JPH09157159A - Composition containing carotinoid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of remarkably enhancing the body absorption of the carotinoid dissolved in a fatty oil and useful for beverages, foods, etc., by using both a polyglycerol fatty acid ester and lecithin as emulsifiers. SOLUTION: (A) An oil phase produced by dissolving (i) a carotinoid in (ii) a fatty oil (e.g. corn oil) is emulsified in (B) an aqueous phase containing (v) a polyhydric alcohol (e.g. glycerol) in the presence of (iii) a polyglycerol fatty acid ester and (iv) lecithin (e.g. soybean lecithin) to obtain the objective composition wherein the average particle diameter of the component A is <=100nm. The component (i) includes a carotinoid obtained by extracting palm oil, and the component (iii) includes the ester of a polyglycerol having a degree of polymerization of 6-10 with a 12-22C fatty acid, concretely, decaglycerol monostearate.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a carotenoid-containing composition having improved carotenoid absorbability in the body.

[0002]

BACKGROUND OF THE INVENTION Carotenoids are used as coloring agents for foods and drinks, pharmaceuticals, etc., or as precursors of vitamin A, and recently as raw materials for health foods which are expected to have antioxidant effects in the body of carotenoids. It is used frequently. However, carotenoids are substances that are hardly dissolved in water, alcohol, etc., and have a relatively high melting point, have low solubility in solvents such as fats and oils, and are easily oxidized, so that carotenoids have been conventionally used. A number of proposals have been made regarding a method for producing a solvent that dissolves carotenoids in a high concentration, a stable emulsion of carotenoids, and a dry powder. For example, carotenoids are supersaturated in edible oils,
There is a method for producing a water-dispersible carotenoid preparation which is emulsified in an aqueous gelatinous substance to obtain an emulsion (Japanese Patent Publication No. 35-8095). Also, although basically similar to this proposal, as a solvent that replaces the above edible oil, for example, flavor oils such as orange oil, lemon oil, and rose oil, terpenes such as limonene, yonon, and menthone, or curcuma oil Terpene-containing oil (Japanese Patent Publication No. 36-21476), essential oil and / or vegetable oil (Japanese Patent Publication No. 37-8532), volatile water-insoluble solvents such as chloroform, methylene chloride, carbon tetrachloride (Japanese Patent Publication No. 37-12428). No.), acetoglyceride (Japanese Patent Publication No. 39-21760), aromatic aldehydes, aromatic alcohols or derivatives thereof (Japanese Patent Publication No. 40).
-18018), castor oil or dehydrated lanolin (Japanese Patent Publication No. 40-24508), monoesters and diesters of higher fatty acids having 10 or more carbon atoms with propylene glycol (Japanese Patent Publication No. 43-6980), hydrogenated castor. Oil polyoxyethylene ether (degree of polymerization of oxyethylene is 60 to 100) (JP-B-44-6986), hydrogenated limonene dimer (JP-B-45-9220), orange oil or lemon oil (JP-B-45). -2
No. 4379 gazette), at least one kind of vegetable oil, mineral oil, essential oil and the like and natural rubber (Japanese Patent Publication No. 48-13687), 1 part amount of natural essential oil and 0.01-500 parts amount of vegetable oil Items 7-12 (Japanese Patent Publication No. 54-28858)
No.), squalene, squalane, or oils and fats containing squalene (Japanese Patent Publication No. 56-12431), vitamin E (Japanese Patent Publication No. 60-102169), and carrier oil to which an aqueous protective colloid is added (Japanese Patent Laid-Open No. 62-2403
No. 64), carotenoids derived from seaweed (JP-A-64-43167), oil-based compositions to which rosin is added (JP-A-5-38273), and the like. In addition, a method for coloring a beverage using a carotenoid extracted from palm oil has also been proposed (JP-A-3-
No. 127970).

However, although the above-mentioned carotenoid emulsions and powder preparations according to the prior art all mention the stability in foods, there is no mention or suggestion of carotenoid absorption in the body.

The present invention has been made in view of the above circumstances, and an object thereof is to provide a carotenoid-containing composition which improves the absorbability of carotenoids in the body.

[0005]

Means for Solving the Problems and Modes for Carrying Out the Invention As a result of earnest studies to achieve the above object, the present inventor has found that in order to improve the absorbability of carotenoids in the body, an oil containing carotenoids is used. It has been found that the type of emulsifier used when emulsifying the phase into the aqueous phase containing the polyhydric alcohol and the size of the oil phase particles thus obtained are important factors. That is, in emulsifying an oil phase obtained by dissolving carotenoids in fats and oils into an aqueous phase containing a polyhydric alcohol and water, a polyglycerin fatty acid ester and lecithin are used together as an emulsifier, whereby the emulsified oil phase The inventors have found that when the average particle diameter is 100 nm or less, the absorbability of carotenoids in the body is improved, and the present invention has been completed.

Accordingly, the present invention comprises an emulsified oil phase obtained by dissolving carotenoids in an oil and fat in an aqueous phase containing a polyhydric alcohol in the presence of polyglycerin fatty acid ester and lecithin, and the average of the above oil phases. Provided is a carotenoid-containing composition having a particle size of 100 nm or less.

The present invention will be described in more detail below. The composition for improving the absorption of carotenoids of the present invention comprises an aqueous phase containing a polyhydric alcohol and an oil phase obtained by dissolving the carotenoids in fats and oils as described above. Is emulsified in the presence of polyglycerin fatty acid ester and lecithin.

The carotenoids used in the present invention are not particularly limited, but carotenoids obtained by extracting palm oil are preferably used. This palm oil extracted carotenoid generally has the following composition. β-carotene: 55-70% (wt%, the same applies below) α-carotene: 40-20% Total amount of α-carotene and β-carotene 85-97% Other natural carotenoids and natural pigments such as lycopene: 3-
15% (typically γ-carotene: 3-5%, lycopene: 3-5%)

By using this carotenoid extracted from palm oil, it is possible to obtain the advantage that the carotenoid extracted from palm oil has a better absorbability when formulated. The method for producing the palm oil-extracted carotenoid is not particularly limited, but for example, palm oil can be produced by the method described in JP-A-61-2657, 63-5073, and 63-5074. Carotenoids collected and concentrated from the above are further described in, for example, JP-A 63-132871, JP-A 63-295551, JP-A No. 1-160953, and JP-A 1-1609.
A method of purifying by the method described in Japanese Patent No. 54, etc. may be mentioned, and it is preferable to use the palm oil extracted carotenoid thus purified.

The fats and oils that dissolve the carotenoids include soybean oil, rapeseed oil, corn oil, olive oil, coconut oil, safflower oil, sunflower oil, which are generally used in foods.
Rice oil, beef tallow, lard, fish oil, edible oils and fats for processing such as medium chain saturated fatty acid triglycerides of C _{6 to} C ₁₂ and sucrose diacetate hexaisobutyrate (SAI)
B), edible oily materials such as rosin can be optionally mixed.

The oil phase may be mixed with an antioxidant such as vitamin E for the purpose of preventing oxidation of carotenoid. Further, orange flavor or the like can be mixed for the purpose of improving the flavor.

The use ratio of the above carotenoids and fats and oils can be arbitrarily selected within the range of 5:95 to 95: 5 by weight, but more preferably 10:90 to 60: 4.
A value of 0 is preferable from the viewpoint of handling the carotenoid / fat mixture.

Next, in the present invention, polyglycerin fatty acid ester and lecithin are used as an emulsifier used to emulsify the above oil phase into an aqueous phase, whereby the average particle diameter of the oil phase is 100 nm or less. A / W type emulsion can be obtained. In this case, it is difficult to obtain an oil phase having an average particle size of 100 nm or less with other emulsifiers such as sugar ester having a high HLB, and the stability is poor.

The polyglycerin fatty acid ester usable in the present invention has a degree of polymerization of 3 or more, preferably 6 to 10.
Polyglycerin of 8 and carbon number 8 or more, preferably 8 to 2
2, and more preferably, an ester with a fatty acid of 12 to 18 and having an HLB of 8 or more, preferably an HLB of 10 or more. The amount used is 0.2 to 3 times by weight, and more preferably 0.5 to 2 times by weight, the weight of the above-mentioned fat or oil containing carotenoids. If it is less than 0.2 times by weight, the emulsion stability of the carotenoid-containing composition is good, but since the particle size is large, the absorbability in the body is poor, and the purpose may not be achieved. If it exceeds the above range, there is a problem in terms of flavor and the intended use may be significantly limited.

Examples of lecithin include soybean lecithin, egg yolk lecithin, enzyme-decomposed lecithin, enzyme-treated lecithin, hydroxylated lecithin, acetylated lecithin, hydrogenated lecithin and the like. The amount used is 0.02-0.5 times by weight, more preferably 0.05-0.4 times by weight, with respect to the above-mentioned fats and oils containing carotenoids. If the amount is less than 0.02 times by weight, the affinity with the biological membrane in the body is poor, the carotenoid absorbency is poor, and the purpose may not be achieved in some cases.
If the amount is more than 5 times by weight, the emulsion may be destroyed and it may be difficult to prepare a preparation.

Further, other emulsifiers such as monoglycerin fatty acid ester, quillaja saponin and soybean saponin can be used for stabilizing the emulsified preparation in addition to the above two kinds of emulsifiers.

Next, the aqueous phase contains a polyhydric alcohol, and water can be mixed if necessary.

Specific examples of the polyhydric alcohol include propylene glycol, glycerin, sorbitol, glucose, maltose, galactose, sucrose, fructose and other sugars, starch syrup, starch decomposition products, and the like. A single phase or a mixture of two or more phases can be mixed with water to form an aqueous phase. However, the types and the mixing ratios are so long as no inconvenience occurs in the step of emulsifying the oil phase into the aqueous phase. It is not particularly limited. The amount of the polyhydric alcohol used is not particularly limited as long as it does not cause any inconvenience in the emulsification step, but is usually 10 to 95% by weight, preferably 50 to 90% by weight based on the whole aqueous phase. %. 10% by weight
If it is less than 100% by weight, the surface tension of the aqueous phase may not be lowered sufficiently, which may make it difficult to emulsify. If it exceeds 95% by weight, emulsification may be carried out favorably, while the obtained carotenoid-containing aqueous composition The oil particles may coalesce during storage, and the carotenoid absorption improving composition itself may not be stable for a long period of time.

The mixing ratio of the water phase and the oil phase can be appropriately selected to obtain the desired carotenoid content, but the weight ratio is usually oil phase: water phase = 1: 2 to 2.
It is preferably 1:25, particularly 1: 3 to 1:20.

As a method for obtaining the carotenoid-containing composition of the present invention, first, an oil phase in which the above carotenoids are uniformly dissolved in fats and oils is prepared. This oil phase can be prepared by mixing carotenoids with fats and oils and dissolving them. The temperature and the like in this case are not particularly limited, but for example, a suspension of carotenoids suspended in the above fats and oils is prepared at room temperature to 170 ° C, preferably 100 to 150 ° C.
The carotenoids can be uniformly dissolved in the oil or fat by stirring for 5 to 30 minutes under the temperature condition of ° C. At this time, in order to suppress oxidative decomposition of carotenoids, dissolution is performed under a nitrogen stream, tocopherols, ascorbic acid fatty acid ester, spice extract, BHT, BHA
1 type, or 2 or more types of antioxidants such as
It is also possible to add 15% by weight, especially about 1 to 10% by weight. In addition, as described above, SAIB,
It is also possible to optionally add edible oily materials such as rosin and flavor components such as limonene, apple flavor and orange flavor.

The aqueous phase can be prepared by using the above polyhydric alcohol and, if necessary, water, and when emulsifying the above oil phase into the aqueous phase, emulsification is performed at a temperature above the melting point of the surfactant used. It is preferable that the temperature condition in this case is 40
It is more preferable that the temperature is not less than 0 ° C, especially 50 to 100 ° C.
If the temperature is lower than 40 ° C, crystallization of carotenoids may occur during the emulsification. Further, at the time of this emulsification, the emulsification can be carried out by a known means using a usual stirring emulsifying machine, a high pressure homogenizer, an ultrasonic emulsifying machine, an ultra mixer, a colloid mill and the like.

In this case, the average particle size of the oil phase (oil particles) must be 100 nm or less, preferably 5 to 100 nm, more preferably 5 to 75 nm. 100n
If it exceeds m, the carotenoid absorbency is poor and the desired effect cannot be obtained.

As a method for adjusting the average particle size of the carotenoid-containing composition to 100 nm or less, as described above, the emulsification time such as the stirring speed and the stirring time can be adjusted, and the amount of the surfactant added can be adjusted. A known emulsion particle size adjusting method can be adopted.

The carotenoid-containing composition of the present invention can be usefully used in foods such as beverages, candy and gummies, health foods, pharmaceuticals, quasi drugs, pet foods, feeds and all other industries.

[0025]

INDUSTRIAL APPLICABILITY The carotenoid-containing composition of the present invention can remarkably enhance the absorbability of oil-soluble carotenoids in the body, and is therefore extremely suitable as an industrially wide range of additives.

[0026]

EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples.

[Example 1] 10 g of palm oil-extracted carotenoid was suspended in 40 g of corn oil, 2 g of vitamin E was mixed, and the mixture was stirred at 140 to 150 ° C for 30 minutes under a nitrogen stream to uniformly dissolve the carotenoid. This solution is cooled to about 80 ° C., 100 g of decaglycerin monostearate (HLB12.5) and 20 g of soybean lecithin are added, uniformly dispersed and mixed, and 728 g of glycerin heated to 80 ° C. and 100 g of water are stirred and poured into a mixed solution. Then, emulsify with TK homogenizer at 12000 rpm for 15 minutes, then 700 kg / c with high pressure homogenizer.
m ² for 1 pass, to obtain a water-soluble emulsion composition containing palm oil extracted carotenoid. The carotenoid content in the obtained preparation was quantified by the following method. About 300 mg of a carotenoid quantitative sample is accurately weighed, diluted with distilled water to make exactly 100 ml, 10 ml of this diluted solution is accurately taken, and 20 ml of ethanol is added. Accurately add 10 ml of cyclohexane, shake well and centrifuge. The lower water layer is not colored. Cyclohexane layer 5m
Exactly 1 l, add cyclohexane and add exactly 50 m
to l. For this solution, cyclohexane is used as a control,
The absorbance (A) at the maximum absorption portion near 450 nm was measured, and the content was determined by the following formula. The result is 1.01%
Met.

[0028]

(Equation 1) The average particle size of the obtained palm oil-extracted carotenoid-containing water-soluble emulsion composition was measured by Super Dynamic Light Scattering Photometer DLS-700 manufactured by Otsuka Electronics Co., Ltd., and the result was 35 nm.

Example 2 A carotenoid-containing water-soluble emulsion composition in the same amount as in Example 1 was obtained in the same manner as in Example 1 except that the palm oil extracted carotenoid was replaced with synthetic β-carotene. It was When the carotenoid content was quantified in the same manner as in Example 1, the carotenoid content in the obtained preparation was 1.02%. As a result of measuring the average particle diameter in the same manner as in Example 1, the average particle diameter of the emulsion composition was 41 nm.

Example 3 10 g of carotenoid extracted from palm oil was suspended in 40 g of medium-chain fatty acid triglyceride,
Vitamin E 2g is mixed and 140-150 under nitrogen stream
The carotenoid was uniformly dissolved by stirring at 30 ° C. for 30 minutes.
This solution is cooled to about 80 ° C., 100 g of decaglycerin monostearate (HLB12.5), 20 g of egg yolk lecithin and 5 g of stearic acid monoglyceride are added,
Glycerin 72 uniformly dispersed and mixed and heated to 80 ° C
A mixture of 3 g and 100 g of water is added by stirring, and emulsified by a TK homogenizer at 12000 rpm for 15 minutes.
Then, it was treated with a high-pressure homogenizer at 700 kg / cm ² for 1 pass to obtain a palm oil-extracted carotenoid water-soluble emulsion composition. When the carotenoid content was quantified in the same manner as in Example 1, the carotenoid content in the obtained preparation was 1.02%. Further, the average particle diameter was measured in the same manner as in Example 1, and as a result, the average particle diameter was 41 nm.

[Comparative Example 1] The same amount of palm oil-extracted carotenoid water-soluble emulsified composition as in Example 1 was used in the same manner as in Example 1 except that a high-pressure homogenizer was not used during emulsification. Obtained. When the carotenoid content obtained in the same manner as in Example 1 was quantified, the carotenoid content in the obtained preparation was 1.01%. The average particle size was measured in the same manner as in Example 1,
The average particle diameter was 120 nm.

Comparative Example 2 Carotenoids extracted from palm oil in the same amount as in Example 1 were prepared in the same manner as in Example 1 except that decaglycerin monostearate (HLB12.5) alone was used as the emulsifier. A water soluble composition was obtained. When the carotenoid content obtained in the same manner as in Example 1 was quantified, the carotenoid content in the obtained preparation was 1.
01%. The average particle size was measured in the same manner as in Example 1, and as a result, the average particle size was 45 nm.

Comparative Example 3 A palm oil-extracted carotenoid water-soluble emulsion composition in the same amount as in Example 1 was obtained in the same manner as in Example 1, except that soybean lecithin alone was used as the emulsifier. . When the carotenoid content obtained in the same manner as in Example 1 was quantified, the carotenoid content in the obtained preparation was 1.00%. The average particle size was measured in the same manner as in Example 1, and as a result, the average particle size was 220 nm.

Comparative Example 4 The same amount as in Example 1 was obtained in the same manner as in Example 1 except that sugar ester (HLB16) was used instead of decaglycerin monostearate (HLB12.5). A palm oil-extracted carotenoid water-soluble emulsion composition was obtained. When the carotenoid content obtained in the same manner as in Example 1 was quantified, the carotenoid content in the obtained preparation was 1.02%. The average particle diameter was measured in the same manner as in Example 1, and as a result, the average particle diameter was 120 nm.

[Comparative Example 5] A palm oil-extracted carotenoid water-soluble emulsion composition in the same amount as in Example 1 was obtained in the same manner as in Example 1 except that all the glycerin was changed to water. . When the carotenoid content obtained in the same manner as in Example 1 was quantified, the carotenoid content in the obtained preparation was 1.01%. Further, as a result of measuring the average particle diameter in the same manner as in Example 1, the average particle diameter was 630.
nm.

The carotenoid-containing compositions of Examples 1 to 3 and Comparative Examples 1 to 5 were subjected to a bioabsorbability test using mice. Carotenoid internal absorbability test 90 ddY 5-week-old male mice were preliminarily bred for 1 week and then divided into 9 groups (10 mice in each group). Experimental group 1 was a palm oil-extracted carotenoid water-soluble emulsion composition prepared according to Example 1, Experimental group 2 was a carotenoid water-soluble emulsion composition, and Experimental group 3 was a palm oil-extracted carotenoid of Example 3. Water-soluble emulsion composition, Experimental group 4 was palm oil-extracted water-soluble emulsion composition of Comparative Example 1, Experimental group 5 was Palm-oil-extracted carotenoid water-soluble emulsion composition of Comparative Example 2, Experimental group 6
Is water-soluble emulsified composition of carotenoid extracted from palm oil of Comparative Example 3, Experimental group 7 is water-soluble emulsified composition of carotenoid extracted from palm oil of Experimental example 7, and Experimental group 8 is water-soluble of carotenoid extracted from palm oil of Comparative example 5. The emulsified composition was added to the drinking water so as to be 0.05% as a carotenoid,
It was given ad libitum. The control group received tap water only. Two weeks and four weeks after the start of administration, 5 animals were sampled from each group, blood was collected, carotenoids were extracted from the serum with hexane, dried, and dissolved in ethanol. Graphography (H
The blood carotenoid concentration was examined by PLC). HPL
The analysis conditions for C are as follows. Column: Shiseido CAPCELL C18 SG120
(4.6 × 15 mm) Mobile phase: acetonitrile / methanol / tetrahydrofuran = 58: 37: 7, v / v / v Detector: Hitachi L4200 (wavelength: 450 nm) Pump: Hitachi L6000 (flow rate: 1.0 ml / min) Calculation of carotenoid: Absolute calibration curve method Table 1 shows the amount of carotenoid in blood after 2 weeks and 4 weeks.

[0037]

[Table 1]

The intakes of drinking water showed no significant difference between the groups, and when the average carotenoid intake of each group was calculated,
2 mg carotenoid / day / mouse. In each of the experimental groups, the amount of carotenoid in blood was elevated, reflecting the administration of carotenoid. Comparing the carotenoid amount of each group, it was revealed that Experimental Groups 1 to 3 had significantly good absorbability in the body.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location A61K 47/24 A61K 47/24 H // C09B 61/00 C09B 61/00 A (72) Inventor Oikawa Gaku 1-3-7, Honjo, Sumida-ku, Tokyo Inside Lion Co., Ltd.

Claims (1)

[Claims] 1. An oil phase obtained by dissolving carotenoids in oil and fat is emulsified into an aqueous phase containing a polyhydric alcohol in the presence of polyglycerin fatty acid ester and lecithin, and the average particle diameter of the oil phase is 100 nm. A carotenoid-containing composition, characterized in that: