Process for the production of a fat composition comprising 1,3-dioleyl-2-palmitoyl glyceride (OPO)

Abstract

It relates to a process for production of a fat composition comprising OPO, comprising: i) provision of a deodorized palm oil having an iodine value (IV) of between 51 and 54; ii) random interesterification of the deodorized palm oil to produce IE palm oil, wherein the proportion of palmitic acid at the Sn-2 position out of total palmitic acid of the IE palm oil is at least 25 wt.%; iii) fractionation of the IE palm oil to obtain a stearin fraction having an iodine value (IV) of less than 48, and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is at least 45 wt.%, and iv) acidolysis of the stearin fraction with oleic acid or derivative thereof in presence of lipase to produce the fat composition.

Description

PROCESS FOR THE PRODUCTION OF A FAT COMPOSITION COMPRISING l,3-DIOLEYL-2-PALMITOYL GLYCERIDE (OPO)CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of European Application No.24156588.6, filed February 8, 2024, the disclosure of which is incorporated by reference herein in its entirety.FIELD OF THE INVENTION

[0002] The present invention relates to a process for the production of a fat composition comprising l,3-dioleyl-2-palmitoyl triglyceride (OPO), a fat composition according to said process and a use of the fat composition in infant formula.BACKGROUND

[0003] Human milk, also known as “breast milk’’ or “mother’s milk”, typically comprises fats, proteins, carbohydrates, vitamins, minerals and other biologically active compounds as its major components. Human milk is considered the optimal nutrition for infants as an energy supply and for providing essential nutrients after birth and during growth. Of these components, fats, which typically comprise only 3.0-5.0% of human milk, are essential as it may provide up to 50% of the energy to an infant.

[0004] As an alternative to human milk, infants may be fed using an infant formula, also known as “baby formula” or “formula”. The infant formula typically comprises the same major components as human milk taking into account e.g. any allergies an infant may have. In most scenarios however, it is important that these infant formulas resemble human milk as best as possible to provide the optimal nutrition for an infant. However, as the components for infant formula are not directly obtained from human milk, the major components need to be obtained from other sources. For example, fats are typically sourced from vegetable oils or cow’s milk. Such sources either lack the same type of fats as human milk, or do not comprise the same quantity of fats found in human milk. Thus, there is a need for providing fats that are present in human milk which are not present, or only present in low levels, in sources other than human milk. By obtaining such lipids, the lipid profile(i.e. the ty pes of lipids in a composition) of human milk can more closely be replicated in an infant formula.

[0005] The fats in human milk mainly comprise triglycerides (TAGs). TAGs are fats with a glycerol ester backbone to which three fatty acids are attached. Fatty acid types are known to be saturated, monounsaturated or polyunsaturated and range from short chain-, medium chain-, long chain- and very long chain fatty acids.

[0006] In a triglyceride molecule, the fatty acids can be attached to the glycerol molecule at different positions, resulting in different isomeric forms. The positions on the glycerol molecule where the fatty acids are attached are referred to as the "Sn" positions. The positions are designated as Sn-1, Sn-2 and Sn-3. Sn positions of the fatty acids in the triglyceride molecules can vary, leading to different triglyceride molecules with distinct properties. The specific combination and types of fatty acids in a triglyceride contribute to factors such as its physical properties, stability, and nutritional characteristics.

[0007] In human milk around 20-25% of fatty acids comprise a palmitic acid (C16H32O2). Palmitic acid is a major component of palm oil.

[0008] More specifically, it is known that in the case of human milk more than 70% of said palmitic acid is located at the middle position of the triglyceride, i.e. at the Sn-2 position. Other fatty acids such as oleic acids (C18H34O2) are located at the outer position, i.e. the Sn-1 and / or Sn-3 position. The triglycerides with an oleic acid at the outer positions (Sn-1.3) and a palmitic acid at the middle position (Sn-2) are also referred to as 1,3-dioleoyl- 2-palmitoyl triglyceride, or “OPO”. This OPO triglyceride makes up an important fraction of fats in human milk.

[0009] The majority of infant formula use vegetable oils such as palm oil and / or bovine milk as a source of fats. These sources of fats have most (> 80 %) of the palmitic acid bound at the Sn-1 and / or Sn-3 position, and an oleic acid at the middle, Sn-2 position. Such triglycerides are l,3-dipalmitoyl-2-oleoyl triglyceride or “POP”. Unfortunately, these sources typically do not contain OPO, or only contain OPO in low amounts. Such sources therefore cannot provide OPO in amounts for industrial applications and thus there is a need for different manners of providing OPO.

[0010] Current technologies to produce OPO are involving usage of palm stearin fraction with a certain IV, followed by random enzymatic interesterification. However, it requires usage of high dosage of polyols such as glycerol.

[0011] In order to obtain palm stearin with a low IV, several fractionation steps are needed. There still remains a need for a way to produce a composition comprising OPO that is efficient and economic at an industrial scale. The present invention addresses this issue.STATEMENT OF THE INVENTION

[0012] In one aspect, the invention relates to a process for the production of a fat composition comprising l,3-dioleyl-2-palmitoyl triglyceride (OPO). the process comprising the steps of: i) provision of a deodorized palm oil having an iodine value (IV) of between 51 and 54; ii) random interesterification of the deodorized palm oil of step i) to produce a randomly interesterified palm oil (IE palm oil), wherein the proportion of palmitic acid at the Sn-2 position out of total palmitic acid of the IE palm oil is at least 25 wt.%, preferably at least 30 wt.%, more preferably at least 35 wt.%, most preferably at least 40 wt.%iii) fractionation of the IE palm oil of step ii) to obtain a stearin fraction having an iodine value (IV) of less than 48, preferably less than 38, more preferably less than 30 and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is at least 45 wt.%, preferably at least 55 wt.%. preferably at least 60 wt.%; and iv) acidolysis of the stearin fraction of step iii) with oleic acid or derivative thereof in the presence of an Sn-l,3-specific triacylglycerol lipase enzyme to produce the fat composition.DETAILED DESCRIPTION

[0013] The present invention is elucidated below with a detailed description. When used in this specification and claims, the terms "comprises" and "comprising" and variations thereof mean that the specified features, steps or integers are included. The terms are not to be interpreted to exclude the presence of other features, steps or components.

[0014] The term " oil" and " fat" will be used interchangeably.

[0015] The “deodorized palm oil” is a refined, bleached, and deodorized (RBD) palm oil; or neutralised, bleached, and deodorized (NBD) palm oil; or palm oil subjected to at least a deodorization step; or mixtures of two or more thereof.

[0016] The “fat composition” is a composition comprising triglycerides, diglycerides, and / or monoglycerides and / or free fatty acids.

[0017] A triglyceride is a molecule composed of three fatty acid chains attached to a glycerol backbone. The carbon number (CN) of a triglyceride refers to the number of carbon atoms in each fatty acid chain. The carbon number of a triglyceride equals the combinedcarbon lengths of its three fatty acid chains. For example, if the three fatty acid chains are each composed of 18 carbon atoms, the triglyceride would have a carbon number of 54 (3 x 18). For example, l,3-dioleyl-2-palmitoyl glyceride (OPO) has a carbon number of 52 (18 + 16 + 18).

[0018] The “iodine value (IV)”, also referred to as also iodine absorption value, iodine number or iodine index, is the common parameter used to identify the amount of unsaturated fatty acids.

[0019] In the context of the present invention, it is understood that M means myristic acid, P means palmitic acid, St means stearic acid, O means oleic acid and L means linoleic acid.

[0020] When the sum of triglycerides under a certain category is reported (for example SSS, S2U, SU2, UUU), the U represents the unsaturated fatty acid residues having from 16 to 24 carbon atoms and S represents a saturated fatty acid residues having from 6 to 24 carbon atoms.Process for the production of a composition comprising OPO

[0021] The aim of the invention is to produce a fat composition comprising 1,3-dioleyl- 2-palmitoyl triglyceride (OPO).

[0022] More details regarding the steps i), ii), iii) iv) and v) of the process according to the invention are disclosed below. These steps are discussed in the order in which they occur in the process.Step i) providing a deodorized palm oil

[0023] Step i) of the process of the present invention is providing a deodorized palm oil having an iodine value (IV) of between 51 and 54.

[0024] The “deodorized palm oil” is defined before. It is obtained by commonly known refining processes that are used to remove impurities and unwanted substances.Step ii) Random interesterification of the deodorized palm oil

[0025] Step ii) of the process of the present invention is random interesterification of the deodorized palm oil provided in step i), to produce a randomly interesterified palm oil (IE palm oil) wherein the proportion of palmitic acid in the Sn-2 position out of total palmiticacid of the randomly interesterified palm oil is at least 25 wt.%, preferably at least 30 wt.%, more preferably at least 35 wt.%, most preferably at least 40 wt.%

[0026] The palmitic acid in the Sn-2 position is determined on the total palmitic acid present in the oil, whereby the oil may comprise triglycerides, diglycerides, and / or monoglycerides and / or free fatty acids. It is measured according to GB30604-2015 method.

[0027] In an aspect, the random interesterification of step ii) according to the invention is performed with an enzymatic esterification step using a lipase enzyme.

[0028] Typically, lipases or esterases are used. The method may offer higher selectivity, yielding desired products with fewer unwanted by-products.

[0029] In a further aspect, the lipase enzyme used in step ii) according to the invention is obtained from a species selected from the group consisting of Thermomyces lanuginosus, Candida antarctica lipase B, Candida cylindracea, Penicillium roqueforti or Burkaholderia cepaciaz, Rhizomucor miehei, Rhizopus oryzea, Rhizopus niveus, Rhizopus delemar and a combination of two or more lipase enzymes obtained from two or more species thereof preferably from Thermomyces lanuginosus, more preferably from Thermomyces lanuginosus, which is immobilized.

[0030] Immobilization of these enzymes is using commonly known process, such as using a carrier, cross-linking technology7, entrapment technology7and the like.

[0031] In an aspect the process according to the invention comprises the interesterified palm oil obtained in step ii) that is having a content of triglycerides with a carbon number of 48 (CN48) of at least 10 wt.%: calculated based on the total amount of triglycerides present in the interesterified palm oil. The total amount of triglycerides is measured according to ISO 23275-1:2012 method.Step iii) Fractionation of the interesterified palm oil

[0032] Step iii) of the process of the present invention is fractionation of the IE palm oil obtained in step ii) to obtain a stearin fraction having an iodine value (IV) of less than 48, preferably less than 38, more preferably less than 30 and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is at least 45 wt.%, preferably at least 55 wt.%, more preferably at least 60 wt.%.

[0033] In an aspect the stearin fraction obtained in step iii) according to the invention has a proportion of palmitic acid in the Sn-2 position out of total palmitic acid content ofthe stearin fraction of at least 45 wt.%. This is measured according to the GB30604-2015 method.

[0034] In an aspect the IE palm oil of step ii) according to the invention comprises a content of triglycerides with a carbon number of 48 (CN48) of at least 10 wt.% calculated based on the total weight of triglycerides and in a further aspect the stearin fraction obtained in step iii) according to the invention comprises a content of triglycerides with a carbon number of 48 (CN48) of at least 30 wt.%, preferably at least 35 wt.%. more preferably at least 40 wt.%, calculated based on the total weight of triglycerides. The total amount of triglycerides is measured according to ISO 23275-1:2012 method.

[0035] In an aspect according to the invention the stearin comprises a content of POO triglycerides (including all positional isomers), having the carbon number of 52 (CN52) of from 8 to 12 wt.%, preferably of from 9 to 11 wt.%.Step iv) Acidolysis of the stearin fraction

[0036] The process according to step iv) of the invention is acidolysis of the stearin fraction obtained in step iii) with oleic acid or derivative thereof, in the presence of an Sn- 1,3-specific triacylglycerol lipase enzyme to produce the fat composition comprising OPO triglycerides.

[0037] In a further aspect, the process according to the invention comprises in step iv) the use of the Snl,3-specific triacylglycerol lipase enzyme; which is obtained from a species selected from the group consisting of Rhizomucor miehei, Rhizopus oryzea, Rhizopus niveus, Rhizopus delemcir and a combination of two or more lipase enzymes obtained from two or more species thereof preferably wherein said lipase enzyme is immobilized.

[0038] In an aspect according to the invention the stearin and the oleic acid or derivative thereof in step iv) is present in a ratio of 25:75 to 35:65.

[0039] Without being bound by any theoretical explanation, it is observed that a higher amount of oleic acid may alter the equilibrium by shifting the reaction toward the product where more OPO triglycerides are produced from PPP triglycerides.

[0040] The inventors have observed that the CN48 content can be reduced from 40.0% to 3.6% after enzymatic reaction of stearin and oleic acid by using the corresponding ratio of 25:75 to 35:65, preferably in a ratio of 25:75 to 30:70.

[0041] In an aspect according to the invention the fat composition comprises a content of triglycerides with a carbon number of 50 (CN50) of at most 30 wt.%, preferably at most25 wt.% based on the total weight of triglycerides. The total triglycerides are measured according to ISO 23275-1 :2012

[0042] In an aspect according to the invention the fat composition comprises a content of triglycerides with a carbon number of 48 (CN48) of at most 10 wt.%, preferably at most 5 wt.%, more preferably at most 4.5 wt.% based on the total weight of triglycerides. The total triglycerides are measured according to ISO 23275-1 :2012

[0043] In an aspect according to the invention the fat composition (e.g. as obtained in step iv)) comprises a content OPO triglycerides of at least 30 wt.%, preferably 35 wt.%, more preferably 40 wt.%, calculated as CN52 triglycerides (viz. based on the total weight of the triglycerides with a carbon number of 52). The content of OPO triglycerides is measured according to the GB30604-2015 method.

[0044] In an aspect according to the invention the fat composition (e.g. as obtained in step iv)) comprises a proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the fat composition of at least 45 wt.%, preferably at least 50 wt.%, at least 52 wt.%, preferably at least 55 wt.%, more preferably at least 60 wt.%.

[0045] This is measured according to the GB30604-2015 method.Step v) Optional distillation of OPO triglycerides

[0046] In a further aspect, the process according to the invention comprises after step iv) a further step wherein the fat composition is subjected to a distillation step for obtaining a fat composition having a content of OPO of at least 30 wt.%, preferably at least 35 wt.%, more preferably at least 40 wt.%, based on the total weight of the triglycerides with a carbon number of is 52 (CN52), and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the fat composition is at least 45 wt.%, preferably at least 50 wt.%, more preferably at least 52 wt.%, most preferably at least 55 wt.%.

[0047] In a further aspect, the process according to the invention comprises after step iv) optional step v) wherein distillation of the fat composition is performed to provide a fat composition wherein the amount of free fatty acids expressed as oleic acid is less than 1 wt.%, preferably less than 0.5 wt. %.

[0048] The distillation can be performed with any commonly known distillation process known in the art. Preferably, a short path distillation is applied. Short-path evaporation, also called short-path distillation or molecular distillation, is a distillation technique that involves the distillate travelling a short distance, often only a few centimetres, and it is normally done at reducedpressure. With short path distillation, a decrease of boiling temperature is obtained by reducing the operating pressure. It is a continuous process with very short residence time. This technique is often used for compounds which are unstable at high temperatures or to purify small amounts of compounds. The advantage is that the heating temperature can be considerably lower (at reduced pressure) than the boiling point of the liquid at standard pressure. Additionally, short-path evaporation allows working at very low pressure.

[0049] Different types of short-path evaporation apparatus can be used that are well known to the skilled person. Examples are, but are not limited to, falling film, centrifugal, or wiped film evaporation apparatus. Preferably, the short-path evaporation of the current process is performed in a wiped film evaporation apparatus.

[0050] The short-path evaporation in step a) of the process according to the invention is performed at a pressure below 1 mbar, preferably below 0.05 mbar, more preferably below 0.01 mbar, most preferably below 0.001 mbar.Optional further purification of QPO triglycerides

[0051] The obtained OPO triglycerides may be further purified by a bleaching and / or deodorization step. Both steps are well-known in the art.Product

[0052] According to the herein described steps and as described above, there is provided for a fat composition comprising 1 ,3-dioleyl-2-palmitoyl glyceride (OPO).

[0053] The product has a content of OPO of at least 30 wt.%, preferably at least 35 wt.%, more preferably at least 40 wt.%, based on the total weight of the triglycerides whose carbon number is 52 (CN52) and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the fat composition is at least 45 wt.%, preferably at least 50 wt.%, more preferably at least 52 wt.%, most preferably at least 55 wt.%.Use of the fat composition

[0054] The obtained fat composition can be used in food product.

[0055] It can be used in food product such as baked goods, dairy alternatives, spreads, confectionery products, preferably infant food product.

[0056] Infant food product is a term well-known in the art and it refers to food that is specifically manufactured for infants and it may be characterized in that is soft, and easilyconsumable by infants and has a nutritional composition adapted to the specific needs at each growth stage.

[0057] The infant food product is available on the market in different forms, i.e. powder, infant base powder, liquid concentrate, and ready -to-feed liquids. When available in the form of a formula base, i.e. a powder or a concentrated liquid, it can be dissolved in water or in another fluid for the preparation of a ready-to-drink infant food product. The infant food product may also be in the form of a pudding or a jelly, or in the form of a cookie or a snack bar, or in any other form.

[0008] It may be a first age infant formula, for infants from birth to age of 6 months, a follow-on formula (also called second age infant formula), for infants from an age of 6 to 18 months, or a growing-up formula (also called third age infant formula) for infants from an age from 1 to 3 years.

[0059] The obtained fat composition may be blended with vegetable oils to form an oil blend to be used in the infant food product.

[0060] The vegetable oil that is used may be derived from one or more vegetable sources and may include oils and / or fats from a single origin or blends of two or more oils and / or fats from different sources or with different characteristics. They may be derived from standard oils or from specialty oils such as oils that have been subjected to fractionation and so on.

[0061] Examples of vegetable oils are amongst others, camelina oil. canola oil, cocoa butter, coconut oil, cottonseed oil, corn oil, groundnut oil, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, rapeseed oil, rice bran oil, sesame oil, safflower oil, shea butter, soybean oil, sunflower oil, single or multiple fractionated oils, such as stearin and / or olein fractions, oil from any variety of oilseeds with increased level of unsaturated fatty acids compared to the original seed variety, such as mid or high oleic sunflower oil. These varieties with increased levels of unsaturated fatty acids can be obtained by natural selection or by genetic modification (GMO). Preferably, the vegetable oil is selected from the group consisting of cottonseed oil, corn oil. groundnut oil, linseed oil, olive oil, rapeseed oil, rice bran oil, sesame oil, safflower oil, soybean oil. sunflower oil. their corresponding high oleic varieties, and mixture of two or more thereof. More preferably, the vegetable oil is selected from the group consisting of com oil, rapeseed oil, soybean oil, sunflower oil, their corresponding high oleic varieties, and mixture of two or more thereof. The high oleic varieties are containing at least 40%, at least 50%, at least 60%, at least 70% and preferablyat least 80% oleic acid in respect of the fatty acid profile. Preferably the vegetable oil is a suitable source of LC- PUFA (long chain poly -unsaturated fatty acids). These sources may provide LC-PUFA selected from the group consisting of arachidonic acid (ARA), docosahexaenoic acid (DHA), eicosapentaenoic acid (EP A), docosapentaenoic acid (DPA), and combinations of two or more thereof.Advantages of the present invention

[0062] Without being bound by any theoretical explanation, it can be seen that the current invention allows to start the process, for preparing a fat composition that is comprising OPO. with deodorized palm oil. This has an economical and technical advantage compared to processes that start with palm oil stearin that might require several fractionation steps, whereupon each of these fractionation steps also result in by-products that may have no clear usage and thus as such reduce the efficiency and effectiveness of the processes.

[0063] Additionally, the current claimed process involves only one fractionation step that is applied on interesterified palm oil and may result in higher yield.

[0064] Current existing technologies to produce OPO are involving usage of palm stearin fraction with a certain IV, followed by random enzymatic interesterification. However, it requires usage of high dosage of polyols such as glycerol.

[0065] The current invention provides for an efficient process wherein in the fractionation step two valuable fractions are obtained. The obtained stearin fraction is used in the current claimed process. At the same time the fractionation step of interesterified palm oil also results in a liquid fraction, an olein fraction. This olein fraction has specific characteristics such as specific solid fat content. This olein fraction can easily be used as milk fat replacer in food applications. It will allow for a significant SAFA reduction in the final food product.

[0066] Although certain aspects of the invention have been described, the scope of the appended claims is not intended to be limited solely to these specific aspects. The claims are to be construed literally, purposively, and / or to encompass equivalents. The scope of the present invention is defined by the appended claims. One or more of the objects of the invention are achieved by the appended claims.EXAMPLES

[0067] The present invention is further elucidated based on the examples below which are illustrative only and not considered limiting to the present invention.1. Analysis methodsDetermination of the triglycerides

[0068] The triglycerides content was determined according to the ISO 23275-1 :2012 method.

[0069] The carbon number (CN) was calculated based on the results obtained with the ISO 23275-1:2012 method.

[0070] In particular the content of CN48. CN50. and CN52 triglycerides was determined with this method.

[0071] The CN52 triglycerides is the sum of POSt, POO, PLSt, PLO, PLL.

[0072] The CN50 triglycerides is the sum of PPSt, POP, MOO, PLP, MLO, PPSt.

[0073] The CN48 triglycerides is the sum of PPP, MOP, MLP.

[0074] In the context of the present invention, it is understood that M means myristic acid, P means palmitic acid, St means stearic acid, O means oleic acid and L means linoleic acid.

[0075] The ISO 23275-1:2012 method allows to measure the total content of triglycerides but does not distinguish between the positional isomers.Determination of mass fraction (= content) of 2-position of palmitic acid accounted for all palmitic acid

[0076] Measurements were preformed according to GB30604-2015 method Annex A.2.Determination of 1,3-Dioleoyl 2-Palmitoyl (OPO) triglyceride content (determination of positional isomer).

[0077] The content of OPO triglycerides is based upon the content of CN52 triglycerides.

[0078] Measurements were preformed according to GB30604-2015 method Annex A.3.Determination of iodine value (IV)The IV value was determined according the AOCS Cd ld-92 method.2. Materials

[0079] RBD Palm Oil with IV 52.5 was obtained from Cargill Palm Product Sdn Bhd, Malaysia. Lipozyme ® TL IM was purchased from Novozyme.

[0080] Lipura ® Select enzyme was purchased from Novozyme.

[0081] Oleic acid was purchased from Oleon NV.3. Example according to the inventionProduction of a fat composition comprising l,3-dioleyl-2-palmitoyl triglyceride (OPO)Step i) providing an RBD palm oil

[0082] A commercially available RBD Palm Oil was used as the feed oil in step ii).Step ii) Random interesterification (IE) of the RBD palm oil

[0083] The interesterification of the palm oil was performed by using a packed bed reactor (packed with Lipozyme® TLIM). The RBD palm oil was heated to 50°C (5 kg of feed oil), blended with 20 gram of enzyme (Lipozyme® TLIM) and pumped through the column in the continuous flow at a feed rate of 2 kg oil / kg enzyme / hour.

[0084] The thus obtained interesterified palm oil (IE palm oil) has am IV value of 52.5. The proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the IE palm oil is 40.3 wt.%, measured according to the GB30604-2015 method.Step Hi) Fractionation of the interesterified palm oil

[0085] The interesterified palm oil (IE palm oil) from step ii) was (re)heated to 60°C in a crystallizer. The heated IE palm oil was held at 60°C for 60 minutes and was then allowed to gradually cool down to a temperature of 36°C (see cooling profile shown below). The obtained crystals in a slurry were subsequently filtered off to obtain a stearin fraction and an olein fraction.Table 1. Cooling Profile

[0086] The stearin fraction obtained has am IV value of 28.6. The proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is 62.1 wt.%, measured according to the GB30604-2015 method.Step iv) Acidolysis of the stearin fraction and Step v) distillation of obtained fat composition

[0087] The stearin from step iii) was mixed with oleic acid in a ratio of stearin to oleic acid of 30:70. The mixture was heated to a temperature of 60 °C under continuous stirring. After heating to 60 °C the mixture was allowed to react with 3 wt.% enzyme Lipura Select®’ for 6 hours, in the presence of 0.11 wt.% of moisture, under continuous stirring. After filtration of the enzyme, thee obtained oil was subsequently subjected to distillation, by using a Short Path Distillation (SPD) at 220°C at 0.003mbar. at a flow rate of 1.5L / hour, in order to obtain the fat composition comprising OPO triglycerides.

[0088] The obtained fat composition has an IV value of 60.1, a content of OPO of 40.7 wt.% based on the total weight of the triglycerides with a carbon number of 52 (CN52), measured according to the GB30604-2015 method. The proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the fat composition is 60.0 wt.%, measured according to the GB30604-2015 method.

[0089] The characterization of the starting material, the intermediate products and claimed fat composition can be seen in Table 2.Table 2. Characterization of the starting material, the intermediate products and claimed fat composition

Claims

CLAIMS1. A process for the production of a fat composition comprising 1 ,3-dioleyl-2- palmitoyl triglyceride (OPO), the process comprising the steps of: i) provision of a deodorized palm oil having an iodine value (IV) of between 51 and 54; ii) random interesterification of the deodorized palm oil of step i) to produce a randomly interesterified palm oil (IE palm oil), wherein the proportion of palmitic acid at the Sn-2 position out of total palmitic acid of the IE palm oil is at least 25 wt.%, preferably at least 30 wt.%, more preferably at least 35 wt.%, most preferably at least 40 wt.% iii) fractionation of the IE palm oil of step ii) to obtain a stearin fraction having an iodine value (IV) of less than 48, preferably less than 38, more preferably less than 30 and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is at least 45 wt.%, preferably at least 55 wt.%, more preferably at least 60 wt.%; and iv) acidolysis of the stearin fraction of step iii) with oleic acid or derivative thereof in the presence of an Sn-l,3-specific triacylglycerol lipase enzyme to produce the fat composition.

2. The process according to claim 1 wherein after step iv) the fat composition is subjected to a distillation step for obtaining a fat composition having a content of OPO of at least 30 wt.%, preferably at least 35 wt.%, more preferably at least 40 wt.%, based on the total weight of the triglycerides with a carbon number of is 52 (CN52), and wherein the proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the fat composition is at least 45 wt.%, preferably at least 50 wt.%, more preferably at least 52 wt.%, most preferably at least 55 wt.%.

3. The process according to claim 1-2, wherein the random interesterification of step ii) is an enzymatic esterification step performed using a lipase enzyme.

4. The process according to any of claims 1-3, wherein the IE palm oil of step ii) comprises a content of triglycerides with a carbon number of 48 (CN48) of at least 10 wt.% based on the total weight of triglycerides.

5. The process according to any of claims 1-4, wherein the IE palm oil of step ii) comprises a content of triglycerides with a carbon number of 48 (CN48) of at least 10 wt.% based on the total weight of triglycerides and / or wherein the stearin fraction obtained in step iii) comprises a content of triglycerides with a carbon number of 48 (CN48) of at least 30 wt.%, preferably 35 wt.%, more preferably 40 wt.%, based on the total weight of triglycerides.

6. The process according to any of claims 1-5, wherein the fat composition comprises a content of triglycerides with a carbon number of 50 (CN50) of at most 30 wt.%, preferably at most 25 wt.% based on the total weight of triglycerides.

7. The process according to any of claims 1-6, wherein the fat composition comprises a content OPO triglycerides of at least 30 wt.%, preferably 35 wt.%, more preferably 40 wt.%, based on the total weight of the triglycerides with a carbon number of 52 (CN52).

8. The process according to any of claims 1-7 wherein the fat composition comprises a proportion of palmitic acid in the Sn-2 position out of total palmitic acid of the stearin fraction is at least 45 wt.%. preferably at least 55 wt.%, more preferably at least 60 wt.%.

9. The process according to any of claims 1-8 wherein after step iv) optional step v) is performed wherein distillation of the fat composition is performed to provide a fat composition wherein the amount of free fatty acids expressed as oleic acid is less than 1 wt. %, preferably less than 0.5 wt.%.

10. The process according to any of claims 1-9, wherein the lipase enzyme used in step ii) is obtained from a species selected from the group consisting of Thermomyces lanuginosus, Candida antarctica lipase B, Candida cylindracea, Penicillium roqueforti or Burkaholderia cepaciaz, Rhizomucor miehei, Rhizopus oryzea, Rhizopus niveus, Rhizopus delemar and a combination of two or more thereof, preferably from Thermomyces lanuginosus , more preferably from Thermomyces lanuginosus that is immobilized.

11. The process according to any of claims 1-10, wherein the Snl,3-specific tri acylglycerol lipase enzyme used in step iv) is obtained from a species selected from the group consisting of Rhizomucor miehei, Rhizopus oryzea, Rhizopus niveus, Rhizopus delemar and a combination of two or more thereof, preferably wherein said lipase enzyme is immobilized on a carrier.

12. The process according to any of claims 1-11, wherein the interesterified stearin and the oleic acid or derivative thereof in step iv) is in a ratio of 25:65 to 35:75.

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