WO2025145409A1

WO2025145409A1 - Deodorized oils with phosphatidylserine

Info

Publication number: WO2025145409A1
Application number: PCT/CN2024/070698
Authority: WO
Inventors: Zhenyu Zhao; Zhukun MA; Weilin XUE; Junyin CHEN; Zhaolin HAO; Jinjin ZHOU
Original assignee: Cargill Inc
Current assignee: Cargill Inc
Priority date: 2024-01-05
Filing date: 2024-01-05
Publication date: 2025-07-10
Anticipated expiration: 2026-07-05
Also published as: WO2025145409A8

Abstract

An oil composition comprises deodorized oil and phosphatidylserine and a food product comprises the said oil composition. It describes a process for reducing the content of glycidyl esters (GE) in a deodorized oil, and the process is comprising the following step: adding phosphatidylserine to a deodorized oil. It further relates to the use of phosphatidylserine to reduce the content of glycidyl esters (GE) in a deodorized oil.

Description

DEODORIZED OILS WITH PHOSPHATIDYLSERINE

Field of the Invention

Use of phosphatidylserine to reduce unwanted contaminants, such as 3-MCPD fatty esters.

Background of the Invention

Crude oils, as extracted from their original source, are not suitable for human consumption due to the presence of high levels of contaminants -such as free fatty acids, phosphatides, soaps and pigments -which may be either toxic or may cause an undesirable color, odor or taste. Crude oils are therefore refined before use. The refining process typically consists of the following major steps: degumming and/or alkali refining, bleaching and deodorizing. An oil obtained after completion of the refining process (called a “NBD” or “RBD oil” ) is normally considered suitable for human consumption and may therefore be used in the production of any number of foods and beverages.

Unfortunately, it has now been found that the refining process itself contributes to the introduction, of high levels of unwanted propanol components into the refined oil.

A lot of efforts have been taken to reduce the levels of these unwanted propanol components such as free epoxypropanols, epoxypropanol fatty acid esters. A lot of diverse processes have been developed in order to avoid, to mitigate or to reduce the content of these unwanted propanol components. These diverse processes each have been concerned with amending the process conditions of at least one or more of the standard refining steps.

There is still a need for a process allowing to obtain a deodorized oil with reduced amounts of these unwanted propanol components, while maintaining high quality in all other aspects of the oil.

The current invention provides such a process and such an oil.

Summary of the Invention

The current invention relates to an oil composition of deodorized oil and phosphatidylserine.

It further relates to a process for reducing the content of glycidyl esters (GE) in a deodorized oil, and the process is comprising the following step: a) Adding phosphatidylserine to a deodorized oil.

The current invention further relates to a food product comprising food ingredients and the oil composition of the present invention.

Finally, it relates to the use of phosphatidylserine to reduce the content of glycidyl esters (GE) in a deodorized oil.

Detailed Description

The deodorized oil is a vegetable oil that has been deodorized. The vegetable oil may be derived from any vegetable oils or vegetable oil blends. 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 seed oil, rice bran oil, coconut oil, canola 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.

The vegetable oil that is derived from palm oil is encompassing palm oil, palm oil fractions such as stearin and olein fractions (single as well as double fractionated, and palm mid fractions) and blends of palm oil and/or its fractions.

Phosphatidylserine is a phospholipid-more specifically a glycerophospholipid-which consists of two fatty acids attached in ester linkage to the first and second carbon of glycerol and serine attached through a phosphodiester linkage to the third carbon of the glycerol.

The current invention relates to the oil composition wherein the phosphatidylserine is present in an amount of from 0.1 to 0.8%, from 0.2 to 0.7%, preferably from 0.3 to 0.5%based on the weight of the deodorized oil.

The current invention relates to the oil composition wherein the oil composition has a content of glycidyl esters (GE) of not more than 0.75 ppm.

Unless specified otherwise, the content of the unwanted propanol components as mentioned above will be determined using Method DGF Standard Methods Section C (Fats) C-VI 18 (10) .

The oil present in the oil composition of the present invention is a deodorized oil.

Deodorising

Deodorization is a process whereby free fatty acids (FFAs) and other volatile impurities are removed by treating (or "stripping" ) a crude or partially refined oil with steam, nitrogen or other inert gasses. The deodorising process and its many variations and manipulations are well known in the art. Preferably, it will include introducing the oil into a deodoriser and contacting it with steam to vaporize and drive off free fatty acids (FFAs) and other volatile impurities, resulting in a deodorised oil and a vapour stream.

The deodoriser may be any of a wide variety of commercially available deodorizing systems, including both multi-chamber deodorisers (such as those sold by Krupp of Hamburg, Germany; De Smet Group, S A. of Brussels, Belgium; Gianazza Technology s.r.l. of Legnano, Italy; Alfa Laval AB of Lund, Sweden, or others) and multi-tray deodorisers (such as those sold by Krupp, DeSmet Group, S.A., and Crown Ironworks of the United States) .

The deodoriser is desirably maintained at an elevated temperature and a reduced pressure to better volatilise the FFAs and other volatile impurities. Most often, the deodoriser will be maintained at a pressure of no greater than 10 mm Hg. Preferably, it will be maintained at a pressure of no greater than 5 mm Hg, e.g., 1-4 mm Hg.

The temperature in the deodorizer may be varied as desired to optimize the yield and quality of the deodorized oil. At higher temperatures, reactions which may degrade the quality of the oil will proceed more quickly. For example, at higher temperatures, cis-fatty acids may be converted into their less desirable trans form. Operating the deodorizer at lower temperatures may minimize the cis-to-trans conversion, and may also reduce the formation of contaminants that are formed in the refining process. The lower deodorization temperature will generally take longer or require more stripping medium or lower pressure to remove the requisite percentage of volatile impurities.

As such, deodorization which is used for obtaining the deodorized oil is performed at a temperature in a range of below 180 to up to 270℃, with temperatures of about 220-260℃ being useful for many oils (note: the temperatures reflect the temperatures reached by the oils in the deodorizer rather than, for example, that of the steam used during the process) .

By conducting the deodorization at a temperature (in the deodoriser) of below 230℃, between 180℃ and 230℃, between from 220℃ to 225℃, the amount of formed contaminants is lower then when conducting the deodorization at higher temperatures.

The present invention relates to a process for reducing the content of glycidyl esters (GE) in a deodorized oil, and the process is comprising the following step: a) adding phosphatidylserine to a deodorized oil.

The deodorized oil of step a) has a temperature of more than 110℃, preferably more than 120℃, more preferably more than 130℃ up to 140℃.

The phosphatidylserine is added to the deodorized oil at a temperature of more than 110℃, preferably more than 120℃, more preferably more than 130℃ up to 140℃, and the thus obtained oil composition is kept for a few minutes, such as 2 to 15 minutes, 5 to 15 minutes at this temperature.

In an aspect of the invention, the process is comprising the sequence of the following steps:

a) Degumming step;

b) Optionally neutralisation step;

c) Bleaching step;

d) Deodorizing step for obtaining refined, deodorized oil;

e) Adding phosphatidylserine to the refined, deodorized oil obtained in step d) ;

f) Collecting the deodorized oil of step e) .

These steps are here outlined below.

Degumming

Any of a variety of degumming processes known in the art may be used. One such process (known as "water degumming" ) includes mixing water optionally containing acid such as citric acid and/or phosphoric acid, with the crude oil and separating the resulting mixture into an oil component and an oil-insoluble hydrated phosphatides component, sometimes referred to as "wet gum" or "wet lecithin" . Alternatively, phosphatide content can be reduced (or further reduced) by other degumming processes, such as acid degumming, enzymatic degumming (e.g., ENZYMAX from Lurgi) or chemical degumming (e.g., SUPERIUNI degumming from Unilever or TOP degumming from VandeMoortele/Dijkstra CS) .

Neutralization Step (optional)

If so desired, crude or degummed oil may be refined via a neutralisation step (= alkali refining) . In alkali refining, the oil is commonly mixed with a hot, aqueous alkali solution, producing a mixture of partially refined or "neutral" oil and soapstock. The soapstock is then separated off and the partially refined oil is delivered to the next refining step.

Bleaching

The crude or partially refined oil may then be delivered to 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 raw or partially refined oil will be mixed with a bleaching agent which combines with oxidation products, trace phosphatides, trace soaps, and other compounds adversely affecting the colour and flavour of the oil. While in general bleaching may have an effect on the colour, it is known in the art that chlorophyll (green) must be reduced during the bleaching process, and carotenoids (orange) are usually reduced in later steps (such as deodorization step) of the oil refining process. As is known in the art, the nature of the bleaching agent can be selected to match the nature of the crude or partially refined oil to yield a desirable bleached oil. Bleaching agents generally include neutral, non-activated bleaching agent, or "activated" bleaching clays, also referred to as "bleaching earths" , activated carbon and various silicates and zeolites. A skilled person will be able to select a suitable bleaching agent from those that are commercially available. Typically, the bleaching temperature ranges from 90 to 110℃.

In a regular bleaching step, the bleaching agent is added in an amount of 0.8 to 1.5%based upon weight of vegetable oil.

Furthermore, the current invention relates to a food product comprising food ingredients and the oil composition of the present invention. More in particular, the food product of the current invention is infant food, food for elderly people, confectionary, frying oil, table oil or salad dressing.

Infant food is a term well-known in the art and it refers to food that is specifically manufactured for infants and it may be characterized in that is soft, and easily consumable by infants and has a nutritional composition adapted to the specific needs at each growth stage.

Food for elderly people is a term well-known in the art and it is taking into account the nutritional needs of elderly people. Food for elderly people is a calorically dense formulation that provides increased energy and nutrition with minimum amount of fluid.

Confectionery or confectionary is a category of food products that are well-known and include without any limitation sweet food products, bakery products, sweets, candies, chocolate and the like.

Frying oil, table oil or salad dressing are oils or blends of oils that are particular suitable for hot preparations such as frying or cold preparations such as table oils and/or oils in dressings such as salad dressings and the like.

Finally, the current invention relates to the use of phosphatidylserine to reduce the content of glycidyl esters (GE) in a deodorized oil.

It relates to the use wherein the content of glycidyl esters (GE) in a deodorized oil is reduced with at least 7%, preferably at least 20%, more preferably at least 50%. IN a specific aspect of the invention, reduction of from 60 to 66%is observed.

In an aspect of the invention it is shown that the oil composition has improved antioxidant properties.

In fact, the current invention clearly has demonstrated that the claimed process allows obtaining an oil composition with reduced content of unwanted propanol components, in particular reduced content of glycidyl esters (GE) . Surprisingly it was found that phosphatidylserine allows reducing content of unwanted propanol components, in particular reduced content of glycidyl esters (GE) , and is improving the oxidative stability of the deodorized oil.

The invention will hereunder be illustrated in following examples.

Examples

Methodology

Acid Value

Weigh about 20 grams of oil, add neutralized isopropyl alcohol solution to dissolve, then use potassium hydroxide standard solution to record the volume required for titration to the end point of the reaction, and calculate it by the following formula:
AV (mg/g) = (V×N×56.1) /W

In the formula:

AV--acid value, in milligrams per gram (mg/g)

V--The volume of standard titration solution consumed for sample measurement, in milliliters (mL)

N--The molar concentration of sodium hydroxide standard titration solution, in moles per liter (mol/L)

56.1--Molar mass of potassium hydroxide, unit is grams per mole (g/mol) ;

W--The weighing quantity of the oil sample, in grams (g) .

Qxidative stability index (OSI)

The oxidative stability index of each oil is tested in accordance with the Rancimat method. The instrument used is 892 Oxidation Stabilizer.

The experimental principle is: pass purified air into a sample that has been heated to a specified temperature and a specified weight. The gas released during the oxidation process is mixed with the air and then introduced into a long-neck bottle. The bottle is pre-filled with deionized water or distilled water and an electrode for measuring conductivity, which is connected to a measuring and recording instrument. During the oxidation process, the conductivity increases rapidly due to the volatile carboxylic acid substances. When the conductivity begins to increase rapidly, it indicates the end of the induction period. Record the time on the instrument, which is the OSI result.

Example 1

The deodorized oil was heated to a temperature of just above 130℃, the corresponding amount (see table) of phosphatidylserine was added, and the oil composition containing the deodorized oil and phosphatidylserine was maintained at temperature above 130℃, while stirring (stirrer speed of 200 rpm) for about 5 to 10 minutes. Phosphatidylserine was evenly dissolved in oil.

The obtained results are shown in table 1

Table 1

RROL58 = Re-Refined Olein 58, Palm oil with an iodine value of 58.

PS = phosphatidylserine

AV mg KOH/g –is acid value in mg KOH/g.

Compared to sample A (Reference) , the OSI of sample B, C, D is increased by 5.86 hours, 10.14hours, 7.42hours respectively.

Compared to sample A (Reference) , the content GE of sample B, C, D is decreased by 136ppb, 230ppb, 302ppb respectively.

Compared to sample A (Reference) , the acid value of sample B, C, D is increased by 0.04mgKOH/g, 0.18mgKOH/g, 0.25mgKOH/g, respectively.

Claims

An oil composition of deodorized oil and phosphatidylserine.
The oil composition of claim 1 wherein the phosphatidylserine is present in an amount of 0.1 to 0.8%.
The oil composition according to claim 1 or 2 wherein the oil composition has a content of glycidyl esters (GE) of not more than 0.75 ppm.
A process for reducing the content of glycidyl esters (GE) in a deodorized oil, and the process is comprising the following step:

a) Adding phosphatidylserine to a deodorized oil.
The process according to claim 4 wherein the deodorized oil of step a) has a temperature of more than 110℃.
The process according to anyone of claims 4 to 5 wherein the process is comprising the sequence of the following steps:

a) Degumming step;

b) Optionally neutralisation step;

c) Bleaching step;

d) Deodorizing step for obtaining refined, deodorized oil;

e) Adding phosphatidylserine to the refined, deodorized oil obtained in step d) ;

f) Collecting the deodorized oil of step e) .
The process according to anyone of claims 4 to 6 wherein the bleaching step is using bleaching agent selected from neutral, non-activated bleaching agent, activated bleaching clay, silicates, zeolites.
The process according to anyone of claims 4 to 7 wherein the degumming is using a degumming agent selected from water, citric acid, phosphoric acid or mixtures thereof.
The process according to anyone of claims 4 to 8 wherein the deodorization step is taking place at a temperature of from 180℃ to 270℃.
A food product comprising food ingredients and the oil composition according to anyone of claims 1 to 3.
The food product according to claim 10 wherein the food product is infant food, food for elderly people, confectionary, frying oil, table oil or salad dressing.
Use of phosphatidylserine to reduce the content of glycidyl esters (GE) in a deodorized oil.
Use according to claim 12 wherein content of glycidyl esters (GE) in a deodorized oil is reduced with at least 10%.