Random intraesterification

Abstract

The present invention relates to a method for modifying one or more types of triglycerides in a fat, comprising subjecting a single fat selected from the group consisting of high stearic high oleic sunflower oil, high stearic high oleic soybean oil, high stearic high oleic rapeseed oil, high stearic high oleic cottonseed oil, palm olein and shea olein to an intraesterification process in which the fatty acids of the triglycerides of said oil or fat are randomly redistributed between the triglycerides to obtain an oil or fat with a modified solid fat content (SFC) profile. Further, the present invention relates to the obtained fats and use thereof.

Claims

1. A method for modifying one or more types of triglycerides in a single fat type, comprising subjecting a single oil or fat type selected from the group consisting of high stearic high oleic sunflower oil, high stearic high oleic soybean oil or olein fraction, high stearic high oleic rapeseed oil or olein fraction, and high stearic high oleic cottonseed oil or olein fraction, to an intraesterification process in which the fatty acids of the triglycerides constituting said single oil or fat type are randomly redistributed within said triglycerides and/or amongst said triglycerides of only said single oil or fat type to obtain an oil or fat with a modified solid fat content (SFC) profile.

2. The method according to claim 1, wherein the random redistribution is carried out by a temperature within the range of 60 to 90° C., in the presence of a sodium methoxide catalyst.

3. The method according to claim 1, wherein the random redistribution is carried out by an enzymatic process.

4. A composition comprising a triglyceride or fat obtainable by a method comprising subjecting a single oil or fat type selected from the group consisting of high stearic high oleic sunflower oil, high stearic high oleic soybean oil or olein fraction, high stearic high oleic rapeseed oil or olein fraction, and high stearic high oleic cottonseed oil or olein fraction, to an intraesterification process in which the fatty acids of the triglycerides constituting said oil or fat are randomly redistributed within said triglycerides and/or amongst said triglycerides of only said single oil or fat type to obtain an oil or fat with a modified solid fat content (SFC) profile.

5. The composition as claimed in claim 4, wherein the composition is a food.

6. The composition as claimed in claim 5, wherein the food is selected from the group consisting of margarines, spreads, coatings, fillings, confectionery products and cooking oils.

7. The method according to claim 1, wherein the method increases an amount of saturated-unsaturated-saturated (SUS) triglycerides, saturated-saturated-unsaturated (SSU), and/or saturated-saturated-saturated (SSS) triglycerides in the oil or fat.

8. The method according to claim 1, wherein the method increases the solid fat content (SFC) profile of the oil or fat.

9. The method according to claim 1, wherein the intraesterification process comprises contacting said single oil or fat type with a catalyst.

10. The method according to claim 1, wherein the intraesterification process comprises contacting said single oil or fat type with an enzyme.

11. The method according to claim 10, wherein the enzyme is a non-specific 1,3 enzyme.

12. A method for modifying one or more types of triglycerides in a single fat type, comprising subjecting a single oil or fat type selected from the group consisting of high stearic high oleic sunflower oil, high stearic high oleic soybean oil or olein fraction, high stearic high oleic rapeseed oil or olein fraction, and high stearic high oleic cottonseed oil or olein fraction, to an intraesterification process in which the fatty acids of the triglycerides of said single oil or fat type are randomly redistributed within said triglycerides and/or amongst said triglycerides of only said single oil or fat type to obtain an oil or fat with a modified solid fat content (SFC) profile, wherein the random redistribution is carried out at temperature within the range of 60 to 90° C. in the presence of a catalyst or by an enzymatic process.

13. The method according to claim 12, wherein the method increases an amount of saturated-unsaturated-saturated (SUS) triglycerides, saturated-saturated-unsaturated (SSU), and/or saturated-saturated-saturated (SSS) triglycerides in the oil or fat.

14. The method according to claim 13, wherein the method increases the solid fat content (SFC) profile of the oil or fat.

15. The method according to claim 14, wherein the random redistribution is carried out at temperature within the range of 60 to 90° C., in the presence of a catalyst.

16. The method according to claim 15, wherein the catalyst is a sodium methoxide catalyst.

17. The method according to claim 14, wherein the random redistribution is carried out by an enzymatic process.

18. The method according to claim 17, wherein the enzyme is a non-specific 1,3 enzyme.

Description

FIGURES

(1) FIG. 1 shows a predictive equation for random intraesterification.

(2) FIG. 2 shows the solid fat content of HSHO oils and oleins by NMR before and after the randomization.

EXAMPLES

Example 1

(3) Predictive Equation

(4) A predictive equation has been obtained to indicate the triglycerides' (TAG) composition after the intraesterification process based on the triglycerides (TAG) and fatty acid (FA) composition of the fat before the intraesterification process. The predictive equation is shown in FIG. 1.

Example 2

(5) Preliminary Trial of Random Intraesterification

(6) 100 g of high stearic high oleic HSHO sunflower oil or olein are placed in the randomization reactor with agitation at 78-82° C. 0.5 g of catalyst sodium methoxide are added to the reactor. Randomization time used: 3.5 hrs. The reaction is stopped by the neutralization of the catalyst with powder citric acid. These products are removed by washing 4 times with 150 ml of warm (about 70° C.) distilled water. The product is dried with anhydrous sodium sulphate.

(7) Chromatographic Analysis of TAGs and Fatty Acids

(8) The TAG composition of the different stearin fractions was determined by GC using an Agilent 6890 gas chromatograph (Palo Alto, Calif.) equipped with a Quadrex Aluminium-Clad 40065HT (30 m length, 0.25 mm i.d., 0.1 μm film thickness (Woodbridge, Conn., USA) and a flame ionization detector. Hydrogen was used as the carrier gas at a linear rate of 50 cm/s and split ratio 1:80. The injector and detector temperatures were 360 and 370° C. respectively, the oven temperature was 335° C., and a head pressure gradient from 100 to 180 kPa was applied. The relative response of the FID was corrected according to the method of Carelli and Cert 1993 (Comparative study of the determination of triacylglycerols in vegetable oils using chromatographic techniques. J. Chromatogr. 630, 213-222).

(9) Fatty acids were analyzed as their methyl esters in a similar chromatograph but equipped with a Supelco SP-2380 fused silica capillary column (30 m length; 0.25 mm i.d.; 0.20 μm film thickness: Bellefonte, Pa.). The analysis conditions were carrier gas (hydrogen) flow at 28 cm.Math.s−1, detector and injector temperature were 200° C., whereas oven temperature was kept at 170° C.

(10) Methylation of the TAG fatty acids was carried out at 80° C. for 1 h after adding a volume of 1.5 mL of methanol/toluene/sulphuric acid (88/10/2; v/v/v) to 5 mg of fat.

(11) For both samples (oil and olein) there are significant increments (about 30 and 60% respectively) in the SUS content by decreasing the SUU content. The increment in SUS yields a better behavior in some applications by an increasing of the solid fat content (SFC) at 15° C. The impact of decreasing SUU, involves a reduction in the solid fat content (SFC) at fridge temperature (below 10° C.)

Example 3

(12) Second and Third Trial of Random Intraesterification

(13) Two more trials were performed as described in Example 2, specifically one additional trial for the olein and 2 additional trials for the oil).

(14) The results of trials 1, 2 and 3 are shown in Table 1 below.

(15) TABLE-US-00001 TABLE 1 TAG type Oil type SUS SUU UUU SSS HSHO oil 9.4 51.8 38.8 0.0 Predicted for oil 12.7 41.3 44.7 1.3 HSHO oil randomized 1 12.4 39.8 47.8 n.d. HSHO oil randomized 2 12.0 40.5 46.9 0.6 HSHO oil randomized 3 12.0 40.5 46.7 0.8 HSHO Olein 7.0 51.9 41.1 0.0 Predicted for olein 11.3 40.1 47.5 1.1 HSHO olein randomized 1 11.5 40.2 48.4 n.d. HSHO olein randomized 2 11.6 40.1 47.6 0.7 n.d. = not detected 1 is preliminary trial of example 2 2 and 3 are new trials of example 3

(16) It follows that in both the oil and the olein the SUU content is significantly decreased and the SUS content is significantly increased by performing the random intraesterification of the invention.

Example 4

(17) Determination of Solid Fat Content

(18) The solid fat content (SFC) of the HSHO oil, HSHO olein fraction and the intraesterified products of examples 2 and 3 were determined using NMR. (Nuclear magnetic resonance)

(19) FIG. 2 shows that the solid fat content of the random intraesterified products of example 2 and 3 is modified compared with the solid fat content of the original HSHO oil and HSHO olein fraction, becoming suitable to be used in some confectionery fillings and as part of the fat phase of margarines and spreads.

Example 5

(20) Determination of Melting Point

(21) The melting point of the HSHO oil, HSHO olein fraction and random intraesterified products of examples 2 and 3 was determined using standard techniques.

(22) Table 2 shows that the melting point of the random intraesterified HSHO oil and HSHO olein fraction are significantly increased when compared to the original HSHO oil and HSHO olein fraction.

(23) TABLE-US-00002 TABLE 2 Melting point Sample (° C.) HSHO 14.3 HSHO olein 12.1 HSHO intraesterified 27.2 HSHO olein intraesterified 24.8