A glyceride composition and a method for its preparation

Abstract

The application belongs to the field of light industry grease, and discloses a glyceride composition with low-temperature anti-coagulation and a preparation method thereof. After chlorogenic acid and propylene glycol are esterified, the esterification product of chlorogenic acid and propylene glycol is applied to peanut oil glyceride, and the peanut oil glyceride with low-temperature anti-coagulation is obtained through dry fractionation. Experimental results show that the esterification product of chlorogenic acid and propylene glycol can promote the aggregation of high-melting-point glyceride in liquid oil, avoid the precipitation of the high-melting-point glyceride at low temperature, improve the coagulation and precipitation phenomenon of peanut oil glyceride at low temperature, and improve the transparency of the product at low temperature.

Description

Technical Field

[0001] This invention belongs to the field of light industrial oils and fats, and specifically relates to a diglyceride composition with low-temperature anticoagulation properties and its preparation method. Background Technology

[0002] Diacylglycerol (DAG) is a structural lipid with only two fatty acyl groups on its glycerol backbone. Its metabolic pathway differs from that of traditional triglycerides; after ingestion, it is difficult to synthesize neutral fats. It is highly effective in controlling body fat accumulation, lowering blood lipids and postprandial blood glucose, and its taste, color, and flavor are indistinguishable from ordinary triglycerides. It is an important component of healthy fats in the future food industry. Currently, diacylglycerol products developed based on vegetable oils such as peanut oil are already on the market in China. Because diacylglycerol contains a hydroxyl group and its fatty acid structure is more loosely arranged, allowing for stronger hydrogen bonds between the hydroxyl groups, its crystal network structure is more compact. Therefore, compared to triglycerides with the same fatty acid composition, diacylglycerol has a higher melting point and the potential to replace saturated solid fats.

[0003] However, the high melting point of peanut oil diglycerides also brings some problems, causing high-melting-point components to precipitate at lower temperatures, resulting in turbidity and precipitation in the oil. This unevenness and non-uniformity significantly affects consumers' perception of the diglyceride product and impacts sales. Traditional solutions to this problem mainly include three points: (1) using dark brown or opaque packaging materials to package the diglycerides. This method does not solve the actual problem; (2) using fractionation technology to extract the high-melting-point components from the diglyceride oil to obtain low-melting-point components, thus solving the problem of easy solidification at low temperatures. However, this method may cause high-melting-point diglycerides to aggregate in the solid fat components, reducing the yield of diglycerides in the liquid oil and lowering the diglyceride content; (3) adding anti-crystallization agents to delay the crystallization of the oil and thus delay the solidification and precipitation of the product. This method is suitable for the anti-coagulation properties of oil at room temperature. If the temperature drops below 10°C, the product will still precipitate. After analysis, none of the above problems can be solved effectively. Summary of the Invention

[0004] To address the problem of peanut oil diglycerides easily solidifying and precipitating at low temperatures, the primary objective of this invention is to provide a method for preparing a diglyceride composition with low-temperature anti-coagulation properties. This invention provides a peanut oil diglyceride derived from the esterification of chlorogenic acid and propylene glycol. After uniformly mixing the esterified chlorogenic acid and propylene glycol with the peanut oil diglyceride, a dry fractionation process is performed. In the resulting liquid oil fraction, the diglyceride content remains unchanged, but the SFC content and melting point at 5°C are significantly reduced. The peanut oil diglyceride obtained by this method exhibits significantly enhanced anti-coagulation properties during refrigeration.

[0005] The present invention provides a diglyceride composition with low-temperature anticoagulation properties prepared by the above method.

[0006] This invention involves esterifying chlorogenic acid and propylene glycol, then applying the resulting esterification product to peanut oil diglycerides. Dry fractionation yields peanut oil diglycerides with low-temperature anti-coagulation properties. Experimental results show that the esterification product of chlorogenic acid and propylene glycol promotes the aggregation of high-melting-point diglycerides in liquid oil while preventing their precipitation at low temperatures, thus reducing the coagulation and precipitation phenomenon of peanut oil diglycerides at low temperatures and improving the transparency of the product at low temperatures.

