CN106900888B - Oil composition containing odd-carbon fatty acid structure fat and application thereof - Google Patents
Oil composition containing odd-carbon fatty acid structure fat and application thereof Download PDFInfo
- Publication number
- CN106900888B CN106900888B CN201510980145.7A CN201510980145A CN106900888B CN 106900888 B CN106900888 B CN 106900888B CN 201510980145 A CN201510980145 A CN 201510980145A CN 106900888 B CN106900888 B CN 106900888B
- Authority
- CN
- China
- Prior art keywords
- odd
- acid
- fat
- fatty acid
- oil
- 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.)
- Active
Links
Classifications
-
- 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
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- 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
Abstract
The invention relates to an oil composition, which comprises the following components: (1)50 to 99.99 weight percent of base oil; (2)0.01 to 50 wt% of an odd-carbon fatty acid structural ester. The invention also relates to the application of the fatty acid structure fat with odd number carbon in reducing the generation of polar compounds in the fat frying process.
Description
Technical Field
The present invention relates to the field of edible oils, in particular frying oils.
Background
The edible oil can generate hydrolysis, oxidation, polymerization and cracking reactions in the continuous high-temperature frying process to generate polar compound molecules containing carbonyl, ketone, aldehyde, carboxyl and the like, and the compounds not only can have adverse effects on the quality of the oil and fat, the flavor and the nutritional value of oil and fat food, but also can generate harm to human health, such as growth stagnation, liver swelling, reproductive function and liver function disorder, human lymphocyte distortion and the like. The content of polar compounds in the frying oil is required to be less than or equal to 27 percent (by mass) according to the national frying oil sanitary standard, and the grease exceeding the value is required to be forcibly discarded.
In actual use or production processes, polar components in frying oil are generally reduced by means of adsorption filtration, and the polar components are also reduced by controlling the content of different types of triglycerides in the oil or adding effective components into the oil base. Patent JP2008054669A provides a method of adding d- (α) -tocopherol to edible oil to reduce the production of polar compounds during frying; the patent CN104171029A achieves the purpose of reducing the generation of polar compounds by controlling the content of different types of triglycerides such as SUS/SSU/SSS/SUU/UUUU (S refers to saturated fatty acid; U refers to unsaturated fatty acid) and the like in the grease; patent EP0797921B1 discloses palm oil with 25 to 48% by weight of saturated fatty acids and 40 to 60% by weight of monounsaturated fatty acids, having good stability for use as frying oil.
Unlike most natural even-numbered fatty acids, the odd-numbered fatty acids are very low in content and are found mainly in humans, animals and milk fat. At present, physiological functions of odd-carbon fatty acids are not comprehensively and comprehensively reported, but some studies show that the odd-carbon fatty acids have the properties and physiological efficacies of different even-carbon fatty acids: compared with the fatty acid with even number, the fatty acid with odd number has a looser crystal structure and weaker intermolecular force; the odd-carbon fatty acid is different from the even-carbon fatty acid in a human body in a metabolic pathway, propionyl CoA generated by beta oxidation has a glycogenic effect, and the propionyl CoA is a dynamic endogenous indicator for human body diet evaluation; pentadecanoic and heptadecanoic acids can be used to assess risk of coronary heart disease and diabetes; pentadecanoic acid and nonadecanoic acid have a strong inhibitory effect on the growth of various cancer cells, and the like. However, there are few reports on the use of lipids containing odd-carbon fatty acids in food processing.
Disclosure of Invention
The invention relates to a method for adding fatty acid structural fat with odd number carbon into frying oil, which can effectively reduce the generation of polar compounds in frying and prolong the service life of the frying oil.
The invention relates to an oil composition, which comprises the following components: (1)50 to 99.99 weight percent of base oil; (2)0.01 to 50 wt% of an odd-carbon fatty acid structural ester. The preferable range is 50-99% of base oil and 1-50% of odd-carbon fatty acid structure fat. More preferably, the range is 50-90% of base oil and 10-50% of odd-carbon fatty acid structure fat.
The present invention relates to an oil and fat composition containing an edible oil and fat containing an odd-carbon fatty acid structure fat.
In one embodiment of the present invention, the fat and oil composition comprises an edible fat and oil to which an odd-carbon fatty acid structural fat is added.
In various embodiments of the present invention, the odd-carbon fatty acid structure fat accounts for 0.01 to 50 wt% of the total weight of the fat composition; the amount of addition in preferred embodiments can be 0.01%, 0.05%, 0.1%, 0.3%, 0.5%, 0.7%, 1%, 1.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, and any interval in between these amounts of addition.
In various embodiments of the present invention, the odd-numbered fatty acids in the odd-numbered fatty acid structural lipids are at least one selected from the group consisting of pentadecanoic acid, heptadecanoic acid, and nonadecanoic acid.
In various embodiments of the present invention, the odd-carbon fatty acid structural ester is formed by randomly distributing odd-carbon fatty acids and even-carbon fatty acids at Sn-1, Sn-3, and Sn-2 positions of the structural ester, and the odd-carbon fatty acids are contained in the odd-carbon fatty acid structural ester in an amount of 10% to 55% by weight.
In various embodiments of the invention, the even-numbered carbon fatty acids are selected from the group consisting of: at least one of lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatetraenoic acid, eicosapentaenoic acid, and docosahexaenoic acid; oleic acid is preferred.
The invention also relates to a method for reducing the generation of polar compounds in the frying process of the oil, which is to add fatty acid structural fat with odd number carbon into edible oil.
In a plurality of specific embodiments of the present invention, the odd-carbon fatty acid structure ester is added to the edible oil, and the weight percentage of the added odd-carbon fatty acid structure ester to the total weight of the composition is 0.01 to 50%; the amount of addition in preferred embodiments can be 0.01%, 0.05%, 0.1%, 0.3%, 0.5%, 0.7%, 1%, 1.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, and any interval in between these amounts of addition.
The invention also relates to application of the fatty acid ester with odd carbon structure in reducing generation of polar compounds in the oil frying process.
The present invention also relates to a food product which is fried or prepared using the fat composition according to the present invention.
The fatty acid content in the invention refers to the content of a certain fatty acid determined by the methods of 'national standard GB/T17376-2008 for preparing animal and vegetable fatty acid methyl ester' and 'national standard GB/T17377-2008 for gas chromatography analysis of animal and vegetable fatty acid methyl ester'. Wherein the content of the odd-carbon fatty acids is the sum of the contents of the odd-carbon fatty acids belonging to each type.
The polar compound of the present invention refers to a compound such as carbonyl, carboxyl, ketone, aldehyde group, etc. generated by the oxidation, polymerization, cracking, hydrolysis, etc. of the oil and fat continuously reused at high temperature during the frying process of the edible oil, and these compounds are called as polar compounds by those skilled in the art because they have higher polarity than normal vegetable oil molecules (triacylglycerides).
In one embodiment of the invention, the base oil used may be selected from palm oil, soybean oil, rapeseed oil, peanut oil, corn oil, sesame oil, high oleic sunflower oil, cottonseed oil, rice bran oil, tea seed oil, safflower seed oil, olive oil, linseed oil, almond oil, walnut oil, fish oil, lard, mutton fat, beef tallow, microalgal oil, margarine, butter, shortening and other oils used for frying, or a combination of two or more of said oils.
The odd-carbon fatty acid refers to fatty acid with odd number of carbon atoms in a carbon chain; similarly, an even number of carbon fatty acids refers to fatty acids in which the number of carbon atoms in the carbon chain is even.
In one embodiment of the present invention, the odd-numbered fatty acids used are selected from the group consisting of pentadecanoic acid, heptadecanoic acid, nonadecanoic acid, and the like, or a mixture of two or more thereof.
In one embodiment of the present invention, the even-numbered fatty acid used is a fatty acid present in a natural oil or fat, and may be a saturated or unsaturated fatty acid such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatetraenoic acid, eicosapentaenoic acid, and docosahexaenoic acid, or a mixture of two or more thereof.
In one embodiment of the present invention, the odd-carbon fatty acid structural ester used is a structural ester in which one or more of the hydroxyl groups of the glycerol form ester bonds with an odd-carbon fatty acid. The odd-carbon fatty acid structure lipid can be obtained by synthesizing odd-carbon fatty acid or derivatives thereof and glycerol or glyceride through an enzymatic method or a chemical method, and removing free fatty acid and a small amount of monoglyceride through methods such as molecular distillation and refining. The obtained fatty acid structure fat with odd carbon can be treated by removing the catalyst in the conventional modes such as centrifugation, filtration or water washing, then removing free fatty acid and partial monoglyceride by molecular distillation, and finally obtaining the fatty acid structure fat with odd carbon by refining and deodorizing processes.
The term "added" as used herein means that the added substance is derived from the outside of the target to be added (in the present invention, it is usually referred to as base oil or edible fat) and is not originally contained in the base oil. It is known that fatty acids in most fatty acid glycerides in natural fats and oils are even-numbered, and although natural fats and oils usually contain trace amounts of odd-numbered fatty acid glycerides, their contents in fats and oils are so small that they do not exhibit the frying advantages of even-numbered fatty acid glycerides. The application of the odd-carbon fatty acid structure fat in reducing the generation of polar compounds in the fat frying process can suggest that research and development personnel can improve the frying performance of the fat by additionally adding a certain amount of odd-carbon fatty acid structure fat in natural fat (namely base oil). The odd-carbon fatty acid glyceride from external sources can be obtained by artificial synthesis or extracted from natural oil and then added into base oil. Therefore, obviously, the odd-carbon fatty acid content of the base oil externally added with the odd-carbon fatty acid structure fat is necessarily larger than that of the original base oil.
