WO2017013966A1 - Inhibiteur de germination pour bactéries sporulées thermophiles, et procédé de production d'ester d'acide gras de saccharose - Google Patents

Inhibiteur de germination pour bactéries sporulées thermophiles, et procédé de production d'ester d'acide gras de saccharose Download PDF

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Publication number
WO2017013966A1
WO2017013966A1 PCT/JP2016/067732 JP2016067732W WO2017013966A1 WO 2017013966 A1 WO2017013966 A1 WO 2017013966A1 JP 2016067732 W JP2016067732 W JP 2016067732W WO 2017013966 A1 WO2017013966 A1 WO 2017013966A1
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Prior art keywords
fatty acid
acid ester
sucrose
sucrose fatty
food
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PCT/JP2016/067732
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English (en)
Japanese (ja)
Inventor
武嗣 中村
祥貴 前田
丈志 川合
大久保　泰宏
直人 伊藤
純一 宇佐美
保徳 塚原
治樹 奥村
径治 木谷
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太陽化学株式会社
マイクロ波化学株式会社
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Priority claimed from JP2015143988A external-priority patent/JP2017025015A/ja
Priority claimed from JP2015225341A external-priority patent/JP5996761B1/ja
Application filed by 太陽化学株式会社, マイクロ波化学株式会社 filed Critical 太陽化学株式会社
Publication of WO2017013966A1 publication Critical patent/WO2017013966A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • 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
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/60—Drinks from legumes, e.g. lupine drinks
    • A23L11/65—Soy drinks
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids

Definitions

  • the present invention relates to a germination inhibitor for heat-resistant spore-forming bacteria and a food or drink containing the germination inhibitor for heat-resistant spore-forming bacteria.
  • the present invention also relates to a method for producing a sucrose fatty acid ester and a food or drink containing the sucrose fatty acid ester obtained thereby.
  • Foods and drinks are usually manufactured through heat sterilization for long-term storage.
  • bacteria that form spores are not killed by heat sterilization treatment, and depending on the storage conditions, food and drink may be degraded through germination and growth.
  • an antibacterial emulsifier such as sucrose fatty acid ester to suppress the growth of spore-forming heat-resistant bacteria. ing.
  • sucrose fatty acid esters have the effect of suppressing the growth of spore-forming heat-resistant bacteria, and among sucrose fatty acid esters, especially those whose constituent fatty acids are palmitic acid have excellent antibacterial properties.
  • sucrose fatty acid esters especially those whose constituent fatty acids are palmitic acid have excellent antibacterial properties.
  • sucrose fatty acid esters are synthesized using sucrose and fatty acids or fatty acid esters as raw materials, but the reaction is very difficult to proceed because of poor reaction efficiency. Therefore, in order to proceed with the reaction, methods such as a reaction at a high temperature using many organic solvents and soaps have been proposed.
  • JP-A-56-18578 Japanese Patent No. 3440545 Japanese Patent No. 3851710 JP 59-76098 A JP-A 61-189289
  • sucrose fatty acid esters can sufficiently provide bactericidal effects and the like when the palmitic acid ratio is about 70 mol%. For this reason, generally, the market distribution of the sucrose fatty acid ester whose palmitic acid ratio is still higher is not seen. In any sucrose fatty acid ester disclosed in the document, the palmitic acid ratio remains at most 80 mol%. Against this background, sucrose fatty acid esters with a low palmitic acid ratio are also used in germination inhibitors for heat-resistant spore-forming bacteria. A quantity is required.
  • one of the objects of the present invention is to provide a germination inhibitor that has a germination inhibitory effect on heat-resistant spore-forming bacteria but has little bitterness peculiar to sucrose fatty acid esters and does not impair the flavor of food and drink. It is to be.
  • sucrose fatty acid ester is produced by reacting at high temperature for a long time, and thus coloring and generation of by-products are observed. Appearance and flavor are not preferred. Therefore, when mix
  • Another object of the present invention is to provide a method for producing a sucrose fatty acid ester for obtaining a flavorful sucrose fatty acid ester and a food or drink containing the sucrose fatty acid ester obtained thereby.
  • the present inventors have synthesized and used a sucrose fatty acid ester in which 90 mol% or more of the constituent fatty acid is palmitic acid.
  • the present invention was completed by finding that the germination inhibitory effect of bacteria was significantly improved. That is, the present invention relates to the following.
  • a germination inhibitor for heat-resistant spore-forming bacteria comprising a sucrose fatty acid ester in which 90 mol% or more of the constituent fatty acids is palmitic acid.
  • sucrose fatty acid ester can obtain sucrose fatty acid ester with few heat deterioration components and favorable flavor by irradiating with a microwave. Accordingly, the present invention further provides [3] A method for producing a sucrose fatty acid ester, comprising a step of irradiating a mixture containing sucrose and a fatty acid ester with microwaves, [4] A method for producing a sucrose fatty acid ester, comprising a step of irradiating a mixture containing sucrose and a fatty acid with microwaves, [5] A food or drink comprising the sucrose fatty acid ester obtained by the production method according to [13] or [24], About.
