CN109984215A - A kind of fat or oil composition and preparation method thereof - Google Patents
A kind of fat or oil composition and preparation method thereof Download PDFInfo
- Publication number
- CN109984215A CN109984215A CN201711480820.5A CN201711480820A CN109984215A CN 109984215 A CN109984215 A CN 109984215A CN 201711480820 A CN201711480820 A CN 201711480820A CN 109984215 A CN109984215 A CN 109984215A
- Authority
- CN
- China
- Prior art keywords
- fat
- acid
- oil
- oleic acid
- oil composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
- A23C9/1528—Fatty acids; Mono- or diglycerides; Petroleum jelly; Paraffine; Phospholipids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
- A23L7/10—Cereal-derived products
- A23L7/198—Dry unshaped finely divided cereal products, not provided for in groups A23L7/117 - A23L7/196 and A23L29/00, e.g. meal, flour, powder, dried cereal creams or extracts
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Abstract
The present invention provides a kind of fat or oil compositions, the fat or oil composition includes 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride (OPL) and 1, bis- oleic acid -2- palmitic acid of 3-, three ester (OPO), and the ingredient of the fat or oil composition and the closer Chinese lacto's rouge structure of content.The present invention also provides the preparation method of the fat or oil composition, the palm stearin that this method is 18 to 36 using iodine number obtains fat A as raw material, through random transesterification；The fat A is subjected to sn-1,3 orientation transesterifications, through isolating and purifying, to obtain fat or oil composition of the invention with containing the fat blend of oleic acid or its nonglyceride and linoleic acid or its nonglyceride again.
Description
Technical field
The invention belongs to food additives manufacture field, in particular to a kind of ingredient and content closer to Chinese
The fat or oil composition and preparation method thereof of newborn ester, the fat or oil composition include 1- oleic acid -2- palmitinic acid -3- linoleic acid three
Ester (following or abbreviation OPL) and bis- oleic acid -2- palmitic acid of 1,3-, three ester (following or abbreviation OPO).
Background technique
Breast milk is infant growth initial stage most important energy source, wherein the energy supply of 50%-60% is from mother
Triglycerides in cream.Therefore, triglycerides plays a crucial role the healthy growth of infant.But due to
The influence of many factors, more and more families, China implement to feed by formula milk to infant in recent years.In order to give
Infant provides most healthy, optimum, most close to the human milk substitution rouge of breast milk, and oil specially for infant milk powder rouge experienced number
Secondary innovation.So far, the fat in Chinese baby formula milk powder mostlys come from vegetable oil allotment, cow's milk fat and contains
Having main component is the fat or oil composition of bis- oleic acid -2- palmitic acid of 1,3-, three ester.
Position distribution rule difference of the fatty acid in fatty acid and vegetable oil on triglycerides skeleton in human milk rouge
Property is very big.Specifically, the saturated fatty acid in human milk rouge is distributed mainly on the position sn-2, in contrast, in vegetable oil
Saturated fatty acid is distributed mainly on sn-1 (3) position.It is existing research (Filer et al., Journal of nutrition,
1999,99:293-298) it proves, the absorption that sn-2 palmitinic acids are more advantageous to infant is distributed in, therefore, compared to human milk
Rouge, vegetable oil allotment grease are unfavorable for absorption of the infant to fat.Further, since the digestion and absorption height of fat relies on pancreas
The hydrolysis of the lipase of glandular secretion, action site deploy grease in sn-1 (3) position of triglycerides, therefore in vegetable oil
Hydrolytic process in, the free saturated fatty acid of high level will be generated in small enteral, these subsequent high-melting-points are saturated free rouge
Fat acid will form calcium soap with calcium ion in the intestine, to directly affect absorption of the infant for calcium.
Secondly, although cow's milk fat is from animal milk, its total fatty acids composition and sn-2 fatty acid compositions
Have with human milk rouge and obviously distinguishes.On total fatty acid content, human milk contains 10% or more polyunsaturated fat
Acid, and cow's milk only contains less than 2%, it is well known that brain and retinal development of the polyunsaturated fatty acid for infant
It plays a crucial role.In addition, in cow's milk sn-2 palmitinic acid only the total palmitic acid content of Zhan 35% or so, well below people
70% in butterfat, therefore, cow's milk can also influence infant to palmitinic acid and calcareous absorption to a certain extent.
In recent years, it deepens continuously, finds in its national human milk rouge to human milk rouge research with developed countries such as America and Europes
Main triglyceride structure be bis- oleic acid -2- palmitic acid of 1,3-, three ester (OPO).Therefore, numerous overseas-funded enterprises, such as Holland
The Crow Luo Desi Ke Lan company and Enzymotec Ltd., Israel are proposed the corresponding commercialized human milk rich in OPO
Fat prod is substituted, and receives the extensive concern of baby formula milk powder industry.Wherein, patent of invention CN101258230B is disclosed
It is raw material by carrying out the preparation method that acidolysis reaction prepares OPO with oleic acid using the palm oil of iodine value 2-12；
It is raw material after random transesterification that CN101679909B, which is disclosed using the palm oil of iodine value 18-40, and it is anti-to carry out acidolysis with oleic acid
The preparation method of OPO should be prepared；CN101198261B discloses a kind of human milk substitute rich in OPO.The above patent of invention is equal
To prepare OPO or production for the purpose of OPO human milk substitution rouge as main component.But as infant matches in nearest China
The attention rate of square milk powder gradually upgrades, we have discovered that, due to the influence of many factors such as eating habit, Chinese population cream
Fat composition and fat composition difference in American-European crowd's milk are extremely obvious in juice.Table 1 summarizes in China and European's butterfat
Important indicator, such as important triglycerides and content of fatty acid:
Table 1
| Index | China | Europe |
| OPO (wt%) | 14%-22% | 13%-28% |
| OPL (wt%) | 22%-33% | 12%-21% |
| Oleic acid (wt%) | 17%-29% | 26%-40% |
| Linoleic acid (wt%) | 16%-27% | 7%-20% |
Above data derive from (1) Lipids, 2009,44,257-271；(2) evaluation model of human milk fat substitutes is established
And its enzyme process preparation；(3) analysis data are had by oneself.Wherein, OPO represents 1,3-Dioleic acid-2-palmitoyl triglyceride；OPL is represented
1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride.
