Deodorized oil containing phosphatidylserine
By adding phosphatidylserine to deodorized oil and treating it at a specific temperature, combined with conventional refining steps, the problem of high GE content in deodorized oil was solved, resulting in reduced GE content and improved oil quality.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- CARGILL INC
- Filing Date
- 2024-01-05
- Publication Date
- 2026-07-31
AI Technical Summary
Existing refining methods can lead to the introduction of high levels of undesirable propanol components, especially glycidyl esters (GE), into deodorized oils, while making it difficult to reduce their content while maintaining oil quality.
Phosphatidylserine is added to deodorized oil and kept at a specific temperature for several minutes, combined with conventional degumming, alkali refining and bleaching steps, to form an oil composition to reduce GE content.
It significantly reduces the glycidyl ester (GE) content in deodorized oil, improves the oxidative stability of the oil, and maintains high quality in other aspects.
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Abstract
Description
Technical Field
[0001] Phosphatidylserine is used to reduce unwanted contaminants such as 3-MCPD fatty esters. Background Technology
[0002] Crude oils extracted from their original sources are unsuitable for human consumption due to the presence of high levels of contaminants—such as free fatty acids, phospholipids, soaps, and pigments—that can be toxic or cause undesirable color, odor, or taste. Therefore, crude oils are refined before use. Refining methods typically consist of the following main steps: degumming and / or alkali refining, bleaching, and deodorization. The oil obtained after refining (referred to as “NBD” or “RBD oil”) is generally considered suitable for human consumption and is therefore suitable for the production of many food and beverage products.
[0003] Unfortunately, it has now been found that the refining process itself can lead to the introduction of high levels of undesirable propanol components into the refined oil.
[0004] Numerous efforts have been made to reduce the levels of these undesirable propanol components, such as free chloropropanol and chloropropanol fatty acid esters. Several different processes have been developed to avoid, mitigate, or reduce the content of these undesirable propanol components. Each of these different processes involves modifying the process conditions of at least one or more steps in the standard refining process.
[0005] There is still a need for methods that can produce deodorized oils with reduced amounts of these undesirable propanol components while maintaining high quality in all other respects of the oil.
[0006] This invention provides such a method and such an oil. Summary of the Invention
[0007] This invention relates to an oil composition of deodorized oil and phosphatidylserine.
[0008] The present invention also relates to a method for reducing the content of glycidyl esters (GE) in deodorized oil, and the method includes the following steps: a) adding phosphatidylserine to the deodorized oil.
[0009] The present invention also relates to a food product comprising food ingredients and the oil composition of the present invention.
[0010] Finally, the present invention relates to the use of phosphatidylserine for reducing the content of glycidyl esters (GE) in deodorized oils. Detailed Implementation
[0011] This invention relates to an oil composition of deodorized oil and phosphatidylserine.
[0012] Deodorized oil is a vegetable oil that has been deodorized. The vegetable oil can be derived from any vegetable oil or blend of vegetable oils. Examples of suitable vegetable oils include: soybean oil, corn oil, cottonseed oil, palm oil, palm kernel oil, peanut oil, rapeseed oil, safflower oil, sunflower oil, sesame oil, rice bran oil, coconut oil, low-erucic acid rapeseed oil, and any fractions or derivatives thereof. According to a particularly preferred aspect of the invention, the vegetable oil will be derived from palm oil.
[0013] Vegetable oils derived from palm oil encompass palm oil, palm oil extracts such as stearic acid and palm oil extracts (both single and double extracts, as well as intermediate palm extracts), and blends of palm oil and / or its extracts.
[0014] Phosphatidylserine is a phospholipid, more specifically a glycerophospholipid, composed of two fatty acids and serine. The fatty acids are linked to the first and second carbons of glycerol via ester bonds, while the serine is linked to the third carbon of glycerol via phosphodiester bonds.
[0015] This invention relates to an oil composition wherein phosphatidylserine is present in an amount of 0.1% to 0.8%, 0.2% to 0.7%, preferably 0.3% to 0.5% based on the weight of the deodorized oil.
[0016] This invention relates to oil compositions having a glycidyl ester (GE) content of not more than 0.75 ppm.
[0017] Unless otherwise specified, the content of the undesirable propanol component as described above will be determined using method DGF standard method section C(Fats)C-VI 18(10).
[0018] The oil present in the oil composition of the present invention is a deodorized oil.
[0019] Deodorize
[0020] Deodorization is a process in which free fatty acids (FFA) and other volatile impurities are removed by treating crude or partially refined oil with steam, nitrogen, or other inert gases (or "back-extraction"). Deodorization processes and their many variations and operations are well known in the art. Preferably, it involves introducing oil into a deodorizer and contacting it with steam to evaporate and remove free fatty acids (FFA) and other volatile impurities, thereby producing a deodorized oil and steam stream.
[0021] The deodorizer can be any of a variety of commercially available deodorization systems, including multi-chamber deodorizers (such as those sold by Krupp (Hamburg, Germany), De Smet Group, SA. (Brussels, Belgium), Gianazza Technology srl (Legnano, Italy), Alfa Laval AB (Lund, Sweden) or others) and multi-disc deodorizers (such as those sold by Krupp, De Smet Group, SA and Crown Ironworks (the United States)).
[0022] The deodorizer is advantageously maintained at high temperature and reduced pressure to allow for better volatilization of FFA and other volatile impurities. Most commonly, the deodorizer will be maintained at a pressure not exceeding 10 mm Hg. Preferably, it will be maintained at a pressure not exceeding 5 mm Hg (e.g., 1-4 mm Hg).
[0023] The temperature within the deodorizer can be adjusted as needed to optimize the yield and quality of the deodorized oil. At higher temperatures, reactions that could potentially reduce oil quality will proceed more rapidly. For example, at higher temperatures, cis fatty acids can be converted to their less desirable trans forms. Operating the deodorizer at lower temperatures minimizes the cis-to-trans conversion and also reduces the formation of contaminants that occur during refining. Lower deodorization temperatures typically require longer processing times or more stripping media or lower pressures to remove the desired percentage of volatile impurities.
[0024] Therefore, the deodorization used to obtain deodorized oil is carried out at temperatures ranging from below 180°C to a maximum of 270°C, of which temperatures of about 220°C-260°C can be used for many oils (Note: the temperature reflects the temperature reached by the oil in the deodorizer, not the temperature of the steam used during the process, for example).
[0025] By deodorizing at temperatures below 230°C, 180°C to 230°C, and 220°C to 225°C (in the deodorizer), the amount of pollutants formed is lower than that formed when deodorizing at higher temperatures.
[0026] The present invention relates to a method for reducing the content of glycidyl esters (GE) in deodorized oil, and the method includes the following steps: a) adding phosphatidylserine to the deodorized oil.
[0027] The deodorized oil in step a) has a temperature of more than 110°C, preferably more than 120°C, more preferably more than 130°C to a maximum of 140°C.
[0028] Phosphatidylserine is added to the deodorized oil at a temperature exceeding 110°C, preferably exceeding 120°C, more preferably exceeding 130°C to a maximum of 140°C, and the resulting oil composition is maintained at that temperature for several minutes, such as 2 to 15 minutes, or 5 to 15 minutes.
[0029] In one aspect of the invention, the method includes the following steps in sequence:
[0030] a) Degumming step;
[0031] b) Optional neutralization steps;
[0032] c) Bleaching steps;
[0033] d) A deodorization step to obtain a refined deodorized oil;
[0034] e) Add phosphatidylserine to the refined deodorized oil obtained in step d);
[0035] f) Collect the deodorized oil from step e).
[0036] These steps are outlined here.
[0037] Degumming
[0038] Any of the various degumming methods known in the art can be used. One such method (referred to as “water degumming”) involves mixing water (optionally containing an acid, such as citric acid or phosphoric acid) with crude oil and separating the resulting mixture into an oil component and an oil-insoluble hydrated phospholipid component, sometimes referred to as “wetting gel” or “wetting lecithin”. Alternatively, the phospholipid content can be reduced (or further reduced) by other degumming methods, such as acid degumming, enzymatic degumming (e.g., ENNYMAX from Lurgi), or chemical degumming (e.g., SUPERIUNI degumming from Unilever or TOP degumming from VandeMoortele / Dijkstra CS).
[0039] Neutralization step (optional)
[0040] If necessary, crude or degummed oils can be refined through a neutralization step (= alkali refining). In alkali refining, the oil is typically mixed with a hot, alkaline aqueous solution, resulting in a mixture of partially refined or "neutral" oil and soap stock. The soap stock is then separated, and a portion of the refined oil is sent to the next refining step.
[0041] bleach
[0042] The crude or partially refined oil can then be fed into a bleaching system. The nature and operation of the bleaching system will depend at least in part on the nature and quality of the oil being bleached. Generally, the crude or partially refined oil will be mixed with a bleaching agent, which is combined with oxidation products, trace amounts of phospholipids, trace amounts of soaps, and other compounds that adversely affect the color and flavor of the oil. Although bleaching can generally affect color, it is known in the art that chlorophyll (green) must be reduced during the bleaching process, and carotenoids (orange) are typically reduced in subsequent steps of the refining process, such as deodorization. As is known in the art, the properties of the bleaching agent can be selected to match the properties of the crude or partially refined oil to produce the desired bleached oil. Bleaching agents typically include neutral, non-activated bleaching agents, or “activated” bleaching clay (also known as “bleaching earth”), activated carbon, and various silicates and zeolites. Those skilled in the art will be able to select a suitable bleaching agent from those commercially available. Typically, the bleaching temperature is in the range of 90°C to 110°C.
[0043] In the standard bleaching process, the bleach is added in an amount of 0.8% to 1.5% of the vegetable oil by weight.
[0044] Furthermore, this invention relates to a food product comprising food ingredients and the oil composition of the present invention. More specifically, the food product of the present invention is infant food, food for the elderly, confectionery, frying oil, edible oil, or salad dressing.
[0045] Infant food is a well-known term in the field, and it refers to food specifically made for infants, characterized by being soft and easy for infants to eat, and having a nutritional composition suitable for the specific needs of each stage of growth.
[0046] Food for the elderly is a well-known term in the field, and it takes into account the nutritional needs of older adults. Food for the elderly is a calorie-dense formula that provides increased energy and nutrition with minimal fluidity.
[0047] Candy or sweets are a well-known category of food products, including but not limited to sweet food products, baked goods, sweet snacks, candies, chocolates, etc.
[0048] Frying oil, cooking oil or salad dressing refers to oil or mixtures of oils that are particularly suitable for use in hot products (such as frying) or cold products (such as cooking oil and / or oils in seasonings such as salad dressings).
[0049] Finally, the present invention relates to the use of phosphatidylserine for reducing the content of glycidyl esters (GE) in deodorized oils.
[0050] This invention relates to the use of deodorized oils in which the content of glycidyl esters (GE) is reduced by at least 7%, preferably at least 20%, and more preferably at least 50%. In one specific aspect of the invention, a reduction of 60% to 66% has been observed.
[0051] In one aspect of the invention, the oil composition is shown to have improved antioxidant properties.
[0052] In fact, the present invention clearly demonstrates that the claimed method allows for obtaining oil compositions with reduced content of undesirable propanol components, particularly reduced content of glycidyl esters (GE). Surprisingly, phosphatidylserine has been found to allow for a reduction in the content of undesirable propanol components, particularly reduced content of glycidyl esters (GE), and to improve the oxidative stability of the deodorized oil.
[0053] The present invention will be described in the following embodiments.
[0054] Example
[0055] method
[0056] acid value
[0057] Weigh approximately 20 grams of oil, dissolve it in neutral isopropanol solution, then titrate to the reaction endpoint using potassium hydroxide standard solution and record the volume required. Calculate the volume using the following formula:
[0058] AV (mg / g) = (V×N×56.1) / W
[0059] In this formula:
[0060] AV—Acid value, expressed in milligrams per gram (mg / g).
[0061] V—The volume of standard titration solution consumed in the sample measurement, in milliliters (mL).
[0062] The molar concentration of the N-sodium hydroxide standard titration solution, expressed in moles per liter (mol / L).
[0063] 56.1 — Molar mass of potassium hydroxide, in grams per mole (g / mol);
[0064] W—Weight of the oil sample, expressed in grams (g).
[0065] Oxidative Stability Index (OSI)
[0066] The oxidation stability index of each oil was tested according to the Rancimat method. The instrument used was an 892 Oxidation Stabilizer.
[0067] The experimental principle is as follows: Purified air is introduced into a sample heated to a specified temperature and weight. Gases released during the oxidation process mix with the air and are then introduced into a long-necked flask. This flask is pre-filled with deionized or distilled water and electrodes for measuring conductivity, which are connected to a measuring and recording instrument. During the oxidation process, conductivity increases rapidly due to volatile carboxylic acids. The point at which conductivity begins to increase rapidly indicates the end of the induction period. The time recorded on the instrument is the OSI result.
[0068] Example 1
[0069] Heat the deodorized oil to a temperature slightly above 130°C, add the appropriate amount of phosphatidylserine (see table), and maintain the oil composition containing the deodorized oil and phosphatidylserine at a temperature above 130°C while stirring (stirrer speed 200 rpm) for about 5 to 10 minutes. The phosphatidylserine is uniformly dissolved in the oil.
[0070] The results are shown in Table 1.
[0071] Table 1
[0072]
[0073] RROL58 = Refined Palm Oil 58, which is palm oil with an iodine value of 58.
[0074] PS = Phosphatidylserine
[0075] AV mg KOH / g — Acid value expressed in mg KOH / g.
[0076] Compared with sample A (reference), the OSI of samples B, C and D increased by 5.86 hours, 10.14 hours and 7.42 hours, respectively.
[0077] Compared with sample A (reference), the GE content of samples B, C and D decreased by 136 ppb, 230 ppb and 302 ppb, respectively.
[0078] Compared with sample A (reference), the acid values of samples B, C, and D increased by 0.04 mg KOH / g, 0.18 mg KOH / g, and 0.25 mg KOH / g, respectively.
Claims
1. An oil composition of deodorized oil and phosphatidylserine.
2. The oil composition according to claim 1, wherein the phosphatidylserine is present in an amount of 0.1% to 0.8%.
3. The oil composition according to claim 1 or 2, wherein the oil composition has a glycidyl ester (GE) content of not more than 0.75 ppm.
4. A method for reducing the content of glycidyl esters (GE) in deodorized oil, the method comprising the following steps: a) Add phosphatidylserine to the deodorized oil.
5. The method according to claim 4, wherein the deodorized oil in step a) has a temperature exceeding 110°C.
6. The method according to any one of claims 4 to 5, wherein the method comprises the following steps in sequence: a) Degumming step; b) Optional neutralization steps; c) Bleaching steps; d) Deodorization step, used to obtain refined deodorized oil; e) Add phosphatidylserine to the refined deodorized oil obtained in step d); f) Collect the deodorized oil from step e).
7. The method according to any one of claims 4 to 6, wherein the bleaching step uses a bleaching agent selected from neutral, non-activated bleaching agents, activated bleaching clays, silicates, and zeolites.
8. The method according to any one of claims 4 to 7, wherein the degumming uses a degumming agent selected from water, citric acid, phosphoric acid, or mixtures thereof.
9. The method according to any one of claims 4 to 8, wherein the deodorization step is performed at a temperature of 180°C to 270°C.
10. A food product comprising food ingredients and an oil composition according to any one of claims 1 to 3.
11. The food product of claim 10, wherein the food product is infant food, food for the elderly, confectionery, frying oil, cooking oil, or salad dressing.
12. Use of phosphatidylserine to reduce the content of glycidyl esters (GE) in deodorized oils.
13. The use according to claim 12, wherein the content of glycidyl esters (GE) in the deodorized oil is reduced by at least 10%.