  • the sucrose fatty acid ester used in the present invention has an effect of suppressing germination of heat-resistant spore-forming bacteria, but since its action is strong, the amount of sucrose fatty acid ester added to food and drink can be reduced. Thereby, it became possible to reduce the bitterness peculiar to sucrose fatty acid ester, and to improve the flavor of food-drinks.
  • the mechanism by which the germination inhibitory effect of heat-resistant spore-forming bacteria is significantly improved by setting the ratio of palmitic acid ester in sucrose fatty acid ester to 90 mol% or more has not been clarified. It is presumed that the antagonistic inhibition of the components is eliminated and the environment in which the effects of sucrose palmitate are easily exerted is obtained.
  • sucrose fatty acid ester for obtaining a sucrose fatty acid ester having a preferable flavor, and a food or drink containing the sucrose fatty acid ester obtained thereby.
  • One aspect of the present invention is a germination inhibitor for thermostable spore-forming bacteria (hereinafter also simply referred to as “germination inhibitor”), which comprises a sucrose fatty acid ester in which 90 mol% or more of the constituent fatty acid is palmitic acid as an active ingredient, and this It is related with the food / beverage products (1st aspect) containing.
  • germination inhibitor for thermostable spore-forming bacteria
  • sucrose fatty acid ester in which 90 mol% or more of the constituent fatty acid is palmitic acid as an active ingredient
  • Sucrose fatty acid ester is a substance obtained by esterifying any of the eight hydroxyl groups in the sucrose molecular skeleton with fatty acid or fatty acid ester.
  • sucrose fatty acid esters there is a method called a solvent method. This is a reaction method using a good solvent for both sucrose and fatty acid derivatives such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO).
  • a microemulsion method In this method, a solution in which sucrose is dissolved in propylene glycol, water and the like and a fatty acid derivative such as fatty acid methyl ester are converted into a very fine dispersion using an emulsifier such as fatty acid soap, that is, a microemulsion. It is the method of making it react after removing.
  • the reaction is efficient by irradiating the mixture with microwaves and ultrasonic waves. It is estimated that it is well promoted and the reaction can be carried out in a short time, so that the generation of heat-degrading components that impair the flavor is reduced.
  • sucrose used in the present invention is not particularly limited, but because it has few impurities such as glucose and fructose and is relatively stable during the reaction, it is granulated sugar, white dichotic sugar, and medium diopterose sugar. Ice sugar and sugar sugar are preferred. Sucrose may be used alone or in combination of two or more.
  • the fatty acid used in the present invention has a palmitic acid ratio of 90 mol% or more, preferably 95 mol% or more.
  • the fatty acid that coexists is not particularly limited. Examples thereof include saturated or unsaturated fatty acids having 8 to 22 carbon atoms, and one or more of these may coexist.
  • Myristic acid is used from the viewpoint of germination inhibitory effect of heat-resistant spore-forming bacteria. Stearic acid is preferred.
  • the fatty acid ester used in the present invention is a fatty acid in which a lower (1 to 4 carbon atoms) alkyl group or vinyl group is esterified, and the fatty acid has a palmitic acid ratio of 90 mol% or more, preferably 95 mol% or more. Is good.
  • the fatty acid that coexists is not particularly limited. Examples thereof include saturated or unsaturated fatty acids having 8 to 22 carbon atoms, and one or more of these may coexist.
  • Myristic acid is used from the viewpoint of germination inhibitory effect of heat-resistant spore-forming bacteria. Stearic acid is preferred.
  • the mixture containing sucrose and fatty acid ester or the mixture containing sucrose and fatty acid can optionally contain additives.
  • the amount of each raw material used in the transesterification reaction or esterification reaction (use ratio) is not particularly limited, and is the same as the amount used in the conventional reaction system.
  • the monoester content of the sucrose fatty acid ester in the present invention is not particularly limited, but in general, the germination inhibitory effect of heat-resistant spore-forming bacteria is desirably higher in monoester content, and 80% by weight or more in view of effectiveness It is preferable that it is 90 wt% or more. When it is less than 80% by weight, it is necessary to increase the amount added as a sucrose fatty acid ester. In addition, the monoester content of sucrose fatty acid ester can be easily determined by using HPLC.
  • additives may be optionally added.
  • Catalysts such as an emulsifier, an alkali catalyst, an acid catalyst, fatty acid soap, etc. are mentioned.
  • the catalyst may be a solid catalyst (heterogeneous catalyst) or a liquid catalyst (homogeneous catalyst).
  • the content of the sucrose fatty acid ester in which 90 mol% or more of the constituent fatty acids is palmitic acid is preferably 10 wt% or more, more preferably 50 wt% or more, and further preferably 90 wt% or more.
  • the germination inhibitor can optionally contain an additive as long as the effects of the present invention are not impaired.
  • Optional additives include known food additives, such as glycerin fatty acid ester, polyglycerin fatty acid ester, organic acid monoglyceride (acetic acid monoglyceride, lactic acid monoglyceride, diacetyltartaric acid monoglyceride, citric acid monoglyceride, succinic acid monoglyceride) Sorbitan fatty acid ester, propylene glycol fatty acid ester, lecithin, enzymatically decomposed lecithin, saponin, polysorbate, saponin and other emulsifiers, guar gum, tara gum, locust bean gum, glucomannan, tamarind gum, xanthan gum, curdlan, gellan gum (Includes both acetyl type), succinoglucan, farseleran, carrageenan ( ⁇ type, ⁇ type, ⁇ type
  • Animal and vegetable proteins and their degradation products (enzymatic degradation, acid degradation), citric acid, succinic acid, tartaric acid, malic acid and other organic acids and their salts, phosphoric acid, pyrophosphoric acid, polyphosphoric acid, metaphosphoric acid and their salts, sodium carbonate Sodium hydrogen carbonate, potassium carbonate, inorganic salts such as potassium hydrogen carbonate, etc., flavoring, coloring, preservatives, and the like.
  • Arbitrary additives may be used alone or in combination of two or more.
  • Second aspect Next, an invention relating to a method for producing a sucrose fatty acid ester (second embodiment) including a step of irradiating microwaves will be described.
  • sucrose fatty acid ester having a preferred flavor
  • the flavor of the sucrose fatty acid ester obtained by reacting the mixture containing sucrose and the fatty acid ester by irradiating with microwaves is increased. I found it preferable.
  • the mechanism by which the flavor becomes preferable is not clear, but the reaction can be efficiently promoted by irradiating the mixture with microwaves, and the reaction can be performed in a short time. It is estimated that the occurrence is reduced.
  • An embodiment of the method for producing a sucrose fatty acid ester of the present invention includes an embodiment including a step of irradiating a mixture containing sucrose and a fatty acid ester with microwaves. By irradiating with microwaves, the transesterification reaction is promoted, and a sucrose fatty acid ester can be obtained in a short time.
  • sucrose fatty acid ester of the present invention there may be mentioned an aspect including a step of irradiating a mixture containing sucrose and a fatty acid with microwaves. By irradiating with microwaves, the esterification reaction is promoted, and a sucrose fatty acid ester can be obtained in a short time.
  • Sucrose is not particularly limited, but because it has few impurities such as glucose and fructose and is relatively stable during the reaction, it is granulated sugar, white dichotose sugar, medium dichotose sugar, ice sugar, Lactose is preferred. Sucrose may be used alone or in combination of two or more.
  • fatty acid examples include saturated or unsaturated fatty acids having 8 to 22 carbon atoms. From the viewpoint of enhancing the antibacterial action of the resulting sucrose fatty acid ester, carbon number 16 (palmitic acid) or 18 (stearic acid) is preferable. .
  • the ratio of palmitic acid to fatty acid is preferably 70 mol% or more from the viewpoint of antibacterial action.
  • fatty acid esters examples include lower (1 to 4) alkyl esters of saturated or unsaturated fatty acids having 8 to 22 carbon atoms and vinyl esters. From the viewpoint of enhancing the antibacterial action of the resulting sucrose fatty acid esters. A methyl ester having 16 carbon atoms (palmitic acid) or 18 (stearic acid) is preferred. The ratio of palmitic acid to fatty acid is preferably 70 mol% or more from the viewpoint of antibacterial action.
  • the mixture containing sucrose and fatty acid ester or the mixture containing sucrose and fatty acid can optionally contain an additive.
  • the amount of each raw material used in the transesterification reaction or esterification reaction (use ratio) is not particularly limited, and is the same as the amount used in the conventional reaction system.
  • Additives include emulsifiers, fatty acid soaps, alkali catalysts and the like.
  • the microwave is irradiated to heat the mixture and promote the reaction.
  • the frequency of the microwave is not particularly limited, but a frequency in the range of 300 MHz to 300 GHz can be used, and examples thereof include 2.45 GHz, 5.8 GHz, 24 GHz, and 915 MHz.
  • the microwave of one frequency may be irradiated, and the microwave of two or more frequencies may be irradiated. In the latter case, for example, microwaves of two or more frequencies may be irradiated at the same time, or may be irradiated at different times.
  • microwaves having two or more frequencies are irradiated at different times, for example, microwaves having a frequency that is easily absorbed by the raw material are irradiated at the start of the reaction, and the product is generated when the reaction proceeds.
  • a microwave having a frequency that is easily absorbed by the light may be irradiated.
  • microwaves having two or more frequencies may be irradiated at the same position or may be irradiated at different positions.
  • microwaves of two or more frequencies are respectively irradiated at different positions, for example, they are easily absorbed by the raw material at a position upstream of the flow reactor, that is, at a position where the ratio of the raw material is higher than that of the product.
  • a microwave having a frequency may be irradiated, and a microwave having a frequency that is easily absorbed by the product may be irradiated at a position downstream of the reactor, that is, at a position where the ratio of the product is higher than that of the raw material.
  • the method of irradiating the microwave is not particularly limited.
  • a waveguide capable of transmitting microwaves is placed in contact with the reactor, and the mixture is microscopically passed through the waveguide and the reactor. You may make it irradiate a wave.
  • the mixture may be heated only by microwaves or arbitrarily combined with heating means other than microwaves. Further, these may be performed in a batch type (batch type) reactor, or may be performed in a flow type reactor.
  • the temperature at the time of synthesis is not particularly limited, but is preferably 60 to 250 ° C, more preferably 80 to 150 ° C.
  • the reaction time is not particularly limited, but is preferably 1 to 20 hours.
  • the synthesis environment may be normal pressure or reduced pressure.
  • the fatty acid composition of the sucrose fatty acid ester thus obtained preferably has a palmitic acid ratio of 70 mol% or more from the viewpoint of antibacterial action, and the monoester content in the sucrose fatty acid ester is preferably 70 mol% or more.
  • the monoester content can be increased by purification with a solvent or the like.
  • a solvent which can be used For example, ethyl acetate, isopropanol, propylene glycol, isobutanol, methyl ethyl ketone, etc. are mentioned.
  • an embodiment further comprising a step of stirring the mixture in advance and / or during synthesis is mentioned.
  • the method of stirring is not particularly limited, and examples thereof include physical stirring by equipment such as paddle stirring and stirring by a homomixer. Further, a high pressure homogenizer may be used. By stirring the mixture, the reaction efficiency of the mixture is improved. An emulsion may be generated by the mixing.
  • an aspect further comprising a step of irradiating the mixture with ultrasonic waves.
  • Ultrasonic waves are irradiated to improve the mixing state of the mixture.
  • An emulsion may be generated by the mixing.
  • the frequency of the ultrasonic wave is not particularly limited, and a frequency in the range of 15 kHz to 10 GHz can be used, and examples thereof include 20 kHz, 25 kHz, and 40 kHz.
  • An ultrasonic wave may be irradiated from a single ultrasonic source, or an ultrasonic wave having the same or different frequency may be irradiated from two or more ultrasonic sources.
  • Ultrasound is irradiated continuously, intermittently, or temporarily during the reaction of the mixture, regardless of the presence or absence of microwave irradiation, and ultrasonic waves with different frequencies depending on the time are irradiated from one ultrasonic source. Also good.
  • the method of irradiating the ultrasonic wave is not particularly limited.
  • an ultrasonic vibrator may be disposed inside the reactor and the mixture may be directly irradiated with the ultrasonic wave from the ultrasonic vibrator.
  • an ultrasonic transducer may be placed in contact with the reactor, and the mixture may be irradiated with ultrasonic waves through the reactor.
  • the microwave and the ultrasonic wave may be irradiated at the same time or may be irradiated at different times. In the latter case, in order to obtain the effect of microwave irradiation and the effect of ultrasonic irradiation at the same time, for example, the microwave irradiation and the ultrasonic irradiation are switched alternately in a short period of time. It may be.
  • FIG. 1 is a diagram showing an example of the configuration of a chemical reaction apparatus 1 used for the above reaction.
  • the chemical reaction apparatus 1 includes a mixing unit 12, a reactor 13, a microwave generator 14, a waveguide 15, a microwave control unit 16, an ultrasonic vibrator 17, an ultrasonic oscillator 18, and an ultrasonic wave.
  • the control part 19 and the process liquid storage tank 20 are provided.
  • the mixing unit 12 the first liquid (sucrose-containing solution) and the second liquid (fatty acid ester-containing solution or fatty acid-containing solution) are premixed before being charged into the reactor 13.
  • the mixing unit 12 may mix the first and second liquids by rotating a blade-shaped member, a wing-shaped member, or a screw-shaped member.
  • the catalyst may be mixed in the mixing unit 12 together with the first and second liquids.
  • the catalyst may be a solid catalyst (heterogeneous catalyst) or a liquid catalyst (homogeneous catalyst).
  • the solid catalyst may, for example, have microwave absorption or microwave sensitivity or not.
  • the solid catalyst When the solid catalyst has microwave absorptivity or microwave sensitivity, the solid catalyst is heated by the microwave when the microwave is irradiated inside the reactor 13 described later, and in the vicinity of the solid catalyst.
  • the chemical reaction will be promoted.
  • carbons other than fullerene eg, graphite, carbon nanotubes, activated carbon, etc.
  • iron, nickel, cobalt, Or there is ferrite when 2.45 GHz microwaves are irradiated, carbons other than fullerene (eg, graphite, carbon nanotubes, activated carbon, etc.), iron, nickel, cobalt, Or there is ferrite.
  • the preheating may or may not be performed in the mixing unit 12.
  • the first and second liquids mixed in the mixing unit 12 are input to the upstream side of the reactor 13.
  • the reactor 13 is a horizontal flow reactor in which the contents flow in the horizontal direction with an unfilled space above.
  • the contents are a mixture of the first and second liquids.
  • the product sucrose fatty acid ester
  • the contents can be said to be the first and second liquids and / or products.
  • the contents are usually liquid.
  • the inner wall of the reactor 13 is preferably made of a material that reflects microwaves. An example of a substance that reflects microwaves is metal. The internal configuration of the reactor 13 will be described later.
  • the microwave generator 14 generates microwaves.
  • the chemical reaction apparatus 1 may include one microwave generator 14 or may include two or more microwave generators 14.
  • the frequency of the microwave is not particularly limited, and may be, for example, 2.45 GHz, 5.8 GHz, 24 GHz, 913 MHz, or the like, and may be other frequencies in the range of 300 MHz to 300 GHz.
  • the waveguide 15 transmits the microwave generated by the microwave generator 14 to the unfilled space of the reactor 13. As shown in FIG. 1, there are usually as many waveguides 15 as the number of microwave generators 14. In addition, it is preferable to use the waveguide 15 having a standard corresponding to the frequency of the microwave generated by the microwave generator 14.
  • the microwave control unit 16 controls the output of the microwave irradiated to the reactor 13 according to the temperature measured by the temperature measurement unit 25 described later. By the control by the microwave control unit 16, the inside of the reactor 13 can be maintained at a desired temperature or a desired temperature range.
  • the ultrasonic transducer 17 generates ultrasonic waves.
  • the ultrasonic transducer 17 is disposed inside the reactor 13 and is connected to the ultrasonic oscillator 18 via a flange or the like. Note that it is preferable that microwaves do not leak in the connection.
  • the ultrasonic vibrator 17 applies ultrasonic vibrations to the contents of the reactor 13 according to the high frequency output received from the ultrasonic oscillator 18. It is preferable that the first and second liquids are mixed with each other according to the ultrasonic vibration. For example, the first and second liquid emulsions may be generated by the ultrasonic vibration.
  • the ultrasonic oscillator 18 generates a high frequency output and supplies it to the ultrasonic transducer 17.
  • the ultrasonic oscillator 18 is controlled by the ultrasonic control unit 19.
  • the ultrasonic control unit 19 controls the high frequency output of the ultrasonic oscillator 18.
  • the control may be, for example, control of output (power) magnitude or on / off control.
  • the ultrasonic control unit 19 uses ultrasonic waves so that the magnitude of the high-frequency output according to the first and second liquids and the on / off pattern of the high-frequency output according to the first and second liquids are obtained.
  • the oscillator 18 may be controlled.
  • a catalyst separation unit for separating the catalyst from the product after the reaction in the reactor 13 between the reactor 13 and the treatment liquid storage tank 20.
  • the solid catalyst may be separated by a filter or precipitation.
  • the solid catalyst may be separated by adsorbing the solid catalyst with a magnet. The separated solid catalyst can be reused as appropriate.
  • the catalyst may be separated by distillation, extraction, or neutralization in the catalyst separation unit.
  • the product discharged from the reactor 13 is placed in the treatment liquid storage tank 20. And it will be divided into final products and by-products as appropriate. That is, a product that is a sucrose fatty acid ester and a by-product such as alcohol and water are obtained, and both are separated in the treatment liquid storage tank 20.
  • a cooler for cooling the substance after the reaction in the reactor 13 may be provided after the reactor 13 or not. In the former case, for example, the cooler may cool the substance after the reaction in the reactor 13 with water.
  • FIG. 2 is a diagram showing an example of the internal structure of the reactor 13 according to the present embodiment.
  • the reactor 13 has a plurality of chambers 31, 32, and 33 that are continuous in series.
  • Each of the chambers 31 to 33 is partitioned by a plurality of partition plates 21 that partition the inside of the reactor 13.
  • the unfilled space 22 exists above the reactor 13.
  • the unfilled space 22 is irradiated with the microwave generated by the microwave generator 14 through the waveguide 15.
  • the partition plate 21 may be microwave transmissive, microwave absorptive, or may reflect microwaves. Examples of the material that transmits microwaves include Teflon (registered trademark), quartz glass, ceramic, and silicon nitride alumina.
  • the partition plate 21 may be comprised by the combination of arbitrary 2 or more materials among a microwave transparent material, a microwave absorptive material, and a microwave reflective material.
  • the contents 30 as the first and second liquids that have entered the reactor 13 circulate between the chambers 31 to 33 and are finally output from the downstream (the right end of the reactor 13 in FIG. 2).
  • the partition plate 21 has a flow path through which the contents flow.
  • the flow path is a flow path in which the contents mainly flow from the upstream side (left side in FIG. 2) to the downstream side (right side in FIG. 2) of the reactor 13, but the short arrows shown in FIG. Thus, a part may flow from the downstream side to the upstream side.
  • the flow path of the partition plate 21 may be, for example, a flow path in which the content overflows above the partition plate 21, or may be a flow path in which the content flows in a gap between the partition plates 21.
  • various partition plates 21 described in International Publication No. 2013/001629 may be used.
  • the reactor 13 may or may not have a slope that decreases from the upstream side toward the downstream side.
  • a stirring means for stirring the contents 30 may or may not exist inside the reactor 13. If stirring means are present, the stirring means may or may not be present for each chamber 31-33.
  • the reactor 13 may also have a temperature measurement unit 25.
  • the temperature inside the reactor 13 is preferably the temperature of the content 30 of the reactor 13.
  • FIG. 2 shows the case where the temperature measuring unit 25 is present in each of the chambers 31 to 33, this need not be the case.
  • the temperature measurement unit 25 may measure temperature using a thermocouple, measure temperature using an infrared sensor, measure temperature using an optical fiber, or measure temperature using other methods. Good.
  • the temperature measured by the temperature measuring unit 25 is passed to the microwave control unit 16 and used for controlling the microwave output by the microwave generator 14.
  • the control is for maintaining the temperature of each of the chambers 31 to 33 at a desired temperature or a desired temperature range as described above.
  • the ultrasonic oscillator 18 outputs a high frequency output to the ultrasonic transducer 17 according to the control by the ultrasonic control unit 19, and the ultrasonic transducer 17 generates an ultrasonic wave according to the high frequency output.
  • the contents 30 are irradiated with ultrasonic waves, and the first and second liquids are mixed.
  • the emulsion of the 1st and 2nd liquid may be produced
  • the contact area between the first and second liquids is increased, and as a result, the reaction between the first and second substances is promoted. This is believed to be particularly noticeable when an emulsion is produced or maintained.
  • the yield is higher than when no ultrasonic wave is irradiated.
  • the reaction time is shorter than when no ultrasonic wave is irradiated.
  • the shape of the reactor 13 does not matter.
  • the reactor 13 may have a cylindrical shape in which the horizontal direction in FIG. 2 is the length direction, may have a rectangular parallelepiped shape, or may have another shape.
  • the wall surface of the reactor 13 may be covered with a heat insulating material. By doing so, it is possible to prevent the heat inside the reactor 13 from being released to the outside.
  • the first and second liquids are supplied to the mixing unit 12 by the pump 11. And it mixes in the mixing part 12, and is thrown into the reactor 13.
  • FIG. The supply speed of the raw material or the like to the reactor 13 may be determined in advance.
  • the raw material supplied to the reactor 13 flows from the upstream side to the downstream side.
  • the microwave generated by the microwave generator 14 is transmitted to the unfilled space 22 of the reactor 13 through the waveguide 15 and irradiated to the contents 30.
  • the content 30 is heated, and the reaction is promoted.
  • the temperatures of the chambers 31 to 33 are measured by the temperature measuring unit 25 and passed to the microwave control unit 16 through a path (not shown).
  • the microwave control unit 16 controls the output of the microwave generator 14 so that the temperature of each of the chambers 31 to 33 becomes a desired temperature or a desired temperature range. Further, the ultrasonic wave generated by the ultrasonic transducer 17 is irradiated to the contents 30.
  • the first and second liquids are mixed, and the reaction of the substances contained in the first and second liquids is promoted.
  • the emulsion of the 1st and 2nd liquid may be produced
  • the product output from the reactor 13 is charged into the processing liquid storage tank 20, and is divided into a target product and a by-product in the processing liquid storage tank 20. In this way, the final product, sucrose fatty acid ester, is obtained. By repeatedly executing such processing, sucrose fatty acid esters are sequentially generated.
  • the ultrasonic transducer 17 is present in each of the chambers 31 to 33 of the reactor 13 , this need not be the case.
  • the ultrasonic vibrator 17 is disposed only in the chamber 31, and the emulsion is stored in the chamber 31. You may make it produce
  • the reactor 13 having three chambers 31 to 33 continuous in series has been described, the number of the chambers is not limited. The number of chambers may be one, two, or four or more.
  • the chemical reaction device 1 including the temperature measurement unit 25 and the microwave control unit 16 has been described, the chemical reaction device 1 may not include the temperature measurement unit 25 and the microwave control unit 16.
  • the temperature of the reactor 13 can be maintained at a desired temperature or temperature range by setting the microwave output to a predetermined value, the microwave output control using the temperature is performed. It is not necessary to perform.
  • the first and second liquids are mixed and charged into the reactor 13
  • the first and second liquids may be charged into the reactor 13 without being premixed.
  • the chemical reaction device 1 may not include the mixing unit 12.
  • the case where the chemical reaction apparatus 1 was provided with the process liquid storage tank 20 was demonstrated, it may not be so.
  • the product may be extracted in another device.
  • the flow reactor 13 having no unfilled space inside may be, for example, a vertical reactor. In the vertical reactor, the contents circulate from below to above or from above to below.
  • the ultrasonic transducer 17 is disposed inside the reactor 13.
  • the ultrasonic transducer 17 is disposed outside the reactor 13, and the reactor 13 itself is disposed by the ultrasonic transducer 17.
  • the contents 30 may be irradiated with ultrasonic waves by vibrating the.
  • the case where the reaction is performed in the flow type reactor 13 has been described.
  • the reaction may be performed in a batch type reactor.
  • first and second liquids may be irradiated with microwaves and ultrasonic waves without causing premixing to react with the first and second substances contained in both liquids.
  • At least one of the first and second liquids to be irradiated with the microwave and the ultrasonic wave is a liquid that is heated when heated.
  • the first solid solidified from the first liquid and the second liquid are mixed, and the first solid contained in the mixture is irradiated with microwaves or ultrasonic waves by preliminary heating. May be melted into the first liquid.
  • the first and second liquids are irradiated with microwaves and ultrasonic waves, and the reaction of the first and second substances contained in both liquids can be promoted. it can.
  • both liquid emulsions are produced and reacted.
  • the area of the liquid interface is increased, and as a result, the reaction is accelerated.
  • the emulsion is not generated by irradiating the first and second liquids with microwaves and ultrasonic waves, both are mixed by the irradiation, and the area of the interface between the two liquids increases.
  • the reaction will be promoted. As a result, a higher yield and a shorter reaction time can be realized, heat-degrading components that cause off-flavors are reduced, and the flavor of the resulting sucrose fatty acid ester is preferable. It is estimated that
  • sucrose fatty acid ester obtained by each aspect is preferable in flavor, it is preferably used for food and drink.
  • food-drinks point out both a drink and solid food.
  • this is suitably used for food and drink as a germination inhibitor of the present invention.
  • the food and drink is not particularly limited, it is preferable to be used for food and drink that is frequently stored for a long time at high temperature, because the food and drink in which heat-resistant spore-forming bacteria are a problem are preferable.
  • a sealed container drink is mentioned.
  • Beverages include coffee, black tea, green tea, oolong tea, barley tea, blended tea, sour flour, zenzai, amazake, cocoa, matcha tea, soy milk, soups (corn soup, consommé soup, vegetable soup, etc.), milk shakes, lactic acid bacteria beverages, milky Examples include beverages, fruit juice beverages, vegetable beverages, sports drinks, carbonated beverages, nutritional drinks, jelly beverages, liquid foods, etc., but are not limited to the exemplified beverages, but the presence of heat-resistant spore-forming bacteria is a problem Coffee, tea, green tea, cocoa, matcha tea, soy milk, soups (corn soup, consommé soup, vegetable soup, etc.), milk shakes, etc. are preferred. Furthermore, since the growth of heat-resistant spore-forming bacteria tends to be improved when a milk component is contained, a beverage containing the milk component is more preferable even if it is the exemplified beverage or other beverages.
  • the packaging form of the food and drink is not particularly limited as long as it is a commonly distributed container such as cans, bottles, PET bottle containers, paper packs, plastic containers, cheer packs, etc. High temperature sales that tend to be problematic, so-called beverages in cans and plastic bottle containers that are often sold as hot vendors are preferred.
  • the addition method of sucrose fatty acid ester to food-drinks, an addition time, the addition method of a germination inhibitor, an addition time, etc. it can add with a well-known addition method and addition time.
  • the amount of the germination inhibitor added to the food or drink is not particularly limited, but is preferably 0.0001% by weight to 0.5% by weight in the food and drink in view of the flavor and the germination inhibitory effect of heat-resistant spore-forming bacteria.
  • Food and drink products can be used in combination with food additives other than sucrose fatty acid esters and germination inhibitors from the viewpoint of safety or to improve the quality of food and drink products.
  • Examples of food additives include glycerin fatty acid ester, polyglycerin fatty acid ester, organic acid monoglyceride (acetic acid monoglyceride, lactic acid monoglyceride, diacetyltartaric acid monoglyceride, citric acid monoglyceride, succinic acid monoglyceride), sorbitan fatty acid ester, propylene glycol fatty acid ester, lecithin, Enzyme-degraded lecithin, emulsifiers such as saponin, polysorbate, saponin, guar gum, tara gum, locust bean gum, glucomannan, tamarind gum, xanthan gum, curdlan, gellan gum (including both native type and deacetylated type), succinoglucan, far celeran, Carrageenan ( ⁇ type, ⁇ type, ⁇ type), microcrystalline cellulose, microfibrous cellulose, sodium alginate, Kuching, carboxymethylcellulose, methylcellulose, starch,
  • Example 1-1 C16 (9080) SE: Palmitic acid ratio 90 mol%, monoester content 80 wt%
  • Examples 1-2, 1-3 Microwave Heating and Ultrasonic Irradiation 34 g of sucrose and 50 g of water were placed in a three-necked flask and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in a microwave reactor equipped with a stirrer and a thermometer (thermocouple), and then an ultrasonic horn was introduced from the top of the three-necked flask.
  • a microwave reactor equipped with a stirrer and a thermometer (thermocouple)
  • Example 1-2 C16 (9580) SE: Palmitic acid ratio 95 mol%, monoester content 80 wt%
  • Example 1-3 C16 (9590) SE: Palmitic acid ratio 95 mol%, monoester content 90 wt%
  • a thermometer thermocouple
  • Example 1-5 a germination inhibitor was obtained in the same manner except that the palmitic acid ratio was 95 mol% in the purification step.