From analysis result, it is apparent that in content of fatty acid level, Chinese's butterfat Linoleic acid content is generally high
In European's butterfat, on the contrary, the oleic acid content in Chinese's butterfat is generally lower than European's butterfat.In triglycerides group stratification
Face, European's butterfat is with OPO for main triglycerides type, and in Chinese's butterfat, the content of OPL is apparently higher than OPO
Content.As previously mentioned, presently disclosed patent is only dedicated to obtaining the fat or oil composition for being rich in OPO, and this kind of grease
Composition not fully agrees with fat in Chinese human milk because it is substantially free of OPL, even if in European countries, it is close from imitating
For the angle of degree, current published patent is still significantly improved space.
Therefore, it is badly in need of exploring while the sn-2 total palmitinic acids of palmitinic acid Zhan and directly fatty close breast milk, it is main sweet
Oily three esters composition meets the preparation method of the human milk substitution rouge of Chinese human milk fat's structure, that is, explores with OPL as primary glycerol
Three ester ingredients, OPO is that the human milk of secondary triglycerides ingredient substitutes rouge, to significantly promote the phase of human milk substitution rouge and breast milk
Like degree.
Summary of the invention
Therefore, the object of the present invention is to provide a kind of ingredient and contents closer to the grease group of Chinese's butterfat structure
Object is closed, wherein 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride (OPL) rich in and 1, bis- oleic acid -2- palmitinic acid of 3-
Triglycerides (OPO).Another object of the present invention, which also resides in, provides the preparation method of above-mentioned fat or oil composition.
Above-mentioned purpose of the invention is achieved through the following technical solutions:
In one aspect, the present invention provides a kind of fat or oil composition, the fat or oil composition includes 1- oleic acid -2- palm
Acid -3- linoleic acid triglyceride and 1,3-Dioleic acid-2-palmitoyl triglyceride, wherein relative to composition total weight and
Speech, the 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride account for 25wt% or more, preferably 25wt%-32wt%；Wherein, phase
For the total weight of composition, the 1,3-Dioleic acid-2-palmitoyl triglyceride accounts for 15wt%-25wt%.
On the other hand, the present invention also provides the preparation method of the fat or oil composition, the method is with iodine number
18 to 36 palm stearin is raw material, and random transesterification is carried out in the presence of the lipase for random transesterification, obtains oil
Rouge A；Then in sn-1, in the presence of 3 orientation lipase, make fat A with containing oleic acid or its nonglyceride and linoleic acid or its
The fat blend of nonglyceride carries out sn-1, and 3 orient transesterifications, then through isolating and purifying, to obtain 1- oil rich in
The fat or oil composition of three ester of acid -2- palmitinic acid -3- linoleic acid triglyceride and bis- oleic acid -2- palmitic acid of 1,3-.
In yet another aspect, the purposes the invention further relates to the fat or oil composition in production infant food, and
Infant food comprising the fat or oil composition.
Specifically, the present invention is achieved through the following technical solutions:
[1] a kind of fat or oil composition, the fat or oil composition include 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride
With bis- oleic acid -2- palmitic acid of 1,3-, three ester；Wherein, for the total weight of composition, the 1- oleic acid -2- palm
Acid -3- linoleic acid triglyceride accounts for 25wt% or more；Wherein, for the total weight of composition, 1,3-, bis- oleic acid-
Three ester of 2- palmitic acid accounts for 15wt%-25wt%.
[2] fat or oil composition as described in paragraph [1], wherein for the total weight of composition, the 1- oil
Acid -2- palmitinic acid -3- linoleic acid triglyceride accounts for 25wt%-32wt%.
[3] fat or oil composition as described in paragraph [1] or [2], wherein sn-2 palmitinic acid accounts for the total content of palmitinic acid
55% or more.
[4] fat or oil composition as described in either segment in paragraph [1]-[3], wherein relative to composition total weight and
Speech, three palmitic acids, three ester account for 10wt% or less.
[5] a kind of method for preparing fat or oil composition described in either segment in paragraph [1]-[4], which comprises
A. the palm stearin for being 18 to 36 using iodine number in the presence of the lipase for random transesterification, makes as raw material
Random ester exchange reaction occurs for raw material, to obtain fat A；
B. fat blend is prepared by oleic acid or its nonglyceride and linoleic acid or its nonglyceride；Or by as oleic acid
Or the oil and fat preparation fat blend in the source of its nonglyceride and linoleic acid or its nonglyceride, wherein with weight ratio meter, institute
State the total amount of the free oleic acid and its residue in fat blend and the total amount of free linoleic acid and its residue ratio be 0.5:1 extremely
2:1, preferably 1:1 are to 1.5:1；Wherein, with weight ratio meter, the ratio of the fat blend and the fat A is 1:1 or more, excellent
Select 1:1-5:1；And
C. in the presence of sn-1,3 orientation lipase, the fat A and the fat blend is made to carry out sn-1,3 is fixed
It to ester exchange reaction, is then isolated and purified, to obtain the fat or oil composition.
[6] method as described in paragraph [5], wherein in step a, the random ester exchange reaction carries out at least 3h；
Wherein, in stepb, the sn-1,3 orientation ester exchange reactions carry out at least 3h.
[7] method as described in paragraph [6], wherein in step a, the random ester exchange reaction carries out at least 6h.
[8] method as described in paragraph [7], wherein in step a, the random ester exchange reaction carries out 6h-8h.
[9] method as described in either segment in paragraph [5]-[8], wherein for the total weight of raw material, for
The dosage of the lipase of machine transesterification is 5wt%-25wt%；
Wherein, for the fat A and the total weight of the fat composition, sn-1, the use of 3 orientation lipase
Amount is 5wt%-25wt%.
[10] method as described in paragraph [9], wherein for the total weight of raw material, for random transesterification
The dosage of lipase is 10wt%.
[11] method as described in paragraph [9], wherein the total weight relative to the fat A and the fat composition
For, the dosage of sn-1,3 orientation lipase are 10wt%.
[12] method as described in either segment in paragraph [5]-[11], wherein the lipase for random transesterification
For Lipozyme TL IM.
[13] method as described in either segment in paragraph [5]-[12], wherein the sn-1,3 orientation lipase are
Lipozyme RL IM。
[14] method as described in either segment in paragraph [5]-[13], wherein the free oleic acid and its residue with it is described
The total amount of free linoleic acid and its residue accounts for the 70wt% or more of the total weight of the fat blend.
[15] method as described in paragraph [14], wherein the free oleic acid and its residue and the free linoleic acid and
The total amount of its residue accounts for the 75wt% or more of the total weight of the fat blend.
[16] method as described in paragraph [15], wherein the free oleic acid and its residue and the free linoleic acid and
The total amount of its residue accounts for the 80wt% or more of the total weight of the fat blend.
[17] method as described in either segment in paragraph [5]-[16], wherein the oleic acid or its nonglyceride derive from
High oleic sunflower oil, high oleic acid rapeseed oil, high oleic acid soybean oil or high oleic acid peanut oil.
[18] method as described in either segment in paragraph [5]-[17], wherein the linoleic acid or its nonglyceride source
In corn oil, soybean oil or walnut oil.
[19] method as described in either segment in paragraph [5]-[18], wherein the palm stearin that the iodine number is 18 to 36
It is obtained by the dry fractionation of palm oil.
[20] method as described in either segment in paragraph [5]-[19], wherein described to isolate and purify use in step c
Molecularly distilled carries out.
[21] method as described in paragraph [20], wherein the reaction condition of the molecularly distilled are as follows: evaporating temperature is
185℃；Condenser temperature is 40 DEG C；Heat exchange temperature is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/
Min, absolute pressure 2Pa.
[22] fat or oil composition described in either segment or as described in either segment in paragraph [5]-[21] in paragraph [1]-[4]
Purposes of the fat or oil composition that method prepares in production infant food, the infant food is preferably that infant matches
Square milk powder or baby formula rice flour.
[23] comprising fat or oil composition described in either segment in paragraph [1]-[4] or by either segment institute in paragraph [5]-[21]
The infant food for the fat or oil composition that the method stated prepares, the infant food be preferably baby formula milk powder or
Baby formula rice flour.
[24] method as described in either segment in paragraph [5]-[21], wherein in stepb, by making as oleic acid or
Hydrolysis occurs for the grease in the source of its nonglyceride and/or linoleic acid or its nonglyceride, prepare corresponding fatty acid or
Fatty acid nonglyceride, and after the hydrolysis, using organic solvent to the fatty acid or fatty acid non-glycerol
Ester is extracted and is dried, to obtain the fat blend；Preferably, the solvent is n-hexane.
[25] method as described in paragraph [24], wherein the hydrolysis carries out in the presence of acid.
[26] method as described in paragraph [25], wherein the acid is selected from hydrochloric acid or sulfuric acid.
Beneficial effect
Present invention firstly provides the necessity for imitating Chinese human milk fat's triglycerides composition, and use oil prodution industry
Conventional products, i.e. iodine value 18 to 36 palm stearin as raw material, random transesterification, and and food are carried out by enzyme method technique
The fat blend in oily source is oriented transesterification, to prepare rich in 1- oleic acid -2- palmitinic acid -3- linoleic acid
The fat or oil composition of three ester (OPO) of three esters (OPL) and bis- oleic acid -2- palmitic acid of 1,3-.
Fat or oil composition produced by the present invention meets following characteristics:
(1) by weight, sn-2 palmitinic acid accounts for 55% or more of palmitinic acid total content；
(2) for the total weight of fat or oil composition, the total amount of OPL and OPO account for 40wt% or more；Wherein, relatively
For the total weight of fat or oil composition, OPL accounts for 25wt% or more；And
(3) for the total weight of fat or oil composition, the content of three palmitic acids, three ester (PPP) is lower than
10wt%.
Rouge, the closer China of the triglycerides ingredient and content of fat or oil composition of the invention are substituted compared to existing human milk
Triglycerides ingredient in human milk fat can be used as human milk substitution rouge and be applied to baby milk powder and other infant foods
In.The similitude of itself and Chinese human milk fat, Chinese Infant and Children preferably is greatly improved in fat or oil composition of the invention
To fat and calcareous absorption and utilization, promote to grow up healthy and sound, nutritive value with higher.
Specific embodiment
Technical solution of the present invention will be hereafter described in detail.
In the present invention, related parameter is all made of national food safety standard-food enrichment 1, bis- oleic acid of 3--
The measurement of the method for inspection provided by three ester of 2- palmitic acid (GB30604-2015) obtains.
Raw material used in the present invention is palm stearin of the iodine value 18 to 36, commercially available.In general, this can also be passed through
Dry fractionation technique known to field, by fractionated palm oil mention obtain comprising three palmitic acids, three ester (PPP) iodine value 18 to
36 palm stearin fraction.Fatty acid composition and the isomers in the palm stearin that iodine value is 18 and 36 are shown in following table 2
Distribution (different batches of product relevant parameter floats less than 5%).
Table 2
Fat blend used in the present invention can be obtained by allotment.The fat blend includes oleic acid or its is non-sweet
Grease and linoleic acid or its nonglyceride.Term oleic acid nonglyceride used herein refers to oleic acid and other than glycerol
Substance be formed by ester.Similarly, term linoleic acid nonglyceride used herein refer to linoleic acid in addition to glycerol with
Outer substance is formed by ester.
In a preferred embodiment, by weight, free oleic acid and its residue and free linoleic acid and its residue is total
Amount accounts for 70% or more, preferably 75% or more, more preferable 80% or more of the total amount of the fat blend.Further preferred
In embodiment, the weight of free oleic acid and its total amount of residue and the total amount of free linoleic acid and its residue in fat blend
Amount is than being 0.5:1 to 2:1, preferably 1:1 to 1.5:1.
Fat blend as used in the present invention is preferably derived from food oil.For example, oleic acid or its nonglyceride can
From high oleic sunflower oil, high oleic acid rapeseed oil, high oleic acid soybean oil or high oleic acid peanut oil.Linoleic acid or its non-glycerol
Ester can derive from corn oil, soybean oil or walnut oil.
In another embodiment, fat blend is also prepared by the following method: by making as oleic acid or its is non-sweet
Hydrolysis occurs for the grease in the source of grease and/or linoleic acid or its nonglyceride, prepares corresponding fatty acid or fatty acid
Nonglyceride, and after the hydrolysis, the fatty acid or fatty acid nonglyceride are carried out using organic solvent
It extracts and dries, to obtain the fat blend.
The grease in the source as oleic acid or its nonglyceride can be times in this field containing oleic acid and its residue
What grease, preferably edible oil.In a preferred embodiment, grease containing free oleic acid and its residue is selected from oleic acid and its residual
The edible oil of the content of base high (for example, 70wt% or more).For example, the oil in the source as linoleic acid or its nonglyceride
Rouge be preferably chosen from one of high oleic sunflower oil, high oleic acid rapeseed oil, high oleic acid soybean oil or high oleic acid peanut oil or
It is a variety of.
The grease in the source of the linoleic acid or its nonglyceride can be times in this field containing linoleic acid and its residue
What grease, preferably edible oil.In a preferred embodiment, grease containing free linoleic acid and its residue be selected from linoleic acid and
The edible oil of the content of its residue high (for example, 70wt% or more).For example, the oil in the source as linoleic acid or its nonglyceride
Rouge is preferably chosen from one of corn oil, soybean oil or walnut oil or a variety of.
Methods known in the art can be used and carry out the hydrolysis.In a preferred embodiment, above-mentioned hydrolysis
For acid hydrolytic reaction.For example, carrying out acid hydrolytic reaction under the heating water bath of certain temperature by using acid.Wherein, acid is optional
Hydrochloric acid and sulfuric acid.
Extraction and the dry methods known in the art that also can be used carry out.For example, can be by extract Rotary Evaporators
It removes solvent and is dried.Preferably, the organic solvent of extraction is n-hexane.
It in the present invention, can will be as oleic acid or the grease in the source of its nonglyceride and linoleic acid or its nonglyceride
The grease mixing in source carries out hydrolysis.Can also by as oleic acid or the grease in the source of its nonglyceride and linoleic acid or its
Reaction is individually hydrolyzed in the grease in the source of nonglyceride.
In addition, in stepb, with weight ratio meter, the ratio of fat blend and fat A is 1:1 or more, preferably 3:1-5:1.
Enzyme used in the present invention is immobilized lipase enzyme preparation or combinations thereof, commercially available.Preferably implementing
In mode, the lipase for random transesterification is Lipozyme TL IM；It is Lipozyme RL that sn-1,3, which orients lipase,
IM。
In step a, reaction temperature is the optimal reactive temperature of Lipozyme TL IM enzyme preparation, such as 55 DEG C -60 DEG C；
Its additive amount is the 5wt%-25wt%, preferably 10wt% or so of palm stearin weight.The reaction time of random transesterification is extremely
Few 3h, preferably at least 6h, more preferable 6h-8h.