[0007] The objective of this invention is achieved through the following technical solution:

[0008] A method for preparing a diglyceride composition with low-temperature anticoagulation properties includes the following steps:

[0009] (1) Chlorogenic acid and propylene glycol are esterified under vacuum to obtain esterified products of chlorogenic acid and propylene glycol;

[0010] (2) Peanut oil diglyceride is mixed with the chlorogenic acid and propylene glycol esterification product obtained in step (1) to obtain an oil mixture;

[0011] (3) The oil mixture is dry fractionated at 15°C to obtain the liquid component, which is the diglyceride composition with low-temperature anticoagulation properties.

[0012] The esterification reaction in step (1) is an enzyme-catalyzed esterification, wherein the enzyme catalyst used is preferably Novozyme 435; the amount of enzyme added is preferably 1 to 5% of the substrate mass, more preferably 3%.

[0013] The reaction temperature of the esterification reaction in step (1) is 50~90℃, preferably 70℃; the reaction time is 60~90min, preferably 80min.

[0014] The vacuum condition described in step (1) is preferably an absolute pressure of 500-2000 Pa.

[0015] The mass ratio of chlorogenic acid to propylene glycol in step (1) is preferably 1:1 to 1:2, and more preferably 1:1.

[0016] The amount of chlorogenic acid and propylene glycol esterification product used in step (2) is such that the mass of chlorogenic acid and propylene glycol esterification product accounts for 0.5-2% of the mass of peanut oil diglyceride, more preferably 1.5%.

[0017] The mixing in step (2) is carried out at 60°C for 10-30 minutes.

[0018] The peanut oil diglyceride in step (2) has a diglyceride content of 40-90% and a solid fat content (SFC) value of 8-30% at 5°C.

[0019] The peanut oil diglyceride described in step (2) is prepared by the following steps: peanut oil is added to glycerol, and then stirred at 50-65℃. Lipase is added and the mixture is reacted under vacuum for 60-90 min. The crude product is then subjected to molecular distillation to remove free fatty acids, glycerol, and monoglycerides to obtain peanut oil diglyceride.

[0020] Preferably, in step (2), the mass ratio of peanut oil to glycerol is 1-3:10; the amount of lipase used is 0.1-0.3% of the substrate mass; the lipase refers to Lipozyme TL IM; the vacuum refers to an absolute pressure of 500-2000 Pa; molecular distillation refers to the heavy phase product obtained by molecular distillation at 150-170℃;

[0021] The dry fractionation method described in step (3) refers to melting the oil mixture at 40-70℃, cooling it down to 15℃ at 1-5℃ / min, maintaining it for 0.5-2h, and then filtering to obtain solid fat and liquid oil.

[0022] A diglyceride composition with low-temperature anticoagulation properties prepared by the above method.

[0023] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0024] This invention is the first to utilize the esterification product of chlorogenic acid and propylene glycol as a crystallization and fractionation regulator for diglycerides. It is applied to peanut oil diglycerides to form a novel composition. After dry fractionation, the diglyceride content in the liquid oil remains unchanged, but the solid fat content and melting point are significantly reduced at low temperatures. It does not become hazy during refrigeration, making it an excellent choice for improving the anti-coagulation properties of vegetable oil diglycerides. Attached Figure Description

[0025] Figure 1 It refers to the change in the diglyceride content of the product.

[0026] Figure 2 This refers to the SFC change of the product at 5°C. Detailed Implementation

[0027] The present invention will be further described in detail below with reference to embodiments, but the embodiments of the present invention are not limited thereto. All raw materials involved in the present invention can be purchased directly from the market. For process parameters not specifically specified, conventional techniques can be referred to.

[0028] The peanut oil diglycerides used in the examples and comparative examples were prepared by the following method: 20g of peanut oil (Kerry Oils & Grains (Guangzhou) Co., Ltd.) was added to 100g of glycerol, and then stirred at 60°C. 0.2% of the substrate weight of lipase Lipozyme TL IM was added, and the mixture was reacted at an absolute pressure of 2000 Pa for 60 min. The crude product was subjected to molecular distillation to remove free fatty acids, glycerol, and monoglycerides to obtain peanut oil diglycerides. The melting point of the obtained peanut oil diglycerides was 25°C, and the diglyceride content was 53.0%.

[0029] This invention aims to esterify chlorogenic acid and propylene glycol, add the esterification product to peanut oil diglycerides, and then perform dry fractionation at 15°C. The fractionated oil showed no significant difference in diglyceride content compared to the fractionated oil, but its melting point decreased, its SFC value at 5°C decreased, and it did not become cloudy after refrigeration at 4°C for 5 hours.

[0030] Example 1.

[0031] (1) Weigh 1 g of chlorogenic acid and 1 g of propylene glycol, heat to melt and mix evenly, then put into a reactor and set the reaction temperature to 70℃. When the temperature is constant, add 3% of Novozyme 435 by weight of the substrate, stir with a magnetic stirrer (300 r / min), and the reaction is carried out under vacuum conditions (absolute pressure = 2000 Pa) with a water circulation pump. After the esterification reaction is completed in 80 min, the reaction solution is centrifuged and the upper layer is collected as the esterification product.

[0032] (2) Heat 100g of peanut oil diglyceride to 60°C and then add the esterification products of chlorogenic acid and propylene glycol at 1.5% of the mass of peanut oil diglyceride to obtain a mixture.

[0033] (3) Stir the composition at 60°C for 30 min at a stirring rate of 100 r / min, set the program to cool down to 15°C for 30 min, and grow crystals at 15°C for 2 h at a stirring rate of 50 r / min. Then filter to obtain liquid oil and solid fat, wherein the liquid oil is peanut oil diglyceride composition, to be tested.

[0034] (4) Melting point determination.

[0035] Melting point is expressed as sliding melting point temperature, determined by the capillary method, referring to ISO 6321 method, using a melting point apparatus, and the sliding melting point is rounded to the integer part.

[0036] (5) Turbidity.

[0037] The turbidity of peanut oil diglycerides and their compositions was determined using a turbidimeter. Caprylic / capric triglyceride (caprylic / capric triglyceride should be less than 0.5 NTU) and the oil sample to be tested were poured into cuvettes, each filling them 2 / 3 full. The cuvette containing the caprylic / capric triglyceride was then placed in the cuvette, the cuvette lid was closed, and the blank button was pressed after stabilization. (The oil sample usually stabilizes in 2-3 seconds. Turbidity is measured in a red light cuvette. Before placing the cuvette into the cuvette, ensure the light-transmitting surface is clean and free of stains.) The oil sample to be tested was then placed in the cuvette, the cuvette lid was closed, and the reading was taken after stabilization; the displayed value is the turbidity of the measured oil sample.

[0038] (6) Solid fat content (SFC).

[0039] The determination of solid fat content was performed according to AOCS Official Method Cd 16-81. 3 mL of oil sample was placed in the solid fat test tube and melted at 60 °C for 30 min to eliminate crystallization memory. Then, the sample was transferred to 0 °C for 60 min and then transferred to 5 °C for 30 min to determine the SFC value.

[0040] (7) Diglyceride content.

[0041] Diglyceride content was determined by gas chromatography. The gas chromatography conditions were as follows: capillary column: RTX-65TG (30m×0.250mm×0.1um); injection volume: 0.2 uL; flame ionization detector temperature: 360 ℃; temperature program: initial temperature 250℃, hold for 1 min, increase to 280 ℃ at 20 ℃ / min, increase to 340 ℃ at 10 ℃ / min, hold for 1 min, increase to 350 ℃ at 1 ℃ / min, hold for 20 min; split ratio: 50:1; carrier gas: hydrogen.

[0042] The composition obtained in Example 1 has a diglyceride content of 54.5%, a melting point of 3.5°C, a turbidity of 0.6 NTU, an SFC of 0.05, and a turbidity of 0.8 NTU after being refrigerated at 4°C for 5 hours.

[0043] Example 2.

[0044] This embodiment is the same as that of Embodiment 1 except for the following technical features: the amount of esterified product added in step (2) is 0.5%.

[0045] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 53.8%, a melting point of 3.8°C, a turbidity of 0.7 NTU, an SFC of 0.09, and a turbidity of 0.9 NTU after being refrigerated at 4°C for 5 hours.

[0046] Example 3.

[0047] This embodiment is the same as that of Embodiment 1 except for the following technical features: the amount of esterified product added in step (2) is 2%.

[0048] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 52.1%, a melting point of 3.2°C, a turbidity of 0.5 NTU, an SFC of 0.08, and a turbidity of 0.7 NTU after being refrigerated at 4°C for 5 hours.

[0049] Example 4.

[0050] This embodiment is the same as Embodiment 1 except for the following technical features: Step (1) Weigh 1 g of chlorogenic acid and 2 g of propylene glycol, heat to melt and mix evenly, and then put into a reactor. Set the reaction temperature to 70°C. When the temperature is constant, add 3% of the substrate weight of Novozyme 435 and stir with a magnetic stirrer (300 r / min). The reaction is carried out under vacuum conditions (absolute pressure = 2000 Pa) with a water circulation pump. After the esterification reaction is completed in 80 min, the reaction solution is centrifuged and the upper layer is collected as the esterification product.

[0051] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 52.8%, a melting point of 4.0°C, a turbidity of 0.8 NTU, an SFC of 0.15, and a turbidity of 1.1 NTU after being refrigerated at 4°C for 5 hours.

[0052] Example 5.

[0053] This embodiment is the same as Embodiment 1 except for the following technical features: Step (1) Weigh 1 g of chlorogenic acid and 1 g of propylene glycol, heat to melt and mix evenly, and then put into a reactor. Set the reaction temperature to 90°C. When the temperature is constant, add 3% of the substrate weight of Novozyme 435 and stir with a magnetic stirrer (300 r / min). The reaction is carried out under vacuum conditions (absolute pressure = 2000 Pa) with a water circulation pump. After the esterification reaction is completed in 80 min, the reaction liquid is centrifuged and the upper layer is collected as the esterification product.

[0054] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 50.0%, a melting point of 4.3°C, a turbidity of 0.9 NTU, an SFC of 0.23, and a turbidity of 1.7 NTU after being refrigerated at 4°C for 5 hours.

[0055] Comparative Example 1.

[0056] This comparative example is the same as Example 1 except for the following technical features: 100g of peanut oil diglyceride is heated to 60°C, and then chlorogenic acid is added to peanut oil diglyceride at 1.5% of the mass of peanut oil diglyceride to obtain a mixture.

[0057] Based on the method described in Example 1 and the calculations performed, the composition obtained in this comparative example has a diglyceride content of 13.0%, a melting point of 3.5°C, a turbidity of 2.6 NTU, an SFC of 0.93, and a turbidity of 5.6 NTU after being refrigerated at 4°C for 5 hours.

[0058] Comparative Example 2.

[0059] This comparative example is the same as Example 1 except for the following technical features: 100g of peanut oil diglyceride is heated to 60°C, and then propylene glycol is added at 1.5% of the mass of peanut oil diglyceride to obtain a mixture.

[0060] Based on the method described in Example 1 and the calculations performed, the composition obtained in this comparative example has a diglyceride content of 15.0%, a melting point of 4.1°C, a turbidity of 2.8 NTU, an SFC of 0.99, and a turbidity of 5.0 NTU after being refrigerated at 4°C for 5 hours.

[0061] Comparative Example 3.

[0062] This comparative example is the same as Example 1 except for the following technical features: 100g of peanut oil diglyceride is heated to 60°C, and then chlorogenic acid and propylene glycol are added to peanut oil diglyceride at 0.75% of the mass of peanut oil diglyceride to obtain a mixture.

[0063] Based on the method described in Example 1 and the calculations performed, the composition obtained in this comparative example has a diglyceride content of 12.0%, a melting point of 3.0°C, a turbidity of 1.8 NTU, an SFC of 0.41, and a turbidity of 4.5 NTU after being refrigerated at 4°C for 5 hours.

[0064] Comparative Example 4.

[0065] This comparative example is the same as Example 1 except for the following technical features: 100g of peanut oil diglyceride was heated to 60°C, and then hydroxystearin was added at 1.5% to obtain a mixture.

[0066] Based on the method described in Example 1 and the calculations performed, the composition obtained in this comparative example has a diglyceride content of 12.8%, a melting point of 6.0°C, a turbidity of 0.8 NTU, an SFC of 1.21, and a turbidity of 1.5 NTU after being refrigerated at 4°C for 5 hours.

[0067] Comparative Example 5.

[0068] This comparative example is the same as Example 1 except for the following technical features: 100g of peanut oil diglyceride was heated to 60°C, and then sucrose ester extract was added at 1.5% of the peanut oil diglyceride to obtain a mixture.

