JP3490657B2 - Edible fats and oils - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention is capable of stably dissolving and containing a plant sterol having a blood cholesterol lowering action, and has less fuming during cooking and less foaming during cooking of fried foods. The present invention relates to an edible oil / fat excellent in food and food and drink containing it.

[0002]

2. Description of the Related Art Plant sterols are known to be effective in lowering blood cholesterol, and are contained in large amounts in plant seeds.
The degree is included. This plant sterol exists in the form of esters such as fatty acids, glycosides linked to sugars, and free plant sterols in natural products, but these are present in the stages of extraction, concentration and purification from natural products. It is hydrolyzed and mostly free. However, this free plant sterol has a solubility in triglycerides,
Ordinary salad oil was as low as about 1.5% by weight, which was a problem when blending a large amount of plant sterols in edible fats and oils.

Therefore, various technical developments have been made to increase the solubility of plant sterols in edible oils and fats. For example, edible oils and fats containing plant sterols and saturated or unsaturated fatty acids having 6 to 18 carbon atoms (JP-B-57-26732), edible liquid oils containing plant sterols and vitamin E (JP-A-57-206336). ), A technique of adding vitamin E and an emulsifier to a plant sterol containing sitosterol to solubilize it in oil (JP-A-10-179086), and a fat containing a plant sterol equivalent having a degree of esterification within a certain range. Based food products (JP-A-11-127779), the use of β-sitostanol fatty acid ester (JP-A-6-506909), and the like.

However, the method of adding a fatty acid having 6 to 18 carbon atoms has a problem that when it is used for heating cooking of fried food, stir-fried food and the like, smoke is generated so much that only dressing and sauce can be used so-called raw use. , The solubilization method using vitamin E has a price problem due to the use of a large amount of expensive vitamin E, and the method of using a plant sterol fatty acid ester is a compound not legally recognized as a food product. There was a problem that was.

On the other hand, medium chain fatty acid triglyceride (MCT) is used as a highly soluble triglyceride of plant sterols.
Is known (Japanese Patent Laid-Open No. 10-179086). However, MCT has a lower smoke point and a lower flash point than long-chain fatty acid triglycerides used for ordinary edible oils and fats and cannot be used for deep-fried foods and stir-fried foods. In addition, when MCT is used by mixing it with ordinary edible oils and fats, the solubility of plant sterols increases depending on the mixing ratio, but when used in fried foods, there is a problem that foaming is severe and it is not suitable for practical use.

Further, Japanese Patent No. 2601104 and Japanese Patent Laid-Open No. 7-179.
In Japanese Patent No. 882 etc., oils and fats introduced with a medium-chain saturated fatty acid residue are also disclosed, but the former improves the freeze resistance of mayonnaise, dressing, etc., and the latter stabilizes the oxidation of mechanical lubricating oils and mechanical softeners. It is intended to improve the heat resistance and low temperature fluidity, and neither the cooking performance nor the plant sterol dissolving performance has been clarified. It has been clarified in our research that these oils and fats cannot achieve the above performances at the same time.

[0007]

Therefore, it can be used not only for raw use of dressing, sauce, etc., but also for cooking of fried food, stir-fried food, etc. in the same manner as general edible oils and fats, and stably dissolves plant sterols. -The development of edible oils and fats that can be contained and that is practical and safe and costly has been desired.

[0008]

Means for Solving the Problems The present inventors have found that edible oils and fats containing a specified amount of medium-chain saturated fatty acids and having a glyceride composition adjusted to a specified range can stably hold plant sterols in a dissolved state. Moreover, it was also found that it is excellent in heat cooking suitability such as fried food and fried food.

That is, according to the present invention, (1) the medium chain saturated acyl group having 8 to 10 carbon atoms is 5 to 5 out of all the constituting acyl groups of fats and oils.
20% by weight, (2) of the triglyceride component, less than 1% by weight of those having a sum of carbon atoms of constituent acyl groups of 30 or less, less than 15% by weight of 32 to 38, and ( 3)
Of all glyceride components, monoglyceride is less than 3% by weight, diglyceride is 2.5% by weight or more and less than 15% by weight, triglyceride is 85% by weight or more and less than 97.5% by weight, and foods and drinks containing the same are provided. Is.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The edible oil / fat of the present invention can be produced by introducing a medium-chain saturated acyl group having 8 to 10 carbon atoms into an animal / vegetable oil / fat and adjusting the glyceride composition thereof.

The animal and vegetable oils and fats used in the production of the edible oils and fats of the present invention may be any animal and vegetable oils and fats generally used for food, but they are liquid at room temperature in consideration of cooking suitability, storage suitability and the like. Those are preferable. Examples of such animal and vegetable oils and fats include rapeseed oil and soybean oil. Also, as the medium-chain saturated fatty acid having 8 to 10 carbon atoms, caprylic acid, capric acid, etc .; fats and oils containing these fatty acids, such as coconut oil, palm kernel oil, medium-chain fatty acid triglyceride (MCT); Esters of fatty acids and lower alcohols having 1 to 3 carbon atoms, such as methyl caprylate, ethyl caprylate, methyl caprate,
Ethyl caprate and the like; a mixture thereof and the like can be used.

As a method for introducing medium-chain saturated fatty acids into animal and vegetable fats and oils, usual ester synthesis reaction or transesterification reaction can be utilized. For example, random transesterification reaction using an alkali catalyst or 1,3 Examples include a selective transesterification reaction using a position-specific lipase. The most preferable production method is a method of transesterifying a liquid animal or vegetable oil and fat with MCT at room temperature, and any of the above random transesterification reaction, 1,3-position specific transesterification reaction, etc. is used for the reaction. You may.

First, the edible oil and fat of the present invention requires that the medium chain saturated acyl group having 8 to 10 carbon atoms is 5 to 20% by weight of all the constituent acyl groups of the oil and fat. It is preferably in the weight%. When the content of the medium-chain saturated acyl group is less than 5% by weight, the solubility of the plant sterol is low, and when it exceeds 20% by weight, the solubility of the plant sterol is increased, but foaming is severe during cooking of fried food and the suitability for heating is poor. Will be things.

Secondly, the edible oil / fat of the present invention is required to have less than 1% by weight of triglyceride components having a sum of carbon atoms of constituent acyl groups of 30 or less, and less than 0.5% by weight. Preferably, and the sum of the carbon numbers is
What is 32 to 38 needs to be less than 15% by weight, preferably less than 7% by weight. If such triglyceride is contained in an amount larger than the above range, foaming and fuming during heating will be severe and the suitability for heating and cooking will be poor.

Thirdly, the edible oil / fat of the present invention comprises, of the total glyceride components, monoglyceride of less than 3% by weight, diglyceride of 2.5% by weight or more and less than 15% by weight, and triglyceride of 85% by weight or more and less than 97.5% by weight. Need that,
It is preferable that the monoglyceride content is less than 1% by weight and the diglyceride content is 2.5% by weight or more and less than 7% by weight. When the content of monoglyceride is 3% by weight or more, fuming during heating is severe and the suitability for cooking becomes poor. Regarding the diglyceride, in conventional fats and oils, even if the diglyceride is contained in the above range, the solubility of the plant sterol and the suitability as edible fat and oil do not change at all, but in the edible fat and oil of the present invention, when the diglyceride is contained in the above range. In addition to increasing the solubility of plant sterols, it is possible to significantly suppress foaming during use of fried foods. Diglyceride is 2.5
If the amount is less than 10% by weight, the effect of this diglyceride cannot be obtained, and if it exceeds 15% by weight, smoke is generated severely and the suitability for cooking with heat becomes poor. From the above, the triglyceride in the total glyceride component is 85% by weight or more and less than 97.5% by weight, which is the remaining amount excluding monoglyceride and diglyceride.

The glyceride composition may be adjusted at any stage in the process for producing the edible oil / fat of the present invention. That is, during the esterification reaction or transesterification reaction for introducing medium-chain saturated fatty acids into animal and vegetable fats or oils, or the subsequent purification process,
For example, the glyceride composition can be adjusted to the above range during the deoxidation, decolorization, deodorization step, or the subsequent mixing operation.

In order to add the diglyceride in the above range to the edible oil / fat of the present invention, the diglyceride is prepared separately,
It is also possible to add it to general edible oils and fats into which medium-chain saturated fatty acids with 8 to 10 carbon atoms have been introduced, but the simplest method is to use the above ester synthesis reaction or transesterification reaction with a small amount of water. And the method performed in the presence of glycerin. The amount of water or glycerin added at this time is determined by the glyceride composition of fats and oils used in the reaction, water contained in raw materials (oils and fatty acids, etc.), catalysts, enzymes, etc. Since it is affected by such factors, it cannot be specified in a general way.

The edible oil / fat of the present invention can contain plant sterols in a stably solubilized state or in a easily solubilized state. The plant sterol used in the present invention is not particularly limited, α-sitosterol,
β-sitosterol, stigmasterol, campesterol, brassicasterol, α-sitostanol, β-
Examples thereof include sitostanol, stigmasteranol, campestanol, cycloartenol and the like, and fatty acid esters thereof, ferulic acid ester, cinnamic acid ester, glycosides and the like, and a mixture thereof.

When the plant sterol is added to the edible oil and fat of the present invention, its content is preferably 6% by weight or less in consideration of the solubility at room temperature. The lower limit of the content is not particularly limited from the viewpoint that the effect is enhanced by the added amount, but 0.3 to 0.7% by weight for general-purpose oils such as rapeseed oil, soybean oil and corn oil, and 1.1 for special edible oils such as rice oil. Since it contains plant sterols in an amount of about wt%, it is desirable that the amount be 1.2 wt% or more from the viewpoint of obtaining the effect more than that of conventional rice oil. In addition, the content of plant sterols here is the total amount of the amount originally contained and the amount newly added.

Further, additives can be added to the edible oil and fat of the present invention within a range not impairing the object of the present invention. As additives, antioxidants such as tocopherols, silicone, vitamin C palmitate, and tea extract; glycerin fatty acid ester, polyglycerin fatty acid ester, polyglycerin polyricinoleic acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol Emulsifiers such as fatty acid esters, organic acid monoglycerides, lecithin, enzyme-treated lecithin, and enzyme-decomposed lecithin;
Other examples include flavoring agents and coloring agents. Among these additives, the emulsifier is preferably added because it improves the blooming of clothes such as tempura during frying, and also improves the solubility of plant sterols, and the addition amount is usually 0.
It is from 02 to 2% by weight.

The edible oil and fat of the present invention can be used in the same manner as general edible oil and fat, and can be widely applied to various foods and drinks using the oil and fat. For example, drinks, desserts, ice creams, dressings, toppings, mayonnaise, processed foods with oil-in-water emulsified oils and fats such as sauce of roasted meats; water-in-oil emulsions processed with oils such as margarine and spreads; peanut butter, flying shortening,
Processed fat foods such as baking shortening; potato chips, snacks, cakes, cookies, pies, bread,
Processed foods such as chocolate, bakery mix,
It can be used for processed meat products, frozen entrees, frozen foods, etc.

[0022]

Example 1 90 parts by weight of rapeseed oil and 10 parts by weight of coconut MT (MCT manufactured by Kao Corporation, fatty acid composition: C8 = 82% by weight, C10 = 18% by weight) were mixed, and in the presence of 300 ppm of water, Sodium methylate
After carrying out a random transesterification reaction at 70 ° C for 1 hour using 0.1% by weight, purification by conventional methods (washing with water, decolorization, deodorization)
The edible oil / fat having the composition shown in Table 1 is obtained. In addition to this, plant sterols (Tama Seikagaku, 95% pure, β-
Sitosterol: 52% by weight, stigmasterol: 25% by weight, campesterol: 20% by weight, brassicasterol: 3% by weight) is added to 4% by weight to obtain a plant sterol-containing edible oil.

Example 2 90% by weight of rapeseed oil and 10 parts by weight of Coconard MT were mixed to obtain 12
A 1,3-position specific transesterification reaction was performed using LIPOZYME (manufactured by Novo Nordisk Co., Ltd.) in the presence of water of 00 ppm, followed by purification in the same manner as in Example 1 to obtain an edible oil / fat having the composition shown in Table 1. And adding the same plant sterol as in Example 1 to 4% by weight to obtain a plant sterol-containing edible oil.

EXAMPLE 3 2000 parts by weight of rapeseed oil fatty acid was mixed with 100 parts by weight of Coconard MT, and 1,3-position specific transesterification reaction was carried out using LIPOZYME (manufactured by Novo Nordisk Co.) under reduced pressure. Purification is performed in the same manner as in Example 1 to obtain an edible oil / fat having the composition shown in Table 1, and the same plant sterol as in Example 1 is added so as to be 4% by weight to obtain a plant sterol-containing edible oil.

Comparative Example 1 Transesterification and purification were carried out in the same manner as in Example 1 except that rapeseed oil 80% by weight and coconard MT 20% by weight were used as raw materials to obtain an edible oil / fat having the composition shown in Table 1 and the plant Add sterol to 4% by weight.

Comparative Example 2 Example 1 except that the water content during transesterification was 150 ppm.
Transesterification and purification are carried out in the same manner as above to obtain an edible oil / fat having the composition shown in Table 1, to which phytosterol is added so as to be 4% by weight.

Test Example 1 Using the phytosterol-containing edible oil obtained in each of the Examples and Comparative Examples, fried food was cooked, its cooking performance (foaming) was evaluated, and the dissolved state of the plant sterol at room temperature was observed. The results obtained are shown in Table 1. The composition of each edible oil / fat is also shown.

<Evaluation Criteria> (1) Foaming evaluation ○: No foaming △: Slight foaming ×: Bubbles

(2) Evaluation of plant sterol dissolution ○: dissolved △: Slightly insoluble ×: insoluble

[0030]

[Table 1]

As is clear from the above results, the edible oil / fat of the present invention has no problem in foaming when cooked and has excellent solubility of plant sterols. On the other hand, in the triglyceride composition, the sum of carbon atoms of the constituent acyl groups is
30% or less 1% by weight or more, 32 to 38% 15% by weight
Even if the edible oil and fat of Comparative Example 1 containing the above contains diglyceride in an amount of 2.5% by weight or more and less than 15% by weight, it foams significantly during heating and cannot be used. Further, in the triglyceride composition, the diglyceride content is less than 2.5% by weight even if the sum of carbon atoms of the constituent acyl groups is 30% or less and 1 to 32% by weight and 32 to 38 are 15% by weight or less. The edible oil / fat of 2 has a low solubility of plant sterols, and has a large amount of foaming during heating and cannot be used.

Example 4 The edible oil / fat of Example 1 was mixed with sorbitan monooleate [O-10
(F), manufactured by Kao Corporation) and 4% by weight of the same plant sterol as in Example 1 are added to obtain a plant sterol-containing oil. This edible oil does not foam when cooked in a deep-fried food, improves the flower bloom of the batter, and improves the solubility of plant sterols at room temperature and low temperature (0 ° C).

[0033]

Industrial Applicability The edible oil and fat of the present invention is capable of stably dissolving and containing plant sterols, and is also excellent in heat cooking suitability such as less fuming during cooking and less foaming during frying. .

Continuation of the front page (56) References JP-A-52-114059 (JP, A) JP-A-8-269478 (JP, A) JP-A-7-16053 (JP, A) JP-A 64-23848 (JP , A) JP-A-2-190146 (JP, A) JP-A-11-243857 (JP, A) JP-A-8-60180 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB) Name) A23D 7/00-9/06

Claims (3)

(57) [Claims] 1. (1) 5 to 20% by weight of a medium-chain saturated acyl group having 8 to 10 carbon atoms among all the constituent acyl groups of fats and oils,
(2) Of the triglyceride components, those in which the sum of carbon atoms of constituent acyl groups is 30 or less are less than 1% by weight, those in the range of 32 to 38 are less than 15% by weight, and (3) the total glyceride component Of these, edible oils and fats containing less than 3% by weight of monoglycerides, 2.5% or more and less than 15% by weight of diglycerides and 85% or more and less than 97.5% by weight of triglycerides. 2. The edible oil and fat according to claim 1, wherein the plant sterol is dissolved. 3. A food or drink containing the edible oil or fat according to claim 1 or 2.