground nut and mustard oils. Acidolysis reaction between individual vegetable oils and capric acid in one is to three molar ratios at 45 degree centigrade temperature was carried out using position specific Candida antarctica lipase so as to protect the Sn-2 position of the oils which are rich in unsaturated fatty acids. The incorporation of capric acid depended on the reaction time showing 6 % within 6 h and 30.8 % in 72 h with rice bran oil. Similarly, in ground nut oil incorporation of capric acid was 34.2 % in 72 h compared to 5.3 % in 6 h. Thus mustard oil showed much lower incorporation than the other two oils, with 3.3 % and 19.5 % in 6 and 72 h respectively. The incorporation of capric acid was influenced by the nature of the fatty acids present in the original oil. The fatty acid composition of Sn-2 position of the structured triacylglycerols of the three oils revealed that capric acid was mainly replacing the fatty acids occupying the Sn-1 and 3 positions of the triglyceride molecule.
Phenyl fatty hydroxamic acids (PFHAs) were synthesized from canola or palm oils and phenyl hydroxylamine (FHA) catalyzed by Lipozyme TL IM or RM IM. The reaction was carried out by shaking the reaction mixture at 120 rpm. The optimization was carried out by changing the reaction parameters, namely; temperature, organic solvent, amount and kind of enzyme, period of reaction and the mol ratio of reactants. The highest conversion was obtained when the reaction was carried out under the following conditions: temperature, 39°C; solvent, petroleum ether; kind and amount of lipase, 80 mg Lipozyme TL IM/mmol oil; reaction period, 72 h and FHA-oil ratio, 7.3 mmol FHA/ mmol oil. The highest conversion percentage of phenyl hydroxylaminolysis of the Ladan and Kristal brands commercial canola oils, palm stearin and palm kernel oils were 55.6, 52.2, 51.4 and 49.7 %, respectively.
Owing to public concern regarding the adverse health effects of trans fatty acids, an alternative technology to trans fats has recently become an important issue. The interesterification of fully hydrogenated vegetable oil and liquid oil blends is one of the most versatile options. This paper reports a physical analysis of high-melting fat (HMF) prepared through the interesterification of fully hydrogenated soybean oil and regular soybean oil, and through fractionation. The thermal and structural properties of the HMF blended with salad oil at a mass ratio of 4:1 (called the HMF blend, hereafter), which was prepared as a model fat blend for margarine, were assessed using X-ray diffraction (XRD), differential scanning calorimetry (DSC), and polarized light microscopy (POM). To observe the polymorphic transformation, all samples were aged after crystallization, and the development of granular crystals during the aging process was observed. We found that the granular crystals are made of SOS/SSO, POS/PSO, and (SOS+POS)/(SSO+PSO) molecular compounds, all of which easily transform into β form with a double-chain-length structure.
Tunisian acid activated clay was investigated as catalyst in the esterification of stearic acid with ethyl alcohol, carried out in a semi-continuous reactor. Kinetic study shows that the reaction is first order with respect to acid concentration. The activation energy found was 21 kJ/mol. This result suggests that the reaction process was controlled by a diffusional step. A kinetic model, giving the apparent constant rate as a function of temperature and catalyst concentration, has been established. This equation has been then successfully applied for a complex mixture of fatty acid.
The genetic diversity of Mesoamerican populations of the biofuel plant Jatropha curcas, using the fatty acids of the seeds as chemical markers was studied. The oil content of the whole seed in 135 accessions from 38 sites varied between 8.020% and 54.28%. The prevalent fatty acids were oleic acid (18:1) and linoleic acid (18:2), and the proportion of unsaturated fatty acids varied between 74.5% and 83.7%. A study with cloned plants grown in common garden showed that both the content of oil as well as the proportion of fatty acids are highly inheritable, therefore these chemical markers are valid for estimating the genetic diversity of the species. An analysis of principal components showed that the fatty acids that contribute more to the variance are stearic, oleic, linoleic, methylpalmitic, gadoleic and ricinoleic. The populations were classified in ten groups when the data were analyzed for fatty acids by analysis of clusters, showing the elevated genetic variation in natural populations of this native species of Mesoamerica. A discriminant analysis separated the populations in accordance with their geographic origin, which was verified with a Mantel test. Using the Monmonier’s algorithm two genetic barriers between the populations were identified. The results are discussed in light of their microevolutionary significance.
The stability of sucrose fatty acid monoesters toward hydrolysis under acidic and basic conditions was evaluated. Mass spectrometric analysis of hydrolysates showed that the glycosidic bond was preferentially hydrolyzed under acidic conditions, whereas the ester bond was selectively hydrolyzed under basic conditions. Under both conditions, the rate of hydrolysis depended on the pH of the solution, the concentration of sucrose monoesters, and the acylated position of the sucrose monoesters. The hydrolysis of the glycosidic bond under acidic conditions was shown to be a first-order process. The rate constants for hydrolysis at various temperatures were measured, and the activation energies were calculated from the slope of the Arrhenius plots. The lifetime of sucrose monoesters estimated from the first-order rate constant for the hydrolysis reaction revealed that the sucrose monoesters have excellent long-term stability over a pH range of 5 to 7 at room temperature.
We investigated the effect of topical application of the glucosylceramide prepared from maize on photoaged mice. Six-week-old hairless female mice were swabbed on the back with glucosylceramide solution or vehicle, following UVA irradiation for 9 weeks. Wrinkle formation was evaluated at 3, 6, and 9 weeks by skin replica analysis by using a three-dimensional (3-D) imaging system. Moreover, epidermal thickness was analyzed at the end of the experiment. Topical application of glucosylceramide significantly reduced UVA-induced wrinkle formation in the skin as well as epidermal hypertrophy. These results suggest that topical glucosylceramide has an inhibitory effect on UVA-induced photoaging.
Previously, Lešová et al. reported the isolation and identification of metabolite OR-1, showing antitrypsin activity, produced during fermentation by Penicillium funiculosum. The structure of OR-1 was a mixture of glyceric acid (GA), esterified with C14-C18 fatty acids, and oleic acid (C18:1) as the most predominant fatty acid (Folia Microbiol. 46, 21–23, 2001). In this study, dioleoyl D-GA and dioleoyl L-GA were synthesized via diesterification with oleoyl chloride, and their antitrypsin activities were evaluated using both a disk diffusion method and spectral absorption measurements. The results show that both compounds and their equivalent mixtures possess antitrypsin activities; however, their IC50 values (approximately 2 mM) are much higher than that of OR-1 (4.25 μM), suggesting that dioleoyl GA does not play a major role in the OR-1 antitrypsin activity.