JP5691037B2 - Oily composition - Google Patents

Description

  The present invention relates to an oily composition that can stably contain carotenoids over a long period of time.

  Carotenoids are yellow-red-purple pigment components produced by green plants, molds, yeasts, mushrooms, bacteria, and the like, and are generally known to have an antioxidant effect. In addition, some carotenoids have various physiological activities. For example, astaxanthin contained in algae such as Haematococcus algae and chlorella and crustaceans such as shrimp and crab is effective against osteoporosis and muscle atrophy disorder. It has been reported that there is an effect (Patent Documents 1 and 2).

  In addition, fucoxanthin contained in brown algae such as mozuku and having the following structure has an antitumor effect (Patent Document 3), a nerve cell protective effect (Patent Document 4), a blood glucose level increase suppressing effect (Patent Document 5), and an anti-tumor effect. It has been reported to have an obesity effect (Non-patent Documents 1 and 2) and the like.

  Focusing on the functionality of these carotenoids, functional foods and cosmetics containing carotenoids have been developed. However, carotenoids are structurally unstable and easily decompose and discolor by heat and light. For this reason, it has been difficult to stably add to foods and cosmetics. For this reason, methods for improving the storage stability of carotenoids have been studied. For example, a method of adding proanthocyanidins (Patent Document 6), a method of combining gallic acid and organic acids (Patent Document 7), etc. are proposed. However, these techniques have not been sufficient to stabilize carotenoids in oily compositions.

JP 2008-303166 A JP 2006-213667 A Japanese Patent Laid-Open No. 10-158156 JP 2001-335480 A JP 2007-297370 A JP 2002-338842 A JP 2002-218940 A

Hayato Maeda, Masashi Hosokawa, Tokutake Sashima, Katsura Funayama, Kazuo Miyashita, "Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues", Biochem. Biophys. Res. Comm. 332, 392-397 (2005). Hayato Maeda, Masashi Hosokawa, Tokutake Sashima, Nobuyuki Takahashi, Yeruo Kawada, Kazuo Miyashita, "Fucoxanthin and its metabolite, Fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells", International Journal of Molecular Medicine, 18,147-152 (2005) .

  Therefore, development of a technique capable of improving the storage stability of carotenoids is desired, and an object of the present invention is to provide a composition that can stably contain carotenoids for a long period of time.

  As a result of diligent research to solve the above problems, the present inventors have found that, by using medium-chain saturated fatty acid triglyceride as an oil base and further adding tocotrienol, decomposition of carotenoids can be remarkably suppressed. The headline and the present invention have been completed.

That is, the present invention provides the following components (A) to (C);
(A) Carotenoids (B) A carotenoid-containing oily composition containing (C) medium chain saturated fatty acid triglyceride (C) and tocotrienol.

  The present invention is also a method for stabilizing carotenoids characterized by dissolving carotenoids and tocotrienol in an oily base containing medium-chain saturated fatty acid triglycerides.

  According to the present invention, decomposition of carotenoids can be suppressed and storage stability can be significantly improved. Accordingly, it is possible to maintain a high carotenoid content and to sufficiently obtain physiological activities such as an antioxidant action, and to maintain a good appearance by suppressing the fading of the carotenoids.

  The carotenoids of component (A) used in the present invention include carotenes as hydrocarbons and xanthophylls containing oxygen in the chemical structure. Specifically, as carotenes, α-carotene, β- Examples of carotene, γ-carotene, ε-carotene, lycopene; xanthophylls include derivatives such as fucoxanthin, lutein, astaxanthin, canthaxanthin, capsanthin, zeaxanthin, anthaxanthin, violaxanthin and esters thereof. Of these, xanthophylls whose various functionalities are becoming clear in recent years are preferable, fucoxanthin and astaxanthin are more preferable, and fucoxanthin is particularly preferable.

  Fucoxanthin is contained in, for example, brown algae belonging to the order of Chloraceae, Fucales, Laminariales, Cytosoniphones, etc., and these can be used as a raw material for extraction. it can. Among these brown algae, the genus Chrysaceae or Chrysaceae, Spermatochaceae, Scarabaceae (Sargassaceae), Crimaceae (Laminariaceae) or Arianoceae (Arianoceae), Brown algae belonging to (Schtosiphonaceae) and the like are preferred, and among the brown algae belonging to the above family, the genus Osalum of the family Nymphalidae (Cladosiphon okamuranus) or the moss (Nemacistus decipiens) of the family A. , Hijiki fusiformis or Akamoku (Sargassum horneri), Eisenia of the kelp family (Eisenia bicyclis (Kjellman) Setchell), Laminaria japonica (Laminaria japonica), Onikonbu (Laminaria diabolica), Rishirikonbu (Laminaria ochotensis), Hosomekonbu (Laminaria religiosa), Mitsuishikonbu (Laminaria angustata), Nagakonbu (Laminaria longissima) or Kagollum combi (Kjellmanella crassiifolia), sea turtle (Undaria pinnatifida), clover (Petalonia binghamiae) Are preferred, especially Nagamatsumo family Cladosiphon okamuranus, the Mozuku family Mozuku, the Habanori of Kayanomori family contains a high concentration of fucoxanthin, also suitably used because it is easy to culture.

  The brown algae used as the raw material for extraction is the release of zoospores from matured bodies, the generation of discoids or filaments from the zoospores, the formation of a solid body by the implantation of a disklike body or a filamentous body, Of the growth cycle of growing into a plate, it may be in any growth stage from a plate-like body or a filamentous body to a mature body, but a plate-like body or a filamentous body is preferred because it contains abundant fucoxanthin. In addition, although a board | plate-like body or a filamentous body is located in the middle of the zoospore and a direct solid in the said growth cycle, and may be called with another name, in the present invention, all of these are included. In addition, the plate-like body or the filamentous body may be naturally derived or artificially cultured, for example, cultured by the method described in JP-A-2004-35528. A board or thread can be used.

  From the above-mentioned brown algae plate or filament, for example, water, alcohols such as methanol, ethanol, propanol, ketones such as acetone, esters such as ethyl acetate, aliphatic hydrocarbons such as hexane, benzene, etc. Fucoxanthin is extracted using an aromatic hydrocarbon, a halogen-based organic solvent such as chloroform, or a mixed solvent thereof. Since fucoxanthin is also used for foods and the like, it is preferably extracted with ethanol or hydrous ethanol. Hydrous ethanol has a mixing ratio of ethanol: water of 40:60 to 99: 1, preferably 80:20 to 90:10 (mass ratio). Use of hydrous ethanol is preferable because the content of impurities such as chlorophyll is small and the yield of fucoxanthin and the like can be improved. These solvents may be added at a mass ratio of 10: 1 to 1: 1, preferably 2: 1 to 4: 1, with respect to the disk or filament.

  The extraction using the above-mentioned solvent can be performed by a conventional method. For example, when ethanol is used as the solvent, the temperature is 15 to 60 ° C., preferably 20 to 40 ° C., preferably 0.5 to 16 hours, preferably Extraction may be performed for 2 to 8 hours. In extraction, if necessary, stirring may be performed with an ultrasonic wave, a stirrer, or the like.

  Since the solvent extract of brown algae obtained as described above contains fucoxanthin at a relatively high concentration, it may be blended as it is in the oily composition of the present invention. The storage stability of fucoxanthin can be improved by further purification using. Examples of such purification means include column chromatography, liquid-liquid partition, etc., but column chromatography can be used because impurities such as chlorophylls contained in the extract can be effectively removed to improve storage stability. preferable. For column chromatography, for example, a reversed-phase synthetic adsorption resin such as styrene-divinylbenzene or methacrylic acid ester is used as a filler, and the adsorbed fraction is eluted with a water-ethanol solvent. . The fraction fractionated by column chromatography may be used as it is, but further concentration, removal of the solvent, etc. may be performed by a conventional method such as concentration under reduced pressure. By repeating such column chromatography, impurities such as chlorophylls are removed, and the storage stability of fucoxanthin can be further improved. Chlorophylls can also be removed by cooling the solvent extract at about 0 to 10 ° C. and filtering off the precipitated solid. Further, by repeating operations such as silica gel column chromatography and recrystallization in addition to these operations, for example, highly pure fucoxanthin having a purity of 90% or more can be obtained.

  The content of the component (A) in the oily composition of the present invention is 1.0 to 40.0% by mass (hereinafter simply indicated by “%”), preferably 3.0 to 10.0%. If it exceeds 40.0%, the solubility of the component (B) in the oil base is limited, which is not realistic.

  In the oily composition of the present invention, component (B) medium chain saturated fatty acid triglyceride is used as the oily base. This medium-chain saturated fatty acid triglyceride is composed of saturated fatty acids having 8 to 10 carbon atoms, and particularly has less body fat accumulation compared to long-chain fatty acids, so that it has 8 carbon atoms and 10 carbon atoms caprylic acid. Tri (capryl / capric acid) glyceryl composed of an acid is preferably used. Commercially available products of medium chain saturated fatty acid triglycerides include O.D. D. Examples thereof include O and scoley (both are tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Group Co., Ltd.). Medium-chain saturated fatty acid triglycerides are reported to have lower body fat accumulation than long-chain fatty acid triglycerides and have an effect of preventing obesity (Michio Kasai, “Medium-chain fatty acids as Foods for Healthy Health Use (FOSHU)). ", J. Lipid Nutr. Vol. 15, No. 1 (2006)).

  Content of the component (B) in the oil-based composition of this invention becomes like this. Preferably it is 50.0-99.0%, More preferably, it is 85.0-95.0%. In addition to the medium-chain saturated fatty acid triglycerides, short-chain fatty acid triglycerides, long-chain fatty acid triglycerides, as well as diglycerides, monoglycerides, and the like are included in the oily base used in the oily composition of the present invention without impairing the effects of the present invention. However, the content of the medium-chain saturated fatty acid triglyceride in the entire oil base is preferably 80.0% or more, more preferably 90.0% or more, and particularly preferably 100%. preferable.

  Furthermore, a component (C) tocotrienol is used for the oil-based composition of this invention. There are four homologues of tocotrienol, α, β, γ and δ −, but any of them can be used in the present invention, and a mixture thereof may be used. Examples of commercially available products of tocotrienols include Tocolit 92 (manufactured by Eisai Food Chemical Co., Ltd.) and Orizatocotrienol-90 (manufactured by Oriza Oil Chemical Co., Ltd.).

  Content of the component (C) in the oil-based composition of this invention is 0.1-6.0% normally, Preferably it is 0.1-5.0%, More preferably, it is 0.5-2. 0%. If it is lower than 0.1%, a sufficient effect may not be obtained. If it is higher than 6.0%, it may be difficult to dissolve in an oily base, or it may not be preferable in terms of cost.

  The oil-based composition of the present invention preferably further contains an oil-soluble antioxidant selected from the group consisting of component (D) tocopherol (D1) and oil-soluble vitamin C derivative (D2). By adding the component (D), the stability of the carotenoids can be further improved. As for tocopherol (D1), there are four homologues of α, β, γ and σ −, any of which can be used, or a mixture thereof. On the other hand, examples of the oil-soluble vitamin C derivative (D2) include L-ascorbic acid fatty acid esters such as vitamin C palmitate and vitamin C stearate. In the present invention, one or more of these can be used. Among these, vitamin C palmitate is preferably used because of its excellent carotenoid stabilizing effect.

  The compounding quantity of the component (D) in the oil-based composition of this invention is 0.1-7.0% normally, Preferably it is 0.5-5.0%, More preferably, it is 0.5-2. 0%. The blending mass ratio with respect to component (C) tocotrienol is preferably 1:50 to 50: 1 (component (C): component (D)).

  When only tocopherol (D1) is used as component (D), the blending mass ratio with respect to component (C) is preferably 1: 0.2 to 8 (component (C): component (D1)). Furthermore, it is preferable to set it as 1: 0.8-5, and it is preferable to set it as 1: 0.4-6 especially. Within such a range, an excellent carotenoid stabilizing effect can be obtained. The total content of the component (C) and the component (D1) in the oily composition is usually 0.2 to 10%, preferably 1.0 to 8.0%, more preferably 1.0 to 4. 0%, especially 2.0-4.0%. This range is preferable because the stability of carotenoids is increased. Further, the total blending mass ratio of the components (C) and (D1) to the component (A) carotenoids may be 1: 0.5 to 8 (component (A): component (C) + (D1)). Preferably, 1: 2-4 is more preferable.

  Moreover, when using a tocopherol (D1) and an oil-soluble vitamin C derivative (D2) together as a component (D), the compounding mass ratio with respect to a component (C) is usually 1: 0.2-8: 0.2. ~ 8, preferably 1: 0.3 to 6: 0.4 to 5, more preferably 1: 0.4 to 5: 0.4 to 2, thereby synergistically stabilizing carotenoids Can be obtained. Further, the total content of the component (C), the component (D1) and the component (D2) in the oily composition is usually 0.2 to 10%, preferably 1.0 to 8.0%, more preferably 1. 0.0 to 4.0%, particularly 2.0 to 4.0%. This range is preferable because the stability of carotenoids increases. Further, the total blending mass ratio of the component (C), the component (D1) and the component (D2) to the component (A) carotenoids is 1: 0.5 to 8 (component (A): component (C) + (D1 ) + (D2)), more preferably 1: 2-4. Furthermore, the blending mass ratio of the component (D1) and the component (D2) is usually 1: 0.5 to 15 (component (D1): component (D2)), preferably 1: 1 to 10, more preferably 1: 1-4.

  In the oily composition of the present invention, an optional component may be blended as necessary within a range not impairing the effects of the present invention. As such an optional component, for example, a fragrance, a cyclodextrin, or the like can be used for the purpose of masking an odor derived from seaweed.

  The oily composition of the present invention is prepared by mixing and dissolving the above components (A), (C) and, if necessary, the component (D) in an oily base containing the component (B) by a conventional method. Can do.

  The oily composition thus obtained can be blended in foods and drinks, pharmaceuticals, cosmetics and the like that are expected to have effects such as antioxidant activity of carotenoids. As foods and drinks, health foods in the form of soft capsules, hard capsules, tablets, granules, etc., or added to other foods and food materials to make foods and drinks such as soft drinks, drinks, jellies, candies, etc. it can. In addition, it can be combined with a known pharmaceutical carrier to form a capsule, liquid, or the like. On the other hand, as cosmetics, various forms such as emulsions, creams, lotions, body gels and the like can be used according to conventional methods.

  For example, an oily composition using fucoxanthin as a carotenoid can be used for a pharmaceutical or the like for the above-mentioned antitumor effect, nerve cell protective effect, blood glucose level increase inhibitory effect and the like. In addition to the anti-obesity effect of fucoxanthin, as described above, the medium-chain fatty acid triglyceride also has an obesity-preventing effect, so that it is possible to make an excellent diet food due to the action of both.

  Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples.

Manufacturing example 1
Preparation of fucoxanthin concentrate (1):
150 L of 86% ethanol (hydrous ethanol) was added to 50 kg of Okinawa mozuku discoids cultured according to the method described in JP-A-2004-35528, followed by extraction with stirring for 6 hours. The clarified extract was obtained by solid-liquid separation of the extract by centrifugation. This extract was loaded onto a column packed with synthetic adsorption resin Diaion HP-20 (Mitsubishi Chemical), adsorbed fucoxanthin, and then washed with 45 L of 70% ethanol, and then into 120 L of 90% ethanol. Fucoxanthin was eluted to obtain a fucoxanthin-containing fraction. This fucoxanthin-containing fraction was concentrated under reduced pressure to obtain a fucoxanthin concentrate. The quantitative analysis of the fucoxanthin content in the concentrate by HPLC under the following conditions was 20%.

(HPLC conditions)
A high performance liquid chromatography LC-20AB system (manufactured by Shimadzu Corporation) was used. The column was COSMOSIL 5C ₂₂ -AR-II (manufactured by Nacalai Tesque, inner diameter 4.6 × 250 mm), and the mobile phase was a mixture of acetonitrile / water (80:20). Fucoxanthin was detected by absorption at a wavelength of 450 nm using a photodiode array, and analysis was performed at a flow rate of 1.5 ml / min.

Example 1
Preparation of fucoxanthin-containing oily composition:
To the fucoxanthin concentrate obtained in Production Example 1, O.D. D. O (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Eulio Co., Ltd.) and Tocolit 92 (Tocotrienol 70%, Tocophenol 30%; manufactured by Eisai Food Chemical Co., Ltd.), fucoxanthin final concentration of 1% Each was added and mixed so that the final concentration was 2%.

Comparative Examples 1-11
An oily composition was prepared in the same manner as in Example 1 except that the oily base and the antioxidant were changed as shown in Table 1 below. The oily base and antioxidant used are as follows.
(Oil base)
O. D. O (tri (caprylic / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.)
Canola oil healthy light (long chain fatty acid triglyceride; Nisshin Oilio Co., Ltd.)
Olive oil (long-chain fatty acid triglyceride; manufactured by Nisshin Eulio)
Salad oil (long-chain fatty acid triglyceride; Nisshin Oilio Co., Ltd.)
(Antioxidant)
Tokorit 92 (70% tocotrienol, 30% tocopherol; manufactured by Eisai Food Chemical Co., Ltd.)
RM-21E (RME; Rosemary extract; manufactured by Mitsubishi Chemical Foods)
Extracted vitamin E emulsion (VE; mixed tocopherol; manufactured by Mitsubishi Chemical Foods)

Test example 1
Fucoxanthin storage stability test:
The oily compositions obtained in Example 1 and Comparative Examples 1 to 11 were each placed in a 25 ml vial and stored in an oven at 40 ° C. The fucoxanthin content in the oily composition after 7 days was measured by HPLC under the above conditions. The results are also shown in Table 1.

  The amount of fucoxanthin after 7 days decreased by 7 to 18% in the comparative example, whereas no decrease was observed in Example 1. In Comparative Examples 3, 6, and 9 in which the same antioxidant as in Example 1 was added, fucoxanthin decreased by 9%, 18%, and 9%, respectively, and Comparative Example using the same oily base as in Example 1 Since 1 and 2 also decreased by 10% and 7%, respectively, it was shown that the medium-chain saturated fatty acid triglyceride and tocotrienol of Example 1 are a particularly highly effective combination.

Examples 2-3
An oily composition was prepared in the same manner as in Example 1 except that the oily base and the antioxidant were changed as shown in Table 2 below. The oily composition was placed in a 25 ml vial and stored in a 50 ° C. oven and a −80 ° C. freezer. The fucoxanthin content in the oily composition after 0, 1, 5, 11, 15 and 26 days was measured by HPLC under the above conditions. The fucoxanthin content was determined as a relative value with the sample stored on the same day at −80 ° C. as 100. The results are shown in Table 3.

  Compared with test 1, in Examples 2 and 3, an accelerated test was conducted over a longer period under higher temperature conditions, which reflects a longer storage stability. Since the amount of fucoxanthin after 26 days remained in Example 3 as compared with Example 2 in comparison with Example 2, it was suggested that the storage stability could be further improved by using vitamin C palmitate together. It was done.

Examples 4-7
Preparation of fucoxanthin-containing oily composition and fucoxanthin storage stability test:
To the fucoxanthin concentrate obtained in Production Example 1, SCORAY 64 (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.), Tocorit 92 (70% tocotrienol, 30% tocopherol; manufactured by Eisai Food Chemical Co., Ltd.) and Tocopherol (manufactured by Nisshin Oillio Co., Ltd.) was added and mixed so that the final concentration of fucoxanthin was 1% and the total final concentration of tocotrienol and tocopherol was 2%. The blending mass ratio of tocotrienol and tocopherol was changed in the range of 1: 0.43 to 4.7.
The resulting oily composition was placed in a 25 ml vial and stored in a 40 ° C. oven and a −80 ° C. freezer. The fucoxanthin content in the oily composition after 15 days was measured by HPLC under the above conditions. The fucoxanthin content was determined as a relative value with the sample stored on the same day at −80 ° C. as 100. In addition, the thing which does not add an antioxidant was set as control. The results are shown in Table 4.

  From Table 4, it was shown that the stability of fucoxanthin is improved by using tocotrienol and tocopherol in combination.

Examples 8-11, Comparative Example 12
Preparation of fucoxanthin-containing oily composition and fucoxanthin storage stability test:
To the fucoxanthin concentrate obtained in Production Example 1, scoray 64 (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.), tocorit 92 (70% tocotrienol, tocopherol 30%; manufactured by Eisai Food Chemical Co., Ltd.), Tocopherol (Nisshin Oilio Co., Ltd.) and Vitamin C palmitate (Mitsubishi Food Chemical Co., Ltd.) so that the final concentration of fucoxanthin is 1%, and the total final concentration of tocotrienol, tocopherol and vitamin C palmitate is 1-8%. Each was added and mixed. The blending mass ratio of tocotrienol, tocopherol and vitamin C palmitate was varied in the range of 1: 0.43: 0.48 to 4.29.
The resulting oily composition was placed in a 25 ml vial and stored in a 40 ° C. oven and a −80 ° C. freezer. The fucoxanthin content in the oily composition after 15 days was measured by HPLC under the above conditions. The fucoxanthin content was determined as a relative value with the sample stored on the same day at −80 ° C. as 100. In addition, the thing which does not add an antioxidant was set as control. The results are shown in Table 5.

  From Table 5, it was shown that a synergistic fucoxanthin stabilizing effect can be obtained by using vitamin C palmitate in addition to tocotrienol and tocopherol.

Manufacturing example 2
Preparation of fucoxanthin concentrate (2):
(Purification 1) 150 L of 86% ethanol (hydrous ethanol) was added to 50 kg of Okinawa mozuku discoids cultured according to the method described in JP-A No. 2004-35528, followed by stirring and extraction for 6 hours. The clarified extract was obtained by solid-liquid separation of the extract by centrifugation. This extract was loaded onto a column packed with synthetic adsorption resin Diaion HP-20 (Mitsubishi Chemical), adsorbed fucoxanthin, and then washed with 45 L of 70% ethanol, and then into 120 L of 90% ethanol. Fucoxanthin was eluted to obtain a fucoxanthin-containing fraction (1). This fucoxanthin-containing fraction (1) was concentrated under reduced pressure to obtain a fucoxanthin concentrate (1). About this concentrate, the fucoxanthin content was analyzed by HPLC in the same manner as in Production Example 1. In addition, chlorophyll a, c ₁ and c ₂ were quantitatively analyzed by HPLC under the following conditions. The results are shown in Table 7.

(HPLC conditions)
A high performance liquid chromatography LC-20AB system (manufactured by Shimadzu Corporation) was used. As the column, Intersil ODS-P 5 μm (GL Science, inner diameter 4.6 × 150 mm) was used. The flow rate is 0.8 ml / min. The analysis was performed with a gradient.
Solvent A: methanol (containing 0.25M ammonium acetate), acetonitrile, water = 4: 3.5: 2.5
Solvent B: acetonitrile, ethyl acetate = 3: 7
The time program for gradient analysis is shown in Table 6 below.

(Purification 2) RO water is added to the fucoxanthin-containing fraction (1) so that the ethanol concentration becomes 70%, and this extract is loaded onto a column packed with synthetic adsorption resin Diaion HP-20. After xanthine was adsorbed and washed with 45 L of 70% ethanol, fucoxanthin was eluted with 90 L of 90% ethanol to obtain a fucoxanthin-containing fraction (2). This fucoxanthin-containing fraction (2) was concentrated under reduced pressure to obtain a fucoxanthin concentrate (2). The contents of fucoxanthin and chlorophyll a, c ₁ and c ₂ in this concentrate were quantitatively analyzed in the same manner as described above. The results are shown in Table 7.

By repeating the column purification twice, the purity of fucoxanthin was 24%, chlorophyll c ₁ was reduced by 17%, c ₂ was reduced by 32%, and a was almost completely removed.

Examples 12-14
Preparation of fucoxanthin-containing oily composition and fucoxanthin storage stability test (light resistance):
To the fucoxanthin concentrates (1) and (2) obtained in Production Example 2, scoray 64 (tri (capryl / capric acid) glyceryl; manufactured by Nisshin Oilio Co., Ltd.), tocorit 92 (tocotrienol 70%, tocopherol 30%; Eisai Food Chemical Co., Ltd.) was added and mixed such that the final concentration of fucoxanthin was 1% and the final concentration of tocotrienol was 2% (Examples 12 and 13). Moreover, it replaced with the fucoxanthin concentrate and prepared the oil-based composition with the same composition using the reagent (The Wako Pure Chemical Industries Ltd. make, purity 94.0% or more) (Example 14).
The obtained oily composition was put in a 25 ml vial and stored under conditions of 5000 Lux and 40 ° C., and the fucoxanthin content in the oily composition after 0, 4, 5, 6, and 7 days was determined according to the conditions of Production Example 1 above. Measured by HPLC. The fucoxanthin content was determined as a relative value with the sample stored on the same day at −80 ° C. as 100. The results are shown in Table 8.

  By repeating the column purification twice, the stability after 7 days was improved by 11%. It is considered that removal of impurities such as chlorophyll a is effective for the storage stability of fucoxanthin.

Example 15
Preparation of fucoxanthin soft capsule:
A soft capsule having the following formulation was prepared.
(Prescription) (per 400mg capsule)
(1) Gelatin (film) 150mg
(2) 250 mg of the oily composition of Example 1
400mg total
This soft capsule has excellent storage stability.

Example 16
Preparation of fucoxanthin-containing beverage:
A beverage having the following formulation was prepared.
(Prescription) (per 100ml)
(1) Oily composition of Example 1 0.5 g
(2) Lecithin (derived from soybean) 0.5g
(3) Green tea extract (Sankyo Lifetech) 0.85g
(4) Fructose 4g
(5) L-ascorbic acid 0.05g
(6) Fragrance 0.1g
(7) Purified water
100g in total (100g with purified water)
This beverage is excellent in storage stability.

  Since the oily composition of the present invention can stably hold carotenoids over a long period of time, it is extremely useful as a raw material for use in health foods and pharmaceuticals.

Claims (9)

The following components (A) to ( D );
(A) Fucoxanthin 1.0-3.0 mass%
(B) Tri (capryl / capric acid) glyceryl 85.0-95.0 mass%
(C) Tocotrienol 0.1-5.0% by mass
(D) From tocopherol (D1) and L-ascorbic acid fatty acid ester (D2)
One or more oil-soluble antioxidants selected from the group consisting of 0.5 to 5.0% by mass
And the blending mass ratio of the component (C) and the component (D) is 1:50 to 50: 1 . Oily composition according to claim 1, wherein fucoxanthin is included in the brown algae extract. A component (D) is tocopherol (D1), mixing mass ratio of component (C) and the component (D1) is 1: claim 1 oleaginous composition wherein 0.2 to 8. Component (D) is tocopherol (D1) and L-ascorbic acid fatty acid ester (D2), and the blending mass ratio of component (C), component (D1) and component (D2) is from 1: 0.2 to 8: 0.2 to 8 is claim 1 oleaginous composition. The oily composition according to any one of claims 1 to 4, wherein the component (D2) is vitamin C palmitate. Food-drinks containing the oil-based composition of any one of Claims 1 thru | or 5 . A pharmaceutical comprising the oily composition according to any one of claims 1 to 5 . A cosmetic comprising the oily composition according to any one of claims 1 to 5 . The following components (A) to (D);
(A) Fucoxanthin 1.0-3.0 mass%
(B) Tri (capryl / capric acid) glyceryl 85.0-95.0 mass%
(C) Tocotrienol 0.1-5.0% by mass
(D) From tocopherol (D1) and L-ascorbic acid fatty acid ester (D2)
One or more oil-soluble antioxidants selected from the group consisting of 0.5 to 5.0% by mass
Containing, the mixing mass ratio of component (C) and the component (D), 1: 50 to 50: In the oil-based composition is 1, fucosyltransferase in an oil base containing a tri (caprylate / caprate), glyceryl A method for stabilizing fucoxanthin in an oily composition, comprising dissolving xanthine, tocotrienol and an oil-soluble antioxidant .