In one embodiment of the invention, the odd-carbon fatty acid structure lipid with different unsaturated fatty acid contents can be obtained by adjusting the proportion of the even-carbon fatty acid and the odd-carbon fatty acid. Therefore, the mixed oil with different unsaturated fatty acid contents can be obtained simply by blending different proportions of the mixed oil.
Since polar compounds are easily generated during heating of edible oils, the oil and fat composition according to the present invention can be applied to any practical application involving heat treatment of edible oils and fats. In some embodiments, applications involving the use of the grease compositions of the present invention include, but are not limited to: frying, baking, shortening and the like, and even additives for heating steps involved in the production and processing of fats and oils. The heating step involved in the production and processing of the grease refers to a process of refining oil at high temperature in a common oil refining process.
In conclusion, the technical scheme provided by the invention can obviously reduce the generation of polar compounds in the frying process and prolong the service life of the frying oil on the premise of not influencing the mouthfeel, flavor and quality of fried food.
Because the grease containing the fatty acid structure fat with odd carbon has good thermal stability and the fatty acid with odd carbon has certain beneficial effect on human body, the grease composition containing the fatty acid structure fat with odd carbon can also be added into grease special for baking, grease special for chocolate candy, grease special for infant formula milk powder, grease special for cold drink, grease special for quick-frozen food, grease special for non-dairy powder, grease special for non-dairy fresh cream, grease special for condiment and the like to provide relevant functionality and improve the product quality.
Although the present description and examples are described in detail primarily with respect to specific edible fats and oils, as well as pentadecanoic acid, heptadecanoic acid, and nonadecanoic acid, one skilled in the art will readily appreciate that routine variations can be made using the methods of the present invention to apply to other similarly demanding applications, such as equivalent substitutions of odd-numbered fatty acids such as tridecanoic acid, heneicosanoic acid, or heptadecenoic acid; or applying the odd-carbon fatty acid structure fat to other fats and oils requiring improvement of frying performance, such as olive oil, peanut oil, butter, etc. Such conventional variations are obviously equivalent to what is claimed in the claims of the invention.
Detailed Description
The present invention will be further described with reference to the following examples. It should be understood that the following examples are illustrative only and are not intended to limit the scope of the present invention.
The edible oil or fat, also referred to as base oil, used in the oil or fat compositions suitable for use in the various aspects of the invention (including contemplated products, methods and uses, hereinafter referred to simply as "various aspects") may be selected from palm oil, soybean oil, rapeseed oil, peanut oil, corn oil, sesame oil, high oleic sunflower oil, cottonseed oil, rice bran oil, tea seed oil, safflower seed oil, olive oil, linseed oil, almond oil, walnut oil, fish oil, lard, mutton fat, tallow, microalgal oil, margarine, butter, shortening and other oils or fats used in frying, or combinations of two or more of such oils or fats. The preferred base oils of the present invention are palm oil and fractionated products, soybean oil, sunflower oil and corn oil.
Odd-numbered fatty acids suitable for use in various aspects of the invention refer to fatty acids having an odd number of carbon chains. The odd-numbered fatty acids in the present invention are preferably selected from pentadecanoic acid, heptadecanoic acid, nonadecanoic acid, and mixtures of two or more thereof.
The even-numbered fatty acids suitable for use in the various aspects of the present invention are those found in natural oils and fats, and may be saturated and unsaturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatetraenoic acid, eicosapentaenoic acid, and docosahexaenoic acid, and the like, or two or more of the above-mentioned fatty acids, preferably palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and more preferably oleic acid.
The odd-numbered fatty acid structural ester suitable for various aspects of the present invention is a structural ester in which any one or more hydroxyl groups on glycerol form ester bonds with odd-numbered fatty acids, and a structural ester in which fatty acids of natural triglycerides undergo an ester exchange reaction with odd-numbered fatty acids. The odd-carbon fatty acid structure lipid can be obtained by synthesizing odd-carbon fatty acid or derivatives thereof and glycerol or glyceride through an enzymatic method or a chemical method, and removing free fatty acid and a small amount of monoglyceride through methods such as molecular distillation and refining. The obtained fatty acid structure fat with odd number carbon can remove catalyst by the conventional modes of centrifugation, filtration or water washing, etc., then free fatty acid and partial monoglyceride are removed by molecular distillation, and finally the fatty acid structure fat with odd number carbon is obtained by the common refining and deodorizing process. In addition, the odd-numbered fatty acid structural fat can also be obtained by obtaining a concentrated substance or a purified substance from the oil naturally containing the structural fat with the molecular structure in the nature through a conventional purification and extraction mode. Or, the odd-numbered fatty acid structure fat can also be obtained by obtaining a concentrated substance or a purified substance from the fat of the structural fat with the molecular structure formed by breaking part of double bond structures in fatty acid chains after the heat treatment processing of the fat through a conventional purification and refining mode.
