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CN105795000B - Oil and fat composition, method for producing same, and food - Google Patents

Oil and fat composition, method for producing same, and food Download PDF

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CN105795000B
CN105795000B CN201410839981.9A CN201410839981A CN105795000B CN 105795000 B CN105795000 B CN 105795000B CN 201410839981 A CN201410839981 A CN 201410839981A CN 105795000 B CN105795000 B CN 105795000B
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oil
composition
weight
general formula
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CN105795000A (en
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谢仕潮
张虹
俞建国
胡鹏
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Shanghai Jiali Food Industry Co ltd
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Kerry Specialty Fats Shanghai Co ltd
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Abstract

The present invention relates to an oil or fat composition, a method for producing the same, and a food. The fat composition of the present invention is characterized by containing not less than 30% by weight of a triglyceride represented by the following general formula (1) based on the total amount of the fat composition, wherein R in the general formula (1)1、R2And R3The definition of (A) is as described in the specification. The composition does not contain trans-fatty acid, has a faster crystallization rate, does not need low-temperature long-time cooling, solidification and molding, reduces production time, has a cool feeling, does not have pasty mouthfeel, and is fast to melt.

Description

Oil and fat composition, method for producing same, and food
Technical Field
The invention provides an oil and fat composition, a preparation method thereof and a food containing the oil and fat composition.
Background
Chocolate is a food with unique flavor and is popular with consumers for many years; fat is an important component of chocolate and determines the solidification and melting characteristics of the chocolate; chocolate grease usually needs to be solidified at a lower temperature, so that chocolate and chocolate products need to pass through a cold air tunnel before being packaged, and the products are fully cooled, solidified and molded. The use of the cold air tunnel increases the investment of fixed equipment on one hand, and the use of cold air also increases the operation cost, so that the method is not economical. On the other hand, the cold air tunnel is usually long and needs to occupy a lot of factory floor area, which is a phenomenon that chocolate producers are not willing to see. Therefore, if the chocolate has the characteristic of quick curing at normal temperature (20-25 ℃), the cost is undoubtedly saved.
In order to provide the crystallization rate of chocolate at normal temperature, the following solutions are available: (1) adding high melting point oil such as fully hydrogenated vegetable oil, and extracting high melting point components. (2) Adding high melting point additives such as saturated glycerin type emulsifier, polyglycerol fatty acid ester, etc. None of these solutions, however, is achieved by mentioning the melting point of chocolate, which sacrifices the chocolate mouthfeel to some extent and is not reimburseable. Therefore, the appearance of chocolate fat which rapidly crystallizes at normal temperature without impairing the taste of the food will largely solve such a contradiction.
Patent document 1 proposes an oil rich in SSO, which can be stabilized in β' crystal form, and which has advantages of non-temperature adjustment, non-hydrogenation and no trans-fatty acid, and has disadvantages of slow crystallization rate, patent document 2 proposes a coated oil produced by transesterification of a lauric acid oil and a fully hydrogenated oil or by full hydrogenation after transesterification of a lauric acid oil and a palmitic acid oil, which has advantages of fast crystallization rate and good heat resistance, and disadvantages of mushy taste of the oil, patent document 3 proposes a method for producing a lauric acid oil, which has advantages of fast crystallization rate, good heat resistance, production by non-hydrogenation or non-hydrogenation processes, low trans-fatty acid content, and disadvantages of mushy taste of the oil, patent document 4 proposes a method for producing an oil with low trans-fatty acid content, which has advantages of non-temperature adjustment, low saturated fatty acid content, and disadvantages of partial hydrogenation, and contains trans-fatty acid, and has slow crystallization rate and poor heat resistance.
Prior art documents:
patent document 1, EP0536824 a1
Patent document 2, WO 2007/129590A 1
Patent document 3. US006033695A
Patent document 4, WO 03/053152 a 2.
Disclosure of Invention
An object of the present invention is to provide an oil or fat composition containing not less than 30% by weight, preferably not less than 50% by weight, more preferably not less than 58% by weight, still more preferably not less than 70% by weight, further preferably not less than 80% by weight, and particularly preferably not less than 88% by weight of a triglyceride represented by the general formula (1),
Figure 604000DEST_PATH_IMAGE001
general formula (1)) In, R1、R2And R3Each being the same or different, R1、R2And R3Any two of them represent a linear or branched saturated hydrocarbon group having 5 to 13 carbon atoms, and the other one represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms.
The fat or oil composition according to, wherein R1、R2And R3Any two of them represent an alkyl group having 7 to 11 carbon atoms.
The fat or oil composition according to, wherein R1、R2And R3Any two of which represent undecyl.
The fat or oil composition according to, wherein R1、R2And R3Any two of which represent a linear undecyl group.
The fat or oil composition according to the above, wherein the triglyceride represented by the general formula (1) is a lauric acid monosaturated acid triglyceride.
The oil or fat composition contains the triglyceride represented by the general formula (2) in an amount of less than 10% by weight, preferably less than 9% by weight, more preferably less than 6% by weight, more preferably less than 4% by weight, and still more preferably less than 2% by weight based on the total amount of the oil or fat composition,
Figure 458824DEST_PATH_IMAGE002
in the general formula (2), R4、R5And R6Each of which is the same or different and represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms, preferably R4、R5And R6Each of which is the same or different and represents a straight-chain alkyl group having 15 to 23 carbon atoms.
The fat and oil composition according to the above, wherein the triglyceride represented by the general formula (2) is at least one selected from the group consisting of 1,2, 3-tristearate triglyceride, 1,2, 3-tripalmitate triglyceride and 1, 2-distearate-3-palmitic triglyceride.
The oil composition of the present invention contains 88.1 wt% of glycerol trilaurate monosaturated acid triglyceride (LLH) and 1.3 wt% of 1,2, 3-tristearate triglyceride (SSS); in the oil composition, the content of the monolauric acid triglyceride (LLH) was 34.6% by weight, and the content of the 1,2, 3-tristearate triglyceride (SSS) was 8.8% by weight; or the oil composition contains 58.9 wt% of the monolauric acid triglyceride (LLH) and 5.5 wt% of the 1,2, 3-tristearic acid triglyceride (SSS).
Another object of the present invention is to provide a method for producing an oil or fat composition, comprising the step of mixing or not mixing other oils or fats with a triglyceride represented by the general formula (1),
Figure 425512DEST_PATH_IMAGE001
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3Any two of them represent a linear or branched saturated hydrocarbon group having 5 to 13 carbon atoms, and the other one represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms.
The production process according to, wherein the triglyceride represented by the general formula (1) is obtained by esterification reaction or transesterification reaction.
Another object of the present invention is to provide a method for producing a fat or oil composition, comprising:
the monoglyceride or a composition comprising monoglyceride is subjected to an esterification reaction with lauric acid or a composition comprising lauric acid.
The manufacturing method according to, wherein the monoglyceride content is not less than 30%, preferably not less than 50%, more preferably not less than 70% by weight of the monoglyceride-containing composition.
The manufacturing method according to, wherein the lauric acid is contained in an amount of not less than 90%, preferably not less than 95%, by weight of the composition containing lauric acid.
According to the production method, the molar ratio of the monoglyceride to the lauric acid in the esterification reaction process is 1:2 to 1:10, preferably 1:3 to 1: 5.
According to the production process, there is further provided a step of subjecting the product of the esterification reaction to distillation, preferably molecular distillation, to remove the reaction raw material, preferably monoglyceride, lauric acid and diglyceride.
Another object of the present invention is to provide a method for producing a fat or oil composition, comprising:
mixing the random ester exchange product of the perhydrostearin with an organic solvent, and carrying out solid-liquid separation.
According to the production method, the random ester exchange product of the perhydrostearin and the organic solvent are mixed in a weight ratio of 1:1 to 1:30, preferably 1:2 to 1:20, more preferably 1:3 to 1: 10.
According to the production method, the fatty acid content of the fat and oil fatty acid carbon chain number of 16 or more in the fully hydrogenated hard butter exceeds 80%. According to the production method, the perhydrogenated stearin is at least one of perhydrogenated palm kernel stearin, perhydrogenated palm stearin, perhydrogenated soybean oil, perhydrogenated rapeseed oil or perhydrogenated peanut oil.
According to the production method, the solid-liquid separation is filtration, centrifugation, or standing separation.
According to the production method, the organic solvent is at least one of acetone, n-hexane, t-butanol, and n-heptane.
Another object of the present invention is to provide a food containing the fat or oil composition or the fat or oil composition produced by the production method. The food is preferably chocolate, whipped cream, cake, biscuit, or sandwich sauce.
An oil or fat composition produced by the production method.
The oil or fat composition or the oil or fat composition prepared by the preparation method is used for preparing food. The food is preferably chocolate, whipped cream, cake, biscuit, or sandwich sauce.
Effects of the invention
Compared with the traditional non-lauric cocoa butter substitute (CBR), the composition does not contain trans fatty acid and is healthier; meanwhile, the composition has a faster crystallization rate, does not need to be cooled at a low temperature for a long time for solidification and molding, and reduces the production time.
The composition of the invention has cool feeling, no pasty mouthfeel and quick melting.
Compared with the traditional lauric acid Cocoa Butter Substitute (CBS), the composition has better heat resistance and is relatively less prone to crack.
The compositions of the invention do not require tempering and reduce chocolate processing steps compared to Cocoa Butter Equivalent (CBE).
Compared with butter or other grease, the composition of the invention can increase the heat resistance stability of the product when being used in the plant grease fresh butter, and simultaneously, the wax taste can not appear, and the foam is stable and has no crack.
The preparation method of the composition is a non-hydrogenation process, and the obtained composition does not contain trans-fatty acid and is healthier.
Detailed Description
The invention provides an oil or fat composition, a method for producing the oil or fat composition, and a food containing the oil or fat composition.
Oil and fat composition
The fat and oil composition of the present invention is characterized by containing not less than 30% by weight of a triglyceride represented by the general formula (1) based on the total amount of the fat and oil composition,
Figure 820721DEST_PATH_IMAGE001
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3Any two of them represent a linear or branched saturated hydrocarbon group having 5 to 13 carbon atoms, and the other one represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms.
In a preferred embodiment of the present invention, R in the formula (1)1、R2And R3Any two of them represent an alkyl group having 7 to 11 carbon atoms.
In the preferred embodiment of the present inventionIn the formula, R in the general formula (1)1、R2And R3Any two of them represent an undecyl group, preferably a linear undecyl group.
In a preferred embodiment of the present invention, R in the formula (1)1、R2And R3Any one of them represents a pentadecyl group.
Preferably, the triglyceride represented by the above general formula (1) is a lauric acid monosaturated triglyceride (LLH) wherein L is lauric acid (C12: 0) and H is a linear or branched fatty acid having not less than 16 carbon atoms in the carbon chain (preferably a linear saturated fatty acid having 16 carbon atoms).
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (1) is contained in an amount of not less than 50% by weight, more preferably not less than 58% by weight, still more preferably not less than 70% by weight, further preferably not less than 80% by weight, and particularly preferably not less than 88% by weight, based on the total amount of the fat or oil composition.