In the present invention, random ester exchange reaction is evaluated using the ratio of the total palmitinic acid of sn-2 palmitinic acid Zhan.Example
Such as, the ratio of the total palmitinic acid of sn-2 palmitinic acid Zhan in pure OPO or OPL is 100wt%, and bis- oil of pure 1- palmitinic acid -2,3-
The total palmitinic acid of sn-2 palmitinic acid Zhan of acid glycerol three ester (POO) or 1- palmitinic acid -2- oleic acid -3- linoleic acid triglyceride (POL)
Ratio be 0wt%.Generally, in the triglycerides containing palmitinic acid of completely random form, the total palmitinic acid of sn-2 palmitinic acid Zhan
Ratio be about 33.3wt%.
In stepb, reaction temperature is the optimal reactive temperature of Lipozyme RL IM enzyme preparation, such as 50 DEG C -55 DEG C；
Its additive amount is the 5wt%-25wt% of the total weight of fat A and fat blend, preferably 10% or so.Sn-1,3 orients ester and hands over
Changing the reaction time is at least 3h.
In the method for the invention, any of method in this field can be used to sn-1, the production of 3 orientation ester exchange reactions
Object is isolated and purified, for example, molecularly distilled, dry fractionation method, chromatography, the crystallizing process under low temperature etc..
In some embodiments, it can be purified by product of the molecular distillation to orientation ester exchange reaction.Preferred
Embodiment in, the specific reaction condition of the molecular distillation is as follows: evaporating temperature be 185 DEG C, condenser temperature be 40 DEG C；
Heat exchange temperature is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/min, absolute pressure 2Pa.It is understood that
, above-mentioned parameter can with conditions such as inventory, environment temperatures and in the reasonable scope appropriate adjustment, do not do especially in the present invention
Limitation.
The fat or oil composition that preparation method through the invention obtains meets following characteristics:
(1) by weight, sn-2 palmitinic acid accounts for 55% or more of palmitinic acid total content；
(2) for the total weight of fat or oil composition, the total amount of OPL and OPO account for 40wt% or more；Wherein, relatively
For the total weight of fat or oil composition, OPL accounts for 25wt% or more；And
(3) for the total weight of fat or oil composition, the content of three palmitic acids, three ester (PPP) is lower than
10wt%.
Rouge, the closer China of the triglycerides ingredient and content of fat or oil composition of the invention are substituted compared to existing human milk
Triglycerides ingredient in human milk fat can be used as human milk substitution rouge and be applied in infant food, infant's food
Product include but is not limited to baby formula milk powder, baby formula rice flour etc..
Embodiment
Invention is further described in detail by the following examples.These embodiments are merely illustrative, without
It is construed as being to limit the scope of the present invention.All technical solutions and its change realized based on above content of the present invention
Shape is within the scope of the present invention.
Preparation example 1: the preparation of fat A
The palm stearin that 100g is 36 by the iodine value that dry fractionation obtains is weighed, is placed in 250ml reactor, at 55 DEG C
It is preheated；After temperature is stablized, the Lipozyme TL IM enzyme preparation for weighing 10g is added into reactor, under stiring instead
It answers 8 hours, obtains fat A.In reaction process, per sampling every other hour from third hour, using in GB30604-2015
A.2 the method for inspection is measured the weight ratio of the sn-2 total palmitinic acids of palmitinic acid Zhan, is as a result shown in Table 3.Table 3
As can be seen from the above table, after random ester exchange reaction, the content of the sn-2 palmitinic acid in triglycerides accounts for palm
The total content of acid obviously rises.After reaction 8 hours, the total palmitinic acid of sn-2 palmitinic acid Zhan of the fat A obtained through random transesterification
Weight ratio close to 33.3%, it is more complete to illustrate that random transesterification carries out.
Preparation example 2: the preparation of fat A
The palm stearin that 100g is 18 by the iodine value that dry fractionation obtains is weighed, is placed in 250ml reactor, at 60 DEG C
It is preheated；After temperature is stablized, the Lipozyme TL IM enzyme preparation for weighing 10g is added into reactor, under stiring instead
It answers 8 hours, obtains fat A.In reaction process, per sampling every other hour from third hour, using in GB30604-2015
A.2 the method for inspection is measured the weight ratio of the sn-2 total palmitinic acids of palmitinic acid Zhan, is as a result shown in Table 4.
Table 4
As can be seen from the above table, after reacting 4 hours, the sn-2 palmitic acid content of the fat A obtained through random transesterification is accounted for
The weight ratio of total palmitic acid content has been approached 33.3%, and it is more complete to illustrate that random transesterification carries out.
Embodiment 1
The grease that the iodine value for weighing 100g respectively is 18 palm stearin, the palm stearin that iodine value is 36, preparation example 1 obtain
The fat A that A and preparation example 2 obtain, is respectively placed in 500ml reactor.
By 22g rapeseed oil, 4.0g corn oil, 35.0g soybean oil, 4.0g coconut oil, 10.0g high oleic sunflower oil,
7.0g peanut oil and 18.0g sunflower oil are mixed to get mixture, and 30ml hydrochloric acid (2mol/L) is added thereto, and 80 DEG C of water-baths add
Hot 50min obtains fatty acid or fatty acid nonglyceride by hydrolysis.After reaction, the water outlet of 100ml n-hexane extraction is added
Product is solved, removes solvent with Rotary Evaporators, drying obtains four groups comprising oleic acid or its nonglyceride and linoleic acid or its is non-sweet
The fat blend B of grease.Wherein, by weight, free oleic acid and its total amount of residue and free linoleic acid and its residue
Total amount exists with equal proportion, and free oleic acid and its residue are mixed with the total fat of the total amount Zhan of free linoleic acid and its residue
The 80wt% of object content.
The above-mentioned fat blend B of four groups of 136g is weighed respectively, is added in above-mentioned each reactor, and is carried out in advance at 55 DEG C
Heat.After temperature is stablized, 23g Lipozyme RM IM enzyme preparation is weighed respectively and is added in each reactor, under stiring instead
It answers 3 hours.Reacting coarse product is through molecular distillation (reaction condition are as follows: evaporating temperature is 185 DEG C, and condenser temperature is 40 DEG C；Heat exchange
Device temperature is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/min, absolute pressure 2Pa) it is isolated and purified,
Four groups of fat or oil compositions are obtained respectively.The composition and content of each fat or oil composition are measured, the results are shown in Table 5.
Table 5
Wherein, the content of C48 triglycerides can characterize PPP content (carbon atom number of PPP is 48).
As can be seen from the above table, the palm stearin for being 18 to 36 relative to iodine value, by the fat A after random transesterification
Be oriented transesterification as raw material, can significantly improve the content of the OPL and OPO in product fat or oil composition, and directly by
PPP content is higher in the fat or oil composition that the palm stearin that iodine value is 18 is obtained as raw material.
Embodiment 2
The fat A for weighing the acquisition of four groups of 100g preparation examples 1, is respectively placed in 500ml reactor.
According to four groups of mixtures of composition preparation shown in table 6,30ml hydrochloric acid (2mol/L) is added into every group of mixture, 80
DEG C heating water bath 50min obtains fatty acid or fatty acid nonglyceride by hydrolysis.After reaction, 100ml n-hexane is added
Hydrolysate is extracted, removes solvent with Rotary Evaporators, drying obtains four groups and includes oleic acid or its nonglyceride and linoleic acid
Or the fat blend B of its nonglyceride.Wherein, by weight, free oleic acid and its total amount of residue and free linoleic acid and
The total amount of its residue exists with equal proportion, in above-mentioned four groups of fat blends, free oleic acid and its residue and the sub- oil that dissociates
The total amount of acid and its residue accounts for 65wt%, 70wt%, 75wt% and 80wt% of fat blend total weight respectively.
The composition of vegetable oil in 6 mixture of table
The above-mentioned four groups of fat blend B of 136g are weighed respectively, are added in each reactor, and preheated at 55 DEG C.To
After temperature is stablized, 23g Lipozyme RM IM enzyme preparation being weighed respectively and is added in each reactor, it is small to react 3 under stiring
When.Reacting coarse product is through molecular distillation (reaction condition are as follows: evaporating temperature is 185 DEG C, and condenser temperature is 40 DEG C；Heat exchanger temperature
Degree is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/min, absolute pressure 2Pa) it is isolated and purified, respectively
Obtain four groups of fat or oil compositions.The content of each fat or oil composition is measured, the results are shown in Table 7.
Table 7
As can be seen from the above table, in the fat blend of use, free oleic acid and its residue and free linoleic acid and its
Ratio shared by the total amount of residue is higher, and the total content of OPL and OPO is higher in the fat or oil composition of acquisition, and the content of PPP is got over
It is low, wherein when free oleic acid in fat blend and its residue and free linoleic acid and its when being less than 70% of residue, institute
PPP content can exceed that 10wt% and the requirement in standard GB30604-2015 is not achieved in the fat or oil composition of acquisition, and
The content of OPL is relatively low.
Embodiment 3
The fat A for weighing the acquisition of seven groups of 100g preparation examples 1, is placed in 500ml reactor.
Fat blend B is prepared using oleic acid and linoleic acid.Wherein, by weight, free oleic acid and its total amount of residue
Ratio with the total amount of free linoleic acid and its residue is respectively 0.2:1,0.5:1,1:1,1.2:1,1.5:1,2:1 and 2.5:1.
The above-mentioned fat blend B of 136g is weighed respectively, is added in above-mentioned each reactor, and preheated at 55 DEG C.To
After temperature is stablized, 23g Lipozyme RM IM enzyme preparation being weighed respectively and is added in each reactor, it is small to react 3 under stiring
When.Through molecular distillation, (reaction condition: evaporating temperature is 185 DEG C to reacting coarse product, and condenser temperature is 40 DEG C；Heat exchange temperature
It is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/min, absolute pressure 2Pa) it is isolated and purified, it obtains respectively
Obtain seven groups of fat or oil compositions.The content of each fat or oil composition is measured, the results are shown in Table 8.
Table 8
As can be seen from the above table, in the fat blend of use, free oleic acid and its residue and free linoleic acid and its
The ratio regular meeting of residue impacts the content of OPL and OPO in the fat or oil composition of acquisition, when containing for free oleic acid and its residue
When measuring too low (being, for example, less than 0.5:1), OPO content is too low (such as less than 15wt%) in fat or oil composition obtained；And work as
When too high levels (being greater than 2:1) of free oleic acid and its residue, the content of OPO may surpass in fat or oil composition obtained
OPL is crossed, the content of the ingredient in Chinese's butterfat is deviated from.
Embodiment 4
The fat A for weighing the acquisition of five groups of 100g preparation examples 1, is placed in 500ml reactor.
The fat blend B being prepared using embodiment 1.Wherein, by weight, free oleic acid and its residue and free
Linoleic acid and its residue equal proportion exist, and the total amount of free oleic acid and its residue and free linoleic acid and its residue accounts for fat
The 80wt% of total weight of the mixture.
The above-mentioned fat blend of 68g, 102g, 136g, 170g and 204g is weighed respectively, is added in each reactor, and 55
It is preheated at DEG C.After temperature is stablized, weigh the 10wt%'s that weight is fat A and fat blend total weight respectively
Lipozyme RM IM enzyme preparation is simultaneously added in each reactor, is reacted 3 hours under stiring.Reacting coarse product is through molecular distillation
(reaction condition: evaporating temperature is 185 DEG C, and condenser temperature is 40 DEG C；Heat exchange temperature is 60 DEG C；Rotating scraped film rate is
120rpm；Charging rate is 2mL/min, absolute pressure 2Pa) it is isolated and purified, five groups of fat or oil compositions are obtained respectively.To each
The content of fat or oil composition is measured, and the results are shown in Table 9.
Table 9
As can be seen from the above table, relative to fat A, when the fat blend ratio of use is higher, the grease group of acquisition
It is higher to close OPL and OPO content in object, and PPP content is lower, and when the weight ratio of fat blend and fat A is less than 2:1,
PPP content can exceed that 10% and the requirement in standard GB30604-2015 is not achieved in fat or oil composition obtained.
Claims (10)
1. a kind of fat or oil composition, the fat or oil composition includes 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride and 1,3-
Two oleic acid -2- palmitic acids, three ester；Wherein, for the total weight of composition, the 1- oleic acid -2- palmitinic acid -3-
Linoleic acid triglyceride accounts for 25wt% or more, preferably 25wt%-32wt%；Wherein, for the total weight of composition, institute
It states bis- oleic acid -2- palmitic acid of 1,3-, three ester and accounts for 15wt%-25wt%.
2. fat or oil composition as described in claim 1, wherein sn-2 palmitinic acid account for the 55wt% of the total content of palmitinic acid with
On；Preferably, for the total weight of composition, three palmitic acids, three ester accounts for 10wt% or less.
3. a kind of method for preparing fat or oil composition of any of claims 1 or 2, which comprises
A. the palm stearin for being 18 to 36 using iodine number in the presence of the lipase for random transesterification, makes raw material as raw material
Random ester exchange reaction occurs, to obtain fat A；
B. fat blend is prepared by oleic acid or its nonglyceride and linoleic acid or its nonglyceride；Or by as oleic acid or its
The oil and fat preparation fat blend in the source of nonglyceride and linoleic acid or its nonglyceride, wherein with weight ratio meter, the rouge
The ratio of the total amount of free oleic acid and its residue in fat mixture and the total amount of free linoleic acid and its residue be 0.5:1 to 2:1,
It is preferred that 1:1 to 1.5:1；Wherein, with weight ratio meter, the ratio of the fat blend and the fat A is 1:1 or more, preferably 1:
1-5:1；And
C. in the presence of sn-1,3 orientation lipase, the fat A and the fat blend is made to carry out sn-1,3 orientation esters
Then exchange reaction is isolated and purified, to obtain the fat or oil composition.
4. method as claimed in claim 3, wherein in step a, the random ester exchange reaction carries out at least 3h, preferably
At least 6h, more preferable 6h-8h；
Wherein, in stepb, the sn-1,3 orientation ester exchange reactions carry out at least 3h.
5. the method as claimed in claim 3 or 4, wherein the rouge for the total weight of raw material, for random transesterification
The dosage of fat enzyme is 5wt%-25wt%, preferably 10wt%；Preferably, the lipase for random transesterification is
Lipozyme TL IM；
Wherein, for the fat A and the total weight of the fat composition, the dosage of sn-1,3 orientation lipase are
5wt%-25wt%, preferably 10wt%；Preferably, the sn-1,3 orientation lipase are Lipozyme RL IM.
6. the method as described in any one of claim 3-5, wherein the free oleic acid and its residue and the free sub- oil
Acid and its residue total amount account for the fat blend total weight 70wt% or more, preferably 75wt% or more, more preferably
80wt% or more；
Preferably, the oleic acid or its nonglyceride derive from high oleic sunflower oil, high oleic acid rapeseed oil, high oleic acid soybean oil
Or high oleic acid peanut oil；
It is highly preferred that the linoleic acid or its nonglyceride derive from corn oil, soybean oil or walnut oil.
7. the method as described in any one of claim 3-6, wherein the palm stearin that the iodine number is 18 to 36 passes through palm
The dry fractionation of oil obtains.
8. such as the described in any item methods of claim 3-7, wherein in stepb, described to isolate and purify using molecularly distilled
It carries out；
Preferably, the reaction condition of the molecularly distilled are as follows: evaporating temperature is 185 DEG C；Condenser temperature is 40 DEG C；Heat exchanger
Temperature is 60 DEG C；Rotating scraped film rate is 120rpm；Charging rate is 2mL/min, absolute pressure 2Pa.
What 9. fat or oil composition of any of claims 1 or 2 or the method as described in any one of claim 3-8 prepared
Purposes of the fat or oil composition in production infant food, the infant food is preferably baby formula milk powder or infant
It is formulated rice flour.
10. being prepared comprising fat or oil composition of any of claims 1 or 2 or the method as described in any one of claim 3-8
The infant food of the fat or oil composition of acquisition, the infant food are preferably baby formula milk powder or baby formula rice
Powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711480820.5A CN109984215A (en) | 2017-12-29 | 2017-12-29 | A kind of fat or oil composition and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711480820.5A CN109984215A (en) | 2017-12-29 | 2017-12-29 | A kind of fat or oil composition and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109984215A true CN109984215A (en) | 2019-07-09 |
Family
ID=67109140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711480820.5A Pending CN109984215A (en) | 2017-12-29 | 2017-12-29 | A kind of fat or oil composition and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109984215A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112741163A (en) * | 2019-10-31 | 2021-05-04 | 内蒙古伊利实业集团股份有限公司 | Oil composition and application thereof in food |
| CN112889923A (en) * | 2021-02-22 | 2021-06-04 | 北京三元食品股份有限公司 | Infant formula milk powder rich in structural fat OPL and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100104694A1 (en) * | 2007-02-28 | 2010-04-29 | Loders Croklaan B.V. | Process for Producing a Glyceride Composition |
| CN102827885A (en) * | 2011-06-17 | 2012-12-19 | 丰益(上海)生物技术研发中心有限公司 | Composition containing 1,3-di-unsaturated fatty acyl-2-saturated fatty acyl glyceryl ester as well as preparation method and application thereof |
-
2017
- 2017-12-29 CN CN201711480820.5A patent/CN109984215A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100104694A1 (en) * | 2007-02-28 | 2010-04-29 | Loders Croklaan B.V. | Process for Producing a Glyceride Composition |
| CN102827885A (en) * | 2011-06-17 | 2012-12-19 | 丰益(上海)生物技术研发中心有限公司 | Composition containing 1,3-di-unsaturated fatty acyl-2-saturated fatty acyl glyceryl ester as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| KALLIO H ET AL.: "Triacylglycerol regioisomers in human milk resolved with an algorithmic novel electrospray ionization tandem mass spectrometry method", 《FOOD CHEMISTRY》 * |
| 金青哲主编: "《功能性脂质》", 31 August 2013, 北京：中国轻工业出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112741163A (en) * | 2019-10-31 | 2021-05-04 | 内蒙古伊利实业集团股份有限公司 | Oil composition and application thereof in food |
| CN112889923A (en) * | 2021-02-22 | 2021-06-04 | 北京三元食品股份有限公司 | Infant formula milk powder rich in structural fat OPL and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101679909B (en) | Process for producing a glyceride composition | |
| CN112522330B (en) | Medium-long carbon chain triglyceride for breast milk to replace fat and preparation method thereof | |
| CN103859065A (en) | Peony seed blend oil for clearing heat and removing toxicity and preparation method thereof | |
| CN111019979B (en) | Grease rich in low saturated fatty acid diglyceride and preparation method thereof | |
| JP2021011576A (en) | Preparation and composition of medium chain triglycerides containing substantial amount of lauric acid | |
| CN109984215A (en) | A kind of fat or oil composition and preparation method thereof | |
| Esonye et al. | Characterization and oxidation modeling of oils from Prunus amygdalus, Dyacrodes edulis and Chrysophyllum albidium | |
| CN109984212A (en) | A kind of fat or oil composition and preparation method thereof | |
| CN108265089A (en) | A kind of fat or oil composition containing bis- oleic acid -2- palmitic acids of 1,3-, three ester and preparation method thereof | |
| CN111802477B (en) | Special grease for hard candies as well as preparation method and application of special grease | |
| CN104783175B (en) | Novel microalgae food composition | |
| CN102585992A (en) | Method for extracting tea oil from tea oilseeds by water substitution | |
| CN109984211A (en) | A kind of fat or oil composition and preparation method thereof | |
| CN109988674A (en) | A kind of fat or oil composition and preparation method thereof | |
| CN113575697B (en) | Preparation method of breast milk fat substitute based on animal milk fat | |
| AU2019204275B2 (en) | A process for producing human milk fat substitutes | |
| TW201234975A (en) | Oil-and-fat composition for processed food of fishery product and processed food of fishery product using the same | |
| CN115197784B (en) | Lard oil substituted grease and preparation method and application thereof | |
| Suaniti et al. | Biodiesel Synthesis from Used frying Oil through Phosphoric Acid Refined and CaO Catalyzed Transesterification | |
| CN104928326A (en) | Preparation method for 1, 3-diglyceride pork fat | |
| CN106135904A (en) | A kind of diglyceride fluid composition rich in calendic acid and its preparation method and application | |
| CN106137944A (en) | A kind of diglyceride fluid composition rich in Cymbidium ensifolium (L.) Sw. acid and its preparation method and application | |
| JP6711572B2 (en) | Noodle loosening improver | |
| CN109984205A (en) | A kind of fat or oil composition and preparation method thereof | |
| CN106615232A (en) | Blend oil with fatty acid in balanced proportion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190709 |