AU2018208993B2 - Stable and liposoluble active ingredient composition, microcapsule, and preparation method and application thereof - Google Patents

Stable and liposoluble active ingredient composition, microcapsule, and preparation method and application thereof Download PDF

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AU2018208993B2
AU2018208993B2 AU2018208993A AU2018208993A AU2018208993B2 AU 2018208993 B2 AU2018208993 B2 AU 2018208993B2 AU 2018208993 A AU2018208993 A AU 2018208993A AU 2018208993 A AU2018208993 A AU 2018208993A AU 2018208993 B2 AU2018208993 B2 AU 2018208993B2
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Prior art keywords
active ingredient
fat
soluble active
vitamin
palmitate
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AU2018208993A1 (en
Inventor
Siping Hu
Huajuan KONG
Chun Li
Zhiping Liang
Fritz Bernhard LÜBBE
Wenxin MA
Guoquan MAO
Li Qian
Qinlan WANG
Shanping WEN
Hongming ZHU
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Zhejiang Medicine Co Ltd Xinchang Pharmaceutical Factory
Zhejiang Medicine Co Ltd Vitamin Factory
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Zhejiang Medicine Co Ltd Xinchang Pharmaceutical Factory
Zhejiang Medicine Co Ltd Vitamin Factory
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Priority claimed from PCT/CN2018/073371 external-priority patent/WO2018133833A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/38—Other non-alcoholic beverages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A23L33/155—Vitamins A or D
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/20—Agglomerating; Granulating; Tabletting
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
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    • A61K31/01—Hydrocarbons
    • A61K31/015—Hydrocarbons carbocyclic
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • A—HUMAN NECESSITIES
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    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5089—Processes
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • B01J13/043—Drying and spraying
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/70—Vitamins
    • A23V2250/708—Vitamin C
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Abstract

A stable and liposoluble active ingredient composition, a microcapsule, and a preparation method and application thereof. The liposoluble active ingredient composition comprises tocopherol, vitamin c palmitate, and a liposoluble active ingredient, wherein a weight ratio of the tocopherol to the vitamin c palmitate is 2-8:1, and a weight ratio of a combination of the tocopherol and the vitamin c palmitate to the liposoluble active ingredient is 7-13:100.

Description

DESCRIPTION
Stable and Liposoluble Active Ingredient Composition, Microcapsule and
Preparation Method and Application Thereof
FIELD OF THE INVENTION The present invention relates to a novel green antioxidant composition for increasing the stability of vitamin A ester. In particular, the present invention relates to a stable fat-soluble active ingredient composition, microcapsule and process of preparation and use thereof.
BACKGROUD OF THE INVENTION Vitamins are necessary for animal nutrition and production and have a very important role on the body's metabolism, growth, development and health. Vitamin A is a very important member of the vitamin A ester family and has a very important function on visual health, bone health, reproduction and cell division and reproduction. It would be inconceivable for the lack of vitamin A in the human body. Vitamin A is a light yellow crystalline solid, insoluble in water, and is soluble in fat and varieties of fat solvents, and is easy to deteriorates in the light, heat and oxygen, and then is easily destroyed. Therefore, it must firstly be esterified in the preparation of vitamin A additive. Generally it would be made into microcapsules powder for use. As for a microencapsulation embedding technology, vitamin A ester as a core material is melted to form an oil phase, and then dissolved with high molecular material as wall material. Small molecule filler and emulsifier in water forms an aqueous phase. The oil phase and the aqueous phase are mixed, and then emulsified, sprayed drying or crosslinked, and finally to obtain a microcapsule product. An antioxidant is added to prevent from oxidation of vitamin A esters in the preparation of vitamin A ester microcapsules of the above process. At present, antioxidants generally includes ethoxyquinoline, tert-butyl hydroxytoluene and butylated hydroxyanisole. But these antioxidants have a trend to be limited uses even prohibited uses in the international food and feed industry due to their associated potential hazards. There are some green safe and healthy antioxidants such as tocopherol or vitamin C palmitate without hidden dangers of limiting or prohibiting uses in the food and feed industry. Tocopherol is a fat-soluble antioxidant for effectively preventing from the formation of active oxides during the oxidation of fat. It would be necessary for normal growth and fertility of animals. Vitamin C palmitate is a highly effective oxygen scavenger and synergist, and evaluated as a nutritious, non-toxic, efficient, safe use food additive by the World Health Organization (WHO) Food Additives Committee and is also the sole antioxidant available for infant food in China, and also used as an antioxidants and has some effects on food color protection, nutrition enhancement for foods.
Chinese Patent CN102362864 ( B) introduces a method for enhancing
free-running property and bulk density of vitamin A or vitamin D3 microcapsules, wherein the antioxidant is tocopherol or vitamin C palmitate. Chinese Patent CN102176833 (A) introduces a preparation method of ready-to-use stable emulsion, wherein the antioxidant is tocopherol, t-butylhydroxytoluene, t-butylhydroxyanisole, ascorbic acid or ethoxyquinoline, wherein the emulsifier is ascorbyl palmitate (vitamin C palmitate).
Chinese Patent CN103181566 (A) describes powder preparation of vitamin A
ester, wherein the water-soluble antioxidant may be ascorbic acid and its salts, such as sodium ascorbate and so on. And the fat-soluble antioxidant may be tocopherol; fatty acid ascorbate, such as ascorbyl palmitate or stearate; BHT; BHA; propyl gallate; ethoxyquinoline. Chinese Patent CN1279112 (A) introduces a carbohydrate matrix comprising a composition of fat-soluble substances, wherein the antioxidant is selected from
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sodium ascorbate, palmitate of ascorbic acid, dl-tocopherol, mixed tocopherol, lecithin and their mixtures. All of above patents mentioned antioxidants comprising tocopherol or vitamin C palmitate, but do not describe a combination of tocopherol with vitamin C palmitate, and do not describe a dose of use and a proportion of the antioxidants.
SUMMARY OF THE INVENTION At present, antioxidants generally include ethoxyquinoline, tert-butyl hydroxytoluene and butylated hydroxyanisole. But these antioxidants have a trend to be limited uses even prohibited uses in the international food and feed industry due to their associated potential hazards. An aspect of the present invention is to eliminate hidden dangers of limited uses of antioxidants such as ethoxyquinoline, t-butylhydroxytoluene and t-butylhydroxyanisole, and to overcome some deficiencies in the fat-soluble active ingredients such as vitamin A ester in microcapsule production. In one aspect the present invention obtains a novel antioxidant composition without hidden dangers for the stability improvement of the fat-soluble active ingredient by screening a combination of antioxidants and adjusting their proportion and dose. According to the first aspect of the present invention, the present invention provides a stable fat-soluble active ingredient composition, the fat-soluble active ingredient composition comprises tocopherol, vitamin C palmitate and a fat-soluble active ingredient; wherein the weight ratio of tocopherol to vitamin C palmitate is 2-8:1, the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 7-13:100. According to another aspect of the present invention, there is provided a fat-soluble active ingredient microcapsule, comprising a stable fat-soluble active
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ingredient composition in which stability of fat-soluble active ingredient is increased; said
stable fat-soluble active ingredient composition comprising tocopherol, vitamin C palmitate and a fat-soluble active ingredient selected from DHA acetate and/or linolenic acid phosphate; wherein the weight ratio of tocopherol to vitamin C palmitate is 2-8:1, and the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 7-13:100. In the technical solution of the fat-soluble active ingredient composition of the present invention, preferably, the stable fat-soluble active ingredient composition is any one of a combination of tocopherol and vitamin C palmitate, a combination of tocopherol and sodium ascorbate, as well as a combination of sodium ascorbate and vitamin C palmitate.
In the technical solution of the fat-soluble active ingredient composition of the present invention, preferably, wherein the weight ratio of tocopherol to vitamin C palmitate is 3-7:1. In the technical solution of the fat-soluble active ingredient composition of the present invention, more preferably, the weight ratio of tocopherol to vitamin C palmitate is 4-6: 1. In the technical solution of the fat-soluble active ingredient composition of the present invention, preferably, the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 8-12: 100. In the technical solution of the fat-soluble active ingredient composition of the present invention, more preferably, the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 9-11: 100. In the technical solution of the fat-soluble active ingredient composition of the present invention, more preferably, tocopherol includes one or more of synthetic or
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natural a-tocopherol, p-tocopherol,'y-tocopherol and 6-tocopherol. In the technical solution of the fat-soluble active ingredient composition of the present invention, preferably, the fat-soluble active ingredient is selected from the group consisting of vitamin A, vitamin D, vitamin K, carotenoid and polyunsaturated fatty acid or ester thereof. More preferably, the vitamin A is vitamin A ester. Most preferably, the vitamin A ester is vitamin A acetate, or vitamin A palmitate, or vitamin A propionate, or vitamin AD 3 , or a mixture of the above
substances, wherein the vitamin AD 3 is a mixture of vitamin A ester and vitamin D 3
. According to another aspect of the present invention, the present invention further provides a fat-soluble active ingredient microcapsule containing the fat-soluble active ingredient composition. According to the third aspect of the present invention, the present invention further provides use of the fat-soluble active ingredient composition in the preparation of foods, beverages, animal feeds, cosmetics or pharmaceuticals. According to a further aspect of the present invention, the present invention provides a process for preparing the fat-soluble active ingredient microcapsule, and the method comprises the following steps: 1) blending and melting a fat-soluble active ingredient with an antioxidant in a certain weight ratio at temperature of 45-85°C under nitrogen protection to form an
oil phase A of a fat-soluble active ingredient molten oil; wherein the antioxidant is tocopherol and vitamin C palmitate, the fat-soluble active ingredient is selected from the group consisting of vitamin A, vitamin D, vitamin K, coenzyme Q10, carotenoid and polyunsaturated fatty acid and ester thereof; 2) dissolving a gelatin or a modified starch as a low molecular filler and a glucose or a white sugar in
water at 60-70°C under nitrogen protection, to obtain an aqueous phase B; 3)
blending the oil phase A of step 1) with the aqueous phase B of step 2) under nitrogen protection, and then high-speed shear emulsifying, degasifying and
21621994.1:DCC- 1/06/2021
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homogenizing under nitrogen protection in closed conditions, to obtain an emulsion; and 4) spraying granulation the emulsion of step 3), and then fluidizing drying , to obtain a fat-soluble active ingredient microcapsule. In another aspect of the present invention there is provided a process of preparing the fat-soluble active ingredient microcapsule as defined above, comprising the following steps: 1) blending and melting a fat-soluble active ingredient with an antioxidant in defined weight ratio at temperature of 45-85°C under nitrogen protection to form an oil phase A of a fat-soluble active ingredient molten oil; wherein the antioxidant is tocopherol and vitamin C palmitate, and the fat-soluble active ingredient is selected from DHA acetate and/or linolenic acid phosphate; 2) dissolving a gelatin or a modified starch as a low molecular filler and a glucose or a white sugar in water at 60-70°C under nitrogen protection, to obtain an aqueous phase B; 3) blending the oil phase A of step 1) with the aqueous phase B of step 2) under nitrogen protection, and then high-speed shear emulsifying, degasifying and homogenizing under nitrogen protection in closed conditions, to obtain an emulsion; and 4) spraying granulation the emulsion of step 3), and then fluidizing drying, to obtain a fat-soluble active ingredient microcapsule. In the technical solution of the process of the present invention, preferably, crosslinking the fat-soluble active ingredient microcapsule of step 4), to obtain a water repelling type fat-soluble active ingredient microcapsule. In the technical solution of the process of the present invention, preferably, the weight ratio of the solution of the aqueous phase B is 30-50wt%. The term "the stability improvement" used in the present invention is referred to improve the stability of the fat-soluble active ingredient (selected from the group consisting of vitamin A, vitamin D, vitamin K, coenzyme Q10, carotenoid and polyunsaturated fatty acids or esters thereof) molten oil or emulsion or microcapsule
21621994.1:DCC- 1/06/2021
6A
by adding the antioxidant (tocopherol and vitamin C palmitate) in the present invention. That is, the antioxidant (such as tocopherol and vitamin C palmitate) can efficiently delay the oxidation of the fat-soluble active ingredient and can increase the antioxidant effect. It can be evaluated by the following simple method. The polyunsaturated fatty acids or esters thereof in the present invention is referred to as a linear polyunsaturated fatty acid of C12-25 or its acetate, glyceride, phosphate; preferably, linoleic acid, linolenic acid, EPA, or DHA. The fat-soluble active ingredient molten oil is placed in a sample bottle and sealed from light, storied at 40°C, and then respectively detected its content in 0, 2, 4, 6 days. Its content retention rate is greater than 96% after 6 days. The fat-soluble active ingredient emulsion is placed in a sample bottle and sealed from light, storied at 40°C, and then respectively detected its content in 0, 1, 2, 3 weeks. Its content retention rate is greater than 95% after 3 weeks. The fat-soluble active ingredient microcapsule is placed in a sample bottle and
2 1540839.1:DCC - 25/05/2021
7
sealed from light, storied at 40°C, and then respectively detected its content in 0, 2,
4, 6 weeks. Its content retention rate is greater than 94% after 6 weeks. The term "screening", "adjusting" used in experiment method of the present invention is to find the optimal combination of antioxidants by an orthogonal experiment.
The orthogonal experiment method conducts an overall design, comprehensive comparison and statistical analysis for the experiment by a table in alignment (such as an orthogonal table) to find out better production conditions by several experiment times to achieve the highest production process effects. The orthogonal experiment method firstly selects an orthogonal table corresponding to experiment factors. It shall start with doing experiment based on the table after establishing an experiment table, and then processing those datum. Processing data is a very important step because number of trials is greatly reduced. Analyzing data is firstly to find out the best data from all of the experiment data. Of course, the data is certainly not the best match data, but it is closest to the best match data. Afterwards, assuming the same level experiment data of each factor up obtains a table of experiment result of each level. It may obtain a group of the optimal factor from the table. And then it may obtain a changing trend of these factors by comparing with former factors in order to guide next experiment. Conducting a calculation such as range and variance among different levels experiment values in each factor learns a sensitivity of the factor. Then it shall make sure next experiment and narrow the scope of the experiment and finally determine an optimal value according to statistical data.
2 1540839.1:DCC - 25/05/2021
7A
In the technical solution of process of preparing the fat-soluble active ingredient composition of the present invention, the weight ratio of combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 5-13:100, preferably 7-13:100. In the technical solution of process of preparing the fat-soluble active ingredient composition of the present invention, the weight ratio of tocopherol to vitamin C palmitate, the weight ratio of tocopherol to sodium ascorbate and the weight ratio of vitamin C palmitate to sodium ascorbate is respectively 1: 1-1:10, respectively, preferably 2-8: 1. The advantages of the present invention are as follows: 1) the antioxidants of the present invention are safe, green and healthy food additives, and can eliminate hidden dangers of limited uses of antioxidants such as ethoxyquinoline, tert-butyl hydroxytoluene and butylated hydroxyanisole; 2) the present invention obtains a novel antioxidant composition without hidden dangers for the stability improvement of the fat-soluble active ingredient (such as vitamin A ester) by screening a combination of antioxidants and adjusting their proportion and dose. Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or
group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.
21540839.1:DCC - 25/05/2021
7B
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTSTHEREOF Hereafter, the present invention will be described specifically with reference to the examples. The examples are given only for illustration of the technical solution of the present invention and should not be construed to limit the present invention.
Example 1
Vitamin A ester crystal, vitamin C palmitate and a-tocopherol are blended and
melted at 75C under nitrogen protection to form a vitamin A molten oil. Factor
level setting table of Table 1 and Orthogonal experiment schedule of Table 1 are determined based on weights of vitamin A ester crystal, vitamin C palmitate and a-tocopherol. The vitamin A ester molten oil is placed in a sample bottle and sealed from light, and stored at 40°C, and respectively detected its content in 0, 2, 4, 6 days.
Table 1: Factor Level Setting Table
r(ratio) A a-tocopherol Vitamin C palmitate B level 1 1% 6% 2 1.5% 8% 3 2% 10% Note: The percentage value of Table 1 is the weigh ratio of antioxidant to vitamin A.
Table 2: Orthogonal experiment schedule Experiment factors NO. A B
2 1 2
3 1 3 4 2 2
5 2 3
6 2 1
7 3 3 8 3 1 9 3 2
Analyzing results of 2, 4, 6 days respectively, conducting a comprehensive judgment as a final experiment result, and conducting a range analysis on a content retention, and selecting a primary and secondary relation and excellent combination.
Table 3: Orthogonal Experiment Analysis Table of Content Retention Rate NO. Experiment factors Content retention rate A B 2days 4days 6days 1 1 1 98.80% 96.10% 95.50% 2 1 2 99.00% 98.20% 97.50% 3 1 3 98.40% 96.50% 96.10% 4 2 2 98.80% 97.90% 97.00% 5 2 3 98.00% 96.50% 95.50% 6 2 1 99.20% 98.00% 97.50% 7 3 3 98.80% 97.20% 97.00% 8 3 1 99.10% 98.10% 97.50% 9 3 2 99.80% 98.30% 97.60% k1 0.987 0.990 content k2 0.987 0.992 retention k3 0.992 0.984 rate in R 0.006 0.008 2days Primary and secondary B>A Excellentcombination A3B2 k1 0.969 0.974 content k2 0.975 0.981 Comprehensive judgment: retention k3 0.979 0.967 Primary and secondary rate in 4 R 0.009 0.014 B>A days Primary and secondary B>A Excellent combination A3B2 Excellentcombination A3B2 k1 0.964 0.968 content k2 0.967 0.974 retention k3 0.974 0.962 rate in 6 R 0.010 0.012 days Primary and secondary B>A Excellent combination A3B2
It may be seen from the Orthogonal experiment table of Table 2 and Table 3 that affecting the stability of vitamin A content is mainly tocopherol, is secondly vitamin C palmitate. According to the comprehensive judgment, the excellent combination is A3B2, namely, 2% vitamin C palmitate and 8% a-tocopherol.
Example 2 Vitamin A palmitate, vitamin C palmitate and p-tocopherol are blended and melted at 65C under nitrogen protection to form vitamin A palmitate molten oil.
Gelatin and glucose are dissolved in water at 65C to form a gelatin and glucose
aqueous phase solution. The vitamin A palmitate molten oil is poured into the gelatin and glucose aqueous phase solution and then emulsified under high-speed shear condition, degassed and homogenized, to obtain a stable emulsion. The stable emulsion (that is, vitamin A palmitate emulsion) is placed in a sample bottle and
sealed from light, stored at 40°C, and respectively detected its content in 0, 1, 2, 3
weeks. Data of content retention rates of different antioxidant ratio emulsion are listed in the Table 4.
Table 4 Statistical Table of Content Retention Rate of Vitamin A Palmitate Emulsion of Different Antioxidant Combination
Vitamin C palmitate Content retention rates of Vitamin A palmitate NO. P-tocopherol 0 week 1 week 2 weeks 3 weeks 1 2.0% 0.0% 100% 92.5% 90.0% 86.1% 2 4.0% 0.0% 100% 92.2% 89.8% 86.5% 3 6.0% 0.0% 100% 92.9% 89.7% 87.5% 4 8.0% 0.0% 100% 93.0% 90.2% 88.2% 5 10.0% 0.0% 100% 93.1% 90.1% 89.5% 6 0.0% 0.5% 100% 92.6% 89.6% 85.8% 7 0.0% 1.0% 100% 92.8% 88.9% 85.9% 8 0.0% 1.5% 100% 92.7% 89.5% 86.5% 9 0.0% 2.0% 100% 93.0% 89.6% 86.8% 10 0.0% 2.5% 100% 92.8% 89.4% 86.6% 11 5.0% 2.5% 100% 97.2% 94.8% 92.8% 12 6.0% 2.0% 100% 97.6% 95.9% 93.6% 13 8.0% 2.0% 100% 98.5% 96.8% 95.2% 14 10.0% 2.0% 100% 98.4% 96.9% 95.3% 15 9.6% 1.6% 100% 98.3% 96.7% 95.1% 16 10.0% 1.4% 100% 97.8% 96.2% 94.2% 17 10.0% 1.2% 100% 97.5% 95.8% 93.3%
It may be obviously seen from datum of Table 4 that ihe content retention rate of the vitamin A palmitate emulsion is higher in the range of formula ratio of the present invention.
Example 3 50kg of vitamin A acetate crystal and 0.5kg of vitamin C palmitate and 3.5kg of synthetic tocopherol are blended and melted at 85°C under nitrogen protection to form a vitamin A acetate molten oil. 75kg of gelatin and 50 kg of glucose are dissolved in 130kg of water at 60 °C, to form a 49% gelatin and glucose aqueous phase solution. The vitamin A acetate molten oil is poured into the 49% gelatin and glucose aqueous phase solution and emulsified under high-speed shear condition, and then degassed and homogenized to obtain a stable emulsion; and then the stable emulsion is delivered into a starch bed to conduct a pray granulation, and then fluidized dried and crosslinked under high temperature to obtain 218 kg of water-repellent vitamin A acetate microcapsule. The content of vitamin A acetate is 520,000 IU/g and the microencapsulated yield is 95%, by the HPLC analysis. The vitamin A ester microcapsule is placed in a sample bottle and sealed from light, stored at 40 °C for 6 weeks, and the content of vitamin A ester is 490,000 IU/g, and the content retention rate is 94.2%.
Example 4 50kg of coenzyme Q10 crystal and 0.5kg of vitamin C palmitate and 3kg of natural y-tocopherol are blended and melted at 45°C under nitrogen protection to form a coenzyme Q10 oil. 75kg of gelatin and 50 kg of glucose are dissolved in 130kg of water at 70 °C, to form a 49% gelatin and glucose aqueous phase solution. The coenzyme Q10 oil is poured into the 49% gelatin and glucose aqueous phase solution and emulsified under high-speed shear condition, and then degassed and homogenized to obtain a stable emulsion, and then the stable emulsion is delivered into a starch bed to conduct a pray granulation, and then fluidized dried and crosslinked under high temperature to obtain 218 kg of water-repellent coenzyme Q10 microcapsule. The content of coenzyme Q10 is 52% and the microencapsulated yield is 95%, by the HPLC analysis. The coenzyme Q10 microcapsules are placed in a sample bottle and sealed away from light, stored at 40 °C for 6 weeks, and the content of coenzyme Q10 is 49%, and the content retention rate is 94.2%.
Examples 5-11 The experiment method is the same as that of Example 1. Preparing different fat-soluble active ingredient oil and the retention rate is determined in the Table 5. Table 5
Fat-soluble Tocopherol Retention rate of fat-soluble Exa tle VC active ingredient ple ingredient Type Weight palmitate 0 1 2 3 ratio week week weeks weeks 5 Vitamin K 5.0% 2.5% 100 98.3% 97.6% 97.0%
6 Xanthin p 6.0% 2.0% 100 98.6% 97.9% 97.0%
7 Astaxanthi y 8.0% 2.0% 100 98.7% 97.8% 96.5% n %
8 Lycopene Synthetic 10.0% 2.0% 100 98.1% 96.5% 95.1%
9 DHA 100 9DAc Natural 9.6% 1.6% 98.5% 97.8% 96.3% Acetate %
10 Linoleic 00 acid Mixted 10.0% 1.4% 1 97.8% 96.6% 96.4% glyceride 11 Linolenic 00 acid Mixted 10.0% 1.2% 1 98.0% 96.3% 95.2% phosphate
It may be obviously seen from Table 5 that the content retention rate of the fat-soluble active ingredient is higher in the range of formula ratio of the present invention.
Although the present invention has been described in connection with the above embodiments, it should be understood that the present invention is not limited to such preferred embodiments and procedures set forth above. The embodiments and procedures were chosen and described in order to best explain the principles of the invention and its practical application, to thereby enable others skilled in the art to best utilize the invention. It will be apparent to those skilled in the art that various substitution, modifications and changes may be thereto without departing from the scope and spirit of the invention. Therefore, the intention is intended to cover all alternative constructions and equivalents falling within the spirit and scope of the invention as defined only by the appended claims and equivalents thereto.

Claims (1)

  1. 21621994.1:DCC- 1/06/2021
    14
    THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS:
    1. A fat-soluble active ingredient microcapsule, comprising a stable fat-soluble active ingredient composition in which stability of fat-soluble active ingredient is
    increased; said stable fat-soluble active ingredient composition comprising tocopherol, vitamin C palmitate and a fat-soluble active ingredient selected from DHA acetate and/or linolenic acid phosphate; wherein the weight ratio of tocopherol to vitamin C palmitate is 2-8:1, and the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat-soluble active ingredient is 7-13:100. 2. The fat-soluble active ingredient microcapsule according to claim 1, wherein the weight ratio of tocopherol to vitamin C palmitate is 3-7:1. 3. The fat-soluble active ingredient microcapsule according to claim 2, wherein the weight ratio of tocopherol to vitamin C palmitate is 4-6:1. 4. The fat-soluble active ingredient microcapsule according to claim 1, wherein the weight ratio of a combination of tocopherol with vitamin C palmitate to the fat soluble active ingredient is 8-12:100. 5. The fat-soluble active ingredient microcapsule according to claim 4, wherein the weight ratio of the combination of tocopherol with vitamin C palmitate to the fat soluble active ingredient is 9-11:100. 6. Use of the fat-soluble active ingredient microcapsule according to any one of claims 1-5 in the preparation of foods, beverages, animal feeds, cosmetics or pharmaceuticals. 7. A process of preparing the fat-soluble active ingredient microcapsule according to any one of claims 1-5, comprising the following steps: 1) blending and melting a fat-soluble active ingredient with an antioxidant in defined weight ratio at temperature of 45-85°C under nitrogen protection to form an oil phase A of a fat-soluble active ingredient molten oil; wherein the antioxidant is tocopherol and vitamin C palmitate, and the fat-soluble active ingredient is selected from DHA acetate and/or linolenic acid phosphate;
    21621994.1:DCC-11/06/2021
    15
    2) dissolving a gelatin or a modified starch as a low molecular filler and a glucose or a white sugar in water at 60-70°C under nitrogen protection, to obtain an aqueous phase B; 3) blending the oil phase A of step 1) with the aqueous phase B of step 2) under nitrogen protection, and then high-speed shear emulsifying, degasifying and homogenizing under nitrogen protection in closed conditions, to obtain an emulsion; and
    4) spraying granulation the emulsion of step 3), and then fluidizing drying, to obtain a fat-soluble active ingredient microcapsule. 8. The process according to claim 7, comprising crosslinking the fat-soluble active ingredient microcapsule of step 4), to obtain a water repelling type fat-soluble active ingredient microcapsule.
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