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (1) is contained in an amount of 50 to 99% by weight, more preferably 58 to 98% by weight, still more preferably 80 to 97% by weight, and particularly preferably 88 to 95% by weight, based on the total amount of the oil or fat composition.
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (2) is contained in an amount of less than 10% by weight based on the total amount of the fat or oil composition,
Figure 572776DEST_PATH_IMAGE002
in the general formula (2), R4、R5And R6Each of which is the same or different and represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms.
In a preferred embodiment of the present invention, R in the formula (2)4、R5And R6Each of which is the same or different and represents a straight-chain alkyl group having 15 to 23 carbon atoms.
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (2) is at least one selected from the group consisting of 1,2, 3-tristearyl triglyceride (SSS), 1,2, 3-tripalmitoyl triglyceride (PPP) and 1, 2-distearoyl-3-palmityl triglyceride (SSP), wherein S is stearic acid (C18: 0) and P is palmitic acid (C16: 0).
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (2) is contained in an amount of less than 9% by weight, preferably less than 6% by weight, more preferably less than 4% by weight, and still more preferably less than 2% by weight based on the total amount of the fat or oil composition.
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (2) is contained in an amount of less than 9 to 0.1% by weight, preferably less than 6 to 0.5% by weight, more preferably less than 2 to 1% by weight, based on the total amount of the fat or oil composition.
In a preferred embodiment of the present invention, the fat or oil composition has a solid fat content of 90% by weight or more, preferably 92% by weight or more, more preferably 95% by weight or more, and still more preferably 96% by weight or more, as measured by a nuclear magnetic instrument, after being left in a water bath at 10 ℃ for 10 minutes. In a specific embodiment of the invention, after the oil and fat composition is placed in a water bath at 10 ℃ for 10 minutes, the solid fat content of the oil and fat detected by a nuclear magnetic instrument is 92.5 wt%, 95.7 wt% and 96.4 wt%.
In one embodiment of the present invention, the content of the monolauric acid triglyceride (LLH) is 88.1% by weight, and the content of the 1,2, 3-tristearic acid triglyceride (SSS) is 1.3% by weight in the grease composition.
In one embodiment of the present invention, the content of the monolauric acid triglyceride (LLH) is 34.6% by weight and the content of the 1,2, 3-tristearic acid triglyceride (SSS) is 8.8% by weight in the grease composition.
In one embodiment of the present invention, the content of the monolauric acid triglyceride (LLH) is 58.9% by weight, and the content of the 1,2, 3-tristearic acid triglyceride (SSS) is 5.5% by weight in the grease composition.
The fat or oil composition of the present invention can be used for producing the following food of the present invention.
The fat or oil composition of the present invention can be produced by the following method for producing a fat or oil composition.
Method for producing fat composition
The method for producing the fat or oil composition of the present invention comprises the step of mixing or not mixing another fat or oil with the triglyceride represented by the general formula (1),
Figure 83654DEST_PATH_IMAGE001
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3Any two of them represent a linear or branched saturated hydrocarbon group having 5 to 13 carbon atoms, and the other one represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms.
In the present invention, the other oil or fat refers to an oil or fat added without affecting the object of the present invention. The oil can be vegetable oil or animal oil. The plant source oil is selected from at least one of rice oil, sunflower seed oil, rape oil, palm oil and a fraction thereof, palm kernel oil and a fraction thereof, peanut oil, rapeseed oil, soybean oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, olive oil, cocoa bean oil, Chinese tallow tree seed oil, almond oil, tung seed oil, rubber seed oil, corn oil, wheat germ oil, sesame seed oil, castor bean oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, glass endive seed oil, sea buckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil and the like. The animal source oil is deep sea fish oil, such as salmon oil, sardine oil, etc.
In a preferred embodiment of the present invention, the triglyceride represented by the general formula (1) is obtained by an esterification reaction or a transesterification reaction.
The esterification reaction can be carried out according to a conventional method. For example, monoglyceride and an organic acid are mixed and heated (e.g., 200 ℃ C.) to react.
The monoglyceride is a monoester of glycerin and a linear or branched fatty acid having 16 or more carbon atoms (preferably a linear saturated fatty acid having 16 carbon atoms), and may be a mixture of glycerin esters having a relatively large monoglyceride content, for example, a glycerin ester having a monoglyceride content of not less than 30%, preferably not less than 40%, preferably not less than 50%, preferably not less than 60%, preferably not less than 70%, preferably not less than 80%, more preferably not less than 90% (for example, a glycerin ester having a monoester content of 60%, a diester content of 35%, and a triester content of 5%).
The organic acid is a linear or branched saturated fatty acid having 6 to 14 carbon atoms, and examples thereof include caprylic acid, capric acid, lauric acid, myristic acid, and the like, and these organic acids may be used singly or in combination, but lauric acid alone is preferable.
The addition amount of the organic acid is monoglyceride in terms of molar ratio: the organic acid is 1: 1-3, preferably 1: 2. the reaction is preferably carried out at 150 to 250 ℃ under heating, particularly preferably at 200 ℃ for 1 to 10 hours, preferably 2 to 4 hours. And filtering to remove unreacted raw materials after reaction to obtain the grease.
The transesterification reaction can be carried out according to a conventional method. For example, at least one kind (first oil and fat) selected from the group consisting of palm kernel oil, coconut oil, palm oil, cottonseed oil, fractionated oil thereof, and hydrogenated oil thereof is mixed with at least one kind (second oil and fat) selected from the group consisting of palm oil, cottonseed oil, fractionated oil thereof, and hydrogenated oil thereof, and reacted. It is particularly preferable to mix the perhydrogenated palm kernel stearin and the perhydrogenated palm stearin and carry out the reaction.
The mixing ratio of the first grease to the second grease may be, by weight: and (3) 70-90% of a second grease: 30-10, preferably 80: 20.
the transesterification reaction may be carried out in the presence of a catalyst. The catalyst comprises a basic catalyst, an acidic catalyst, a biological enzyme catalyst and the like. Wherein the alkaline catalyst comprises a readily alcohol soluble catalyst (e.g., NaOH, KOH, NaOCH)3Organic bases, etc.) and various solid base catalysts; the acidic catalyst includes catalysts which are readily soluble in alcohols (e.g., sulfuric acid, sulfonic acid, etc.) and various solid acid catalysts. Preferably NaOCH3(sodium methoxide). The amount of catalyst usedIs 0.05-2.0 wt%, preferably 0.1 wt% of the total reactant.
The reaction is preferably carried out at 50 to 250 ℃ under heating, particularly preferably at 100 ℃ for 0.1 to 5 hours, preferably 0.5 to 2 hours. After the reaction, the reaction mixture is preferably washed with an organic solvent (preferably acetone, n-hexane, t-butanol, n-heptane).
The method for producing the fat composition of the present invention comprises:
the monoglyceride or a composition comprising monoglyceride is subjected to an esterification reaction with lauric acid or a composition comprising lauric acid.
The monoglyceride is a monoester of glycerin and a linear or branched fatty acid having 16 or more carbon atoms (preferably a linear saturated fatty acid having 16 carbon atoms). In the monoglyceride-containing composition, the monoglyceride content is not less than 30%, preferably not less than 40%, preferably not less than 50%, preferably not less than 60%, preferably not less than 70%, preferably not less than 80%, more preferably not less than 90% by weight of the monoglyceride-containing composition (for example, monoglyceride having a monoester content of 60%, a diester content of 35%, and a triester content of 5%).
The manufacturing method according to, wherein the lauric acid is contained in an amount of not less than 90%, preferably not less than 95%, by weight of the composition containing lauric acid.
According to the production method, the molar ratio of the monoglyceride to the lauric acid in the esterification reaction process is 1:2 to 1:10, preferably 1:3 to 1: 5. The specific amount or ratio of monoglyceride-containing composition and lauric acid-containing composition used may be determined according to the amount of monoglyceride and monoglyceride-containing composition to be used, the amount of lauric acid to be used, and the amount of lauric acid in the lauric acid-containing composition.
According to the production process, there is further provided a step of subjecting the product of the esterification reaction to distillation, preferably molecular distillation, to remove the reaction raw material, preferably monoglyceride, lauric acid and diglyceride.
The esterification, distillation or molecular distillation process is well known to those skilled in the art, and those skilled in the art can adjust specific parameters, such as 200 ℃ molecular distillation, according to the purpose to be achieved.
The preparation method of the grease composition provided by the invention comprises the following steps:
mixing the random ester exchange product of the perhydrostearin with an organic solvent, and carrying out solid-liquid separation.
According to the production method, the random ester exchange product of the perhydrostearin and the organic solvent are mixed in a weight ratio of 1:1 to 1:30, preferably 1:2 to 1:20, more preferably 1:3 to 1: 10.
According to the production method, the fatty acid content of the fat and oil fatty acid carbon chain number of 16 or more in the fully hydrogenated hard butter exceeds 80%. According to the production method, the perhydrogenated stearin is at least one of perhydrogenated palm kernel stearin, perhydrogenated palm stearin, perhydrogenated soybean oil, perhydrogenated rapeseed oil or perhydrogenated peanut oil.
According to the production method, the solid-liquid separation is filtration, centrifugation, or standing separation.
According to the production method, the organic solvent is at least one of acetone, n-hexane, t-butanol, and n-heptane.
In the process of the present invention, the random transesterification step may employ any method that enables random transesterification of the perhydrostearin, such as chemical random transesterification or enzymatic random transesterification.
The random transesterification step is carried out, for example, by dehydrating the fats and oils under heating, and adding a chemical catalyst or lipase under heating. The dehydration is performed, for example, under vacuum at 90 to 120 ℃ such as 105 ℃ for 0.5 to 2 hours such as 1 hour. After the catalyst is added, the reaction is preferably carried out at 60 to 90 ℃, for example, 80 ℃.
The random transesterification step may be carried out in the presence of a chemical catalyst. The chemical catalyst is at least one of hydroxide, carbonate, bicarbonate and alkoxide of alkali metal or alkaline earth metal. The hydroxide of an alkali metal or alkaline earth metal is selected from KOH, NaOH, Ca (OH)2At least one of (1). The carbonate of an alkali metal is selected from K2CO3、Na2CO3At least one of (1). The alkali metal bicarbonate is selected from KHCO3、NaHCO3At least one of (1). Alkoxides of alkali metals, e.g. NaOCH3. The amount of the catalyst to be added is not particularly limited, and for example, 0.1 to 2% by weight, for example, 0.5% by weight of the catalyst is added to the oil and fat.
The random transesterification step may also be carried out in the presence of a lipase. The lipase enzyme is a non-specific lipase, and may be a commercially available enzyme (e.g., lipzyme TL IM from novacin), a self-fermenting enzyme, or an enzyme solution in which enzyme powder is dissolved in a buffer. The lipase may be derived from animals or plants, or from microorganisms such as Thermomyces lanuginosus (Thermomyces lanuginosus) (II)Thermomyces lanuginosus) Rhizopus oryzae (A) and (B)Rhizopus oryzae) Rhizomucor miehei (A), (B), (CRhizomucor miehei) Candida antarctica (C.), (Candida antarctica) Aspergillus nigerAspergillus niger) Burkholderia bacterium (B.), (B.)Burkholderia sp.) Candida rugosa (C.), (Candida rugosa) Alcaligenes, Alcaligenes (II) and (III)Alcaligenes sp.) Mucor javanicus (A) and (B)Mucor javanicus) Rhizopus niveus (A) and (B)Rhizopus niveus) Geotrichum candidum (A), (B), (C), (B), (C), (Cryytococcus neoformans) Etc. or a genetically modified strain thereof.
The reaction of the random transesterification step is preferably terminated with a terminator. The terminator may be an organic acid or an inorganic acid. Examples of the organic acid include citric acid and tartaric acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid. 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, 10 to 30% by weight, for example, 20% by weight of the reaction mixture is added.
In one embodiment of the present invention, the molecular distillation type monoglyceride and lauric acid are mixed in a molar ratio of 1:2 mixing, heating and carrying out an esterification reaction for 2 hours, and removing unreacted lauric acid, monoglyceride and diglyceride by molecular distillation to obtain the oil or fat composition. The temperature of the heating esterification is 200 ℃, and the molecular distillation is carried out at 200 ℃. The obtained oil and fat composition had a content of glycerol trilaurate monosaturated acid (LLH) of 88.1 wt% and a content of glycerol 1,2, 3-tristearate (SSS) of 1.3 wt%.
In one embodiment of the invention, the fully hydrogenated palm kernel stearin and the fully hydrogenated palm stearin are mixed in a weight ratio of 4: 1, adding 0.1 weight percent of sodium methoxide, carrying out transesterification reaction at 100 ℃ to obtain ester-exchanged oil, mixing the obtained ester-exchanged oil and acetone according to the weight ratio of 1:4, and filtering to obtain the oil composition. The obtained oil and fat composition had a content of unsaturated acid triglyceride dilaurate (LLH) of 34.6 wt% and a content of 1,2, 3-tristearate triglyceride (SSS) of 8.8 wt%.
In one embodiment of the present invention, monoglyceride (monoester content 60 wt%, diester content 35 wt%, and triester content 5 wt% in the monoglyceride) is mixed with lauric acid in a molar ratio of 1:2 mixing, heating and esterifying for 2 hours, and removing unreacted lauric acid, monoglyceride and diglyceride by molecular distillation to obtain the oil and fat composition. The temperature of the heating esterification is 200 ℃, and the molecular distillation is carried out at 200 ℃. The obtained oil and fat composition had a content of glycerol trilaurate monosaturated acid (LLH) of 58.9 wt% and a content of glycerol 1,2, 3-tristearate (SSS) of 5.5 wt%.
In a preferred embodiment of the present invention, the fat composition obtained by the above-described method for producing a fat composition of the present invention has a solid fat content of 90% by weight or more, preferably 92% by weight or more, more preferably 95% by weight or more, and still more preferably 96% by weight or more, as measured by a nuclear magnetic instrument, after being left in a water bath at 10 ℃ for 10 minutes. In a specific embodiment of the invention, after the oil and fat composition is placed in a water bath at 10 ℃ for 10 minutes, the solid fat content of the oil and fat detected by a nuclear magnetic instrument is 92.5 wt%, 95.7 wt% and 96.4 wt%.
In the present invention, the oil or fat composition of the present invention can be produced by the above-described method for producing an oil or fat composition of the present invention. The fat or oil composition produced by the above-described method for producing a fat or oil composition of the present invention can be used for producing the food of the present invention described below.
Food product
The food of the present invention contains the fat or oil composition of the present invention or the fat or oil composition produced by the method for producing the fat or oil composition. In the food of the present invention, the content of the fat or oil composition is determined according to the flavor and actual need of the food. The content of the oil or fat composition is usually 0.1 to 50% by weight, preferably 1 to 45% by weight, more preferably 5 to 40% by weight, and particularly preferably 10 to 35% by weight, based on the total amount of the food.
The food products of the present invention include, but are not limited to, chocolate (e.g., sweet chocolate, milk chocolate, semi-sweet chocolate, buttermilk chocolate, white chocolate or colored chocolate and various types of chocolate foods), chocolate also including chocolate coatings having a chocolate flavor (coating chocolate) and other substances that function as chocolate substitutes; vegetable cream and other substances acting as substitutes for vegetable cream, chocolate, whipped cream, cake, biscuit, sandwich sauce, etc.
The food of the present invention can be prepared by contacting the fat or oil composition with a food-acceptable carrier according to a conventional method.
In a preferred embodiment of the present invention, cocoa powder, white sugar, the fat or oil composition of the present invention, lecithin are finely ground (e.g., for 1 hour) with a ball mill to have an average particle size of less than 26 microns; after the resulting chocolate mass is placed in an oven (e.g. 50 ℃) to melt sufficiently, the chocolate mass is poured into a plastic mould and, after cooling, a chocolate mass is formed.
In the preferred embodiment of the invention, the oil and the oil phase material are heated (for example, 70 ℃) for standby, and the oil phase material comprises the oil, tween 60, span 60, lecithin, sodium stearoyl lactylate and propylene glycol fatty acid ester. Heating until all substances are dissolved, adding sodium caseinate, and dispersing in oil to obtain an oil phase; the glucose syrup is added to water and the temperature is raised (e.g., 65 ℃ C. to 70 ℃ C.). Uniformly mixing xanthan gum, guar gum, microcrystalline cellulose, sucrose, salt and dipotassium hydrogen phosphate, adding into water, and stirring (for example, 1200 rpm) until all materials are dispersed to obtain a water phase; slowly adding the oil phase into the water phase, and stirring at 2000 rpm (for example, 2000 rpm for 30 min); homogenizing; cooling the materials (for example, 2-4 ℃) by using an ice cream machine, aging the materials in a refrigerator (for example, 2-4 ℃ for 5 hours), and then storing the materials in the refrigerator (for example, 20 ℃ below zero); taking frozen and hard non-dairy cream, thawing with warm water (such as 5 ℃) and stirring until no ice crystal exists, beating with a beater at a medium speed (such as 160 rpm), and obtaining an optimal foam structure when the liquid cream becomes thick, the surface gloss disappears and soft peaks are formed; the cream was extruded from the piping bag and placed in an oven (e.g., 27 degrees, 30 minutes).
In the present invention, the food-acceptable carrier includes, but is not limited to, for example, starch, cellulose, dextrin, milk fat, animal and vegetable oils and fats such as sesame oil, soybean oil, peanut oil, palm oil, olive oil, corn oil, rapeseed oil, lard, beef tallow and the like, edible gums such as gum arabic, gelatin, carrageenan, xanthan gum, guar gum, sodium alginate and the like, phospholipids such as lecithin, cephalin and the like, baking powder and the like, emulsifiers such as glycerin fatty acid ester, sucrose fatty acid ester, sorbitol fatty acid ester, lecithin and the like, antioxidants, colorants, flavors and the like.
The following detailed description of various aspects of the present invention is provided in connection with examples to enable those skilled in the art to better understand the present invention, but the scope of the present invention is not limited by the examples.
The following examples use instrumentation conventional in the art. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers. In the following examples, various starting materials were used, and unless otherwise specified, conventional commercially available products were used. In the description of the present invention and the following examples, "%" represents weight percent unless otherwise specified.
Examples
In the following examples of the invention, FHPKST (fully hydrogenated palm kernel oil stearin), PKST (palm kernel oil stearin), PKO (palm kernel oil), PO (palm oil) were used, all from the oil and fat chemical industry, California (Shanghai) Co.
Example 1:
mixing 10 mol parts of molecular distillation type monoglyceride (Jia Li oil chemical industry (Shanghai) Co., Ltd.) and 20 mol parts of lauric acid (Yihai (Lianhong) oil chemical industry Co., Ltd.), putting into a three-neck flask, heating to 200 ℃, carrying out esterification reaction for 2 hours, and naturally cooling for 2 hours; the oil and fat obtained from the reaction was subjected to molecular distillation at 200 ℃ to remove unreacted lauric acid, monoglyceride and diglyceride, and the oil and fat obtained (sample 1) was referred to as TAG: the AOCS offical method Ce 5-86 is adopted for detection, wherein the detection results of the contents of LLH and SSS are shown in Table 1.
Example 2:
mixing 800g of fully hydrogenated palm kernel stearin (Jia Li special oil and fat Co., Ltd.) and 200g of fully hydrogenated palm kernel stearin (Jia Li special oil and fat Co., Ltd.), putting into a three-neck flask, adding 0.1% sodium methoxide, reacting at 100 ℃ for 40 minutes, and naturally cooling for 2 hours to obtain ester exchange oil and fat A; mixing the obtained ester exchange oil A with acetone at a weight ratio of 1:4, cooling to 22 deg.C, and filtering; the filtrate was further cooled to 10 ℃, filtered, the filter cake was rinsed clean with acetone, the solid fat was collected, and the obtained solid fat (sample 2) was referenced TAG: the AOCS offical method Ce 5-86 is adopted for detection, wherein the detection results of the contents of LLH and SSS are shown in Table 1.
Example 3:
monoglyceride (AOCS official method Ce 5-86 and AOCS official method Cd 11d-96, both of which are available from carlix oil and fat chemical industry (shanghai) limited) was detected, and as a result, 10 moles of monoglyceride in the monoglyceride were mixed with 20 moles of lauric acid, and esterification and molecular distillation were performed, which were the same as in example 1, to obtain sample 3, and the obtained sample 3 was referred to as TAG: the method of AOCSoffical method Ce 5-86 detects the content of LLH and SSS, and the detection results are shown in Table 1.
Comparative example 1: perhydrogenated palm kernel oil was used as comparative sample 1.
Comparative example 2: the ester-exchanged fat A not fractionated in example 2 was used as comparative sample 2.
Comparative example 3: sample 1 (80 parts by mole) was mixed with perhydrogenated palm stearin (Jia Li specialty fats Co., Ltd.) (20 parts by mole) and melted to obtain comparative sample 3.
Respectively referring the comparison samples 1-3 to TAG: the content of LLH and SSS in the AOCS official method Ce 5-86 is detected, and the detection result is shown in Table 1.
TABLE 1
LLH% SSS%
Sample 1 88.1 1.3
Sample 2 34.6 8.8
Sample 3 58.9 5.5
Comparative sample 1 15.2 11.5
Comparative sample 2 9.8 4.3
Comparative sample 3 70.5 21.1
Comparison of crystallization rates
And (3) loading the grease samples 1-3 and the comparative samples 1-3 into a glass tube, placing the glass tube in a water bath at 10 ℃ for 10 minutes, and detecting the solid fat content of the grease on a nuclear magnetic instrument. The results are shown in Table 2.
TABLE 2
Oil solid fat content after 10 minutes (%)
Sample 1 96.4
Sample 2 92.5
Sample 3 95.7
Comparative sample 1 87.5
Comparative sample 2 88.4
Comparative sample 3 95.7
The higher the fat content, the faster the crystallization rate at the same time at a given temperature. As can be seen from the results in table 2, the crystallization rates of samples 1,2,3 and 3 were faster than those of comparative samples 1 and 2.
Application example 1
Chocolate
The chocolate formula comprises: 10% cocoa powder, 55% white sugar, 34.6% fat (sample 1, sample 2, sample 3, comparative sample 1, comparative sample 2 or comparative sample 3), 0.4% lecithin. The entire batch was placed in a ball mill and ground for 1 hour to an average particle size of less than 26 microns (as measured by a screw micrometer). The chocolate liquor was placed in an oven at 50 ℃ to melt thoroughly. The chocolate mass is poured into plastic modules and, after cooling, chocolate pieces of about 5 grams each are produced. The chocolate pieces were kept at 20 ℃ for 3 days and then their mouth solubility was evaluated by tasting by 20 researchers. Table 3 shows the average evaluation results of the oral solubility evaluation.
Evaluation criteria for oral solubility: melting rate, pasty mouthfeel, and refreshing feeling;
wherein ○ indicates fast thawing, it indicates slow thawing, and the two indicate no thawing basically or long thawing time;
○ indicates no paste taste, it indicates slight paste taste, and the other indicates obvious paste taste;
○ indicates strong cooling, and it indicates a cooling but not obvious, and the other indicates weak or no cooling.
TABLE 3
Rate of melting Paste taste Feeling of coolness
Sample 1
Sample 2
Sample 3
Comparative sample 1
Comparative sample 2
Comparative sample 3
The experimental results show that the samples 1,2 and 3 have good mouthfeel; and the comparative samples 1,2 and 3 have slow melting rate, paste taste and poor taste.
Application example 2
Vegetable fat fresh cream
Fresh non-dairy cream was prepared according to the formulation of table 4, wherein the fats and oils used are shown in table 5. The preparation method of the plant fat fresh cream comprises the following steps:
heating oil and oil phase material to 70 deg.C. The oil phase material comprises oil, Tween 60, span 60, lecithin, sodium stearyl lactate, and propylene glycol fatty acid ester. Heating until all substances are dissolved, adding sodium caseinate, and dispersing in oil to obtain an oil phase;
adding the glucose syrup into water, and heating to 65-70 ℃. Uniformly mixing xanthan gum, guar gum, microcrystalline cellulose, sucrose, salt and dipotassium hydrogen phosphate, adding into water, and stirring at 1200 rpm until all materials are dispersed to obtain a water phase;
slowly adding the oil phase into the water phase, and stirring at 2000 rpm for 30 min; homogenizing;
cooling the materials to 2-4 ℃ by using an ice cream machine, aging the materials in a refrigerator at 2-4 ℃ for 5 hours, and then storing the materials in a refrigerator at-20 ℃;
taking 900g of frozen and hard non-dairy cream, unfreezing the non-dairy cream to 5 ℃ by using warm water, stirring the non-dairy cream until no ice crystal exists, and stirring the non-dairy cream by using a stirrer at a medium speed (160 rpm) until the liquid cream becomes thick and thick, the surface gloss disappears, and an optimal foam structure can be obtained when a soft peak is formed;
the cream was extruded from a piping bag, placed in a 27-degree oven for 30 minutes, and observed for changes in surface and internal foam, with the results shown in Table 6.
TABLE 4 vegetable fat fresh cream ingredient table
Model number Ratio of
Oil and fat 20.10%
Casein sodium salt sodium casenate 2.05%
Xanthan gum Grindsted Xantan 200 0.10%
Guar gum Grindsted Guar 250 0.10%
Microcrystalline cellulose MCC 3282 0.30%
Sucrose 13.00%
Glucose syrup 16%
Salt (salt) 0.50%
Dipotassium hydrogen phosphate 0.10%
Tween 60 Crillet3 0.15%
Span 60 Grindsted SMS-M 0.43%
Lecithin 0.30%
Sodium stearoyl lactylate SLL P55VEG 0.20%
Propylene glycol fatty acid ester PGMS90 0.20%
Water (W) 46.47%
TABLE 5 fats and oils used in the experiments
Sample No. 4 Sample No. 5 Sample No. 6 Comparative sample 4 Comparative sample 5 Comparative sample 6
Sample 1 100% 80% 75%
FHPKST 100%
PKST 50% 40%
PKO 20% 10% 50% 30%
PO 15% 30%
TABLE 6 stability test results for vegetable fat fresh cream
Sample No. 4 Sample No. 5 Sample No. 6 Comparative sample 4 Comparative sample 5 Comparative sample 6
In Table 6, the change was evaluated according to the following criteria:
○ foam stability, no cracking;
slight cracking of the foam is expected;
and obvious breakage and collapse of foam appear in the opposite aspect.
The application experiment result of the plant fat fresh cream shows that the samples 4, 5, 6 and 4 are stable in foam and free of rupture; whereas the foam showed significant collapse using comparative samples 5 and 6.

Claims (38)

1. An oil or fat composition characterized by containing 50 to 99 wt% of a triglyceride represented by the general formula (1) based on the total amount of the oil or fat composition and containing less than 9 to 0.1 wt% of a triglyceride represented by the general formula (2) based on the total amount of the oil or fat composition,
Figure DEST_PATH_IMAGE002
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3Any two of them represent an undecyl group, and the other represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms,
Figure DEST_PATH_IMAGE004
in the general formula (2), R4、R5And R6Each of which is the same or different and represents a linear or branched saturated hydrocarbon group having 15 to 29 carbon atoms,
the oil and fat composition is obtained by performing esterification reaction on monoglyceride or a composition containing monoglyceride and lauric acid or a composition containing lauric acid, wherein the monoglyceride content is not lower than 30% by weight of the monoglyceride-containing composition, and the lauric acid content is not lower than 90% by weight of the lauric acid-containing composition, or
The grease composition is obtained by mixing a random transesterification product of a perhydro stearin with an organic solvent and performing solid-liquid separation, wherein the perhydro stearin is at least one of perhydro palm kernel stearin, perhydro palm stearin, perhydro soybean oil, perhydro rapeseed oil or perhydro peanut oil.
2. The fat and oil composition according to claim 1, wherein the triglyceride represented by the general formula (1) is contained in an amount of not less than 80% by weight based on the total amount of the fat and oil composition.
3. The fat and oil composition according to claim 1, wherein the triglyceride represented by the general formula (1) is contained in an amount of not less than 88% by weight based on the total amount of the fat and oil composition.
4. The fat and oil composition according to claim 1, wherein the triglyceride represented by the general formula (1) is contained in an amount of 58 to 98 wt% based on the total amount of the fat and oil composition.
5. The fat and oil composition according to claim 1, wherein the triglyceride represented by the general formula (1) is contained in an amount of 80 to 97% by weight based on the total amount of the fat and oil composition.
6. The fat and oil composition according to claim 1, wherein the triglyceride represented by the general formula (1) is contained in an amount of 88 to 95% by weight based on the total amount of the fat and oil composition.
7. The grease composition according to any one of claims 1 to 6, wherein R in the general formula (1)1、R2And R3Any one of them represents a pentadecyl group.
8. The fat and oil composition according to claim 1, which contains less than 4% by weight of the triglyceride represented by the general formula (2) based on the total amount of the fat and oil composition.
9. The fat and oil composition according to claim 1, which contains less than 2% by weight of the triglyceride represented by the general formula (2) based on the total amount of the fat and oil composition.
10. The fat and oil composition according to claim 1, which contains the triglyceride represented by the general formula (2) in an amount of less than 6 to 0.5 wt% based on the total amount of the fat and oil composition.
11. The fat and oil composition according to claim 1, which contains the triglyceride represented by the general formula (2) in an amount of less than 2 to 1 wt% based on the total amount of the fat and oil composition.
12. The oil or fat composition according to any one of claims 1 to 6, wherein R in the general formula (2)4、R5And R6Each of which is the same or different and represents a straight-chain alkyl group having 15 to 23 carbon atoms.
13. The fat and oil composition according to any one of claims 1 to 6, wherein the triglyceride represented by the general formula (2) is at least one selected from the group consisting of 1,2, 3-tristearate triglyceride, 1,2, 3-tripalmitate triglyceride and 1, 2-distearate-3-palmitate triglyceride.
14. The fat composition according to any one of claims 1 to 6, which has a fat solid fat content of 90% by weight or more as measured by a nuclear magnetic instrument after being left in a water bath at 10 ℃ for 10 minutes.
15. The fat composition according to any one of claims 1 to 6, which has a fat solid fat content of 92% by weight or more as measured by a nuclear magnetic instrument after being left in a water bath at 10 ℃ for 10 minutes.
16. The fat composition according to any one of claims 1 to 6, which has a fat solid fat content of 95% by weight or more as measured by a nuclear magnetic instrument after being left in a water bath at 10 ℃ for 10 minutes.
17. The fat composition according to any one of claims 1 to 6, which has a fat solid fat content of 96% by weight or more as measured by a nuclear magnetic instrument after being left in a water bath at 10 ℃ for 10 minutes.
18. The method for producing the grease composition according to claim 1, comprising:
the monoglyceride or a composition comprising monoglyceride is subjected to an esterification reaction with lauric acid or a composition comprising lauric acid.
19. The method of claim 18, wherein the monoglyceride comprises an amount of not less than 50% by weight of the composition.
20. The method of claim 18, wherein the monoglyceride comprises an amount of not less than 70% by weight of the composition.
21. The preparation method according to claim 18, wherein the lauric acid is contained in an amount of not less than 95% by weight of the composition containing lauric acid.
22. The preparation method according to claim 18, wherein the molar ratio of the monoglyceride to the lauric acid during the esterification reaction is 1:2 to 1: 10.
23. The preparation method according to claim 18, wherein the molar ratio of the monoglyceride to the lauric acid during the esterification reaction is 1:3 to 1: 5.
24. The method of claim 18,
further comprising the step of distilling the product of the esterification reaction to remove the reaction raw material.
25. The method of claim 24, wherein the distillation is molecular distillation.
26. The method of claim 24, wherein monoglycerides, lauric acid and diglycerides are removed.
27. The method for producing the grease composition according to claim 1, comprising:
mixing the random ester exchange product of the perhydrostearin with an organic solvent, and carrying out solid-liquid separation.
28. The method according to claim 27, wherein the random transesterified product of the perhydrostearin is mixed with an organic solvent at a weight ratio of 1:1 to 1: 30.
29. The method according to claim 27, wherein the random transesterification product of the perhydrostearin is mixed with the organic solvent in a weight ratio of 1:2 to 1: 20.
30. The method according to claim 27, wherein the random transesterification product of the perhydrostearin is mixed with the organic solvent in a weight ratio of 1:3 to 1: 10.
31. The production method according to any one of claims 27 to 30,
the fatty acid content of the fatty acid carbon chain number of the grease in the fully hydrogenated stearin is equal to or more than 16 and exceeds 80 percent.
32. The production method according to any one of claims 27 to 30, wherein the solid-liquid separation is filtration, centrifugation, or standing separation.
33. The method according to any one of claims 27 to 30, wherein the organic solvent is at least one of acetone, n-hexane, t-butanol, and n-heptane.
34. A food product comprising the oil or fat composition according to any one of claims 1 to 17 or the oil or fat composition produced by the production method according to any one of claims 18 to 33.
35. The food product of claim 34, which is chocolate, whipped cream, cake, biscuit, or sandwich.
36. An oil or fat composition produced by the production method according to any one of claims 18 to 33.
37. Use of the oil or fat composition according to any one of claims 1 to 17 or 36 for producing a food.
38. The use according to claim 37, wherein the food product is chocolate, whipped cream, cake, biscuit, or sandwich sauce.
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