WO2024041525A1 - 一种组合物及其制备方法和用途 - Google Patents
一种组合物及其制备方法和用途 Download PDFInfo
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- WO2024041525A1 WO2024041525A1 PCT/CN2023/114223 CN2023114223W WO2024041525A1 WO 2024041525 A1 WO2024041525 A1 WO 2024041525A1 CN 2023114223 W CN2023114223 W CN 2023114223W WO 2024041525 A1 WO2024041525 A1 WO 2024041525A1
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- aminobutyric acid
- cyclodextrin
- aqueous solution
- wall material
- starch
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- 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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- 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
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
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- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
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- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2303/00—Characterised by the use of starch, amylose or amylopectin or of their derivatives or degradation products
- C08J2303/02—Starch; Degradation products thereof, e.g. dextrin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2303/00—Characterised by the use of starch, amylose or amylopectin or of their derivatives or degradation products
- C08J2303/04—Starch derivatives
- C08J2303/10—Oxidised starch
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/16—Cyclodextrin; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
- C08J2405/16—Cyclodextrin; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
Definitions
- This application belongs to the field of raw material processing technology and relates to a composition, preparation method and use.
- GABA ⁇ -aminobutyric acid
- GABA has strong hygroscopicity, so its powder has poor dispersibility and is not easy to mix evenly with other ingredients during use. Especially during the processing of food powders, due to the presence of free amino compounds in GABA, the Maillard reaction easily occurs with reducing sugars or carbonyl compounds, resulting in brown or even brown-black macromolecules, resulting in discoloration of the product.
- the wall material is selected from one or more of ⁇ -cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose.
- the DE value of the maltodextrin is 5-10, and the starch is oxidized starch.
- composition consists of wall material and gamma-aminobutyric acid.
- the mass ratio of the wall material to the ⁇ -aminobutyric acid is (1-4):1, preferably (2-4):1.
- the wall material includes ⁇ -cyclodextrin and its derivatives and maltodextrin;
- the mass ratio of the maltodextrin to the ⁇ -cyclodextrin and its derivatives is 1:(0.01-0.5), preferably 1:(0.2-0.3).
- the wall material includes ⁇ -cyclodextrin and its derivatives and starch;
- the mass ratio of the starch to the ⁇ -cyclodextrin and its derivatives is 1:(0.01-0.5), preferably 1:(0.2-0.3).
- aqueous solution of ⁇ -aminobutyric acid and the aqueous solution of the wall material are mixed to obtain aqueous solution C, stirred, and spray-dried to obtain the composition.
- the mass ratio of the sum of the masses of the wall material and the ⁇ -aminobutyric acid to the aqueous solution C is (0.5-2.5):10, preferably (1-2):10.
- a complex including the composition described in any one of items 1 to 5 or the composition prepared by the method of any one of items 6 to 7.
- composition in this application can prevent ⁇ -aminobutyric acid from reacting with reducing sugar or carbonyl under the action of water.
- the Maillard reaction of the base compound will not produce brown or brown-black macromolecular substances, nor will it cause the product to change color.
- the wall material in the composition of the present application can effectively block moisture from participating in the browning reaction and effectively protect ⁇ -aminobutyric acid.
- the wall material in the composition of the present application has strong water absorption and can competitively absorb water to slow down the Maillard reaction of water participating in ⁇ -aminobutyric acid in the formula food to achieve a more significant effect.
- Figure 1 shows the content stability results of some examples
- Figure 2 shows the color change of Maillard reaction in some examples.
- ⁇ -Aminobutyric acid is a white or slightly yellow crystalline powder. It has strong hygroscopicity, is easily soluble in water, is slightly soluble in hot ethanol, and is insoluble in benzene, cold ethanol, ether and other organic solvents. It has a slight odor and no optical activity. It is a polar substance with a melting point of 203-205°C, a relative molecular mass of 103.12, and a molecular formula of CHNO.
- ⁇ -Aminobutyric acid usually exists in the form of zwitterions in aqueous solutions.
- ⁇ -Aminobutyric acid is a non-protein amino acid that has some special chemical properties of amino acids and can undergo hydrocarbylation reactions, acylation reactions, ninhydrin color reactions, etc.
- ⁇ -aminobutyric acid As a new type of food functional factor, ⁇ -aminobutyric acid has attracted more and more attention. Studies have found that ⁇ -aminobutyric acid can enhance the permeability of nerve cell membranes to Na, hyperpolarize the cell membrane, and increase the initiation threshold of action potentials. Therefore, ⁇ -aminobutyric acid is an important component of the nerve center of humans and mammals. It is an important inhibitory neurotransmitter in the system, can participate in various metabolic activities in the body, and has strong physiological activity. Its production and application are becoming a hot research direction in the fields of food, medicine, animal feed, and agriculture. The main physiological functions of ⁇ -aminobutyric acid include the following:
- ⁇ -aminobutyric acid As an important inhibitory transmitter in the central nervous system, ⁇ -aminobutyric acid has a good regulatory effect on cardiovascular activity, mainly by regulating heart rate, lowering blood pressure and blood sugar, etc.
- Gamma-aminobutyric acid has certain pharmacological effects in lowering blood pressure. The reason may be that there are specific neuroreceptors in the cerebral blood vessels that can bind to gamma-aminobutyric acid. When the neuroreceptors bind to gamma-aminobutyric acid, time, you can reach to lower blood pressure.
- Mao Zhifang and others found that long-term drinking of green tea containing ⁇ -aminobutyric acid in spontaneously hypertensive rats can significantly reduce blood pressure.
- ⁇ -Aminobutyric acid can also inhibit the activity of glutamic acid decarboxylase, effectively preventing glutamic acid decarboxylation, thereby reducing blood ammonia levels and ensuring human health; at the same time, ⁇ -aminobutyric acid can also promote glutamic acid decarboxylation in the blood. Acid combines with ammonia to form urea, which effectively removes ammonia poisoning in the body and improves liver and kidney function.
- epilepsy According to reports, the number of epilepsy patients in my country has reached about 9 million.
- the causes of epilepsy are diverse, the mechanisms are complex, and they are closely related to central neurotransmitters.
- epilepsy has become the second most common disease in my country, seriously affecting people's work and life.
- ⁇ -aminobutyric acid As an important inhibitory neurotransmitter in the human body, ⁇ -aminobutyric acid has an improving effect on the treatment of epilepsy, insomnia, Parkinson's syndrome and other diseases.
- amino acids in the central nervous system excitatory amino acids and inhibitory amino acids. If the content of excitatory amino acids is too high, the nerve inhibitory effect will decrease, which may cause epilepsy.
- ⁇ -aminobutyric acid can increase the body's anticonvulsant threshold and can effectively treat intractable epilepsy.
- ⁇ -aminobutyric acid can promote sleep, calm nerves, resist anxiety, etc., and can help improve mental disorders in the elderly and symptoms of menopausal syndrome in women.
- ⁇ -aminobutyric acid content in cerebrospinal fluid is negatively correlated with the severity of epilepsy patients, and the ⁇ -aminobutyric acid content is low. Therefore, epilepsy can be treated by directly increasing the content of ⁇ -aminobutyric acid in cerebrospinal fluid.
- ⁇ -aminobutyric acid can also reduce the neurological excitement caused by glutamate, thereby reducing damage to nerve cells.
- ⁇ -aminobutyric acid also has certain effects on the treatment of stiffness and Parkinson's disease.
- ⁇ -Aminobutyric acid regulates the secretion of growth hormone, growth hormone mediators, thyroid hormones, sex hormones and other hormones in the endocrine system, and can effectively improve the body's metabolic level.
- ⁇ -ammonia Butyric acid can directly stimulate the body to secrete the required hormones and is safer than taking exogenous hormones directly. Research shows that ⁇ -aminobutyric acid can regulate gonadotropin secretion by inhibiting the excitation of certain nerves in the hypothalamus.
- ⁇ -aminobutyric acid In addition to inhibiting the decarboxylation of glutamic acid to reduce blood ammonia, ⁇ -aminobutyric acid also has a diuretic effect, allowing excess salt to be excreted from the body and effectively relieving the pressure on the liver and kidneys. Studies have shown that gamma-aminobutyric acid can activate kidney function. At the same time, ⁇ -aminobutyric acid can also inhibit alkaline phosphatase activity, and an important indicator for evaluating liver function activation is the activity of alkaline phosphatase.
- ⁇ -aminobutyric acid also has physiological functions such as preventing obesity, promoting lipid metabolism, preventing vascular sclerosis, repairing skin, and delaying aging. Clinically, ⁇ -aminobutyric acid can also treat uremia, carbon monoxide poisoning and other diseases. In addition, ⁇ -aminobutyric acid also has insecticidal and deodorizing effects.
- the present application provides a composition, including a wall material and ⁇ -aminobutyric acid.
- the wall material is selected from one of ⁇ -cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose. Or two or more.
- the maltodextrin is a maltodextrin with a low DE value.
- the DE value of the maltodextrin is 5-10;
- the DE value of maltodextrin can be 5, 6, 7, 8, 9, 10, or any range therebetween.
- the DE value refers to the percentage of reducing sugars (measured as glucose) in the dry matter of the syrup. According to national standards, the higher the DE value, the higher the grade of glucose syrup.
- the DE value is measured using any method known to those skilled in the art.
- the specifications of maltodextrin in my country's light industry standards are divided into three categories, namely DE value ⁇ 10, ⁇ 15 and ⁇ 20.
- Low DE value maltodextrin is a widely used food ingredient. It has low sweetness, low hygroscopicity and good solubility. It is often used as a carrier of flavor substances, moisturizer, film-forming agent and fat substitute.
- the DE value is determined using an iodometric method.
- the starch is amylose and amylopectin and related modified starches, preferably oxidized starch.
- Natural starch is found in nature in all plants (especially in plant seeds, roots and tubers A carbohydrate present in ) in which it acts as a reserve of nutrients for the new growing season.
- Starch is a glucose polymer in which anhydroglucose units are linked to each other by an ⁇ -D-glycosidic bond.
- Glucose chains are linear or slightly branched amylose, or highly branched amylopectin.
- amylose molecules have a degree of polymerization of 1000 to 5000 and amylopectin molecules have an average degree of polymerization of 1,000,000 or higher.
- Starch can be isolated from, among other things: rice, corn, potato, wheat, cassava (genus Cassava), cassava, barley, oats, millet, and sorghum.
- Modified starch is a starch prepared by at least partially degrading native starch, such as by treating native starch with inorganic acids, alkaline compounds, bleaches, oxidants, enzymes, or acetylating agents.
- Oxidized starch is a modified starch obtained by oxidizing starch by reacting with oxidants in acid, alkali or neutral media. Oxidized starch lowers the starch gelatinization temperature, reduces the viscosity of the hot paste and increases the thermal stability.
- the product is white in color, transparent in paste, has good film-forming properties, and has good freeze-thaw resistance. It is a low-viscosity and high-concentration thickener and is widely used. In the textile, paper, food and fine chemical industries.
- the determination of oxidized starch is carried out using any method known to those skilled in the art.
- the determination of oxidized starch is carried out using a neutralization titration method.
- Cyclodextrin is formed by the action of cyclodextrin glucose residue transferase on glucose polymers such as starch, glycogen, and malto-oligosaccharides.
- the most common ones are cyclodextrin ⁇ , ⁇ , and ⁇ . kind.
- ⁇ -cyclodextrin ⁇ -Cyclodex, referred to as ⁇ -CD
- ⁇ -CD ⁇ -cyclodextrin
- ⁇ -CD is a water-soluble, non-reducing white crystal or amorphous powder with a main configuration like a hole in the middle and unclosed ends. conical cylinder.
- the inner cavity is hydrophobic and can contain many guest molecules, such as organic molecules, inorganic molecules, complexes, and inert gas molecules. Therefore, they can form various inclusions through weak interactions of non-covalent bonds. substances to change the physical, chemical and biological properties of guest molecules.
- the derivative of ⁇ -cyclodextrin is selected from the group consisting of carboxymethyl- ⁇ -cyclodextrin, glucosyl- ⁇ -cyclodextrin, ethylenediamine- ⁇ -cyclodextrin, hydroxyl- ⁇ -cyclodextrin, One or more of ethyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, sulfonate- ⁇ -cyclodextrin and quaternary ammonium- ⁇ -cyclodextrin.
- the composition consists of wall material and gamma-aminobutyric acid.
- the mass ratio of the wall material to the ⁇ -aminobutyric acid is (1-4):1, preferably (2-4):1;
- the mass ratio of the wall material to the ⁇ -aminobutyric acid may be 1:1, 2:1, 3:1, 4:1 or any range therebetween.
- the wall material includes ⁇ -cyclodextrin and its derivatives and malt Dextrin; preferably, the mass ratio of the maltodextrin to the ⁇ -cyclodextrin and its derivatives is 1: (0.01-0.5), preferably 1: (0.2-0.3);
- the mass ratio of the maltodextrin to the ⁇ -cyclodextrin and its derivatives may be 1:0.5, 1:0.45, 1:0.4, 1:0.35, 1:0.3, 1:0.25, 1: 0.2, 1:0.15, 1:0.1, 1:0.05, 1:0.01 or any range in between.
- the wall material is composed of ⁇ -cyclodextrin and its derivatives and maltodextrin.
- the wall material is composed of ⁇ -cyclodextrin and maltodextrin.
- the wall material is composed of ⁇ -cyclodextrin and maltodextrin with a DE value of 5-10.
- the wall material includes ⁇ -cyclodextrin and its derivatives and starch; preferably, the mass ratio of the starch to the ⁇ -cyclodextrin and its derivatives is 1: (0.01 ⁇ 0.5), preferably 1:(0.2-0.3); for example, the mass ratio of the starch to the ⁇ -cyclodextrin and its derivatives can be 1:0.5, 1:0.45, 1:0.4, 1:0.35, 1:0.3, 1:0.25, 1:0.2, 1:0.15, 1:0.1, 1:0.05, 1:0.01 or any range in between.
- the wall material is composed of ⁇ -cyclodextrin and its derivatives and starch.
- the wall material is composed of ⁇ -cyclodextrin and starch.
- the wall material is composed of ⁇ -cyclodextrin and oxidized starch.
- the present application provides a preparation method of the above composition, wherein,
- aqueous solution of ⁇ -aminobutyric acid and the aqueous solution of the wall material are mixed to obtain aqueous solution C, stirred, and spray-dried to obtain the composition.
- the mass ratio of the sum of the masses of the wall material and the gamma-aminobutyric acid to the aqueous solution C is (0.5-2.5):10, preferably (1- 2):10;
- the sum of the masses of the wall material and the gamma-aminobutyric acid and the mass of the aqueous solution C can be 0.5:10, 0.75:10, 1:10, 1.25:10, 1.5:10, 1.75:10, 2 :10, 2.25:10, 2.5:10, or any range in between.
- the mass ratio of the sum of the masses of the wall material and the gamma-aminobutyric acid to the aqueous solution C also refers to the solid content, that is, in the aqueous solution C,
- the solid content is 5-25%, preferably 10-20%;
- the solid content in aqueous solution C, can be 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25% or any range therebetween.
- the stirring temperature is 60-70°C, preferably 60-65°C;
- the stirring temperature may be 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C or any range therebetween.
- the inlet air temperature of spray drying is 140-145°C, and the outlet air temperature of spray drying is 95-105°C;
- the inlet air temperature of spray drying can be 140°C, 141°C, 142°C, 143°C, 144°C, 145°C or any range in between;
- the air outlet temperature of spray drying can be 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C or any range in between.
- an aqueous solution A of wall material is configured, wherein the wall material includes ⁇ -cyclodextrin and its derivatives and maltodextrin; preferably, the maltodextrin and the ⁇ -cyclodextrin are The mass ratio of cyclodextrin and its derivatives is 1: (0.01-0.5), or the wall material includes ⁇ -cyclodextrin and its derivatives and starch; preferably, the starch and the ⁇ -cyclodextrin The mass ratio of dextrin and its derivatives is 1: (0.01 ⁇ 0.5).
- the wall material solution is dissolved in deionized water at 70 ⁇ 80°C, stirred for 10 ⁇ 15 minutes, and cooled to 60 ⁇ 65°C to obtain a uniform solution;
- aqueous solution B of ⁇ -aminobutyric acid mix the aqueous solution of ⁇ -aminobutyric acid and the aqueous solution of the wall material to obtain aqueous solution C.
- stirring temperature should be 60-65°C, which is the temperature before spray drying.
- the mass ratio of the sum of the masses of the wall material and the gamma-aminobutyric acid to the aqueous solution C is (1-2):10, ensuring that the spray drying yield reaches 80 %above.
- the present application provides a complex including the above composition.
- This application also provides a use of the above composition in food, health care products, and pharmaceutical formulations.
- This application also provides a use of the above composition in food, health products, and pharmaceutical raw materials.
- This application also provides a use of the above composition in slowing down the Maillard reaction.
- the wall material used can partially wrap ⁇ -aminobutyric acid, and on the other hand, the wall material used can competitively absorb water, reducing the risk of ⁇ -aminobutyric acid coming into contact with water. Probability, good barrier to moisture to slow down the participation of moisture in the Maillard reaction in formula foods.
- the ingredients used in this application are safe and reliable. This method can effectively improve the browning problem caused by the Maillard reaction between ⁇ -aminobutyric acid and reducing sugars in formula foods, and expands the application of ⁇ -aminobutyric acid in the food field.
- the application of the product is pure and odorless, can be dissolved in water-soluble products, the preparation process is simple, the raw materials are easily available, the yield is high, and it is easy to promote and apply.
- aqueous solution A of wall material dissolve 90g oxidized starch and 22.5g ⁇ -cyclodextrin in 900mL deionized water at 75°C, stir for 10 minutes, and cool to 60°C to obtain an aqueous solution of wall material, oxidized starch and ⁇ -cyclodextrin.
- the mass ratio of essence is 1:0.25, and the sum of the masses of oxidized starch and ⁇ -cyclodextrin is 112.5g;
- aqueous solution B of ⁇ -aminobutyric acid Prepare the aqueous solution B of ⁇ -aminobutyric acid, weigh 37.5g ⁇ -aminobutyric acid and dissolve it in 100 mL of deionized water to obtain the aqueous solution B of ⁇ -aminobutyric acid.
- the weight percentage of ⁇ -aminobutyric acid in the aqueous solution B is 37.5%;
- aqueous solution B of ⁇ -aminobutyric acid Slowly add the aqueous solution B of ⁇ -aminobutyric acid to the aqueous solution A of the wall material in proportion to obtain solution C.
- the mass ratio of the wall material to ⁇ -aminobutyric acid is 3:1
- the mass ratio of the wall material to ⁇ -aminobutyric acid is 3:1.
- the mass ratio of the sum of the masses of aminobutyric acid to aqueous solution C is 1.5:10
- the solid content is 15%, stir and homogenize, continue stirring and homogenizing for 30 minutes after the addition is completed; the stirring temperature is controlled at 62°C, and then sprayed
- the dryer is used for spray drying.
- the inlet air temperature of the spray dryer is 140°C
- the air outlet temperature of the spray dryer is 100°C. 136.8g of powdery solid is obtained, and ⁇ -aminobutyric acid S1 is prepared.
- Example 1 The yield of Example 1 was 91.2%.
- Example 2 The only difference between Example 2 and Example 1 is that the aqueous solution A of the wall material is configured, 60g of oxidized starch and 15g of ⁇ -cyclodextrin are dissolved in 900 mL of deionized water at 75°C, and the mass ratio of the oxidized starch and ⁇ -cyclodextrin is The mass ratio of oxidized starch and ⁇ -cyclodextrin is 75g, the mass ratio of wall material to ⁇ -aminobutyric acid is 2:1, the solid content is 11.25%, and the other conditions are the same.
- Example 3 The only difference between Example 3 and Example 1 is that the aqueous solution A of the wall material is configured, 120g of oxidized starch and 30g of ⁇ -cyclodextrin are dissolved in 900 mL of deionized water at 75°C, and the mass ratio of the oxidized starch and ⁇ -cyclodextrin is The mass ratio of oxidized starch and ⁇ -cyclodextrin is 150g, the mass ratio of wall material to ⁇ -aminobutyric acid is 4:1, the solid content is 18.75%, and the other conditions are the same.
- Example 4 The only difference between Example 4 and Example 1 is that the aqueous solution A of the wall material is prepared, and 90g maltodextrin (the DE value of maltodextrin is 5-10) and 22.5g ⁇ -cyclodextrin are dissolved in 900mL of 75°C.
- the mass ratio of maltodextrin and ⁇ -cyclodextrin with a DE value of 5-10 is 1:0.25
- the sum of the masses of maltodextrin and ⁇ -cyclodextrin with a DE value of 5-10 is 112.5g.
- the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1
- the solid content is 15%
- the other conditions are the same.
- Example 5 The only difference between Example 5 and Example 1 is that the aqueous solution A of the wall material is prepared, and 90g of oxidized starch and 22.5g ⁇ -cyclodextrin are dissolved in 1200 mL of deionized water at 75°C; the aqueous solution B of ⁇ -aminobutyric acid is prepared, Weigh 37.5g of ⁇ -aminobutyric acid and dissolve it in 300 mL of deionized water to obtain aqueous solution B of ⁇ -aminobutyric acid; the mass ratio of oxidized starch and ⁇ -cyclodextrin is 1:0.25, and the mass ratio of oxidized starch and ⁇ -cyclodextrin is 1:0.25.
- the total mass is 112.5g, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content in the obtained aqueous solution C is 10%, and the other conditions are the same.
- Example 6 The only difference between Example 6 and Example 1 is that the aqueous solution A of the wall material is prepared, and 90g of oxidized starch and 22.5g ⁇ -cyclodextrin are dissolved in 650 mL of deionized water at 75°C; the aqueous solution B of ⁇ -aminobutyric acid is prepared, Weigh 37.5g of ⁇ -aminobutyric acid and dissolve it in 100 mL of deionized water to obtain aqueous solution B of ⁇ -aminobutyric acid; the mass ratio of oxidized starch and ⁇ -cyclodextrin is 1:0.25, and the mass ratio of oxidized starch and ⁇ -cyclodextrin is 1:0.25.
- the total mass is 112.5g, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content in the obtained aqueous solution C is 20%, and the other conditions are the same.
- Example 7 The only difference between Example 7 and Example 1 is that the aqueous solution A of the wall material is configured, 75g of oxidized starch and 37.5g of ⁇ -cyclodextrin are dissolved in 900 mL of deionized water at 75°C, and the mass of the oxidized starch and ⁇ -cyclodextrin is The ratio is 1:0.5, the sum of the masses of oxidized starch and ⁇ -cyclodextrin is 112.5g, in aqueous solution C, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content is 15%, and the remaining conditions same.
- Example 8 The only difference between Example 8 and Example 1 is that the aqueous solution A of the wall material was prepared. 111.3g of oxidized starch and 1.2g of ⁇ -cyclodextrin were dissolved in 900 mL of deionized water at 75°C. The mass ratio is 1:0.011, the sum of the masses of oxidized starch and ⁇ -cyclodextrin is 112.5g, in aqueous solution C, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content is 15%, and the rest Conditions are the same.
- Example 9 The only difference between Example 9 and Example 1 is that the aqueous solution A of the wall material is prepared, and 112.5g of maltodextrin (the DE value of maltodextrin is 5-10) is dissolved in 900 mL of deionized water at 75°C, and the solid content is 15%, other things being equal.
- Example 10 The only difference between Example 10 and Example 1 is that the aqueous solution A of the wall material was prepared. 112.5 g of oxidized starch was dissolved in 900 mL of deionized water at 75° C. with a solid content of 15%. The other conditions were the same.
- Example 11 The only difference between Example 11 and Example 1 is that the aqueous solution A of the wall material was prepared by dissolving 112.5g ⁇ -cyclodextrin in 900 mL of deionized water at 75° C. with a solid content of 15%, and the other conditions were the same.
- Example 12 The only difference between Example 12 and Example 1 is that the aqueous solution A of the wall material was prepared. 112.5 g of corn starch was dissolved in 900 mL of deionized water at 75° C. with a solid content of 15%. The remaining conditions were the same.
- Example 13 The only difference between Example 13 and Example 1 is that the aqueous solution A of the wall material was prepared by dissolving 112.5g of maltodextrin in 900 mL of deionized water at 75°C, with a solid content of 15%, and the other conditions were the same.
- Example 14 The only difference between Example 14 and Example 1 is that the aqueous solution A of the wall material was prepared, and 90g of oxidized starch and 22.5g of ⁇ -cyclodextrin were dissolved in 1675mL of deionized water at 75°C;
- aqueous solution B of ⁇ -aminobutyric acid weigh 37.5g ⁇ -aminobutyric acid and dissolve it in 200 mL deionized water to obtain aqueous solution B of ⁇ -aminobutyric acid; in the obtained aqueous solution C, oxidized starch and ⁇ -
- the total mass of cyclodextrin is 112.5g.
- the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content is 8%, and the other conditions are the same.
- Example 15 The only difference between Example 15 and Example 1 is that the aqueous solution A of the wall material is prepared, and 90g of oxidized starch and 22.5g ⁇ -cyclodextrin are dissolved in 500 mL of deionized water at 75°C; the aqueous solution B of ⁇ -aminobutyric acid is prepared, Weigh 37.5g of ⁇ -aminobutyric acid and dissolve it in 100 mL of deionized water to obtain aqueous solution B of ⁇ -aminobutyric acid; in the obtained aqueous solution C, the sum of the masses of oxidized starch and ⁇ -cyclodextrin is 112.5g.
- aqueous solution C the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content is 25%, and the other conditions are the same.
- Example 16 The only difference between Example 16 and Example 1 is that the aqueous solution A of the wall material is configured, 90g corn starch and 22.5 g ⁇ -cyclodextrin are dissolved in 900 mL deionized water at 75°C, and the masses of corn starch and ⁇ -cyclodextrin are The ratio is 1:0.25, the sum of the masses of corn starch and ⁇ -cyclodextrin is 112.5g, in aqueous solution C, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, the solid content is 15%, and the remaining conditions same.
- Example 17 The only difference between Example 17 and Example 1 is that the aqueous solution A of the wall material is prepared. 90g maltodextrin and 22.5g ⁇ -cyclodextrin are dissolved in 900 mL of deionized water at 75°C. Maltodextrin and ⁇ -cyclodextrin are The mass ratio of maltodextrin and ⁇ -cyclodextrin is 112.5g. In aqueous solution C, the mass ratio of wall material to ⁇ -aminobutyric acid is 3:1, and the solid content is 15%. , other conditions are the same.
- Example 1 The parameters of Example 1 to Example 17 are shown in Table 2.
- the samples of Examples 1-4, 7-13 and 16-17 were respectively mixed with maltose, lactose, glucose, fructose and arabinose at a ratio of 1:1 and subjected to a high temperature accelerated test at 60°C to observe the color change after 14 days. , and conduct GABA content detection according to the following method.
- Instrument High-performance liquid chromatograph equipped with UV detector, automatic sampler and data processing system; Chromatographic column: Hypersil ODS C18, 5 ⁇ m, 4.6 ⁇ 250mm (chromatographic column with equal or above separation effect); analytical balance : Accuracy 0.1mg; ultrasonic dissolver.
- Reagents methanol: chromatography grade; acetonitrile: chromatography grade; o-phthalaldehyde (OPA); crystalline sodium acetate; glacial acetic acid; ⁇ -aminobutyric acid standard: purity ⁇ 99.0%; boric acid; sodium hydroxide
- Preparation of standard solution Precisely weigh 0.5g of ⁇ -aminobutyric acid standard, dissolve it in water and adjust the volume to 100mL. After mixing evenly, take 10mL and adjust the volume to 100mL. Filter with a 0.22 ⁇ m filter membrane and collect the filtrate as the standard solution.
- sample solution Precisely weigh 0.5 ⁇ 2.0g sample, dissolve it in water and adjust the volume to 100mL. After mixing evenly, take 10mL and adjust the volume to 100mL. Filter with a 0.22 ⁇ m filter membrane and collect the filtrate as the sample solution to be tested.
- boric acid buffer Preparation of 0.4mol/L boric acid buffer: Weigh 2.47g of boric acid, add about 80mL of water, adjust the pH to 10.2 with sodium hydroxide, and adjust the volume to 100mL with water.
- Preparation of derivatization reagent Weigh 0.1g o-phthalaldehyde (OPA) and dissolve it in 1mL acetonitrile, add 130 ⁇ L mercaptoethanol, and adjust the volume to 10mL with 0.4mol/L boric acid buffer.
- OPA o-phthalaldehyde
- Mobile phase A Weigh 7.5g of crystalline sodium acetate, dissolve it in water and adjust the volume to 1000mL, add 5% acetic acid dropwise to adjust the pH to 7.20 ⁇ 0.02, filter and set aside.
- Phase B filter chromatographically pure acetonitrile and set aside. The mobile phase ratio when running the method is: 75% phase A + 25% phase B. Flow rate: 1.0mL/min. Detection wavelength: 338nm. Column temperature: 40°C.
- Peak area obtain the area ratio between the peak area and the concentration of the standard solution (based on dry product), repeat the operation 6 times, and the relative standard deviation should be less than 3%.
- X 1 The content of ⁇ -aminobutyric acid in the sample
- a i peak area of ⁇ -aminobutyric acid in the sample
- n S Drying weight loss of ⁇ -aminobutyric acid standard
- V S diaminobutyric acid standard, in milliliters (mL);
- a S peak area of ⁇ -aminobutyric acid standard
- n The weight loss on drying of the sample
- V The dilution volume of the sample, in milliliters (mL).
- the wall materials are composed of individual low DE value maltodextrin (S9), oxidized starch (S10) and ⁇ -cyclodextrin (S11) and various sugars respectively.
- S9 maltodextrin
- S10 oxidized starch
- S11 ⁇ -cyclodextrin
- the effect Very good.
- the ⁇ -aminobutyric acid content in the samples of experimental examples S7 and S8 was reduced to about 80%; sample S16 was prepared by compounding corn starch and maltodextrin with ⁇ -cyclodextrin as wall materials. and S17, after being compounded with glucose and arabinose and accelerated under high temperature conditions, the content dropped to 75-80% and 10% respectively.
- the experimental results can show that the compounding ratio of oxidized starch and ⁇ -cyclodextrin is 1:0.2 ⁇ 1:0.3
- the sample prepared by spray drying the wall material and ⁇ -aminobutyric acid has better stability and can effectively slow down the Maillard reaction.
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Abstract
Description
Claims (10)
- 一种组合物,其中,包括壁材和γ-氨基丁酸;所述壁材选自β-环糊精及其衍生物、麦芽糊精、淀粉、壳聚糖、葡萄糖中的一种或两种以上。优选的,所述麦芽糊精的DE值为5-10,所述淀粉为氧化淀粉。
- 根据权利要求1所述的组合物,其中,所述壁材与所述γ-氨基丁酸的质量比为(1~4):1,优选为(2~4):1。
- 根据权利要求1所述的组合物,其中,所述壁材包括β-环糊精及其衍生物和麦芽糊精;优选地,所述麦芽糊精与所述β-环糊精及其衍生物的质量比为1:(0.01~0.5),优选为1:(0.2~0.3)。
- 根据权利要求1所述的组合物,其中,所述壁材包括β-环糊精及其衍生物和淀粉;优选地,所述淀粉与所述β-环糊精及其衍生物的质量比为1:(0.01~0.5),优选为1:(0.2~0.3)。
- 一种如权利要求1-4任一项所述组合物的制备方法,其中,配置壁材的水溶液A;配置γ-氨基丁酸的水溶液B;将γ-氨基丁酸的水溶液与壁材的水溶液进行混合得到水溶液C,搅拌,喷雾干燥,得到所述组合物。
- 根据权利要求5所述的方法,其中,在水溶液C中,所述壁材与所述γ-氨基丁酸的质量之和与水溶液C的质量比为(0.5-2.5):10,优选为(1-2):10。
- 一种复合物,包括权利要求1-4任一项所述组合物或权利要求5-6任一项方法制备的组合物。
- 权利要求1-4任一项所述组合物或权利要求5-6任一项方法制备的组 合物在食品、药品配方中的用途。
- 权利要求1-4任一项所述组合物或权利要求5-6任一项方法制备的组合物在食品、药品原料中的用途。
- 权利要求1-4任一项所述组合物或权利要求5-6任一项方法制备的组合物在减缓美拉德反应中的用途。
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| JP2025511988A JP2025527755A (ja) | 2022-08-25 | 2023-08-22 | 組成物及びその調製方法及び使用 |
| EP23856615.2A EP4578905A4 (en) | 2022-08-25 | 2023-08-22 | COMPOSITION, PREPARATION PROCESS AND USE |
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| CN119818654A (zh) * | 2025-03-18 | 2025-04-15 | 北京青藤谷禧干细胞科技研究院有限公司 | 一种促进膝关节修复的间充质干细胞制剂、制备方法及应用 |
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| JP2008150350A (ja) * | 2006-12-20 | 2008-07-03 | Unitika Ltd | γ−アミノ酪酸含有組成物 |
| US20100196542A1 (en) * | 2007-07-19 | 2010-08-05 | Roquette Freres | Encapsulation agent comprising a pea maltodextrin and/or a pea glucose syrup, compositions containing it and its preparation method |
| CN104055788A (zh) * | 2014-06-12 | 2014-09-24 | 黑龙江八一农垦大学 | 一种肉牛用抗运输应激复合制剂 |
| CN112568429A (zh) * | 2020-12-18 | 2021-03-30 | 广州白云山汉方现代药业有限公司 | 一种γ-氨基丁酸灵芝多糖保健食品组合物及其制备方法 |
| CN115322450A (zh) * | 2022-08-25 | 2022-11-11 | 华熙生物科技股份有限公司 | 一种组合物及其制备方法和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4144357A (en) * | 1977-06-22 | 1979-03-13 | Johnson & Johnson | Preventing the Maillard reaction in synthetic dietary compositions |
| KR101059482B1 (ko) * | 2008-09-04 | 2011-08-25 | (주)마린바이오프로세스 | 해조류의 발효에 의한 gaba의 제조방법 |
| CN103305561A (zh) * | 2012-03-15 | 2013-09-18 | 江苏纳克生物工程有限公司 | 一种利用微生物发酵法生产γ-氨基丁酸的方法 |
| CN102796779B (zh) * | 2012-08-24 | 2013-11-20 | 南通励成生物工程有限公司 | 生物法制备γ-氨基丁酸的方法 |
| CN105614779A (zh) * | 2015-12-30 | 2016-06-01 | 福建舜远农业技术开发有限公司 | 一种富硒、富γ-氨基丁酸辣木淮山复合营养粉制造工艺 |
| CN105614766A (zh) * | 2015-12-30 | 2016-06-01 | 福建舜远农业技术开发有限公司 | 一种富硒、富γ-氨基丁酸辣木枣片休闲食品的制造工艺 |
| CN105639706A (zh) * | 2015-12-30 | 2016-06-08 | 福建舜远农业技术开发有限公司 | 一种富硒、富γ-氨基丁酸辣木咀嚼片的制造工艺 |
| JP6946039B2 (ja) * | 2016-04-08 | 2021-10-06 | 高砂香料工業株式会社 | 酢酸含有飲食品組成物 |
| CN108771115A (zh) * | 2018-05-21 | 2018-11-09 | 天津市食品研究所有限公司 | 一种gaba富集粉制备方法 |
| CN114317628B (zh) * | 2021-12-28 | 2024-03-08 | 华熙生物科技股份有限公司 | 一种低刺激性的γ-氨基丁酸产品及其制备方法和降低刺激性的应用 |
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| JP2008150350A (ja) * | 2006-12-20 | 2008-07-03 | Unitika Ltd | γ−アミノ酪酸含有組成物 |
| US20100196542A1 (en) * | 2007-07-19 | 2010-08-05 | Roquette Freres | Encapsulation agent comprising a pea maltodextrin and/or a pea glucose syrup, compositions containing it and its preparation method |
| CN104055788A (zh) * | 2014-06-12 | 2014-09-24 | 黑龙江八一农垦大学 | 一种肉牛用抗运输应激复合制剂 |
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| CN115322450A (zh) * | 2022-08-25 | 2022-11-11 | 华熙生物科技股份有限公司 | 一种组合物及其制备方法和用途 |
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