CN105724601B - Oil and fat composition and use thereof - Google Patents
Oil and fat composition and use thereof Download PDFInfo
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- CN105724601B CN105724601B CN201410759653.8A CN201410759653A CN105724601B CN 105724601 B CN105724601 B CN 105724601B CN 201410759653 A CN201410759653 A CN 201410759653A CN 105724601 B CN105724601 B CN 105724601B
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Abstract
The present invention relates to an oil or fat composition and use thereof. The fat composition of the present invention comprises a fat and an oil and fat-soluble flavonoid compound, and is characterized in that the fat-soluble flavonoid compound has a hydroxyl radical half-inhibitory rate IC500.1 to 1.0 g/L. The grease composition of the invention has excellent oxidation resistance, inhibits the hazy solidification in long-term storage under low-temperature environment, maintains good flow property and has good stability.
Description
Technical Field
The invention provides an oil composition which has the characteristics of no fogging and no solidification at low temperature, good flowing performance and excellent oxidation resistance.
Background
Rice oil, olive oil, peanut oil, cottonseed oil, corn oil, soybean oil, and the like contain a considerable amount of saturated fatty acids, and are prone to clouding or even solidification in a low-temperature environment. In addition, the external wall-hanging grease is easy to oxidize to generate substances harmful to human bodies. Some fats and oils that become hazy or set at low temperatures are not acceptable to a portion of the average consumer, and this phenomenon, while normal, affects the marketing and daily use of these fats and oils. Therefore, the problem that the grease is hazy and solidified during low-temperature refrigeration storage is solved, and the method has important significance for the use and the market of the grease.
At present, the problem of haziness caused by excessive wax content in the grease can be solved by dewaxing processes, such as rapeseed oil dewaxing. The problem of low temperature hazy solidification has not been solved for oils and fats with high solid fat content such as palm oil, rice oil, peanut oil and the like.
The patent CN103118546 of kao corporation proposes that polyglycerol ester can inhibit the crystal precipitation of grease compositions containing diglyceride at low temperature, but polyglycerol ester only can bring crystal inhibition effect when applied to grease, and does not bring other better performance improvement effect.
Liu Heng Li et al teach that sucrose fatty acid esters can extend the freezing time of palm olein at 5 ℃. However, the application of sucrose fatty acid ester in edible oil can affect the cooking effect, so that the cooked food has a greasy feeling and a heavy fragrance, and the flavor of the food is affected (the sucrose ester affects the cold resistance of the super palm olein in the storage process, and the 11 th period 37-42 of volume 38 of 2013 of Chinese oil).
Omari J. Bandel et al indicate that fat-soluble flavonoid compounds have various physiological activities such as antibiosis, antiphlogosis, antivirus, antioxidation, antitumor, arteriosclerosis prevention and the like, however, the lipophilicity is poor, and the antioxidant performance of the flavonoid compounds in a non-aqueous system is limited (Bioflavonoids as solids of Human Topoisomerase II α and II β, Biochemistry,2007, 46 (20), pp 6097-.
The fat-soluble flavonoid compounds are prepared by introducing long-chain fatty acid into phenolic hydroxyl of flavonoid compounds (such as tea polyphenol, rutin, quercetin, procyanidin, etc.) through chemical or enzymatic molecular modification to increase oil solubility. Jana Viskupcova et al have discussed that fat-soluble flavonoids not only improve the lipid solubility of the flavonoids, but also improve their biological activities, such as antioxidant, antibacterial, antioxidant, anticancer, etc. (Lipophitic cutin derivatives for antioxidant protection of oil-based foods, Food Chemistry 123 (2010) 45-50).
Disclosure of Invention
An object of the present invention is to provide an oil or fat composition containing an oil or fat and a fat-soluble flavonoid compound, wherein the fat-soluble flavonoid compound has a hydroxyl radical half-inhibitory rate IC500.1 to 1.0 g/L.
In a particular embodiment of the invention, the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.2 to 0.9 g/L. In a particular embodiment of the inventionThe hydroxyl radical half inhibition rate IC of the fat-soluble flavonoid compound500.45-0.75 g/L.
The fat composition according to the above, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 2 to 23, preferably 5 to 15.
The fat or oil composition according to, wherein the saturated fatty acid content of the fat or oil is more than 10% by weight.
In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 11-40 wt%. In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 15-20 wt%.
The oil or fat composition has a content ratio of saturated fatty acids to fat-soluble flavonoids of 1-10000: 1, preferably 10-5000: 1, more preferably 50-3000: 1, and still more preferably 80-2000:1, in terms of weight ratio.
The fat and oil composition according to, wherein the fat and oil is a vegetable-derived fat and oil.
The oil composition according to, wherein the vegetable-derived oil is at least one selected from the group consisting of soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower seed oil, rice bran oil, palm oil and cottonseed oil.
The fat composition, wherein the fat-soluble flavonoid compound is at least one selected from the group consisting of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin, and fat-soluble rutin.
The fat-soluble flavonoid compound is an esterification product of a flavonoid compound and a fatty acid or a derivative thereof.
In a specific embodiment of the present invention, the esterification of the flavonoid compound with the fatty acid or the derivative thereof is chemical esterification.
In a specific embodiment of the present invention, the esterification of said flavonoid with fatty acid or derivative thereof is an enzymatic esterification.
The oil or fat composition according to the present invention, wherein the fatty acid is selected from a linear or branched, saturated or unsaturated, mono-or poly-fatty acid having 10 to 30 carbon atoms, and preferably at least one selected from myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid, and erucic acid.
In a particular embodiment of the invention, the fatty acid derivative is an acid halide of the fatty acid. In a particular embodiment of the invention, the fatty acid derivative is an acyl chloride of the fatty acid. In a specific embodiment of the present invention, the fatty acid derivative is at least one of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride, or erucic acid chloride.
Another object of the present invention is to provide a method for lowering the freezing point of fat or oil, characterized by bringing the fat or oil into contact with a fat-soluble flavonoid compound having a hydroxyl radical half-inhibition ratio IC500.1 to 1.0 g/L.
In a particular embodiment of the invention, the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.2 to 0.9 g/L. In a particular embodiment of the invention, the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.45-0.75 g/L.
In a specific embodiment of the present invention, the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 2 to 23, preferably 5 to 15.
In a particular embodiment of the invention, the fat has a saturated fatty acid content of greater than 10% by weight.
In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 11-40 wt%. In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 15-20 wt%.
In a specific embodiment of the present invention, the content ratio of the saturated fatty acid to the fat-soluble flavonoid compound is 1 to 10000:1, preferably 10 to 5000:1, more preferably 50 to 3000:1, and further preferably 80 to 2000:1 by weight.
In a specific embodiment of the present invention, the fat-soluble flavonoids are selected from at least one of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin and fat-soluble rutin.
In a particular embodiment of the invention, the fat-soluble flavonoid is an esterification product of a flavonoid with a fatty acid or a derivative thereof.
In a specific embodiment of the present invention, the esterification of the flavonoid compound with the fatty acid or the derivative thereof is chemical esterification.
In a specific embodiment of the present invention, the esterification of said flavonoid with fatty acid or derivative thereof is an enzymatic esterification.
In one embodiment of the present invention, the fatty acid is selected from linear or branched, saturated or unsaturated, mono-or poly-fatty acids having 10 to 30 carbon atoms, preferably at least one selected from myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid or erucic acid.
In a particular embodiment of the invention, the fatty acid derivative is an acid halide of the fatty acid. In a particular embodiment of the invention, the fatty acid derivative is an acyl chloride of the fatty acid. In a specific embodiment of the present invention, the fatty acid derivative is at least one of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride, or erucic acid chloride.
Another object of the present invention is the use of fat-soluble flavonoids for lowering the freezing point of lipids, wherein the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.1 to 1.0 g/L.
In a particular embodiment of the invention, the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.2 to 0.9 g/L. In a particular embodiment of the invention, the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.45-0.75 g/L.
In a specific embodiment of the present invention, the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 2 to 23, preferably 5 to 15.
In a particular embodiment of the invention, the fat has a saturated fatty acid content of greater than 10% by weight.
In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 11-40 wt%. In a specific embodiment of the invention, the content of saturated fatty acid in the grease is 15-20 wt%.
In a specific embodiment of the present invention, the content ratio of the saturated fatty acid to the fat-soluble flavonoid compound is 1 to 10000:1, preferably 10 to 5000:1, more preferably 50 to 3000:1, and further preferably 80 to 2000:1 by weight.
In a specific embodiment of the present invention, the fat-soluble flavonoids are selected from at least one of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin and fat-soluble rutin.
In a particular embodiment of the invention, the fat-soluble flavonoid is an esterification product of a flavonoid with a fatty acid or a derivative thereof.
In a specific embodiment of the present invention, the esterification of the flavonoid compound with the fatty acid or the derivative thereof is chemical esterification.
In a specific embodiment of the present invention, the esterification of said flavonoid with fatty acid or derivative thereof is an enzymatic esterification.
In one embodiment of the present invention, the fatty acid is selected from linear or branched, saturated or unsaturated, mono-or poly-fatty acids having 10 to 30 carbon atoms, preferably at least one selected from myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid or erucic acid.
In a particular embodiment of the invention, the fatty acid derivative is an acid halide of the fatty acid. In a particular embodiment of the invention, the fatty acid derivative is an acyl chloride of the fatty acid. In a specific embodiment of the present invention, the fatty acid derivative is at least one of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride, or erucic acid chloride.
Effects of the invention
The fat-soluble flavonoid compound with a specific proportion is added into the grease composition, so that the grease composition not only can help the grease to improve the oxidation resistance, but also can inhibit the hazy solidification of the grease in a low-temperature environment for long-term storage and keep good flowing property compared with polyglycerol ester and sucrose ester.
Therefore, compared with the polyglycerol ester and the sucrose ester, the fat-soluble flavonoid compound not only can inhibit haziness of the grease and improve the frost resistance of the grease, but also can improve the oxidation resistance of the grease. The grease composition has good stability.
Detailed Description
The fat composition of the present invention comprises a fat and an oil and fat-soluble flavonoid compound, and is characterized in that the fat-soluble flavonoid compound has a hydroxyl radical half-inhibitory rate IC500.1 to 1.0 g/L.
In a preferred embodiment of the present invention, the fat or oil is a vegetable-derived fat or oil. Preferably, the plant-derived oil is at least one selected from soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower seed oil, rice bran oil, palm oil and cottonseed oil. For example, in one embodiment of the present invention, the oil is soybean oil, peanut oil, or a mixed oil of soybean oil and palm oil (for example, soybean oil: palm oil 4:1 by weight, and palm oil iodine number 56).
The grease may be crude oil or refined oil obtained by refining the corresponding crude oil by a conventional refining method.
In a preferred embodiment of the present invention, the fat or oil composition of the present invention has a saturated fatty acid content of more than 10% by weight. The content of saturated fatty acids in the oil is preferably 11 to 40% by weight, more preferably 12 to 30% by weight, still more preferably 14 to 25% by weight, and particularly preferably 15 to 20% by weight. In a specific embodiment of the present invention, the content of saturated fatty acids in the fat or oil composition of the present invention is 12.867 wt%, 15.482 wt%, 19.932 wt%.
The saturated fatty acid is a straight chain or branched chain, monobasic or polybasic saturated fatty acid with 12-18 carbon atoms. For example, dodecanoic acid (C12: 0), tetradecanoic acid (C14: 0), hexadecanoic acid (C16: 0), octadecanoic acid (C18: 0), and the like can be given.
In a preferred embodiment of the present invention, the content of unsaturated fatty acids in the fat or oil composition of the present invention is 70 to 90% by weight, preferably 75 to 80% by weight. In a specific embodiment of the present invention, the content of unsaturated fatty acids in the fat or oil composition of the present invention is 77.067 wt%, 77.151 wt%, 83.161 wt%.
The saturated fatty acid is a linear chain or branched chain, monobasic or polybasic unsaturated fatty acid with 16-20 carbon atoms. Examples thereof include octadecenoic acid (C18: 1), octadecadienoic acid (C18: 2), octadecatrienoic acid (C18: 3), and the like.
In the following examples of the present invention, the fatty acid content was measured by subjecting the fat or oil to methyl esterification and then gas chromatography. The methyl esterification method is carried out according to the method of the national standard GB/T17376-2008 for preparing the animal and vegetable oil fatty acid methyl ester; the gas chromatographic analysis is carried out according to the method of the national standard GB/T17377-2008 of the gas chromatographic analysis of the animal and vegetable oil fatty acid methyl ester.
In a preferred embodiment of the present invention, the fat-soluble flavonoid compound preferably has a hydroxyl radical half-inhibitory rate IC50Is 0.2 to 0.9g/L, more preferably 0.25 to 0.85g/L, still more preferably 0.3 to 0.8g/L, and still more preferably 0.45 to 0.75 g/L. For example, in a specific embodiment of the present invention, the fat-soluble flavonoid compound has a hydroxyl radical half-inhibition ratio IC500.12g/L, 0.32g/L, 0.44g/L, 0.96 g/L.
The half-inhibition rate of the hydroxyl free radical is determined by adopting a Feton spectrophotometry according to the color army and the like (the hydroxyl free radical generated by a Fenton reaction is determined by the spectrophotometry, and the Feton spectrophotometry is adopted in the 2 nd period 91-93 of the 6 th month of 2009, the university of Chengdu university (Nature science edition).
In a preferred embodiment of the present invention, the fat-soluble flavonoids are at least one selected from the group consisting of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin, and fat-soluble rutin.
In a preferred embodiment of the present invention, the fat-soluble flavonoid compound may be a mixture of flavonoid compounds that have been partially esterified or fully esterified, or may be a commercially available product.
In a preferred embodiment of the present invention, the fat-soluble flavonoid may be an esterification product of a flavonoid and a fatty acid or a derivative thereof. The fatty acid is selected from straight chain or branched chain, saturated or unsaturated, mono-or poly-fatty acid with 10-30 carbon atoms, and preferably is selected from at least one of myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid and erucic acid. The fatty acid derivative is an acid halide, such as an acid chloride, of the fatty acid. The fatty acid derivative is preferably at least one of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride or erucic acid chloride.
The fat-soluble flavonoid compound can be prepared, for example, as follows. And contacting the water-soluble flavonoid compound with the fatty acid or the derivative thereof in the presence of a solvent.
In a preferred embodiment of the present invention, the content ratio of the saturated fatty acids to the fat-soluble flavonoids in the fat and oil composition of the present invention is 1 to 10000:1, preferably 10 to 5000:1, more preferably 50 to 3000:1, further preferably 80 to 2000:1, and particularly preferably 200 to 1000:1, by weight. For example, in a specific embodiment of the present invention, the content ratio of saturated fatty acids to fat-soluble flavonoids is 499:1, 999:1, 1999:1, 4999:1, 9999:1, in terms of weight ratio.
In a preferred embodiment of the present invention, the fat-soluble flavonoid compound is contained in the fat composition of the present invention in an amount of 0.0001 to 10 wt%, preferably 0.001 to 5 wt%, more preferably 0.01 to 1 wt%, further preferably 0.02 to 0.8 wt%, further preferably 0.05 to 0.5 wt%, particularly preferably 0.1 to 0.2 wt%, based on the total weight of the fat composition. For example, in a specific embodiment of the present invention, the content of the fat-soluble flavonoid compound is 0.01 wt%, 0.02 wt%, 0.05 wt%, 0.1 wt%, 0.2 wt% based on the total weight of the fat and oil composition.
In a preferred embodiment of the present invention, the number of hydroxyl residues (non-esterified hydroxyl groups) contained in the fat-soluble flavonoid compound is 2 to 23, preferably 5 to 15.
In the invention, the anti-freezing performance of the grease is measured by adopting a freezing test, the temperature is considered to be selected from-5 ℃ to 5 ℃, and the conditions of haziness and solidification of the grease are observed. The freezing experiments were performed according to the method of AOCS Cc 11-53. The specific method comprises the following steps: the using instrument is a Julabo constant-temperature water bath kettle, 100ml of grease is weighed, heated to 130 ℃, filtered while hot, cooled to room temperature, added into a freezing test tube, then placed into the water bath kettle, and the frost resistance of the grease is observed.
The frost resistance of the grease was evaluated by the clouding time, and the longer the clouding time, the better the frost resistance of the grease. The oil or fat composition of the present invention has a clouding time, as measured at-5 ℃, of 100 minutes or longer, preferably 130 minutes or longer, more preferably 145 minutes or longer, still more preferably 190 minutes or longer, still more preferably 240 minutes or longer, and particularly preferably more than 600 minutes.
The oil or fat composition of the present invention has a clouding time, as measured at 5 ℃, of 70 minutes or more, preferably 150 minutes or more, more preferably 200 minutes or more, further preferably more than 500 minutes, and still more preferably more than 600 minutes.
In the present invention, an 743 Rancimat oil oxidation stability tester (Switzerland, 743 type oil oxidation stability tester) was used to measure the antioxidant properties of the oil and fat composition. Specifically, the induction time of the sample is measured by the above instrument under the conditions of the temperature of 100 ℃ and the air flow rate of 20L/h, and the longer the induction time of the sample is, the stronger the antioxidant capacity of the sample is. The induction time of the oil or fat composition of the present invention is 19 hours or more, preferably 19 to 30 hours, more preferably 20 to 22 hours. In one embodiment of the invention, the induction time is, for example, 20.54 hours, 21.03 hours.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.99% by weight of a fat and oil and 0.01% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the content of saturated fatty acid in the oil is 12.867 wt%, and the content of unsaturated fatty acid in the oil is 83.161 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 2 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.95% by weight of a fat and oil and 0.05% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the content of saturated fatty acid in the oil is 12.867 wt%, and the content of unsaturated fatty acid in the oil is 83.161 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 2 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.9% by weight of a fat and oil and 0.1% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the content of saturated fatty acid in the oil is 12.867 wt%, and the content of unsaturated fatty acid in the oil is 83.161 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, water-soluble procyanidin,in a molar ratio of 1: 2 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.99% by weight of a fat and oil and 0.01% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the content of saturated fatty acid in the oil is 15.482 wt%, and the content of unsaturated fatty acid in the oil is 77.067 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 2 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.95% by weight of a fat and oil and 0.05% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the content of saturated fatty acid in the oil is 15.482 wt%, and the content of unsaturated fatty acid in the oil is 77.067 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 2 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.9% by weight of a fat and oil and 0.1% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the content of saturated fatty acid in the oil is 15.482 wt%, and the content of unsaturated fatty acid in the oil is 77.067 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 2 (Water-soluble flower)B, green element: palmitoyl chloride) with palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.99% by weight of a fat and oil and 0.01% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compounds is 0.12 +/-0.03 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is mixed oil of soybean oil and palm oil (in weight ratio, the ratio of soybean oil to palm oil is 4:1, and the iodine value of the palm oil is 56), the content of saturated fatty acids in the oil is 19.932 wt%, and the content of unsaturated fatty acids in the oil is 77.151 wt%. The fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, water-soluble tea polyphenol is mixed according to a molar ratio of 1: 2 (water-soluble tea polyphenol: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.95% by weight of a fat and oil and 0.05% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compounds is 0.12 +/-0.03 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is mixed oil of soybean oil and palm oil (in weight ratio, the ratio of soybean oil to palm oil is 4:1, and the iodine value of the palm oil is 56), the content of saturated fatty acids in the oil is 19.932 wt%, and the content of unsaturated fatty acids in the oil is 77.151 wt%. The fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, water-soluble tea polyphenol is mixed according to a molar ratio of 1: 2 (water-soluble tea polyphenol: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.8% by weight of a fat and oil and 0.2% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC500.12 +/-0.03 g/L, the fat-soluble flavonoid compound is fat-soluble tea polyphenol, the oil is mixed oil of soybean oil and palm oil (in weight ratio, the ratio of soybean oil to palm oil is 4:1, and the iodine value of the palm oil is 56), and the fat-soluble flavonoid compound is fat-soluble tea polyphenol, and the oil is mixed oil of soybean oil and palm oilThe content of saturated fatty acid in the oil is 19.932 wt%, and the content of unsaturated fatty acid in the oil is 77.151 wt%. The fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, water-soluble tea polyphenol is mixed according to a molar ratio of 1: 2 (water-soluble tea polyphenol: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.99% by weight of a fat and oil and 0.01% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.96 +/-0.08 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the content of saturated fatty acid in the oil is 12.867 wt%, and the content of unsaturated fatty acid in the oil is 83.161 wt%. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 6 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.99% by weight of a fat and oil and 0.01% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the fat-soluble flavonoid compound is 0.32 +/-0.05 g/L, the fat-soluble flavonoid compound is fat-soluble tea polyphenol, the oil is mixed oil of soybean oil and palm oil (in weight ratio, the ratio of soybean oil to palm oil is 4:1, and the iodine value of the palm oil is 56), the content of saturated fatty acid in the oil is 19.932 wt%, and the content of unsaturated fatty acid in the oil is 77.151 wt%. The fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, water-soluble tea polyphenol is mixed according to a molar ratio of 1: 4 (water-soluble tea polyphenol: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.98% by weight of a fat and oil and 0.02% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50Is 0.96 +/-0.08 g/L, and the fat-soluble flavonoid compound is a fat-soluble sourceAnthocyanin, wherein the oil is soybean oil without antioxidant. The fat-soluble procyanidin is prepared as follows: in the presence of a solvent, the water-soluble procyanidin is mixed in a molar ratio of 1: 6 (water-soluble procyanidin: palmitoyl chloride) and palmitoyl chloride.
In one embodiment of the present invention, the fat and oil composition of the present invention comprises 99.98% by weight of a fat and oil and 0.02% by weight of a fat-soluble flavonoid compound having a hydroxyl radical half-inhibitory rate IC50The content of the lipid-soluble flavonoid compound is 0.32 +/-0.05 g/L, the lipid-soluble flavonoid compound is lipid-soluble tea polyphenol, and the oil is soybean oil without antioxidant. The fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, water-soluble tea polyphenol is mixed according to a molar ratio of 1: 6 (water-soluble tea polyphenol: palmitoyl chloride) and palmitoyl chloride.
In the invention, the inventor finds that the fat-soluble flavonoid compound can be used for lowering the freezing point of the grease. By contacting the grease with the fat-soluble flavonoid compound, the oxidation resistance of the grease can be improved, the hazy solidification of the grease in a low-temperature environment can be inhibited, and the good flowing property can be maintained.
In the present invention, the freezing point of the fat or oil can be lowered by bringing the fat or oil into contact with the fat-soluble flavonoid compound. Wherein the fat-soluble flavonoid compound can be the fat-soluble flavonoid compound disclosed in the invention.
The hydroxyl radical half-inhibition rate IC of the fat-soluble flavonoid compound500.1 to 1.0 g/L. In a preferred embodiment of the present invention, the fat-soluble flavonoid compound preferably has a hydroxyl radical half-inhibitory rate IC50Is 0.2 to 0.9g/L, more preferably 0.25 to 0.85g/L, still more preferably 0.3 to 0.8g/L, and still more preferably 0.45 to 0.75 g/L. For example, in a specific embodiment of the present invention, the fat-soluble flavonoid compound has a hydroxyl radical half-inhibition ratio IC500.12g/L, 0.32g/L, 0.44g/L, 0.96 g/L.
In a preferred embodiment of the present invention, the fat or oil is a vegetable-derived fat or oil. Preferably, the plant-derived oil is at least one selected from soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower seed oil, rice bran oil, palm oil and cottonseed oil. The fat may be the fat described in the present invention.
In a preferred embodiment of the present invention, the fat or oil has a saturated fatty acid content of more than 10% by weight. The content of saturated fatty acids in the oil is preferably 11 to 40% by weight, more preferably 12 to 30% by weight, still more preferably 14 to 25% by weight, and particularly preferably 15 to 20% by weight.
The saturated fatty acid is a straight chain or branched chain, monobasic or polybasic saturated fatty acid with 12-18 carbon atoms. For example, dodecanoic acid (C12: 0), tetradecanoic acid (C14: 0), hexadecanoic acid (C16: 0), octadecanoic acid (C18: 0), and the like can be given.
In a preferred embodiment of the present invention, the content of unsaturated fatty acids in the fat or oil is 70 to 90% by weight, preferably 75 to 80% by weight.
The saturated fatty acid is a linear chain or branched chain, monobasic or polybasic unsaturated fatty acid with 16-20 carbon atoms. Examples thereof include octadecenoic acid (C18: 1), octadecadienoic acid (C18: 2), octadecatrienoic acid (C18: 3), and the like.
In a preferred embodiment of the present invention, the ratio of the saturated fatty acid to the fat-soluble flavonoid compound is 1 to 10000:1, preferably 10 to 5000:1, more preferably 50 to 3000:1, further preferably 80 to 2000:1, and particularly preferably 200 to 1000:1, by weight. For example, in the specific embodiment of the present invention, the ratio of the saturated fatty acid to the fat-soluble flavonoid is 499:1, 999:1, 1999:1, 4999:1, 9999: 1.
In a preferred embodiment of the present invention, the fat-soluble flavonoid compound is added in an amount of 0.0001 to 10 wt%, preferably 0.001 to 5 wt%, more preferably 0.01 to 1 wt%, further preferably 0.02 to 0.8 wt%, further preferably 0.05 to 0.5 wt%, particularly preferably 0.1 to 0.2 wt%, based on the total weight of the fat and oil of the present invention and the fat-soluble flavonoid compound. For example, in a specific embodiment of the present invention, the amount of the fat-soluble flavonoid compound added is 0.01 wt%, 0.02 wt%, 0.05 wt%, 0.1 wt%, 0.2 wt% based on the total weight of the fat and oil and the fat-soluble flavonoid compound.
In the invention, the anti-freezing performance of the grease is measured by adopting a freezing test, the temperature is considered to be selected from-5 ℃ to 5 ℃, and the conditions of haziness and solidification of the grease are observed. The freezing experiments were performed according to the method of AOCS Cc 11-53. The specific method comprises the following steps: the using instrument is a Julabo constant-temperature water bath kettle, 100ml of grease is weighed, heated to 130 ℃, filtered while hot, cooled to room temperature, added into a freezing test tube, then placed into the water bath kettle, and the frost resistance of the grease is observed.
The frost resistance of the grease was evaluated by the clouding time, and the longer the clouding time, the better the frost resistance of the grease. In the present invention, the haze time is measured at-5 ℃ for 100 minutes or more, preferably 130 minutes or more, more preferably 145 minutes or more, further preferably 190 minutes or more, still more preferably 240 minutes or more, particularly preferably more than 600 minutes according to the above method.
In the present invention, the clouding time measured at 5 ℃ according to the above method is 70 minutes or more, preferably 150 minutes or more, more preferably 200 minutes or more, further preferably more than 500 minutes, still more preferably more than 600 minutes.
In the present invention, an 743 Rancimat oil oxidation stability tester (Switzerland, 743 type oil oxidation stability tester) was used to measure the antioxidant properties of the oil and fat composition. Specifically, the induction time of the sample is measured by the above instrument under the conditions of the temperature of 100 ℃ and the air flow rate of 20L/h, and the longer the induction time of the sample is, the stronger the antioxidant capacity of the sample is. In the present invention, the fat-soluble flavonoid compound is added to the oil-and-fat composition, so that the induction time of the oil-and-fat composition is 19 hours or more, preferably 19 to 30 hours, and more preferably 20 to 22 hours. In one embodiment of the invention, the induction time is, for example, 20.54 hours, 21.03 hours.
The following detailed description of various aspects of the present invention is provided in connection with examples to provide a better understanding of the present invention, but the scope of the present invention is not limited thereto.
The following examples use instrumentation conventional in the art. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers. In the following examples, various starting materials were used, and unless otherwise specified, conventional commercially available products were used. In the description of the present invention and the following examples, "%" represents weight percent unless otherwise specified.
Example (b):
in the following examples of the present invention, the fat a used was soybean oil (available from shanghai jiali food industry co., ltd.); the grease B is peanut oil (purchased from Shanghai Jiali food industry Co., Ltd.); the fat C is a mixed fat of soybean oil (purchased from Shanghai Jiali food industry Co., Ltd.) and palm oil (purchased from Shanghai Jiali food industry Co., Ltd.), wherein the ratio of the soybean oil to the palm oil is 4:1 (weight ratio), and the iodine value of the palm oil is 56; the oil D is soybean oil without antioxidant, and is prepared according to the preparation method of oil preparation and processing technology (Liuyulan weaving), wherein the green soybean oil is commercially available. The fat E was obtained by adding an antioxidant (t-butylhydroquinone (TBHQ)) to the fat D, wherein the amount of t-butylhydroquinone used was 80 ppm.
In the following examples of the present invention, the fat-soluble tea polyphenol used is an esterification product of water-soluble tea polyphenol, which is available from Jiang industries, Ltd, with fatty acid. The fat-soluble procyanidin is an esterification product of water-soluble procyanidin and fatty acid, wherein the water-soluble procyanidin is purchased from naturex commerce and trade company Limited, France. See below for specific methods.
Measurement of fatty acid composition of fat and oil
The fatty acid composition of the fat A, B, C shown in Table 1 was determined, and the fatty acid composition of each fat was determined by using the GB/T17377-.
TABLE 1
| C12:0(%) | C14:0(%) | C16:0(%) | C18:0(%) | C18:1(%) | C18:2(%) | C18:3(%) | |
| Oil A | 0 | 0 | 9.355 | 3.512 | 34.328 | 43.867 | 4.966 |
| Oil B | 0 | 0 | 11.517 | 3.965 | 42.073 | 34.994 | 0 |
| Oil C | 0.135 | 0.520 | 15.752 | 3.525 | 37.198 | 36.154 | 3.799 |
Preparation of fat-soluble tea polyphenol and fat-soluble procyanidin and determination of half inhibition rate of hydroxyl free radical
Preparation of fat-soluble tea polyphenol and fat-soluble procyanidin
The fat-soluble tea polyphenol and the fat-soluble procyanidin are prepared by quantitatively esterifying water-soluble tea polyphenol and procyanidin. The preparation method comprises the following steps: in a 100ml three-necked flask, 2.00g of each flavonoid compound shown in Table 2 was charged, 20ml of pyridine was added to dissolve the flavonoid compound, and 10ml of ethyl acetate and 5ml of pyridine were charged into a constant pressure dropping funnel, followed by addition of palmitoyl chloride in an amount shown in Table 2. Dropping the mixture into a three-neck flask at constant pressure, reacting for a period of time, and adding 10ml of 90% ethanol solution to quench the reaction. And then adding 20ml of ethyl acetate and 30ml of 2mol/L diluted hydrochloric acid solution into the reaction solution for extraction and liquid separation, taking an ethyl acetate layer, washing the ethyl acetate layer for 3 times by using the 2mol/L diluted hydrochloric acid solution with the same volume, drying for 5 hours by using anhydrous sodium sulfate, and performing vacuum spin-drying on the solvent to obtain 1-3 parts of fat-soluble tea polyphenol and 1-3 parts of fat-soluble procyanidine.
TABLE 2
| Water-soluble flavonoid compounds: palmitoyl chloride (mol/mol) | Reaction time (h) | |
| Fat-soluble tea polyphenol 1 | 1:2 | 4 |
| Fat-soluble tea polyphenol 2 | 1:4 | 8 |
| Fat-soluble tea polyphenol 3 | 1:8 | 16 |
| Fat-soluble procyanidin 1 | 1:2 | 4 |
| Fat-soluble procyanidin 2 | 1:6 | 8 |
| Fat-soluble procyanidin 3 | 1:15 | 16 |
Hydroxyl radical half-inhibition rate measurement according to the Yanjun et al, the hydroxyl radical generated by Fenton reaction is measured by spectrophotometry, and is measured by adopting the Feton spectrophotometry in the 2 nd 91-93 of volume 28 of 6 months of 2009, university of Chengdu university (Nature science edition). The half-inhibitory ratios of hydroxyl radicals of the fat-soluble flavonoids used in the examples are shown in table 3.
TABLE 3
| Half-inhibition ratio IC of hydroxyl radical50（g/L） | |
| Fat-soluble tea polyphenol 1 | 0.12±0.03 |
| Fat-soluble tea polyphenol 2 | 0.32±0.05 |
| Fat-soluble tea polyphenol 3 | 1.12±0.05 |
| Fat-soluble procyanidin 1 | 0.44±0.02 |
| Fat-soluble procyanidin 2 | 0.96±0.08 |
| Fat-soluble procyanidin 3 | 1.26±0.04 |
Preparation of oil and fat composition
According to the composition ratios shown in the following tables 4 to 9, the fat-soluble flavonoids and the oil are heated and dissolved at 60 ℃ to obtain the oil compositions of examples 1 to 13 and comparative examples 1 to 13, wherein the fat-soluble flavonoids are not added in the oil compositions of comparative examples 1 to 3.
TABLE 4
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Example 7 | Example 8 | Example 9 | |
| Fat and oil A (%) | 99.99 | 99.95 | 99.9 | ||||||
| Fat and oil B (%) | 99.99 | 99.95 | 99.9 | ||||||
| Fat and oil C (%) | 99.99 | 99.95 | 99.8 | ||||||
| Fat-soluble procyanidin 1(%) | 0.01 | 0.05 | 0.1 | 0.01 | 0.05 | 0.1 | |||
| Fat-soluble tea polyphenol 1(%) | 0.01 | 0.05 | 0.2 |
TABLE 5
| Example 10 | Example 11 | |
| Fat and oil A (%) | 99.99 | |
| Fat and oil C (%) | 99.99 | |
| Fat-soluble procyanidin 2(%) | 0.01 | |
| Fat-soluble tea polyphenol 2(%) | 0.01 |
TABLE 6
| Example 12 | Example 13 | |
| Fat and oil D (%) | 99.98 | 99.98 |
| Fat-soluble procyanidin 2(%) | 0.02 | |
| Fat-soluble tea polyphenol 2(%) | 0.02 |
TABLE 7
| Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Fat and oil A (%) | 100 | ||
| Fat and oil B (%) | 100 | ||
| Fat and oil C (%) | 100 |
TABLE 8
| Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | Comparative example 9 | Comparative example 10 | Comparative example 11 | |
| Fat and oil A (%) | 99.995 | 99.75 | 99.99 | |||||
| Fat and oil B (%) | 99.995 | 99.75 | ||||||
| Fat and oil C (%) | 99.995 | 99.75 | 99.99 | |||||
| Fat-soluble procyanidin 1(%) | 0.005 | 0.25 | 0.005 | 0.25 | ||||
| Fat-soluble tea polyphenol 1(%) | 0.005 | 0.25 | ||||||
| Fat-soluble procyanidin 3(%) | 0.01 | |||||||
| Fat-soluble tea polyphenol 3(%) | 0.01 |
TABLE 9
| Comparative example 12 | Comparative example 13 | |
| Fat and oil D (%) | 99.98 | 99.98 |
| Fat-soluble procyanidin 3(%) | 0.02 | |
| Fat-soluble tea polyphenol 3(%) | 0.02 |
Determination of anti-freezing performance of grease composition
The frost resistance of the grease composition is measured by adopting a freezing test, the temperature is selected from-5 ℃ to 5 ℃ under the investigation, and the conditions of haziness and solidification of the grease are observed. The freezing experiment is measured according to the method of AOCS Cc 11-53, and the used instrument is a Jumbo constant temperature water bath kettle, and the specific method is as follows: weighing 100ml of grease, heating to 130 ℃, filtering while hot, cooling the grease to room temperature, adding the grease into a freezing test tube, then putting the tube into a water bath kettle, and observing the frost resistance of the grease.
Results of freezing experiments
1. Freezing experiment of fat-soluble flavonoid compounds with different concentrations.
TABLE 10-1
| Freezing experiment at-5 deg.C | Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 4 | Comparative example 5 |
| Time to become cloudy (min) | 130 | >600 | >600 | 60 | 80 | 40 |
TABLE 10-2
| Freezing experiment at 5 deg.C | Example 4 | Example 5 | Example 6 | Comparative example 2 | Comparative example 6 | Comparative example 7 |
| Time to become cloudy (min) | 150 | >600 | >600 | 62 | 86 | 50 |
Tables 10-3
| Freezing experiment at 5 deg.C | Example 7 | Example 8 | Example 9 | Comparative example 3 | Comparative example 8 | Comparative example 9 |
| Time to become cloudy (min) | 70 | 200 | >500 | 20 | 38 | 18 |
2. Freezing experiments of flavonoids compounds with different hydroxyl free radical inhibition rates.
TABLE 11-1
| Freezing experiment at-5 deg.C | Example 1 | Example 10 | Example 12 | Example 13 | Comparative example 1 | Comparative example 10 | Comparative example 12 | Comparative example 13 |
| Time to become cloudy (min) | 130 | 145 | 190 | 240 | 60 | 80** | 50** | 40** |
Precipitate as a flocculent solid.
TABLE 11-2
| Freezing experiment at 5 deg.C | Example 7 | Example 11 | Comparative example 3 | Comparative example 11 |
| Time to become cloudy (min) | 70 | 83 | 30 | 45** |
Precipitate as a flocculent solid.
From the results of freezing experiments, it is obvious that (1) the fat-soluble flavonoid compound with the content ratio of the saturated fatty acid to the fat-soluble flavonoid compound of 80-2000:1 is added to obviously improve the anti-freezing performance of the grease, and effectively solve the problems of poor and solidified grease during low-temperature long-term storage; (2) after the half inhibition rate of hydroxyl free radicals exceeds a certain range of 1.0g/L, the freezing resistance of the composition is weakened, and the phenomenon of precipitation of fat-soluble flavonoid compounds appears.
Antioxidant effect (Rancimat oxidation stability determination)
The induction time of a 743 Rancimat grease oxidation stability tester (Switzerland, 743 type grease oxidation stability tester) was measured at 100 ℃ and an air flow rate of 20L/h, and the longer the induction time of the sample, the stronger the oxidation resistance.
The Rancimat result shows that the higher the half inhibition rate of the hydroxyl radical of the fat-soluble flavonoid compound in the comparative example is, the weaker the grease oxidation resistance is, and even no antioxidant effect is achieved. The fat-soluble flavonoid compound used in the invention not only has excellent performances of preventing the oil from becoming cloudy and coagulating and keeping good fluidity, but also has the effect of helping to improve the oxidation resistance of the oil. The results of detection of example 12, example 13, comparative example 12, comparative example 13, fat D, and fat E are shown in table 12.
TABLE 12
| Oil E | Oil and fat D | Example 12 | Example 13 | Comparative example 12 | Comparative example 13 | |
| Time(h) | 23.27 | 16.34 | 20.54 | 21.03 | 16.12 | 17.48 |
Claims (55)
1. A fat composition comprising a fat and a fat-soluble flavonoid compound, characterized in that the fat-soluble flavonoid compound has a half-inhibitory rate of hydroxyl radicals IC500.1-1.0 g/L, wherein the content ratio of saturated fatty acid to fat-soluble flavonoid compound in the oil is 80-2000: 1; the oil is a vegetable-derived oil, and the saturated fatty acid content of the oil is more than 10 wt% and less than 25 wt%.
2. The fat and oil composition according to claim 1, wherein the fat-soluble flavonoid compound has a hydroxyl radical half-inhibitory rate IC500.2 to 0.9 g/L.
3. The fat or oil composition according to claim 1 or 2, wherein the fat-soluble flavonoid compound has a half inhibitory rate on a hydroxyl radicalIC500.45-0.75 g/L.
4. The fat or oil composition according to claim 1 or 2, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 2 to 23.
5. The fat or oil composition according to claim 1 or 2, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 5 to 15.
6. The oil or fat composition according to claim 1 or 2, wherein the oil or fat has a saturated fatty acid content of 15 to 20% by weight.
7. The fat composition according to claim 1, wherein the vegetable-derived fat is selected from at least one of soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower seed oil, rice bran oil, palm oil, and cottonseed oil.
8. The fat and oil composition according to claim 1 or 2, wherein the fat-soluble flavonoids are at least one selected from the group consisting of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin, and fat-soluble rutin.
9. The fat or oil composition according to claim 1 or 2, wherein the fat-soluble flavonoid is an esterification product of a flavonoid and a fatty acid or a derivative thereof.
10. The fat or oil composition according to claim 9, wherein the fatty acid is selected from linear or branched, saturated or unsaturated, mono-or polybasic fatty acids having 10 to 30 carbon atoms.
11. The fat and oil composition according to claim 9, wherein the fatty acid is at least one selected from myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid, and erucic acid.
12. The fat or oil composition according to claim 9, wherein the fatty acid derivative is an acid halide of the fatty acid.
13. The fat or oil composition according to claim 9, wherein the fatty acid derivative is an acid chloride of the fatty acid.
14. The fat or oil composition according to claim 9, wherein the fatty acid derivative is at least one selected from the group consisting of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride and erucic acid chloride.
15. A method for lowering the freezing point of oil or fat features that the oil or fat is contacted with liposoluble flavone compound whose half-suppressing rate of hydroxy radical is IC500.1-1.0 g/L, wherein the content ratio of saturated fatty acid to fat-soluble flavonoid compound is 80-2000:1 in terms of weight ratio, the oil is plant-derived oil, and the content of saturated fatty acid in the oil is more than 10 wt% and less than 25 wt%.
16. The method for lowering the freezing point of fats and oils according to claim 15, wherein said fat-soluble flavonoids have a half-inhibitory rate of hydroxyl radicals IC500.2 to 0.9 g/L.
17. The method for lowering the freezing point of fats and oils according to claim 15 or 16, wherein said fat-soluble flavonoids have a half-inhibitory rate of hydroxyl radical IC500.25 to 0.85 g/L.
18. The method for lowering the freezing point of fats and oils according to claim 15 or 16, wherein said fat-soluble flavonoids have a half-inhibitory rate of hydroxyl radicals IC500.3 to 0.8 g/L.
19. According toThe method for lowering the freezing point of fats and oils according to claim 15 or 16, wherein said fat-soluble flavonoids have a half inhibition ratio of hydroxyl radicals IC500.45-0.75 g/L.
20. The method for lowering the freezing point of fat and oil according to claim 15 or 16, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 2 to 23.
21. The method for lowering the freezing point of fat and oil according to claim 15 or 16, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid compound is 5 to 15.
22. The method for lowering the freezing point of fats and oils according to claim 15 or 16, wherein the saturated fatty acid content of said fats and oils is 15 to 20% by weight.
23. The method for lowering the freezing point of oils and fats according to claim 15 or 16, wherein said oils and fats of vegetable origin are selected from at least one of soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower oil, rice bran oil, palm oil and cottonseed oil.
24. The method for lowering the freezing point of fat and oil according to claim 15 or 16, wherein the fat-soluble flavonoids are at least one selected from the group consisting of fat-soluble tea polyphenols, fat-soluble procyanidins, fat-soluble quercetin and fat-soluble rutin.
25. The method for lowering the freezing point of fats and oils according to claim 15 or 16, wherein said fat-soluble flavonoids are esterification products of flavonoids with fatty acids or derivatives thereof, said fatty acid derivatives being acyl halides of said fatty acids.
26. The method for lowering the freezing point of fats and oils according to claim 25, wherein said fatty acid is selected from the group consisting of linear or branched, saturated or unsaturated, mono-or polybasic fatty acids having 10 to 30 carbon atoms.
27. The method of lowering the freezing point of fats and oils of claim 25, wherein said fatty acid is selected from at least one of myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid or erucic acid.
28. The method for depressing the freezing point of fats and oils of claim 25 wherein said fatty acid derivative is an acyl chloride of said fatty acid.
29. The method for lowering the freezing point of oils and fats according to claim 25, wherein said fatty acid derivative is at least one selected from the group consisting of myristic acid chloride, lauric acid chloride, palmitic acid chloride, stearic acid chloride, oleic acid chloride, behenic acid chloride and erucic acid chloride.
30. Use of fat-soluble flavonoids for lowering the freezing point of fats and oils, wherein the fat-soluble flavonoids have a hydroxyl radical half-inhibition ratio IC500.1-1.0 g/L, wherein the content ratio of saturated fatty acid to fat-soluble flavonoid compound is 80-2000:1 in terms of weight ratio, the oil is plant-derived oil, and the content of saturated fatty acid in the oil is more than 10 wt% and less than 25 wt%.
31. The use according to claim 30, wherein the fat-soluble flavonoid has a hydroxyl radical half-inhibition ratio IC500.2 to 0.9 g/L.
32. Use according to claim 30 or 31, wherein the fat-soluble flavonoid has a hydroxyl radical half-inhibition ratio IC500.45-0.75 g/L.
33. The use according to claim 30 or 31, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid is 2 to 23.
34. The use according to claim 30 or 31, wherein the number of hydroxyl residues contained in the fat-soluble flavonoid is 5 to 15.
35. Use according to claim 30 or 31, wherein the oil or fat has a saturated fatty acid content of 15 to 20% by weight.
36. The use according to claim 30 or 31, wherein the vegetable-derived oil is selected from at least one of soybean oil, olive oil, rapeseed oil, peanut oil, corn oil, sunflower seed oil, rice bran oil, palm oil and cottonseed oil.
37. The use according to claim 30 or 31, wherein the fat soluble flavonoids are selected from at least one of fat soluble tea polyphenols, fat soluble procyanidins, fat soluble quercetin and fat soluble rutin.
38. Use according to claim 30 or 31, wherein the fat-soluble flavonoid is the esterification product of a flavonoid with a fatty acid or a derivative thereof, said fatty acid derivative being an acid halide of said fatty acid.
39. The use according to claim 38, wherein the fatty acid is selected from linear or branched, saturated or unsaturated, mono-or polybasic fatty acids having 10 to 30 carbon atoms.
40. Use according to claim 38, wherein the fatty acid is selected from at least one of myristic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid or erucic acid.
41. The use of claim 38, wherein the fatty acid derivative is an acyl chloride of the fatty acid.
42. The use according to claim 38, wherein the fatty acid derivative is selected from at least one of myristoyl chloride, lauric acid acyl chloride, palmitic acid acyl chloride, stearic acid acyl chloride, oleic acid acyl chloride, behenic acid acyl chloride or erucic acid acyl chloride.
43. An oil and fat composition comprising 99.99 wt% of an oil and fat and 0.01 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC500.44 +/-0.02 g/L, wherein the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the saturated fatty acid content of the oil is 12.867 wt%, the unsaturated fatty acid content of the oil is 83.161 wt%, and the fat-soluble procyanidin is prepared from the following components in percentage by weight: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
44. An oil and fat composition comprising 99.95 wt% of an oil and fat and 0.05 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC500.44 +/-0.02 g/L, wherein the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the saturated fatty acid content of the oil is 12.867 wt%, the unsaturated fatty acid content of the oil is 83.161 wt%, and the fat-soluble procyanidin is prepared from the following components in percentage by weight: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
45. An oil and fat composition comprising 99.9 wt% of an oil and fat and 0.1 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50Is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the saturated fatty acid content of the oil is 12.867 wt%, the unsaturated fatty acid content of the oil is 83.161 wt%, and the fat-soluble procyanidin is as followsPreparation: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
46. An oil and fat composition comprising 99.99 wt% of an oil and fat and 0.01 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50Is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the saturated fatty acid content of the oil is 15.482 wt%, the unsaturated fatty acid content of the oil is 77.067 wt%, and the fat-soluble procyanidin is prepared by the following steps: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
47. An oil and fat composition comprising 99.95 wt% of an oil and fat and 0.05 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50Is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the saturated fatty acid content of the oil is 15.482 wt%, the unsaturated fatty acid content of the oil is 77.067 wt%, and the fat-soluble procyanidin is prepared by the following steps: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
48. An oil and fat composition comprising 99.9 wt% of an oil and fat and 0.1 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50Is 0.44 +/-0.02 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is peanut oil, the saturated fatty acid content of the oil is 15.482 wt%, the unsaturated fatty acid content of the oil is 77.067 wt%, and the fat-soluble procyanidin is prepared by the following steps: dissolving water soluble procyanidinIn the presence of an agent, with a water-soluble procyanidin: palmitoyl chloride = 1: 2 with palmitoyl chloride.
49. An oil and fat composition comprising 99.99 wt% of an oil and fat and 0.01 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50The content of the fat-soluble flavonoid compounds is 0.12 +/-0.03 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is mixed oil of soybean oil and palm oil, and the weight ratio of the mixed oil is as follows: the palm oil iodine value of the mixed oil is 56, the saturated fatty acid content of the oil is 19.932 wt%, the unsaturated fatty acid content of the oil is 77.151 wt%, and the fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, mixing water-soluble tea polyphenol: palmitoyl chloride = 1: 2 with palmitoyl chloride.
50. An oil and fat composition comprising 99.95 wt% of an oil and fat and 0.05 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50The content of the fat-soluble flavonoid compounds is 0.12 +/-0.03 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is mixed oil of soybean oil and palm oil, and the weight ratio of the mixed oil is as follows: the palm oil iodine value of the mixed oil is 56, the saturated fatty acid content of the oil is 19.932 wt%, the unsaturated fatty acid content of the oil is 77.151 wt%, and the fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, mixing water-soluble tea polyphenol: palmitoyl chloride = 1: 2 with palmitoyl chloride.
51. An oil and fat composition comprising 99.8 wt% of an oil and fat and 0.2 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC500.12 +/-0.03 g/L, the fat-soluble flavonoid compound is fat-soluble tea polyphenol, and the oil is largeA mixed oil of soybean oil and palm oil, the mixed oil comprising, by weight: the palm oil iodine value of the mixed oil is 56, the saturated fatty acid content of the oil is 19.932 wt%, the unsaturated fatty acid content of the oil is 77.151 wt%, and the fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, mixing water-soluble tea polyphenol: palmitoyl chloride = 1: 2 with palmitoyl chloride.
52. An oil and fat composition comprising 99.99 wt% of an oil and fat and 0.01 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50Is 0.96 +/-0.08 g/L, the fat-soluble flavonoid compound is fat-soluble procyanidin, the oil is soybean oil, the saturated fatty acid content of the oil is 12.867 wt%, the unsaturated fatty acid content of the oil is 83.161 wt%, and the fat-soluble procyanidin is prepared by the following steps: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 6 with palmitoyl chloride.
53. An oil and fat composition comprising 99.99 wt% of an oil and fat and 0.01 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50The content of the fat-soluble flavonoid compounds is 0.32 +/-0.05 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is mixed oil of soybean oil and palm oil, and the weight ratio of the mixed oil is as follows: the palm oil iodine value of the mixed oil is 56, the saturated fatty acid content of the oil is 19.932 wt%, the unsaturated fatty acid content of the oil is 77.151 wt%, and the fat-soluble tea polyphenol is prepared by the following steps: in the presence of a solvent, mixing water-soluble tea polyphenol: palmitoyl chloride = 1: 4 with palmitoyl chloride.
54. An oil and fat composition comprises 99.98 wt% of oil and fat and 0.02 wt% of fatSoluble flavonoid compound, and hydroxyl radical half-inhibition rate IC of the soluble flavonoid compound50The content of the lipid-soluble flavonoid compound is 0.96 +/-0.08 g/L, the lipid-soluble flavonoid compound is lipid-soluble procyanidin, the oil is soybean oil without antioxidant, and the lipid-soluble procyanidin is prepared by the following steps: in the presence of a solvent, mixing a water-soluble procyanidin: palmitoyl chloride = 1: 6 with palmitoyl chloride.
55. An oil and fat composition comprising 99.98 wt% of an oil and fat and 0.02 wt% of a fat-soluble flavonoid compound having a half-inhibitory rate of hydroxyl radical IC50The content of the fat-soluble flavonoid compounds is 0.32 +/-0.05 g/L, the fat-soluble flavonoid compounds are fat-soluble tea polyphenols, the oil is soybean oil without antioxidant, and the fat-soluble tea polyphenols are prepared as follows: in the presence of a solvent, mixing water-soluble tea polyphenol: palmitoyl chloride = 1: 6 with palmitoyl chloride.
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| CN103891922A (en) * | 2012-12-26 | 2014-07-02 | 丰益(上海)生物技术研发中心有限公司 | Edible oil composition containing water soluble antioxidant and preparation method thereof |
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