US-12616218-B2 - Breast milk structured lipid simulating the composition of triglycerides and method for preparing the same

Abstract

The present invention provides a breast milk structured lipid simulating the composition of triglycerides and the method for preparing the same. The breast milk structured lipid exhibits a similarity of over 90% to breast milk lipid, including the contents of less than 0.3 mg/kg of esterified propenyl glycerol, less than 0.5 mg/kg of chloropropanol esters, and less than 0.3 g/100 g of trans fatty acids. The final product of the present invention exhibits a composition highly similar to breast milk while also meeting the requirements of the national food safety standard GB30604-2015.

Inventors

• Qin Wang
• Danqiong WU
• Yawen JIANG
• Xiaoqiang ZOU
• Zhonghao CHAO
• Yao YANG

Assignees

• Kerisom Food Biotechnology Enterprises Limited

Dates

Publication Date

20260505

Application Date

20230728

Priority Date

20220729

Claims (7)

1. 1 . A method for preparing a structured lipid simulating a composition of triglycerides in breast milk, wherein the method comprises the following steps: based on fatty acid composition of breast milk lipid, determining a range of required sn-2 fatty acid composition during a lipid blending process and a range of required sn-1,3 fatty acid composition for an acidolysis reaction between a palm stearin and blended fatty acids, and establishing a lipid blending model to determine a molar ratio of selected lipids to the palm stearin, establishing an acidolysis equilibrium model to determine a composition of free fatty acids required for the acidolysis reaction under different substrate ratios, and establishing a fatty acid blending model to determine the proportions of fatty acids from different lipid sources; performing the acidolysis reaction between the palm stearin and the blended fatty acids under the catalysis of a sn-1,3 lipase, wherein composition of the blended fatty acids is determined by the acidolysis equilibrium model and the fatty acid blending model, and a molar ratio of the palm stearin to the blended fatty acids is determined by the lipid blending model; after the completion of the acidolysis reaction, performing fractionation and extraction in the presence of free fatty acids to adjust the content of tripalmitin in the acidolysis reaction product and remove a part of the glyceride, and removing the fatty acids via vacuum distillation to obtain a substitute lipid product similar to the breast milk lipid in terms of fatty acid composition and distribution, as well as the triglyceride composition, wherein the lipid blending model is as follows: sn - 2 ⁢ FA ⁢ % = Y 1 ⁢ ( sn - 2 ) + ∑ i = 2 n Y i ⁡ ( sn - 2 ) ⁢ X i 1 + ∑ i = 2 n X i , ( 1 ) wherein sn-2 FA % is the sn-2 fatty acid composition in mixed lipids, Y represents different fatty acids, Y 1(sn-2) and Y i(sn-2) are molar percentages of each fatty acid at sn-2 position of the palm stearin and the lipids, respectively, X i represents a molar ratio of the lipids to the palm stearin; the compositions of total fatty acids and sn-1,3 fatty acids are also obtained, as shown below: FA ⁢ % = Y 1 + ∑ i = 2 n Y i ⁢ X i 1 + ∑ i = 2 n X i , ( 2 ) sn - 1.3 FA ⁢ % = 3 × ( Y 1 + ∑ i = 2 n Y i ⁢ X i ) - ( Y 1 ⁢ ( sn - 2 ) + ∑ i = 2 n Y i ⁡ ( sn - 2 ) ⁢ X i ) 2 × ( 1 + ∑ i = 2 n X i ) , ( 3 ) wherein FA % is the fatty acid composition in the mixed lipids, sn-1,3 FA % is the sn-1,3 fatty acid composition in the mixed lipids, Y 1 and Y i are molar percentages of each fatty acid in the palm stearin and the lipids, respectively, wherein the acidolysis equilibrium model is as follows: the content of Xi fatty acids in the triglycerides sn-1,3 (sn-1/3Xi) at reaction equilibrium is as follows: sn - 1 / 3 ⁢ FA ⁢ % = 2 ⁢ mM sn - 1 / 3 ⁢ Xi + hM Xi ∑ i = 1 n ( 2 ⁢ mM sn - 1 / 3 ⁢ Xi + hM Xi ) , ( 4 ) wherein m is the amount of the triglycerides, h is the amount of the fatty acids, n is the type of the fatty acids, Xi represents different fatty acids, M sn-1/−3Xi is a molar percentage of Xi fatty acids on a sn-1,3 position of triglycerides, MX i is a molar percentage of free fatty acids Xi; since ∑ i = 1 n M sn - 2 ⁢ Xi = 1 , ∑ i = 1 n M Xi = 1 , and ⁢ therefore ∑ i = 1 n ( 2 ⁢ m ⁢ M s ⁢ n - 1 / 3 ⁢ X ⁢ i + h ⁢ M X ⁢ i ) = 2 ⁢ m + h , and the acidolysis equilibrium model is further simplified as: sn - 1 / 3 ⁢ FA ⁢ % = 2 ⁢ mM sn - 1 / 3 ⁢ Xi + hM Xi 2 ⁢ m + h , ( 5 ) if h/m=S, a molar ratio between the free fatty acids to the triglycerides is S:1, and the content of Xi fatty acids in the triglycerides sn-1,3 at reaction equilibrium is further simplified as: sn - 1 / 3 ⁢ FA ⁢ % = 2 ⁢ M sn - 1 / 3 ⁢ Xi + SM Xi 2 + S , ( 6 ) wherein the fatty acid blending model is as follows: FA ⁢ % = ∑ i = 2 n Y i ⁢ X i ∑ i = 2 n X i , ( 7 ) wherein Y i is a molar percentage of each fatty acid in the selected lipids, and X i is a molar ratio of the selected lipids.
2. 2 . The method of claim 1 , wherein an acidolysis product of the palm stearin has a maximum removal amount of palmitic acid of 15-25%.
3. 3 . The method of claim 1 , wherein an edible vegetable oil is selected to regulate the sn-2 fatty acid composition of the palm stearin based on the range of the required sn-2 fatty acid composition, the edible vegetable oil is selected from a group consisting of sunflower oil, soybean oil, tea seed oil, coconut oil, palm kernel oil, and flaxseed oil.
4. 4 . The method of claim 1 , wherein a fatty acid proportion is calculated based on a fatty acid balance from the acidolysis reaction of the lipids, and one or more of the fatty acids from sunflower seed oil, rapeseed oil, coconut oil, flaxseed oil, tea seed oil, and palm kernel oil are selected as acyl donors for the acidolysis reaction, and the type and proportion of the acyl donors are determined by establishing the fatty acid blending model.
5. 5 . The method of claim 1 , wherein the acidolysis reaction product is obtained by catalyzing the acidolysis reaction of the palm stearin with mixed fatty acids using a sn-1,3 specific lipase via a packed bed or batch reactor.
6. 6 . The method of claim 1 , wherein the fractionation and extraction process involves two-stages, wherein a first stage comprises heating the lipid to 60-70° C. for 20-45 minutes, and reducing the lipid to 26-35° C. at a rate of 5-15° C./h for 2-8 hours, so that palmitic acid and tripalmitin crystallize to form crystal nucleus.
7. 7 . The method of claim 6 , wherein a second stage comprises reducing the lipid to 13-24° C. at the rate of 4-10° C./h and keeping for 4-12 hours to facilitate crystallization of partial glycerides containing two palmitic acids.

Description

CROSS-REFERENCES TO RELATED APPLICATIONS This application claims priority from Chinese patent application number 2022109120253 filed on Jul. 29, 2022; the disclosure of which is incorporated herein by reference in its entirety. FIELD OF THE INVENTION The present invention relates to the technical field of oil and lipid. More specifically, the present invention relates to a breast milk structured lipid that mimics the composition of triglycerides, and the method for preparing the same. BACKGROUND OF THE INVENTION Breast milk lipid is the primary source of energy for infants when they are breastfed, accounting for over 50% of the total energy intake. Additionally, it provides active substances such as fat-soluble vitamins and polyunsaturated fatty acids, which are crucial for the health, development, and growth of the infants. Triglycerides are the predominant substance in breast milk lipid, constituting over 98% of its content. They possess unique fatty acid composition and molecular structures, which vary depending on the lactation stage, the mother's dietary habits, individual circumstances, and genetic characteristics. The major fatty acids (present in amounts greater than 1%) found in breast milk lipid include oleic acid, palmitic acid, linoleic acid, stearic acid, myristic acid, lauric acid, linolenic acid, and decanoic acid, in which over 60% of palmitic acid is located at the sn-2 position, while the majority of unsaturated fatty acids are primarily found at the sn-1,3. The composition of triglyceride of breast milk lipid is rather complex, and based on its fatty acid distribution, it can be inferred that one of the major types of triglycerides in breast milk lipid is 1,3-diunsaturated fatty acid-2-palmitic acid triglyceride (UPU). The triglycerides with this specific structure may enhance the absorption of fats and calcium, and they also influence the metabolism of triglycerides within the infant's body. The composition and content of the triglycerides in breast milk lipid are the result of long-term evolution. Due to underdeveloped growth, infants have a different digestive and metabolic environment compared to adults. Among these differences, the gastric lipase activity in infants is similar to that of adults, but the concentration of pancreatic lipase is only 5-10% of that in adults, and the bile salt content is less than 50%. Meanwhile, the enzymatic activity of fatty acid desaturases and elongases in infants is also lower. Therefore, the composition of triglycerides in lipids is closely related to the digestion, absorption, and metabolism in infants. Infant formula is a substitute for breast milk lipid, and its composition is based on breast milk as the gold standard. It is primarily made from cow's milk (or goat's milk) and its processed products, and processed by adjusting the levels of protein, lipid, and other components, along with adding appropriate amounts of vitamins, minerals, and other additives. When the infants are temporarily unable to receive breastfeeding, the infant formula becomes the best alternative food for them. Infant formula typically contains around 25% lipid content, serving as a primary source of energy and functional lipids for infants, just like breast milk lipid does. Currently, the lipid mainly used to modulate the lipid structure in formula milk is 1,3-diacylglycerol-2-palmitic acid triglyceride (OPO). By adding this structured lipid, the lipid composition in formula milk can achieve a certain level of similarity to breast milk lipid in terms of fatty acid distribution. However, due to the complexity of triglycerides in breast milk lipid, the enhancement of similarity in the triglyceride composition of formula milk lipid is limited. In the current industrial production processes, due to the relatively low content of OPO, it is challenging to meet the requirements of both national food safety standard GB30604-2015 “Food Nutrition Fortifier 1,3-diacylglycerol-2-palmitic acid triglyceride” and the composition of breast milk lipid simultaneously. Considering the unique physiological environment of infants and their specific digestion, absorption, and metabolic processes of triglycerides, a new process that utilizes triglyceride composition to produce a product that meets both the requirements of the national food safety standard GB30604-2015 and also satisfies the composition demands of breast milk lipid. SUMMARY OF THE INVENTION This section aims to summarize some aspects of the embodiments of the present invention and to briefly describe some preferred embodiments. Simplification or omission may be made in this section, the abstract of the specification, and the title to avoid obscuring the purposes of this section, the abstract of the specification, and the title. Such simplification or omission may not be used to limit the scope of the present invention. The present invention is made in view of the technical problems of breast milk structured lipid as above-mention