[0069] According to the method described in Example 1, the composition obtained in this comparative example has a diglyceride content of 21.0%, a melting point of 5.1°C, a turbidity of 0.6 NTU, an SFC of 1.01, and a turbidity of 1.3 NTU after being refrigerated at 4°C for 5 hours.

[0070] Comparative Example 6.

[0071] This comparative example is the same as Example 1 except for the following technical features: in step (1), chlorogenic acid is replaced with decanoic acid.

[0072] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 23.8%, a melting point of 6.8°C, a turbidity of 0.7 NTU, an SFC of 2.09, and a turbidity of 1.9 NTU after being refrigerated at 4°C for 5 hours.

[0073] Comparative Example 7.

[0074] This comparative example is the same as Example 1 except for the following technical features: in step (1), propylene glycol is replaced with glycerol.

[0075] Based on the method described in Example 1 and the calculations performed, the composition obtained in this example has a diglyceride content of 19.6%, a melting point of 4.0°C, a turbidity of 0.8 NTU, an SFC of 0.50, and a turbidity of 0.9 NTU after being refrigerated at 4°C for 5 hours.

[0076] Table 1 shows the melting point changes of the products in the examples and comparative examples.

[0077] Table 2 shows the turbidity changes of the products in the examples and comparative examples.

[0078] Table 1.

[0079] .

[0080] Table 2.

[0081] .

[0082] Conclusion: Adding the esterified product obtained by esterification of chlorogenic acid and propylene glycol as a crystallization extraction regulator to peanut oil diglycerides proved effective. Compared to traditional crystallization regulators, which only promote the enrichment of high-melting-point components in solid fats and reduce the turbidity of liquid oil but fail to retain high-melting-point diglycerides in the liquid component, the chlorogenic acid-propylene glycol esterified product showed a decrease in the melting point of the liquid oil in diglyceride extraction tests, while retaining the content of high-melting-point diglycerides, and significantly reducing the overall product turbidity.

[0083] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A method for preparing a diglyceride composition with low-temperature anticoagulation properties, characterized in that, Includes the following steps: (1) Chlorogenic acid and propylene glycol were esterified under vacuum to obtain the esterified product of chlorogenic acid and propylene glycol. (2) The esterification product is stirred and mixed with peanut oil diglyceride to obtain a mixture; (3) The mixture is dry fractionated at 15°C to obtain a liquid oil component which is a diglyceride composition with low-temperature anticoagulation properties.

2. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, The esterification reaction described in step (1) is an enzyme-catalyzed esterification, wherein the catalyst used is Novozyme 435; the amount of catalyst added is 1 to 5% of the substrate mass.

3. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, The absolute pressure of the vacuum condition described in step (1) is 500-2000 Pa; The reaction temperature of the esterification reaction in step (1) is 50~90℃; the reaction time is 60~90 min.

4. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, The mass ratio of chlorogenic acid to propylene glycol in step (1) is 1:1 to 1:

2.

5. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, In step (2), the mass percentage of chlorogenic acid and propylene glycol esterification products is 0.5-2% of the mass of peanut oil diglycerides.

6. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, The peanut oil diglyceride in step (2) has a diglyceride content of 40-90% and a solid fat content (SFC) value of 8-30% at 5°C.

7. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that, The peanut oil diglyceride described in step (2) is prepared by the following steps: peanut oil is added to glycerol, and then stirred at 50-65℃. Lipase is added and the mixture is reacted under vacuum for 60-90 min. The crude product is then subjected to molecular distillation to remove free fatty acids, glycerol, and monoglycerides to obtain peanut oil diglyceride.

8. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 7, characterized in that, The mass ratio of peanut oil to glycerol is 1-3:10; the amount of lipase added is 0.1-0.3% of the substrate mass; the lipase refers to Lipozyme TL IM; the absolute pressure of the vacuum is 500-2000 Pa; molecular distillation refers to obtaining a heavy phase product by molecular distillation at 150-170℃.

9. The method for preparing the diglyceride composition with low-temperature anticoagulation properties according to claim 1, characterized in that: The dry fractionation described in step (3) refers to melting the mixture at 40-70℃, cooling it down to 15℃ at 1-5℃ / min, maintaining it for 0.5-2h, and then filtering to obtain solid lipid components and liquid oil components.

10. A diglyceride composition having low-temperature anticoagulation properties, characterized in that... It is prepared by the method described in any one of claims 1-9.

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