Enzymatic synthesis refers to a reaction in which lipase acts as a catalyst. The lipase may be selected from the following microorganisms: candida Antarctica (Candida Antarctica), Aspergillus niger (Aspergillus niger), Candida rugosa (Candida rugosa), Thermomyces lanuginosus (Thermomyces lanuginosus), Rhizomucor miehei (Rhizomucor meihei), and Pseudomonas (Pseudomonas sp.), among others.
Chemical synthesis refers to the reaction of a lewis acid or a basic or acidic compound as a catalyst. The Lewis acid catalyst includes boron trifluoride, aluminum chloride, tin tetrachloride, antimony pentachloride, etc.; the alkali catalyst is hydroxide of lithium, sodium, potassium, calcium, etc.; the acid catalyst includes methyl benzene sulfonic acid, sulfuric acid, etc.
"decolorization" refers to: and (3) removing pigments in the grease by adopting an adsorption method. "deodorization" means: the process of eliminating bad smell from oil and fat in certain method. The "deodorization" and "decolorization" processes are well known to those skilled in the art, and the specific methods and parameters thereof can be performed by conventional methods in the art. In the above-described treatment, those skilled in the art may make adjustments and changes according to the actual conditions, and the adjustment method is well known to those skilled in the art.
The decolorizing step can be carried out using methods conventional in the art. "decolorization" can be, but is not limited to, by adsorption. Generally, the decolorizing step comprises maintaining vacuum at elevated temperature to 80-90 deg.C, breaking the vacuum and adding a decolorizing agent; then heating to 90-110 ℃, and keeping vacuum stirring for 30-45 minutes; followed by filtration to remove decolorizing agents. Decolorizing agents include, but are not limited to, natural clays, activated carbons, attapulgite, and the like; preferably a more neutral acid-activated clay, such as a sulfuric acid-activated clay. The amount of decolorizing agent added can also be determined by one skilled in the art as a matter of practice.
The "deodorization" may be carried out by, but not limited to, steam distillation. Optionally adding citric acid solution into decolorized oil during deodorization treatment, wherein the citric acid solution contains citric acid not less than 0.01 wt% of the oil. Various commercially available citric acid solutions can be used, and citric acid solutions can also be formulated by themselves. Citric acid can be a variety of commercially available products. The citric acid solution has a mass concentration of 2-60%, for example, 2-40%, 2-30%, 5-20%. Typically, the citric acid solution is added in an amount of 0.01 to 50%, preferably 0.1 to 10%, more preferably 0.1% to 2% by weight of the oil.
The deodorization may be performed at a temperature of about 180 to 220 ℃, for example, about 180 to 200 ℃, about 200 to 220 ℃, or about 180 ℃, about 200 ℃ or about 220 ℃. The vacuum degree of deodorization is conventional deodorization vacuum degree, preferably below about 20mbar, such as below about 10-20 mbar, or below about 15mbar, or below about 10 mbar. In embodiments, the time for deodorization may be about 60 to 90min, about 60 to 80min, about 60 to 70min, such as about 60min, about 65min, about 70min, about 75min, about 80min, etc., wherein about 60min is preferred. Furthermore, the deodorizing medium may be any conventional deodorizing medium, such as nitrogen, steam or an inert gas, preferably nitrogen or steam, more preferably nitrogen. After the deodorization treatment is finished, the vacuum can be broken at the temperature below 50 ℃, and the filtration is carried out.
In one embodiment, the method for separating the odd-numbered fatty acid structural lipids may employ molecular distillation, vacuum distillation, fractionation, supercritical CO2 extraction, and the like, but is not limited thereto. In one embodiment of the invention, molecular distillation is used to remove most of the lipid impurities. Molecular distillation is a distillation process operated under high vacuum, with the mean free path of the vapor molecules being greater than the distance between the evaporation and condensation surfaces, so that the difference in the evaporation rates of the components in the feed solution can be used to separate liquid mixtures.
In the present invention, "vacuum" means: in a given space, a gaseous state with a pressure lower than 101325 pascal (Pa), the "vacuum degree" being: the degree to which the pressure in the system is lower than atmospheric pressure is generally expressed in Pa. In the present invention, the evacuation by vacuum pump means a dry screw vacuum pump, a water ring pump, a reciprocating pump, a slide valve pump, a rotary vane pump, a roots pump, a diffusion pump and the like so that the absolute pressure of the reaction system is 1 to 500mbar, preferably 1 to 50mbar, more preferably 1 to 10 mbar.
In some embodiments, in order to further improve the performance of the grease, some other common additives, such as an emulsifier, an antioxidant, etc., may be added to the grease mixture of the present invention. In one embodiment, the emulsifier is selected from the group consisting of: one or more of sucrose fatty acid ester, monoglyceride fatty acid, polyglycerol fatty acid ester, propylene glycol fatty acid ester, and sorbitan fatty acid ester. In one embodiment, the antioxidant is selected from: tea polyphenols, butyl hydroxy eggplant ether, dibutyl hydroxy toluene, licorice antioxidant, ascorbyl palmitate, phosphorus ester, dilauryl thiodipropionate, propyl gallate, Madaoxiang extract, hydroxystearyl (oxystearyl), sorbic acid and potassium salt thereof, tert-butyl hydroquinone, vitamin E, phytic acid, sodium phytate, bamboo leaf antioxidant, D-isoascorbic acid and sodium salt thereof, ascorbic acid, sodium ascorbate, calcium ascorbate and one or more of sodium lactate.
Since polar compounds are easily generated during heating of edible oils, the oil and fat composition according to the present invention can be applied to any practical application involving heat treatment of edible oils and fats. In some embodiments, applications involving the use of the grease compositions of the present invention include, but are not limited to: frying, baking, shortening and the like, and even additives for heating steps involved in the production and processing of fats and oils. The heating step involved in the production and processing of the grease refers to a process of refining oil at high temperature in a common oil refining process.
In the present invention, additional food additives may be added, including but not limited to one or more of leavening agents, flavoring agents, antioxidants, anticaking agents, flavor enhancers, nutrient supplements, preservatives, thickeners, enzyme preparations, colorants, flavors, pigments, surfactants, and the like.
In another preferred example of the invention, the grease composition further comprises optional components, wherein the optional components are one or more of edible additives and food raw and auxiliary materials.
In another preferred embodiment of the present invention, the food additive is selected from one or more of a defoaming agent and an antioxidant.
In another preferred embodiment of the present invention, the defoamer is a polyether defoamer, a silicon defoamer, or a higher alcohol defoamer, and preferably the defoamer is one or more of polymethylsilicone, polysiloxane resin, and polydimethylsiloxane.
In the present invention, if not specifically stated, the antioxidant in the present invention includes, but is not limited to, one or more of TBHQ (t-butylhydroquinone), BHT (2, 6-di-t-butyl-4-methylphenol), BHA (butylhydroxyanisole), vitamin C, vitamin E, carotenoids, ascorbic acid, ascorbyl palmitate, erythorbic acid, PG (propyl gallate), rosemary, and tea polyphenols.
In the present invention, "anticaking agent" refers to a substance added to a granular or powdery food to prevent the granular or powdery food from aggregating and agglomerating, and to keep it loose or free-flowing. The anticaking agent used in the present invention may include potassium ferrocyanide, sodium aluminosilicate, tricalcium phosphate, silicon dioxide, microcrystalline cellulose.
In the present invention, "flavor enhancer" means a substance capable of enhancing or improving the flavor of a food. The odorant used in the present invention includes amino acid type and nucleotide type odorants, specifically, including, but not limited to, disodium 5 ' -guanylate, disodium 5 ' -inosinate, disodium 5 ' -tasting nucleotide, capsicum oleoresin.
In the present invention, the "nutrient supplement" refers to a natural or synthetic food additive belonging to the natural nutrient range, which is added to food to enhance the nutrient components. Nutritional supplements for use in the present invention include, but are not limited to, vitamins (e.g., including but not limited to vitamin A, beta-carotene, B vitamins (thiamine hydrochloride, riboflavin, niacin), vitamin C), mineral supplements (e.g., including but not limited to calcium, iodine, iron, zinc), lysine supplements (e.g., including but not limited to L-lysine hydrochloride, L-lysine, L-aspartate, L-lysine-L-glutamate, taurine), proteins (e.g., including but not limited to soy protein, whey protein, skim milk powder, yeast powder, fish meal)
In the present invention, the term "preservative" means a substance which inhibits growth and propagation of microorganisms to prolong the shelf life of food and inhibit the spoilage of substances. Preservatives useful in the present invention include, but are not limited to, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, calcium propionate.
In the present invention, the "thickener" is a substance for improving and increasing the viscosity of food, maintaining the color, flavor, taste and stability of fluid food and jelly food, improving the physical properties of food, and giving the food a smooth and palatable feeling. Thickeners useful in the present invention include, but are not limited to, inorganic thickeners, cellulosics, polyacrylates, and associative polyurethane thickeners.
The grease containing the fatty acid structure fat with odd carbon has good thermal stability, and the fatty acid structure fat with odd carbon also has certain beneficial effect on human bodies, so the grease composition containing the fatty acid structure fat with odd carbon can be added into grease special for baking, grease special for chocolate candies, grease special for infant formula milk powder, grease special for cold drinks, grease special for quick-frozen foods, grease special for non-dairy powder, grease special for non-dairy fresh cream, grease special for seasonings and the like to provide relevant functionality and improve the product quality.
The experimental methods of the following examples, which are not specified under specific conditions, are generally determined according to national standards. If there is no corresponding national standard, it is carried out according to the usual international standards, to the conventional conditions or to the conditions recommended by the manufacturer. Unless otherwise indicated, all parts are parts by weight and all percentages are percentages by weight.
Unless otherwise specified, various starting materials of the present invention are commercially available; or prepared according to conventional methods in the art. Unless defined or stated otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention.
In the following examples of the invention, the immobilized lipases Novozyme435 and NS40086 were purchased from novicent; AlCl3NaOH and toluenesulfonic acid were purchased from pharmaceutical group chemicals ltd; n-pentadecanoic acid, n-heptadecanoic acid, and n-nonadecanoic acid were obtained from Shanghai Tuo Yang Biotech, Inc.; glycerol and oleic acid were provided by the harvest oil chemistry (shanghai) ltd; refined palm oil, refined soybean oil, refined 24-degree palm olein (melting point about 24 ℃), refined high oleic sunflower oil, and refined corn oil are all provided by jagli food industry ltd.
Preparation of odd-carbon fatty acid structure ester
Example 1:
weighing 180 g of n-pentadecanoic acid, 270 g of oleic acid and 37 g of glycerol, dissolving in a 1000 ml three-neck round-bottom flask at 75 ℃, uniformly mixing, adding 50 g of immobilized lipase Novozyme435, vacuumizing the reaction flask to about 0.3KPa by using a vacuum pump, and stirring for reacting for 8 hours.
Example 2:
20.2 g of n-heptadecanoic acid, 114 g of oleic acid, 37 g of glycerol and 1.7 g of anhydrous AlCl are weighed out3In a 500 ml three-neck round-bottom flask, the vacuum in the reaction flask is pumped by a vacuum pump to about 0.3KPa at the temperature of 70 ℃, and the reaction is stirred for 4 hours.
Example 3:
104 g of n-nonadecanoic acid, 127 g of oleic acid, 37 g of glycerol and 5.4 g of NaOH are weighed into a 500 ml three-neck round-bottom flask, nitrogen is filled into the flask at the temperature of 230 ℃ for protection, and the mixture is stirred and reacted for 3 hours.
Example 4:
11.2 g of n-pentadecanoic acid, 11.2 g of n-heptadecanoic acid, 201.2 g of oleic acid, 37 g of glycerol and 2.6 g of methylbenzenesulfonic acid were weighed into a 1000 ml three-neck round-bottom flask, and nitrogen gas was introduced into the flask at 180 ℃ to react for 6 hours with stirring.
Example 5:
weighing 14 g of n-pentadecanoic acid, 14 g of n-heptadecanoic acid and 100 g of high oleic acid sunflower seed oil in a 500 ml round bottom flask, uniformly stirring at 70 ℃, adding 12 g of immobilized lipase NS40086, and reacting for 8 hours under stirring.
The reaction product is firstly subjected to centrifugation and filtration to remove the catalyst, then molecular distillation is carried out to remove free fatty acid and part of monoglyceride, and finally refining, decoloring and deodorizing processes are carried out to obtain the fatty acid structure ester with odd carbon number. And finally, analyzing the components of the fatty acid structure fat with odd carbon and analyzing the components of the fatty acid.
Wherein the conditions selected for molecular distillation are as follows: the distillation temperature is 180 ℃ and 200 ℃, and the vacuum degree is 10-3mbar, scraper speed of 300rpm, and feeding speed of 5-8 mL/min; decoloring conditions: the consumption of activated clay is 3%, the decolorizing temperature is 90-100 ℃, the vacuum degree is 5mbar, and the decolorizing time is 120 min; deodorizing conditions: deodorizing at 240 deg.C under vacuum degree of 3mbar for 100 min.
The analysis method of the components and the content of the contained fatty acid comprises the following steps:
the methyl esterification method comprises the following steps: according to the method of the national standard GB/T17376-2008 for preparing the animal and vegetable oil fatty acid methyl ester;
fatty acid component analysis: according to the national standard GB/T17377-2008 of gas chromatographic analysis of animal and vegetable fat fatty acid methyl ester.
The content of triglyceride, diglyceride and monoglyceride was measured by high performance liquid chromatography.
TABLE 1 analysis of the composition and fatty acids of the fatty acid esters with odd number of carbon atoms
The application example is as follows:
according to table 2, the base oil corresponding to the column of "base oil/structural fat" in the table and the odd-carbon fatty acid structural fat prepared in the corresponding examples 1 to 5 were weighed, and the odd-carbon fatty acid structural fat was added to the base oil according to the following steps: (1) heating the base oil to 50-80 ℃; (2) the odd-carbon fatty acid structure ester was added to the base oil, and stirred uniformly to form examples 6 to 35 and comparative examples 1 to 5, in which the weight ratios of the base oil to the odd-carbon fatty acid structure ester are shown in table 2 as the weight% of the base oil and the weight% of the odd-carbon fatty acid structure ester, respectively.
TABLE 2 composition of each comparative example and example
The fat compositions containing odd-numbered fatty acid structure fats obtained in examples 6 to 35 and the fats and oils of comparative examples 1 to 5 were used to conduct a fry test of potato chips. The frying method comprises the following steps: weighing 2.5 kg of the oil or the oil composition in a frying pan, heating to 180 +/-5 ℃, adding 200 g of chips for frying, and taking out after 3 minutes. In the morning, after frying 10 pots, the mixture is air-fried for 2 hours; in the afternoon, the pan was again fried for 10 g, and 100 g of the oil sample was taken out. The frying operation was continued the next day according to this method for a total of 40 batches fried for two days. After the completion of the frying, the extracted oil samples of 20-batch frying and 40-batch frying were subjected to the measurement of polar compounds, and the results are shown in table 3.
The polar compounds were determined as follows:
polar compound: the measurement was carried out according to the national standard GB/T5009.202-2003.
TABLE 3 content of polar compounds after frying experiments in the respective proportions and examples
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the scope of the invention, which is defined by the claims appended hereto, and any implementation or method that is within the scope of the claims appended hereto is intended to be covered by the claims if it is the same or equivalent to the scope of the claims appended hereto.
Claims (12)
1. The oil composition comprises edible oil and is characterized in that an odd-carbon fatty acid structure fat is added into the edible oil and is 0.01-50 wt% of the total weight of the oil composition, the odd-carbon fatty acid structure fat is formed by randomly distributing odd-carbon fatty acids and even-carbon fatty acids on Sn-1, Sn-3 and Sn-2 positions of the structure fat, the weight content of the odd-carbon fatty acids in the odd-carbon fatty acid structure fat is 10% -55%, and the oil composition is used for frying food; the odd-carbon fatty acid structure ester is a structure ester in which any one or more hydroxyl groups on the glycerol and the odd-carbon fatty acid form ester bonds.
2. The composition of claim 1, wherein the odd-carbon fatty acid structure fat accounts for 1-40 wt% of the total weight of the grease composition.
3. The composition according to claim 1 or 2, wherein the odd-carbon fatty acid structure fat accounts for 5-35% of the total weight of the grease composition.
4. The composition of claim 1, wherein the odd-numbered fatty acids in the odd-numbered fatty acid structure lipids are at least one selected from the group consisting of pentadecanoic acid, heptadecanoic acid, and nonadecanoic acid.
5. The composition of claim 1, wherein the even-numbered carbon fatty acids are selected from the group consisting of: at least one of lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatetraenoic acid, eicosapentaenoic acid, and docosahexaenoic acid.
6. The composition of claim 5, wherein the even-numbered fatty acid is oleic acid.
7. A method for reducing the generation of polar compounds in the frying process of oil is characterized in that fatty acid structural fat with odd number carbon is added into edible oil.
8. The method according to claim 7, wherein the odd-carbon fatty acid structure fat is added to the edible fat, and the weight percentage of the odd-carbon fatty acid structure fat added to the edible fat is 0.01 to 50% of the total weight of the composition.
9. The method according to claim 8, wherein the odd-carbon fatty acid structure fat is added to the edible fat, and the weight percentage of the odd-carbon fatty acid structure fat added to the edible fat is 1 to 40% of the total weight of the composition.
10. The method according to claim 8, wherein the odd-carbon fatty acid structure fat is added to the edible fat, and the weight percentage of the odd-carbon fatty acid structure fat added to the edible fat is 5 to 35% of the total weight of the composition.
11. Use of an odd-carbon fatty acid structured fat for reducing the formation of polar compounds during fat frying.
12. A fried food, characterized in that the fried food is fried using the fat composition according to any one of claims 1 to 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510980145.7A CN106900888B (en) | 2015-12-23 | 2015-12-23 | Oil composition containing odd-carbon fatty acid structure fat and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510980145.7A CN106900888B (en) | 2015-12-23 | 2015-12-23 | Oil composition containing odd-carbon fatty acid structure fat and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106900888A CN106900888A (en) | 2017-06-30 |
| CN106900888B true CN106900888B (en) | 2021-12-24 |
Family
ID=59200158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510980145.7A Active CN106900888B (en) | 2015-12-23 | 2015-12-23 | Oil composition containing odd-carbon fatty acid structure fat and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106900888B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107873864A (en) * | 2017-09-28 | 2018-04-06 | 山东巧妻食品科技有限公司 | A kind of frying oil and preparation method thereof |
| CN111067886A (en) * | 2019-12-10 | 2020-04-28 | 石河子大学 | Free fatty acid capable of effectively reducing morbidity risk of type 2 diabetes and application thereof |
| CN117396592A (en) * | 2021-04-16 | 2024-01-12 | 丰益国际有限公司 | Triacylglycerol (TAG) compositions, their manufacture and use |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0392798A2 (en) * | 1989-04-11 | 1990-10-17 | Nabisco Brands, Inc. | Partially digestible sucrose esters as low calorie fat mimetics |
| CN1642435A (en) * | 2002-03-22 | 2005-07-20 | 石油加工体系股份有限公司 | Cooking oil antioxidant composition, method of preparation and use |
| CN102215839A (en) * | 2008-11-18 | 2011-10-12 | 贝朗医疗有限公司 | Fat emulsion for artificially feeding seriously ill intensive care patients |
| CN103319323A (en) * | 2013-02-20 | 2013-09-25 | 上海晶纯实业有限公司 | Odd-carbon saturated higher fatty acids, and preparation method for esters thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5169670A (en) * | 1990-05-23 | 1992-12-08 | The Procter & Gamble Company | Low saturate frying oil with fried flavor |
| US5104678A (en) * | 1990-05-23 | 1992-04-14 | The Procter & Gamble Company | Low saturate frying oil with meat flavor |
| US6403144B1 (en) * | 1999-04-30 | 2002-06-11 | The Procter & Gamble Co. | Food preparation compositions |
| CN103798417A (en) * | 2012-11-07 | 2014-05-21 | 丰益(上海)生物技术研发中心有限公司 | Method used for reducing oil content of fried food, and applications of diacylglycerol in reducing oil content of fried food |
| CN104247782A (en) * | 2013-06-26 | 2014-12-31 | 孙志刚 | Ortho nutrition animal and plant oil mixed general healthy doublet edible oil |
| JP2015033343A (en) * | 2013-08-08 | 2015-02-19 | 日清フーズ株式会社 | Oil-and-fat composition for cooking |
-
2015
- 2015-12-23 CN CN201510980145.7A patent/CN106900888B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0392798A2 (en) * | 1989-04-11 | 1990-10-17 | Nabisco Brands, Inc. | Partially digestible sucrose esters as low calorie fat mimetics |
| CN1642435A (en) * | 2002-03-22 | 2005-07-20 | 石油加工体系股份有限公司 | Cooking oil antioxidant composition, method of preparation and use |
| CN102215839A (en) * | 2008-11-18 | 2011-10-12 | 贝朗医疗有限公司 | Fat emulsion for artificially feeding seriously ill intensive care patients |
| CN103319323A (en) * | 2013-02-20 | 2013-09-25 | 上海晶纯实业有限公司 | Odd-carbon saturated higher fatty acids, and preparation method for esters thereof |
Non-Patent Citations (4)
| Title |
|---|
| A Review of Odd-Chain Fatty Acid Metabolism and the Role of;Benjamin Jenkins等;《Molecules》;20150130;第20卷(第2期);2425-2444 * |
| Oxidative stability of structured lipids;Diana Martin等;《European Food Research and Technology》;20100721;第231卷;635-653 * |
| 奇数碳脂肪酸的代谢与营养;张大昕;《生理科学进展》;19791001;第10卷(第3期);250-255 * |
| 煎炸油食品卫生指标研究——煎炸油中极性化合物的实验研究;王瑞卿等;《中国公共卫生》;19870630;第6卷(第6期);322-323 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106900888A (en) | 2017-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5636398B2 (en) | Oil composition | |
| EP2115107B1 (en) | Process for producing a glyceride composition | |
| EP1928990B1 (en) | Process for producing dioleyl palmitoyl glyceride | |
| EP2721131B1 (en) | Method for manufacturing refined fats and oils | |
| KR101832001B1 (en) | Production process for refined fats and oils | |
| JP5100974B2 (en) | Oil composition | |
| CN106900888B (en) | Oil composition containing odd-carbon fatty acid structure fat and application thereof | |
| US7604966B2 (en) | Process for the production of structured lipid mixtures | |
| EP2219476A2 (en) | Infant formula composition | |
| EP2894215B1 (en) | Fat composition | |
| EP2173197B1 (en) | Process | |
| CN1656907A (en) | Oil and fat composition containing diglyceride and crean frging oil and food containing said oil and fat composition | |
| EP3561030B1 (en) | Fat composition | |
| CN106479682B (en) | Oil and fat composition, preparation method and application thereof | |
| JP5809818B2 (en) | Oil composition | |
| KR102169417B1 (en) | Method for improving efficiency of enzymatic esterification by addition of ethanol | |
| KR102143203B1 (en) | Method for improving efficiency of enzymatic esterification by adjustment of peroxide value of reaction mixture | |
| JP6797269B2 (en) | Oil composition | |
| KR102548822B1 (en) | Composition | |
| WO2020050304A1 (en) | Production method for docosahexaenoic acid-containing glyceride using a lipase hydrolysis reaction | |
| JP2021078450A (en) | Sweetness enhancer | |
| JP2021078451A (en) | Sweetness enhancer | |
| KR20200083772A (en) | Method for improving efficiency of enzymatic esterification by adjustment of iodine value of triacylglyceride | |
| KR20210035942A (en) | Method for preparing triglyceride utilizing fractionation byproduct | |
| KR20210031014A (en) | Method for preparing triglyceride utilizing distillation byproduct |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |