KR20240087358A - A composition for reducing hazardous substances in oils - Google Patents

Abstract

This application relates to a composition for reducing hazardous substances derived from fatty acids in oil and fat.

Description

{A composition for reducing hazardous substances in oils}

This application relates to a composition for reducing hazardous substances derived from fatty acids in oil and fat.

Generally, when producing edible oil, a refining process including degumming, deacidifying, decolorizing, and deodorizing steps is performed. Among edible oils, many vegetable oils such as palm oil contain fatty acids, which are converted into glycidyl fatty acid esters (GEs) and 3-monochloropropane during the high-temperature refining process (over 160°C or 200°C). It is converted to diol esters (3-Monochloropropane-1,2-diol esters, 3-MCPDE). In particular, the GEs and 3-MCPDE are known to be produced in large quantities under high temperature conditions during deodorization during the purification process.

The generated GEs and 3-MCPDE are decomposed in the body when ingested and absorbed in the form of non-ester forms of glycidol and 3-monochloropropanediol (3-MCPD), respectively, which are reported by the International Agency for Research on Cancer (IARC). It is a carcinogen classified as Group 2A and Group 2B, and all are hazardous substances. Specifically, 3-MCPD and glycidol have been reported to cause tumors in animal experiments, and have recently been reported to be toxic to humans (P.-W. Liu et al., Journal of Hazardous Materials 405, 2021). In addition, the WHO's Food Additives Subcommittee recognizes GEs and 3-MCPDE as 'undesirable contaminants whose concentrations should be reduced as much as possible.'

As these substance evaluation and risk research results accumulate, the European Union (EU) is establishing and managing 'permission standards for hazardous substances derived from fatty acids in food', and discussions on reducing hazardous substances derived from fatty acids are continuing in Korea.

Accordingly, edible oil manufacturers are taking various methods, such as changing the manufacturing process, adjusting process conditions (temperature, time, etc.), and using emulsifiers, adsorbents, and enzymes to reduce the generation of hazardous substances such as 3-MCPDE and GEs. . When changing process conditions and using adsorbents, the occurrence of GEs was effectively reduced. However, there is still no significant reduction method for 3-MCPDE.

One object of the present application is to provide a composition for reducing the content of 3-monochloropropanediol ester in oil containing rosemary extract and vitamin C.

Another object of the present application is to reduce the 3-monochloropropanediol ester content, including adding a composition for reducing the 3-monochloropropanediol ester content in oil and fat containing rosemary extract and vitamin C during the purification process of oil and fat. A method for producing this reduced fat and oil is provided.

Another object of the present application is to produce 3-monochloropropanediol ester in oil and fat, prepared by adding a composition for reducing the content of 3-monochloropropanediol ester in oil and fat containing rosemary extract and vitamin C during the refining process of oil and fat. The aim is to provide fats and oils with reduced content.

This is explained in detail as follows. Meanwhile, each description and embodiment disclosed in this application may also be applied to each other description and embodiment. That is, all combinations of the various elements disclosed in this application fall within the scope of this application. Additionally, the scope of the present application cannot be considered limited by the specific description described below. Additionally, numerous papers and patent documents are referenced and citations are indicated throughout this specification. The disclosures of the cited papers and patent documents are incorporated by reference into this specification in their entirety to more clearly explain the content of this application and the level of technical field to which this application belongs.

One aspect of the present application provides a composition for reducing the content of 3-monochloropropane-1,2-diol esters (3-MCPDE) in oil containing rosemary extract and vitamin C.

In this application, the term "3-Monochloropropane-1,2-diol esters (3-MCPDE)" refers to an ester bonded to 3-monochloropropanediol (3-MCPD), When ingested, it is decomposed in the body and absorbed in the form of non-esterified 3-monochloropropanediol. These are carcinogens classified as Group 2A and Group 2B by the International Agency for Research on Cancer (IARC), respectively, and are all hazardous substances.

Among edible oils, many vegetable oils such as palm oil contain fatty acids, and during the high-temperature refining process, fatty acids are converted into hazardous substances such as 3-monochloropropanediol ester and glycidyl fatty acid esters (GEs). It is known to be converted. Accordingly, edible oil manufacturers are using various methods such as changing the manufacturing process, adjusting process conditions (temperature, time, etc.), and using emulsifiers, adsorbents, and enzymes to reduce the generation of hazardous substances such as 3-monochloropropanediol ester. However, there is still no significant reduction method for 3-monochloropropanediol ester.

Accordingly, the present application is significant in providing a composition that can reduce the content of 3-monochloropropanediol ester in oil produced during the refining process of edible oil.

In the present application, the oil may be edible. As an example, the oil of the present application may be an edible oil containing fatty acids. For example, the oil of this application may be palm olein oil, palm oil, brown rice oil, soybean oil, sunflower oil, grape seed oil, canola oil, etc., but is not limited thereto.

The composition of the present application may contain 70 to 90% by weight of rosemary extract based on the total weight of the composition for reducing the content of 3-monochloropropanediol ester in fat.

As an example, the rosemary extract is 70% by weight or more, 71% by weight or more, 72% by weight or more, 73% by weight or more, 74% by weight or more, 75% by weight based on the total weight of the composition for reducing the content of 3-monochloropropanediol ester in fat. One lower limit selected from wt% or more, 76 wt% or more, 77 wt% or more, 78 wt% or more and 79 wt% or more and/or 90 wt% or less, 89 wt% or less, 88 wt% or less, 87 wt% or less. , may be included in a range consisting of one upper limit selected from 86 wt% or less, 85 wt% or less, 84 wt% or less, 83 wt% or less, 82 wt% or less, and 81 wt% or less.

The term "extract" in this application refers to a liquid component obtained by immersing the target material in various solvents and then extracting it at room temperature, low temperature, or heated state for a certain period of time, and a liquid component obtained by removing the solvent from the liquid component. It refers to the result of solid content, etc. In addition, in addition to the above results, it can be comprehensively interpreted to include all dilutions of the results, concentrates thereof, crude preparations, purifications, etc. of the above results.

In the present application, the extract may be an extract of rosemary ( Salvia rosmarinus ). The extract can be obtained by extraction with water or various organic solvents such as media and alcohol. At this time, the organic solvent used is not particularly limited as long as it can obtain an extract, but may specifically be water, a polar solvent, or a non-polar solvent, and more specifically, water, a medium, or a low-grade solvent with 1 to 6 carbon atoms. It may be alcohol (C1 to C6, for example, methanol, ethanol, propanol, or butanol, etc.), or a mixed solvent thereof.

In addition, the method for obtaining the extract is not particularly limited as long as the extract of rosemary can be obtained, and extraction can be performed according to a method commonly used in the art. For example, the above methods include hot water extraction, ultrasonic extraction, filtration, reflux extraction, and supercritical extraction, and may be performed alone or in combination of two or more methods, but are not limited thereto.

The rosemary extract can be purchased and used commercially, or an extract obtained from rosemary collected or cultivated in nature can be used. Alternatively, various compositions containing rosemary extract can be used. For example, the rosemary extract may be Kemin's FORTIUM R40 product, but is not limited thereto.

Rosemary of the present application may be included in the composition of the present application in the form of not only its extract, but also rosemary itself, its dried product, fermented broth, or fraction, but is not limited thereto.

The composition of the present application may contain 10 to 30% by weight of vitamin C based on the total weight of the composition for reducing the content of 3-monochloropropanediol ester in fat.

As an example, the vitamin C is 10% by weight or more, 11% by weight or more, 12% by weight or more, 13% by weight or more, 14% by weight or more, 15% by weight or more, based on the total weight of the composition for reducing the content of 3-monochloropropanediol ester in fat. One lower limit selected from wt% or more, 16 wt% or more, 17 wt% or more, 18 wt% or more and 19 wt% or more and/or 30 wt% or less, 29 wt% or less, 28 wt% or less, 27 wt% or less. , 26 wt% or less, 25 wt% or less, 24 wt% or less, 23 wt% or less, 22 wt% or less, and 21 wt% or less.

The vitamin C may be naturally derived vitamin C extracted from plants that contain vitamin C and are collected or cultivated in nature. Alternatively, the vitamin C may be chemically synthesized synthetic vitamin C. The vitamin C can be purchased and used commercially. For example, the vitamin C may be a synthetic vitamin C product from DSM, or it may be vitamin C prepared by freeze-drying an extract from acerola ( Malpighia emarginata ) containing vitamin C, but is not limited thereto.

The purity of vitamin C may be 10% or more, specifically 20% or more.

If the composition of the present application contains the rosemary extract and vitamin C in amounts outside the above content range, a problem may occur in which the effect of reducing the 3-monochloropropanediol ester content in the oil is reduced.

The composition of the present application may be added during the refining process of fats and oils.

The purification process of the fat may include one or more, two or more or three or more steps selected from the group consisting of a degumming step, a deacidifying step, a decolorizing step and a deodorizing step, and any purification process known in the art may be included within the scope of the present invention. there is.

In the present application, there is no time interval between the steps such as the degumming step, the deoxidizing step, the decolorizing step, and the deodorizing step, or they may be performed simultaneously, or may be performed at arbitrary intervals such as several seconds, several minutes, and several hours. .

The degumming, deacidification, decolorization, and deodorization can be performed by methods known in the art, and are not particularly limited as long as the degumming, deacidification, decolorization, and deodorization methods can produce food.

In one embodiment, the composition of the present application may be added before the deodorization step during the oil refining process.

In another embodiment, the composition of the present application may be added to fats and oils at a concentration of 500 ppm or less.

As an example, the composition of the present application is 500ppm or less, 490ppm or less, 480ppm or less, 470ppm or less, 460ppm or less, 450ppm or less, 440ppm or less, 430ppm or less, 420ppm or less, 410ppm or less, 400ppm or less, 380ppm or less, 370ppm or less, 360ppm or less, and It may be added to the fat or oil at a concentration ranging from 350 ppm or less to a selected upper limit.

In another embodiment, the composition of the present application may reduce the content of 3-monochloropropanediol ester in oil to 2,000 μg/kg or less.

As an example, the composition of the present application has a content of 3-monochloropropanediol ester in the oil of 2,000 ㎍/kg or less, 1,995 ㎍/kg or less, 1,990 ㎍/kg or less, 1,980 ㎍/kg or less, 1,970 ㎍/kg or less, 1,960 ㎍/㎏ or less, 1,950 ㎍/㎏ or less, 1,900 ㎍/㎏ or less, 1,850 ㎍/㎏ or less, 1,800 ㎍/㎏ or less, 1,750 ㎍/㎏ or less, 1,700 ㎍/㎏ or less, 1,650 ㎍/ Less than 1 kg and 1,600 ㎍ It can be included in a range consisting of one upper limit selected from /kg or less.

Another aspect of the present application includes the step of adding a composition for reducing the 3-monochloropropanediol ester content in oil and fat containing rosemary extract and vitamin C during the purification process of oil and fat, 3-monochloropropanediol ester content. A method for producing this reduced fat and oil is provided.

The rosemary extract, vitamin C, and 3-monochloropropanediol ester are as described above.

The composition of the present application may be added before the deodorization step during the oil refining process. The purification process of the fat may include a degumming step, a deacidifying step, a decolorizing step, and a deodorizing step, which are as described above.

In one embodiment, the method

a) carrying out degumming, deacidifying and decolorizing steps on oils and fats;

b) adding the composition of the present application to the maintenance of a) above; may include.

In the method of the present application, there is no time interval between steps such as the degumming, deacidification, and decolorization steps of step a), or they may be performed simultaneously, or may be performed at arbitrary intervals such as several seconds, several minutes, and several hours. there is.

In the method of the present application, in step b), the composition of the present application may be added to the fat or oil at a concentration of 500 ppm or less, as described above.

In another embodiment, the method may further include the step of deodorizing the oil to which the composition of the present application has been added.

Another aspect of the present application is a 3-monochloropropanediol ester in oil and fat, prepared by adding a composition for reducing the content of 3-monochloropropanediol ester in oil and fat containing rosemary extract and vitamin C during the purification process of oil and fat. Provides oil with reduced content.

The rosemary extract, vitamin C, and 3-monochloropropanediol ester are as described above.

In the present application, the oil may be edible, as described above.

The composition of the present application may reduce the content of 3-monochloropropanediol ester in fats and oils to 2,000 μg/kg or less, and this is as described above.

When a deodorizing process is performed by adding the composition of the present application to edible oil and fat, 3-monochloropropanediol ester (3-Monochloropropane-1) in the edible oil and fat is compared to edible oil and fat where the deodorizing process is performed without adding the composition of the present application. , 2-diol esters, 3-MCPDE) are significantly reduced, making it possible to provide edible oil with reduced fatty acid-derived hazardous substances.

Hereinafter, the present application will be described in more detail through examples. However, the following examples are merely preferred embodiments for illustrating the present application and are therefore not intended to limit the scope of the present application thereto. Meanwhile, technical matters not described in this specification can be fully understood and easily implemented by anyone skilled in the technical field of this application or a similar technical field.

Example: Preparation of a composition for reducing hazardous substances in fats and oils

Example 1: Composition containing rosemary extract and vitamin C-1

Mix 80% (w/w) of rosemary extract (FORTIUM R40, Kemin) and 20% (w/w) of vitamin C (synthetic vitamin C (purity 20% or more), DSM) and mix with a homomixer (T.K. Homomixer mark) at 50°C. Example 1 was prepared by stirring at 1,000 rpm for 30 minutes using a II F model (Tokushu Kika Kogyo).

Example 2: Composition containing rosemary extract and vitamin C-2

Example 2 was prepared by mixing 90% (w/w) of rosemary extract and 10% (w/w) of vitamin C and stirring at 1,000 rpm for 30 minutes using a homomixer at 50°C.

Example 3: Composition containing rosemary extract and vitamin C-3

Example 3 was prepared by mixing 70% (w/w) of rosemary extract and 30% (w/w) of vitamin C and stirring at 50°C at 1,000 rpm for 30 minutes using a homomixer.

Example 4: Emulsifier-containing composition-1

Soy lecithin (Seyang Trading) 10 to 30% (w/w), glycerol monostearate (Glyceryl monooleate, GMS) (Ilshin Wells) 10 to 30% (w/w) and polyglycerol polyricinoleate Example 4 was prepared by mixing 40 to 80% (w/w) of (polyglycerol polyricinoleate, PGPR) (Ilshin Wells) and stirring at 1,000 rpm for 30 minutes at 50°C using a homomixer.

Example 5: Emulsifier-containing composition-2

Example 5 was prepared by mixing 30 to 50% (w/w) of soy lecithin and 50 to 70% (w/w) of PGPR and stirring at 1,000 rpm for 30 minutes at 50°C using a homomixer.

Example 6: Emulsifier-containing composition-3

Example 6 was prepared by mixing 30 to 50% (w/w) of soy lecithin and 50 to 70% (w/w) of GMS and stirring at 1,000 rpm for 30 minutes at 50°C using a homomixer.

Manufacturing examples and comparative examples

Examples 1 to 6, tocopherol, rosemary extract, vitamin C, antioxidant, lecithin, GMS or PGPR alone were added to edible oil (palm olein oil) before and after the deodorization process as shown in Table 1 below, and Preparation Examples 1 to 3, comparison. Examples 1 to 12 were prepared.

Manufacturing example
One Manufacturing example
2 Production example 3 Comparative Example 1 Comparative example
2 Comparative example
3 Comparative example
4 Comparative example
5 Comparative example
6 Comparative Example 7 Comparative Example 8 Comparative example
9 Comparative example
10 Comparative example
11 Comparative example
12 Palm olein oil (before deodorization process) O O O O O O O O O O O O O O Palm olein oil (deodorization process completed) O tocopherol O rosemary extract O Vitamin C O Olist O lecithin O GMS O PGPR O Example 1 O Example 2 O Example 3 O Example 4 O Example 5 O Example 6 O

The manufacturing methods of specific manufacturing examples and comparative examples are as follows.

Preparation Examples 1 to 3: Addition of Examples 1 to 3 to edible oil before deodorizing process

Palm olein oil (CJ CheilJedang) was prepared before the deodorization process, in which the purification process, degumming, deacidification, and decolorization processes were completed, but the deodorization process was not performed.

Examples 1 to 3 were added to the palm olein oil before the deodorization process to a concentration of 500 ppm, and then stirred at 1,000 rpm for 30 minutes using a magnetic stirrer (Daihan science SMH S-6 model).

Comparative Example 1: Preparation of edible oil before deodorization process

Palm olein oil before the deodorization process was prepared in Comparative Example 1.

Comparative Examples 2 to 4 and 7 to 10: Addition of raw materials alone to edible oil before deodorization process

Tocopherol (Kemin), rosemary extract, Olist (antioxidant, CJ Cheil Jedang), lecithin, vitamin C, PGPR or GMS were added to the palm olein oil before the deodorization process to a concentration of 500 ppm, and then stirred at 1,000 rpm with a magnetic stirrer. It was stirred for 30 minutes.

Comparative Example 6: Preparation of edible oil after deodorization process

Palm olein oil for which the deodorization process was completed was prepared in Comparative Example 6.

Comparative Examples 5 and 11-12: Addition of Examples 4-6 to edible oil before deodorization process

Examples 4 to 6 were added to the palm olein oil before the deodorization process to a concentration of 500 ppm, and then stirred at 1,000 rpm for 30 minutes using a magnetic stirrer.

Experiment example

Experimental Example 1: Analysis of 3-Monochloropropanediol esters (3-Monochloropropane-1,2-diol esters, 3-MCPDE) content after deodorization process

A deodorization process was performed on Preparation Examples 1 to 3 and Comparative Examples 1 to 12, and the 3-MCPDE content after the deodorization process was analyzed.

To perform the deodorization process, use a laboratory-scale deodorization pilot (glass glassware, self-made) to set the conditions to temperature 210°C, vacuum 3.5 torr, and steam input amount of 30 ml/hr per hour, and then deodorize for 1 hour. Deodorized oil was prepared for each production example and comparative example.

3-MCPDE content analysis was performed in accordance with the 'Ministry of Food and Drug Safety Report 18161Food Commission 007 Test Method' (Study on the risk of hazardous substances derived from fatty acids in foods - Focusing on conjugated 3-MCPD and glycidol, Korea Food and Drug Safety Evaluation Institute, 2018, pages 27-28). The analysis results are shown in Table 2 below.

division Manufacturing Example 1 Manufacturing example 2 Production example 3 Comparative Example 1 Comparative example 2 Comparative Example 3 Comparative example 4 Comparative Example 5 3-MCPDE content
(㎍/kg) 1,972 2,088 2,135 2,406 2,305 2,513 2,238 2,159 division Comparative Example 6 Comparative Example 7 Comparative Example 8 Comparative Example 9 Comparative Example 10 Comparative Example 11 Comparative Example 12 3-MCPDE content (㎍/kg) 2,194 2,019 2,187 2,537 2,057 2,126 2,101

As a result, as shown in Table 2, after deodorizing Preparation Example 1 to which the composition of Example 1 containing 80% (w/w) of rosemary extract and 20% (w/w) of vitamin C was added, the 3-MCPDE content was 1,972. It was confirmed that it was significantly lower than Preparation Examples 2 to 3 and Comparative Examples 1 to 12.

Accordingly, it was confirmed that the composition containing rosemary extract and vitamin C reduced the 3-MCPDE content of edible oil and fat after the deodorization process.

From the above description, a person skilled in the art to which this application belongs will be able to understand that this application can be implemented in other specific forms without changing its technical idea or essential features. In this regard, the embodiments described above should be understood in all respects as illustrative and not restrictive. The scope of the present application should be interpreted as including the meaning and scope of the patent claims described below rather than the detailed description above, and all changes or modified forms derived from the equivalent concept thereof are included in the scope of the present application.

Claims (15)

A composition for reducing the content of 3-monochloropropanediol ester in fat containing rosemary extract and vitamin C.
The composition according to claim 1, wherein the composition contains 70 to 90% by weight of rosemary extract based on the total weight of the composition.
The composition of claim 1, wherein the composition contains 10 to 30% by weight of vitamin C based on the total weight of the composition.
The composition of claim 1, wherein the oil is edible.
The composition according to claim 1, wherein the composition is added during the refining process of oil and fat.
The composition of claim 5, wherein the purification process of the fat or oil includes at least one selected from the group consisting of a degumming step, a deacidifying step, a decolorizing step, and a deodorizing step.
The composition according to claim 5, wherein the composition is added before the deodorizing step during the fat refining process.
The composition of claim 5, wherein the composition reduces the content of 3-monochloropropanediol ester in the oil to 2,000 μg/kg or less.
The composition of claim 5, wherein the composition is added to fats and oils at a concentration of 500 ppm or less.
A method for producing oil with reduced 3-monochloropropanediol ester content, comprising adding a composition for reducing the 3-monochloropropanediol ester content in oil and fat containing rosemary extract and vitamin C during the purification process of the oil.
The method of claim 10, wherein the composition is added before the deodorization step during the fat refining process.
The method of claim 10, wherein the method further comprises the step of deodorizing the oil to which a composition for reducing the content of 3-monochloropropanediol ester in the oil containing rosemary extract and vitamin C has been added.
Oil and fat with reduced 3-monochloropropanediol ester content in fat and oil, manufactured by adding a composition for reducing the 3-monochloropropanediol ester content in oil and fat containing rosemary extract and vitamin C during the refining process of oil and fat.
The oil of claim 13, wherein the oil is edible.
The fat or oil of claim 13, wherein the content of 3-monochloropropanediol ester is reduced to 2,000 ㎍/kg or less.