CN114431306A

CN114431306A - Breast milk-like fat composition and preparation method and application thereof

Info

Publication number: CN114431306A
Application number: CN202011187427.9A
Authority: CN
Inventors: 万建春; 许淑芳; 祁柯宇; 张虹; 张明瑞
Original assignee: Wilmar Shanghai Biotechnology Research and Development Center Co Ltd
Current assignee: Wilmar Shanghai Biotechnology Research and Development Center Co Ltd
Priority date: 2020-11-02
Filing date: 2020-11-02
Publication date: 2022-05-06

Abstract

The application provides a breast milk-like fat composition which has the following characteristics in percentage by weight of the components: the OPO content is 11.01-17.92%, the OPL content is 11.10-20.45%, the content ratio of OPL/OPO is 0.92-1.71, the MLCT content is 19-38%, and the CN52 content is 37.53-52%. The application also provides a preparation method and application of the breast milk oil composition.

Description

Breast milk-like fat composition and preparation method and application thereof

Technical Field

The present application relates to the field of food, in particular infant formula; specifically, the application provides a breast milk-like oil composition, a preparation method and an application thereof.

Background

Breast milk is the only natural food which is recognized to be the most natural, the safest and the most complete for the growth of infants, is called as the 'gold standard', and contains various physiological active substances required by the growth of infants and comprehensive and sufficient nutrition. Breast milk contains around 5% of lipid components, and about 99% of the lipids are triglycerides. Therefore, breast milk fat is the most important energy source for the life growth of infants, and can provide 50% of energy and essential fatty acid and other substances for the growth of infants.

Research shows that fatty acids in breast milk lipid mainly contain palmitic acid (P), oleic acid (O), linoleic acid (L) and other fatty acids, the content of the triglyceride sn-2 palmitic acid in the total palmitic acid is more than 70%, and the main triglyceride component of breast milk is a triglyceride with the carbon number of 52(CN 52): 1, 3-dioleic acid 2-palmitic acid triglyceride (OPO), 1-oleic acid 2-palmitic acid 3-linoleic acid triglyceride (OPL), 1, 3-dilinoleic acid 2-palmitic acid triglyceride (LPL), 1-oleic acid 2-palmitic acid 3-stearic acid triglyceride (OPS), and 1-linoleic acid 2-palmitic acid 3-stearic acid triglyceride (LPS), and the like. These triglycerides are most abundant in OPO and OPL. Recent studies have shown that breast milk lipids contain medium and long carbon chain triglycerides (MLCT) in addition to OPO and OPL triglycerides.

This unique structure and composition of breast milk lipids provides a strong guarantee of a healthy infant's success. The OPO in the breast milk can promote absorption of fatty acid and calcium by infants, enhance skeleton strength, soften feces strength, reduce intestinal inflammation and reduce crying of infants. Meanwhile, the MLCT in the breast milk lipid can rapidly provide energy for the infant, medium-chain fatty acid generated by MLCT hydrolysis promotes the growth of lactobacillus and bifidobacteria, and monoglyceride generated by hydrolysis also has strong antibacterial and antiviral activities, so that the establishment of early intestinal flora of the infant is influenced.

Although breast milk is the most perfect choice for nutrition for infant growth, infant mothers have partially or completely replaced breast milk with infant formula for some specific reasons. The infant formula milk powder is based on the components of breast milk as the 'gold standard', and simulates the components contained in breast milk as much as possible. The vegetable oils in infant formula are one of the important ingredients for mimicking human milk fat, which can approach human milk fat on a macro scale (fatty acid composition) by mixing various vegetable oils and fats, but which are greatly different from human milk fat on a micro scale (triglyceride structure). Mainly because the triglyceride component of common vegetable oils in infant formula powders is mainly 1, 3-dipalmitoyl-2-oleic acid (POP) type triglycerides and Medium Chain Triglycerides (MCT).

CN101258230, CN101679909, CN102827885 and CN101198261 report methods for synthesizing OPO, and the country has issued national standards for food nutrition fortifiers OPO (GB 30604-2015). CN201711481008.4 discloses a method for preparing OPO and OPL. Although the fat and oil composition prepared by the method is close to breast milk lipid, the composition hardly contains MLCT component. CN109666541 discloses a preparation method of high purity MLCT, but the prepared oil and fat almost contains no OPO and OPL components.

Accordingly, it would be desirable in the art to provide infant formula components, such as lipids, that are similar in structure and composition to breast milk.

Disclosure of Invention

In a first aspect, the present application provides a human milk-like fat composition having the following characteristics, in weight percent, of the components:

the OPO content is 11.01-17.92%,

the content of OPL is 11.10-20.45%,

the content ratio of OPL/OPO is 0.92 to 1.71,

the MLCT content is 19-38%, and

the content of CN52 is 37.53-52%.

In some embodiments, the human breast-milk-like oil and fat composition has an OPO content of 11.01 to 17.89%.

In some embodiments, the human milk-like fat composition has an OPL content of 11.10 to 19.87%.

In some embodiments, the human breast-milk-like oil and fat composition has an OPL/OPO content ratio of 1.02 to 1.71.

In some embodiments, the breast-milk-like fat composition has an MLCT content of 20-35%.

In some embodiments, the breast-milk-like fat composition has a CN52 content of 40-52%.

In some embodiments, the human milk-like fat composition further has one or more of the following characteristics, in weight percent of the components:

the content of the Sn-2-position palmitic acid accounts for 69-86% of the total palmitic acid content,

the content of M2L is 0.5-5%,

the content of ML2 is 10-30%,

the content of CN40 is 0.5-4%,

the content of CN42 is 1-9%,

the content of CN44 is 1-9%,

the content of CN46 is 10-20%,

the content of CN48 is 5-20%,

the content of CN50 is 10-20%.

In some embodiments, the amount of Sn-2 palmitic acid in the breast-like oil and fat composition is 70-86% of the total palmitic acid content.

In some embodiments, the breast-milk-like fat composition has an M2L content of 1-4%. In some embodiments, the breast-milk-like fat composition has an M2L content of 1.96 to 3.81%.

In some embodiments, the breast-milk-like fat composition has an ML2 content of 15-30%. In some embodiments, the breast-milk-like fat composition has a ML2 content of 19.15 to 29.73%.

In some embodiments, the breast-milk-like fat composition has a CN40 content of 0.5 to 3%. In some embodiments, the breast-milk-like fat composition has a CN40 content of 0.7-2%. In some embodiments, the breast-milk-like fat composition has a CN40 content of 0.71-1.82%.

In some embodiments, the breast-milk-like fat composition has a CN42 content of 1-5%. In some embodiments, the breast-milk-like fat composition has a CN42 content of 1.42-2.36%.

In some embodiments, the breast-milk-like fat composition has a CN44 content of 1-8%. In some embodiments, the breast-milk-like fat composition has a CN44 content of 1-5%. In some embodiments, the breast-milk-like fat composition has a CN44 content of 1.5-4%. In some embodiments, the breast-milk-like fat composition has a CN44 content of 1.81-3.76%.

In some embodiments, the breast-milk-like fat composition has a CN46 content of 10-18%. In some embodiments, the breast-milk-like fat composition has a CN46 content of 10.25 to 17.26%.

In some embodiments, the breast-milk-like fat composition has a CN48 content of 5-15%. In some embodiments, the breast-milk-like fat composition has a CN48 content of 8.35 to 13.15%.

In some embodiments, the breast-milk-like fat composition has a CN50 content of 10-18%. In some embodiments, the breast-milk-like fat composition has a CN50 content of 11-18%. In some embodiments, the breast-milk-like fat composition has a CN50 content of 11.47-17.17%.

In some embodiments, the breast-milk-like fat composition of the first aspect is obtained by the method of the second aspect.

In a second aspect, the present application provides a method of preparing a breast-milk-like fat composition comprising the steps of:

(a) providing a transesterified fat composition, wherein the transesterified fat composition is prepared from 77% or more of palm stearin, 2% or more of linoleic acid-rich vegetable oil and 5% or more of lauric acid type fat by weight of the transesterified fat composition by a random transesterification reaction;

(b) providing a fatty acid mixture, wherein the fatty acid mixture comprises, based on the weight of the fatty acid mixture, 40% or more oleic acid, 3% or more lauric acid, and 47% or more linoleic acid-rich vegetable oil-rich fatty acid;

(c) subjecting the transesterified fat composition of step (a) and the fatty acid mixture of step (b) to a selective sn1-3 transesterification reaction to obtain the breast-milk-like fat composition.

In some embodiments, in step (a), the combined weight of palm stearin, linoleic acid rich vegetable oil and lauric acid type fats comprises 84% to 100% of the transesterified fat composition.

In some embodiments, in step (a), the linoleic acid-rich vegetable oil is sunflower oil, or safflower oil, or a mixture of sunflower and safflower oil.

In some embodiments, in step (a), the lauric acid type oil is one or a mixture of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil, and hydrogenated coconut oil, or the lauric acid type oil is one or a combination of one or more of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil, and hydrogenated coconut oil, which is physically mixed or transesterified with other oils.

In some embodiments, in step (a), the random transesterification reaction occurs catalyzed by a chemical catalyst or in the presence of a lipase. In some embodiments, the chemical catalyst is one or more of an alkali or alkaline earth metal hydroxide, carbonate, bicarbonate, alkoxide, such as sodium methoxide.

In some embodiments, in step (a), the transesterified fat composition comprises 77-93% palm oil stearin.

In some embodiments, in step (a), the transesterified oil and fat composition comprises 2-10% linoleic acid rich vegetable oil.

In some embodiments, in step (a), the transesterified fat composition comprises 5-18% lauric fats.

In some embodiments, in step (a), the palm oil stearin has an iodine value of no greater than 22. In some embodiments, the palm oil stearin has an iodine value of 8 to 22.

In some embodiments, in step (b), the total weight of oleic acid, lauric acid, and linoleic acid-rich vegetable oil comprises 90% to 100% of the fatty acid mixture.

In some embodiments, in step (b), the linoleic acid rich vegetable oil fatty acid is selected from sunflower oil fatty acid, safflower oil fatty acid, or a mixture of sunflower oil fatty acid and safflower oil fatty acid.

In some embodiments, in step (b), the fatty acid mixture comprises 40-43% oleic acid.

In some embodiments, in step (b), the fatty acid mixture comprises 3-12% lauric acid.

In some embodiments, in step (b), the fatty acid mixture comprises 47-55% fatty acids rich in linoleic acid vegetable oil.

In some embodiments, in step (c), the selective sn1-3 transesterification reaction is catalyzed by an enzyme. In some embodiments, the enzyme that catalyzes a selective sn1-3 transesterification reaction is a sn-1, 3-position obligate lipase. In some embodiments, the lipase is an immobilized lipase.

In some embodiments, in step (c), the weight of the transesterified fat composition and the fatty acid mixture is from 1:6 to 1: 9. In some embodiments, the weight of the transesterified fat composition and the fatty acid mixture is from 1:7 to 1: 8.

In a third aspect, the present application provides a breast-milk-like fat composition prepared by the method of the second aspect.

In some embodiments, the human milk-like fat composition, in weight percent of the components, has one or more of the following characteristics:

the OPO content is 11.01-17.92%,

the content of OPL is 11.10-20.45%,

the content ratio of OPL/OPO is 0.92 to 1.71,

the content of the MLCT is 19-38%,

the content of CN52 is 37.53-52%,

the content of M2L is 0.5-5%,

the content of ML2 is 10-30%,

the content of CN40 is 0.5-4%,

the content of CN42 is 1-9%,

the content of CN44 is 1-9%,

the content of CN46 is 10-20%,

the content of CN48 is 5-20%,

the content of CN50 is 10-20%.

In some embodiments, the amount of Sn-2 palmitic acid in the breast-like oil composition is 70-86% of the total palmitic acid content.

In some embodiments, the breast-milk-like fat composition has an M2L content of 1-4%. In some embodiments, the breast-milk-like fat composition has an M2L content of 1.96-3.81%.

In some embodiments, the breast-milk-like fat composition has an ML2 content of 15-30%. In some embodiments, the breast-milk-like fat composition has an ML2 content of 19.15 to 29.73%.

In some embodiments, the breast-milk-like fat composition has a CN44 content of 1-8%. In some embodiments, the amount of CN44 in the breast-milk-like fat composition is 1-5%. In some embodiments, the breast-milk-like fat composition has a CN44 content of 1.5-4%. In some embodiments, the breast-milk-like fat composition has a CN44 content of 1.81-3.76%.

In a fourth aspect, the present application provides use of the human milk-like fat composition of the first aspect or the human milk-like fat composition of the third aspect in the preparation of a food product. In some embodiments, the food product is an infant formula or a breast milk fat substitute or a dietary ingredient or an infant food product. In some more specific embodiments, the food product is an infant formula. In some embodiments, the human milk-like fat composition is added to the food product in the form of an emulsion, a powder, an fortifier, or a dietary supplement.

In a fifth aspect, the present application provides a food product comprising the human milk-like fat composition of the first aspect or the human milk-like fat composition of the third aspect. In some embodiments, the food product is an infant formula or a breast milk fat substitute or a dietary ingredient or an infant food product. In some more specific embodiments, the food product is an infant formula. In some embodiments, the human milk-like fat composition is added to the food product in the form of an emulsion, a powder, an fortifier, or a dietary supplement.

Detailed Description

As mentioned above, in infant formulas, in particular formula powders, simulation of breast milk is a consistent appeal in the art. The inventors of the present application have made extensive studies, developments and efforts to obtain an oil and fat composition highly similar to breast milk in a number of important parameters of breast milk oil and fat (OPO content, OPL/OPO content ratio, MLCT content, CN52 content, etc.), which is used for example in the manufacture of infant formula powder. In addition, the process of the breast milk-like fat composition is relatively simple, and the main reaction can be realized through one-step enzyme catalytic reaction.

Definition of

The following definitions are provided to better define the present application and to guide those of ordinary skill in the art in the practice of the present application. Unless otherwise indicated, the terms in this application have the same meaning as commonly understood by one of ordinary skill in the art, e.g., in reference to starting materials and products, operating steps, process parameters, equipment and tools used, and numerical units. All patent documents, academic papers, and other publications cited herein are incorporated by reference in their entirety.

The term "human milk-like fat composition" herein refers to an artificially prepared fat composition similar in structure and composition to human milk, prepared from an isolated or synthetic fat raw material (typically a vegetable fat raw material). Aspects of structural and compositional parameters that exhibit "similarity" of interest to the present application include, but are not limited to, OPO content, OPL/OPO content ratio, MLCT content, CN52 content, and the like.

The term "MLCT" as used herein refers to medium to Long Chain Triglycerides (Middle to Long Chain Triglycerides) which are structural lipids containing both medium Chain fatty acids (M) and Long Chain fatty acids (L) on the glycerol backbone, wherein medium Chain fatty acids refer to fatty acids having 6 to 12 carbon atoms and Long Chain fatty acids refer to fatty acids having more than 12 carbon atoms. MLCT can be classified into, for example, two types of single medium chain triglycerides (LLM/LML, ML2) and double medium chain triglycerides (MML/MLM, M2L) according to the number of M and L in the molecular structure of triglycerides.

The term "CNXX" herein refers to a triglyceride having a carbon number XX.

The term "palm stearin" as used herein is a high melting point palm oil refined from palm oil by a fractionation process.

The term "palm kernel stearin" as used herein is a high melting point palm kernel oil obtained by refining palm kernel oil in a fractionation process.

Non-limiting examples of the term "linoleic acid rich vegetable oil" herein are sunflower or safflower oil or a mixture of sunflower and safflower oil.

Non-limiting examples of the term "fatty acids rich in linoleic acid vegetable oil" herein are sunflower oil fatty acids, safflower oil fatty acids, or mixtures of sunflower oil fatty acids and safflower oil fatty acids. The fatty acid rich in linoleic acid can be obtained by hydrolysis reaction of linoleic acid rich vegetable oil. By way of non-limiting example, safflower seed oil fatty acid or sunflower seed oil fatty acid can be prepared by the following method: adding water into sunflower seed oil or safflower seed oil, heating and stirring to 30-60 deg.C, and adding appropriate amount of hydrolase into the oil-water mixture; after reacting for several hours, centrifugally separating the oil-water mixture, and taking an oil phase; the oil phase is obtained after vacuum drying and molecular distillation purification.

Non-limiting examples of the term "lauric-type fats" herein are mixtures of one or more of palm kernel oil, coconut oil, palm kernel oil fractionated fat, coconut oil fractionated fat, hydrogenated palm kernel oil, hydrogenated coconut oil, or fats obtained by physically mixing or transesterifying one or more of palm kernel oil, coconut oil, palm kernel oil fractionated fat, coconut oil fractionated fat, hydrogenated palm kernel oil, hydrogenated coconut oil with other fats.

The term "random transesterification reaction" herein refers to a reaction of redistribution of acyl groups between or within the triglyceride molecules of the oil and fat, eventually reaching a random distribution of fatty acids within the triglyceride mixture. The random transesterification reaction may be carried out in the presence of a chemical catalyst. Non-limiting examples of chemical catalysts include one or more of hydroxides, carbonates, bicarbonates, alkoxides of alkali or alkaline earth metals. The hydroxide of an alkali or alkaline earth metal may be selected from KOH, NaOH, Ca (OH)₂. The carbonate of an alkali metal may be selected from K₂CO₃、Na₂CO₃. The alkali metal bicarbonate can be chosen from KHCO₃、NaHCO₃. Alkali metal alkoxides such as sodium methoxide. The amount of the chemical catalyst to be added is not particularly limited, and may be, for example, 0.01 to 1 wt%, for example, 0.1 wt% based on the total amount of the fats and oils to be added. The random transesterification reaction may also be carried out in the presence of a lipase. Lipases suitable for random transesterification reactions are commercially availablePurchased (e.g., Lipzome RM IM by Novoxin), or prepared by itself. The lipase may be from animals, plants or microorganisms. Microbial sources of lipases include, but are not limited to, Thermomyces lanuginosus, Rhizopus oryzae (Rhizopus oryzae), Rhizomucor miehei (Rhizomucor miehei), Candida antarctica (Candida antarctica), Aspergillus niger (Aspergillus niger), Burkholderia plantarii (Burkholderia sp.), Candida rugosa (Candida rugosa), Alcaligenes Alcaligenes (Alcaligenes sp.), Mucor javanicus, Rhizopus niveus (Rhizopus niveus), Geotrichum candidum (Cryptococcus neoformans), and the like, as well as genetically modified species thereof. The random transesterification reaction may be terminated with a terminating agent. The terminating agent may be an organic acid or an inorganic acid. Examples of organic acids include citric acid, tartaric acid, and the like. Examples of the inorganic acid include hydrochloric acid, phosphoric acid, sulfuric acid, and the like. Citric acid is preferred. The amount of the terminator to be added is not particularly limited as long as the reaction can be terminated, and for example, 0.1 to 1% by weight, for example, 0.3% by weight of the terminator may be added to the total amount of the fat and oil (reaction mixture).

The term "selective sn1-3 transesterification" as used herein is a reaction mode in which transesterification occurs at a specific site, and its meaning is understood by those skilled in the art. Typically, the selective sn1-3 transesterification reaction is catalyzed by an enzyme, such as a sn-1, 3-position obligate lipase. The term "sn-1, 3-position specific lipase" herein is a lipase that selectively hydrolyzes the sn-1 position and the sn-3 position of triglycerides, and microbial sources thereof include, but are not limited to, Thermomyces lanuginosus, Rhizopus oryzae (Rhizopus oryzae), Rhizomucor miehei (Rhizomucor miehei), Candida antarctica (Candida antarctica), Aspergillus niger (Aspergillus niger), hall Burkholderia (Burkholderia), Candida rugosa (Candida rugosa), Alcaligenes sp.), Mucor javanicus (Mucor javanicus), Rhizopus niveus (Rhizopus niveus), geotrichus (Cryytococcus neoformans) and the like, and genetic modifications thereof. Specific examples include NS40086 manufactured by novicent.

Unless otherwise indicated, the various percent amounts (X%) and ratios between ingredients (X: Y) used in this application are on a weight/weight basis.

It is to be understood that the terms "substantially", "about" (e.g., in component amounts and reaction parameters) as used herein are to be interpreted in a manner that is generally understood by those skilled in the art. In general, the terms "substantially" and "about" may be understood to mean any value within plus or minus 5% of the given value, for example, about X or substantially X may represent any value in the range of 95% X to 105% X.

It should also be understood that specific values given herein (e.g., in proportions, temperatures, and times) are not to be construed as exclusive, but are to be construed to provide only the endpoints of a range, and that other ranges may be provided in combination with each other.

the OPO content is 11.01-17.92%,

the content of OPL is 11.10-20.45%,

the content ratio of OPL/OPO is 0.92 to 1.71,

the MLCT content is 19-38%, and

the content of CN52 is 37.53-52%.

In some embodiments, the breast-milk-like fat composition further has one or more of the following characteristics, in weight percent of the components:

the content of M2L is 0.5-5%,

the content of ML2 is 10-30%,

the content of CN40 is 0.5-4%,

the content of CN42 is 1-9%,

the content of CN44 is 1-9%,

the content of CN46 is 10-20%,

the content of CN48 is 5-20%,

the content of CN50 is 10-20%.

In some embodiments, the breast-milk-like fat composition has a CN40 content of 0.5 to 3%. In some embodiments, the amount of CN40 in the breast-milk-like fat composition is 0.7-2%. In some embodiments, the breast-milk-like fat composition has a CN40 content of 0.71-1.82%.

In some embodiments, the breast-milk-like fat composition has a CN50 content of 10-18%. In some embodiments, the breast-milk-like fat composition has a CN50 content of 11-18%. In some embodiments, the breast-milk-like fat composition has a CN50 content of 11.47 to 17.17%.

As non-limiting examples, the content of each group of triglyceride in the oil and fat composition can be detected by a GC-MS detection method, and the content range of the sn-2 position palmitic acid in the total palmitic acid can be detected by a method in the national standard GB30604 appendix A.

(a) providing a transesterified fat composition, wherein based on the weight of the transesterified fat composition, the transesterified fat composition is prepared from 77% or more (e.g., 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92% or 93%) of palm stearin, 2% or more (e.g., 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17% or 18%) of linoleic acid-rich vegetable oil, and 5% or more (e.g., 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20% or 21%) of lauric acid type fat by a random transesterification reaction;

(b) providing a fatty acid mixture, wherein the fatty acid mixture comprises, based on the weight of the fatty acid mixture, greater than 40% (e.g., 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, or 50%) oleic acid, greater than 3% (e.g., 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, or 13%) lauric acid, and greater than 47% (e.g., 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, or 57%) fatty acids of a linoleic acid-rich vegetable oil;

It will be appreciated by those skilled in the art that steps (a) and (b) need not be performed in a particular chronological order.

In some embodiments, in step (a), the lauric acid type oil is one or a mixture of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil, and hydrogenated coconut oil, or the lauric acid type oil is oil obtained by physically mixing or transesterifying one or a combination of one or more of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil, and hydrogenated coconut oil with other oils.

In some embodiments, in step (a), the transesterified oleo-fat composition comprises 77-93% (e.g., 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, or 93%) palm oil stearin.

In some embodiments, in step (a), the transesterified fat composition comprises 2-10% (e.g., 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%) of a linoleic acid-rich vegetable oil.

In some embodiments, in step (a), the transesterified fat composition comprises 5-18% (e.g., 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%) of lauric acid type fats.

In some embodiments, in step (a), the palm oil stearin has an iodine value of not greater than 22. In some embodiments, the palm oil stearin has an iodine value of from 8 to 22, for example 22, 15, 8.

In some embodiments, step (a) comprises one or more pretreatment steps of mixing the specified amounts of the various components (palm stearin, vegetable oil rich in linoleic acid, lauric acid type grease), heating, dehydrating, chemical random transesterification catalysis reaction treatment (catalysis of sodium methoxide), citric acid water washing treatment, soaping removal, drying, refining and the like, which are easily understood and implemented by those skilled in the art and can be adjusted according to actual needs and conditions, equipment and the like.

By way of non-limiting example, step (a) may be carried out as follows:

the specified amounts of the various components were mixed, heated to 105 ℃ and dehydrated under vacuum with stirring for 30 min. Adding a proper amount of sodium methoxide (one thousandth of the weight of oil), stirring and reacting for 30min under vacuum at 105 ℃, adding a proper amount of citric acid aqueous solution (15 mass percent), and stirring for 20min to terminate the reaction. The reactant was washed repeatedly with hot water to remove soap. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating, drying, and refining to obtain ester-exchanged oil and fat composition.

In some embodiments, in step (b), the total weight of the fatty acids of oleic acid, lauric acid, and linoleic acid-rich vegetable oil comprises 90% to 100% of the fatty acid mixture.

In some embodiments, in step (b), the fatty acids of the linoleic acid-rich vegetable oil are selected from sunflower oil fatty acids, safflower oil fatty acids, or a mixture of sunflower and safflower oil fatty acids.

In some embodiments, in step (b), the fatty acid mixture comprises 40-43% (e.g., 40%, 41%, 42%, 43%) oleic acid.

In some embodiments, in step (b), the fatty acid mixture comprises 3-12% (e.g., 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%) lauric acid.

In some embodiments, in step (b), the fatty acid mixture comprises 47-55% (e.g., 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%) of linoleic acid rich fatty acids.

In some embodiments, step (b) includes the step of subjecting the specified amounts of the various components (oleic acid, lauric acid, sunflower oil fatty acid or safflower oil fatty acid or a mixture of sunflower oil fatty acid and safflower oil fatty acid) to heated agitation (e.g., 60 ℃).

In some embodiments, in step (c), the weight of the transesterified fat composition and the fatty acid mixture is from 1:6 to 1:9 (e.g., 1:6, 1: 6.5, 1:7, 1: 7.5, 1:8, 1: 8.5, 1: 9). In some embodiments, the weight ratio of the transesterified fat composition to the fatty acid mixture is from 1:7 to 1: 8.

In some embodiments, in step (c), the selective sn1-3 transesterification reaction is catalyzed by an enzyme. In some embodiments, the enzyme that catalyzes a selective sn1-3 transesterification reaction is a sn-1, 3 position obligate lipase. In some embodiments, the lipase is an immobilized lipase, such as NS40086 (novacin).

In some embodiments, after step (c), refining the obtained breast-milk-like fat composition, for example, deacidifying, decolorizing and/or deodorizing, etc. is further included.

By way of non-limiting example, step (c) may be carried out as follows:

the transesterified fat composition and the fatty acid mixture are added to the reaction vessel in the prescribed weight ratio, and an appropriate amount of immobilized lipase (for example, NS40086 which is about 6% by weight of the reaction substrate) is added at a reaction temperature of 60 ℃ and a stirring speed of 300 rpm. After 5h of reaction, transferring the oil into a centrifuge tube, centrifuging for 2min at 2000r/min, separating lipase and oil, neutralizing and removing free fatty acid in the oil by an alkaline method, and purifying to obtain the breast-milk-like oil composition.

the OPO content is 11.01-17.92%,

the content of OPL is 11.10-20.45%,

the content ratio of OPL/OPO is 0.92 to 1.71,

the content of the MLCT is 19-38%,

the content of CN52 is 37.53-52%,

the content of M2L is 0.5-5%,

the content of ML2 is 10-30%,

the content of CN40 is 0.5-4%,

the content of CN42 is 1-9%,

the content of CN44 is 1-9%,

the content of CN46 is 10-20%,

the content of CN48 is 5-20%,

the content of CN50 is 10-20%.

In some embodiments, the amount of CN48 in the breast-milk-like fat composition is 5-15%. In some embodiments, the breast-milk-like fat composition has a CN48 content of 8.35 to 13.15%.

The process of preparing a food product (e.g., an infant formula, such as an infant formula) using the breast-milk-like fat composition of the present application can be according to conventional practice in the art.

Examples

The invention of the present application is described below by way of example with reference to the following examples, but the contents of the examples section do not limit the inventions of the present application in any way.

The palm stearin, sunflower seed oil, palm kernel stearin, coconut oil used in the following examples were obtained from Jiali special fat (Shanghai) Inc., and safflower seed oil was commercially available (brand: red fruit, manufacturer: Xinjiang red fruit biologics, Inc.). Oleic acid (C18: 1 content: 85%), linoleic acid and lauric acid (C12: 0 content: 99%) are all from Fengyi oil science and technology Limited, sunflower oil fatty acid (C18: 2 content: 58.4%) and safflower oil fatty acid (C18: 2 content: 75%) are self-made by a laboratory through an enzymatic hydrolysis process, and the preparation method is as follows: 2kg of water was added to 2kg of sunflower or safflower oil, heated and stirred to 35 ℃ and 2g of hydrolase TL 100L (Novoxin (China) Biotechnology Co., Ltd.) was added to the oil-water mixture after the temperature reached 35 ℃. After 24h of reaction, the oil-water mixture is centrifuged and the oil phase is taken. Vacuum drying the oil phase at 90 deg.C, and purifying by molecular distillation to obtain oleum Helianthi fatty acid (C18: 2 content is 58.4%) or oleum Carthami tinctorii fatty acid (C18: 2 content is 75%).

Sodium methoxide was from Sigma-Aldrich, immobilized sn-1, 3-specific lipase NS40086 from novacin (china) biotechnology limited. In the embodiment, a GC-MS detection method is adopted for TAG composition, and a national standard GB30604 appendix A method is adopted for the sn-2 site palmitic acid accounting for the total palmitic acid content.

Example 1: establishment of fat composition according to breast milk

The study subjects were: 50 samples of mature breast milk were from Chengdu, Danyang, Beijing, and Guangzhou.

Breast milk lipid extraction: the lipid in the breast milk sample is extracted by an extraction method reported in the literature (fatty acid composition and distribution research [ J ] of breast milk in different lactation periods in Shanghai and Zhejiang areas, Chinese food science, 2019, 19 (04): 249-257.).

And (3) detection: the composition of breast milk Triglyceride (TAG) is detected by adopting a GC-MS detection method, and the content of sn-2 palmitic acid in the total palmitic acid is detected by adopting a method in GB30604 annex A of the national standard.

The results are shown in tables 1 and 2

TABLE 1 Main triglyceride content Range in Breast milk

TABLE 2 Breast milk CN52, MLCT content, ratio of sn-2 palmitic acid to total palmitic acid content and OPL/OPO Range

Index (I)	Content (%)
		CN52 content	40～52
MLCT content	19～38
		The content of sn-2-position palmitic acid in the total palmitic acid	70～86
Content ratio of OPL/OPO	0.92～1.71

Example 2: preparation, testing and comparison of grease compositions

Preparation and testing of examples

Preparation of transesterified fat and oil compositions: mixing 77% palm oil stearin (IV15), 5% sunflower oil and 18% palm kernel stearin, heating to 105 deg.C, and stirring under vacuum for 30min for dehydration. Adding one thousandth of sodium methoxide based on the weight of oil, stirring and reacting for 30min under vacuum at 105 ℃, adding a proper amount of citric acid aqueous solution (15 mass percent), and stirring for 20min to terminate the reaction. The reactant was washed repeatedly with hot water to remove soap. Heating to 105 deg.C, vacuum stirring for 30min for dehydration and drying, and refining to obtain ester-exchanged oil.

Preparation of fatty acid mixture: mixing 40% oleic acid, 8% lauric acid and 52% sunflower seed oil fatty acid at 60 deg.C under stirring to obtain mixed fatty acid.

Enzymatic acidolysis reaction: the ester-exchanged oil and fat and the mixed fatty acid are added into a reaction kettle according to the weight ratio of 1:7, 6 percent (weight ratio of reaction substrates) of immobilized lipase NS40086 is added, the reaction temperature is 60 ℃, and the stirring speed is 300 r/m. And after 5h of reaction, transferring the oil into a centrifugal tube, centrifuging at 2000r/min for 2min, separating lipase and oil, neutralizing by an alkaline method to remove free fatty acid in the oil, and purifying to obtain the grease composition I.

Grease compositions II to XVII were obtained according to the similar procedures as above, and the following tables show the differences in the procedures.

TAG compositions and sn-2 palmitic acid content in total palmitic acid content of the grease compositions I to XVII were measured in the same manner as in example 1, and the results are shown in tables 3 and 4.

In summary, the oil and fat compositions I to XVII substantially meet the range of breast milk parameters determined in example 1 in terms of the oil and fat structure and composition parameters of interest in the present application (OPO content, OPL/OPO content ratio, MLCT content, CN52 content, Sn-2 palmitic acid to total palmitic acid content), except that the oil and fat compositions II, VII and XII have a slightly lower CN52 content, the oil and fat composition II has a slightly lower Sn-2 palmitic acid to total palmitic acid content, and the oil and fat composition XVII has a slightly higher OPO and OPL content). Based on the comparison of the processes and results of fat compositions II, VII, XII, XVII with other fat compositions in combination with the range of breast milk parameters determined in example 1, the inventors of the present application further propose a more optimized process comprising:

in the acidolysis reaction by the enzyme method, the weight ratio of the ester-exchanged oil-fat composition to the fatty acid mixture is controlled to be 1:7 to 1: 8; and/or

Controlling the lauric acid content in the fatty acid mixture to be less than 13%; and/or

The palm oil stearin used has an iodine value of less than 27, for example, not higher than 22.

Comparative examples

Comparative grease compositions a-F were prepared and tested in this example and the following table shows the differences in the preparation process of comparative grease compositions a-F from grease composition I above. The main objective of comparative example A, B, F was to reveal the importance of linoleic acid-rich vegetable oil in the transesterified fat composition and linoleic acid-rich sunflower oil fatty acid or safflower oil fatty acid or mixtures thereof in the fatty acid mixture to achieve the desired effect. Comparative example C, D, E was from a process reported in some literature having a similar purpose to the present application.

TAG compositions and sn-2 palmitic acid content in total palmitic acid content of comparative grease compositions a to F were measured in the same manner as in example 1, and the results are shown in tables 5 and 6. As shown in the results of tables 5 and 6, the comparative oil and fat compositions a to F were far from the range of breast milk parameters measured in example 1 in terms of the oil and fat structure and composition parameters of interest in the present application (the content of OPO, the content of OPL, the content ratio of OPL/OPO, the MLCT content, the CN52 content, and the content of palmitic acid in Sn-2 position to total palmitic acid).

TABLE 5 triglyceride content (%)

Note: cy (C8: 0, octanoic acid), Cp (C10: 0, decanoic acid), La (C12: 0, lauric acid), M (C14: 0, myristic acid), P (C16: 0, palmitic acid), S (C18: 0, stearic acid), O (C18: 1, oleic acid), L (C18: 2, linoleic acid)

TABLE 6 characteristic value contents (%)

ML 2: single medium chain triglycerides, M2L double medium chain triglycerides. The MLCT content is the sum of the ML2 and M2L contents.

The invention has been described in detail with respect to a general description and specific embodiments thereof, but it will be apparent to those skilled in the art that modifications and improvements can be made based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims

1. The breast milk-like oil composition has the following characteristics in percentage by weight of the components:

OPO content of 11.01-17.92%, preferably 11.01-17.89%,

the OPL content is 11.10-20.45%, preferably 11.10-19.87%,

the content ratio of OPL/OPO is 0.92 to 1.71, preferably 1.02 to 1.71,

the MLCT content is 19-38%, preferably 20-35%, and

the content of CN52 is 37.53-52%, preferably 40-52%.

2. The breast-milk-like fat composition of claim 1, further comprising one or more of the following characteristics, in weight percent, of the components:

the content of the Sn-2-position palmitic acid accounts for 69-86%, preferably 70-86% of the total content of the palmitic acid; and/or

The content of M2L is 0.5-5%, preferably 1-4%, more preferably 1.96-3.81%; and/or

ML2 content of 10-30%, preferably 15-30%, more preferably 19.15-29.73%; and/or

CN40 content of 0.5-4%, preferably 0.5-3%, more preferably 0.7-2%, and further preferably 0.71-1.82%; and/or

CN42 content of 1-9%, preferably 1-5%, more preferably 1.42-2.36%; and/or

A CN44 content of 1-9%, preferably 1-8%, more preferably 1-5%, further preferably 1.5-4%, most preferably 1.81-3.76%; and/or

CN46 content of 10-20%, preferably 10-18%, more preferably 10.25-17.26%; and/or

CN48 content of 5-20%, preferably 5-15%, more preferably 8.35-13.15%; and/or

The content of CN50 is 10-20%, preferably 10-18%, more preferably 11-18%, and still more preferably 11.47-17.17%.

3. A method for preparing a breast-milk-like fat composition, comprising the steps of:

(c) subjecting the transesterified fat composition of step (a) and the fatty acid mixture of step (b) to a selective sn1-3 transesterification reaction to obtain the breast-milk-like fat composition,

wherein said steps (a) and (b) are performed in any order.

4. The method of claim 3, wherein in step (a),

the vegetable oil rich in linoleic acid is sunflower seed oil, or safflower seed oil, or a mixture of sunflower seed oil and safflower seed oil; and/or

The lauric acid type oil is one or a mixture of more of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil and hydrogenated coconut oil, or the lauric acid type oil is oil obtained by physically mixing or carrying out ester exchange reaction on one or a combination of more of palm kernel oil, coconut oil, palm kernel oil fractionated oil, coconut oil fractionated oil, hydrogenated palm kernel oil and hydrogenated coconut oil and other oil; and/or

The random transesterification reaction is catalyzed by a chemical catalyst or takes place in the presence of a lipase, for example, the chemical catalyst is one or more of a hydroxide, a carbonate, a bicarbonate, an alkoxide of an alkali metal or an alkaline earth metal, such as sodium methoxide.

5. A process as claimed in claim 3 or 4, wherein in step (a) the process is carried out in the presence of a catalyst

The transesterified fat composition comprises 77-93% palm stearin; and/or

The ester-exchanged oil-fat composition comprises 2-10% of vegetable oil rich in linoleic acid; and/or

The ester-exchanged oil-fat composition comprises 5-18% of lauric acid type oil-fat; and/or

The palm oil stearin has an iodine value of not higher than 22, and preferably, the iodine value of the palm oil stearin is 8 to 22.

6. The method of any one of claims 3-5, wherein in step (b),

the fatty acid rich in linoleic acid is selected from sunflower seed oil fatty acid, safflower seed oil fatty acid, or a mixture of sunflower seed oil fatty acid and safflower seed oil fatty acid; and/or

The fatty acid mixture comprises 40-43% oleic acid; and/or

The fatty acid mixture comprises 3-12% lauric acid; and/or

The fatty acid mixture comprises 47-55% fatty acids rich in linoleic acid vegetable oil.

7. The process according to any one of claims 3 to 6, wherein in step (c) the weight ratio of the transesterified fat composition to the fatty acid mixture is from 1:6 to 1:9, preferably from 1:7 to 1: 8.

8. The breast-milk-like fat composition prepared by the method of any one of claims 3-7, optionally, the breast-milk-like fat composition, in weight percent of components, having one or more of the following characteristics:

the content of OPO is 11.01-17.92%, preferably 11.01-17.89%;

the content of OPL is 11.10-20.45%, preferably 11.10-19.87%;

the content ratio of OPL/OPO is 0.92-1.71, preferably 1.02-1.71;

the MLCT content is 19-38%, and preferably 20-35%;

the content of CN52 is 37.53-52%, preferably 40-52%;

the content of the Sn-2-position palmitic acid accounts for 69-86%, preferably 70-86% of the total content of the palmitic acid;

ML2 content of 10-30%, preferably 15-30%, more preferably 19.15-29.73%; and/or

CN42 content of 1-9%, preferably 1-5%, more preferably 1.42-2.36%; and/or

CN46 content of 10-20%, preferably 10-18%, more preferably 10.25-17.26%; and/or

CN48 content of 5-20%, preferably 5-15%, more preferably 8.35-13.15%; and/or

9. Use of the human milk-like fat composition of claim 1 or 2 or the human milk-like fat composition prepared by the method of any one of claims 3-7 for the preparation of a food product, such as an infant formula (e.g. infant formula) or a human milk fat substitute or a dietary ingredient or an infant food product; optionally, the human milk fat-like composition is added to the food product in the form of an emulsion, a powder, an fortifier or a dietary supplement.

10. Food product comprising the breast-milk-like fat composition of claim 1 or 2 or the breast-milk-like fat composition prepared by the method of any one of claims 3 to 7, for example the food product is an infant formula (e.g. infant formula) or a breast milk fat substitute or a dietary ingredient or an infant food product; optionally, the human milk fat-like composition is added to the food product in the form of an emulsion, a powder, an fortifier or a dietary supplement.