  • Comparative Example 1-1 a germination inhibitor was obtained in the same manner except that the palmitic acid ratio was 70 mol% in the purification step.
  • Comparative Example 1-2 a germination inhibitor was obtained in the same manner except that the palmitic acid ratio was 80 mol% in the purification step.
  • Example 1-4 C16 (9080) SE: Palmitic acid ratio 90 mol%, monoester content 80 wt%
  • Example 1-5 C16 (9580) SE: palmitic acid ratio 95 mol%, monoester content 80 wt% Comparative Example 1-1: C16 (7080) SE: Palmitic acid ratio 70 mol%, monoester content 80 wt% Comparative Example 1-2: C16 (8080) SE: Palmitic acid ratio 80 mol%, monoester content 80 wt%
  • the weight-adjusted coffee mix was homogenized at a pressure of 15 MPa at a temperature of 65 to 75 ° C. using a high-pressure homogenizer, filled in a can and retort sterilized at 121 ° C. for 30 minutes.
  • the pH of the coffee mix after sterilization was 6.6.
  • Test Example 1-1 ⁇ Bacteriostatic test (germination inhibition test)> To the prepared beverages, Morella thermoacetica, Thermonerobacter maslanii, and Geobacillus stearothermophilus staurostro buds, which were activated at 100 ° C. for 30 minutes, Inoculate each solution to a concentration of 1 ⁇ 10 4 cells / ml, take 2 ml ⁇ 5 beverages inoculated with each spore suspension in a glass tube, seal the open end with a flame, and seal the glass ampoule. It was.
  • F 0 10 ⁇ 20 equivalent, that is, heat treatment at 121 ° C for 10-20 minutes, then store at 55 ° C for 4 weeks, then check for deterioration Judged. The determination was made based on the difference in pH from the non-inoculated bacteria group. The one whose pH was lowered by 0.4 or more compared to the uninoculated beverage was regarded as deterioration. Of the five glass ampoules of the same beverage, when even one of them was degraded, the bacteriostatic property was evaluated as “ ⁇ ”, and when it was not degraded, it was evaluated as “ ⁇ ”. The results of this test are shown in Tables 1-3.
  • Test Example 1-2 Hot water extraction (extraction efficiency 25%) was performed using 65 g of roasted coffee beans with an L value of 20 to obtain 550 g of a Bx3.0 coffee extract. To this, 150 g of milk, 50 g of granulated sugar, and 60 ° C. warm water were added a solution in which the germination inhibitors of Examples and Comparative Examples were added and adjusted so that the palmitic acid content was 240 ppm, and the pH was adjusted to 6. with sodium bicarbonate. After adjusting to 9, water was further added to bring the total amount to 1000 g to obtain a coffee mix. The weight-adjusted coffee mix was homogenized at a pressure of 15 MPa at a temperature of 65 to 75 ° C.
  • the milk coffee beverage to which each sucrose fatty acid ester is added in an amount showing bacteriostatic properties has a less bitter taste than the sucrose fatty acid ester having a higher palmitic acid ratio can suppress the addition amount.
  • the flavor was good.
  • synthesis using microwaves or ultrasonic waves can suppress the taste and improve the flavor. I understand. In Examples 1-4 and 1-5, although they had a slightly different taste, they were of a level that would not cause a problem as a beverage.
  • Example 2-2 Microwave Heating A three-necked flask was charged with 34 g of sucrose, 2 g of sucrose palmitate as an emulsifier, and 50 g of water, and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in a microwave reactor equipped with a stirrer and a thermometer (thermocouple). Then, microwaves (2.45 GHz) were irradiated while stirring, and a transesterification reaction was performed for 5 hours while maintaining the temperature at 90 ° C. ⁇ 2 ° C. After completion of the reaction, sucrose palmitate was purified from the mixture using water, methyl ethyl ketone, and ethyl acetate, and subjected to evaluation in the following test examples.
  • Comparative Example 2-1 Normal Heating A three-necked flask was charged with 34 g of sucrose, 2 g of sucrose palmitate as an emulsifier, and 50 g of water, and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in an oil bath, and a transesterification reaction was carried out for 30 hours while maintaining the temperature measured with a thermometer (thermocouple) at 90 ° C. ⁇ 2 ° C. while stirring. In this comparative example, microwave irradiation was not performed.
  • a thermometer thermocouple
  • the liquid during the transesterification reaction was a two-layer liquid.
  • sucrose palmitate was purified from the mixture using water, methyl ethyl ketone, and ethyl acetate, and subjected to evaluation in the following test examples.
  • Test Example 2-1 Hot water extraction (extraction efficiency 25%) was performed using 65 g of roasted coffee beans with an L value of 20 to obtain 550 g of a Bx3.0 coffee extract.
  • Test Example 2-2 Hot water extraction (extraction efficiency 25%) was performed using 30 g of roasted coffee beans with an L value of 20, and 250 g of Bx3.0 coffee extract was obtained. To this, 300 g of milk, 60 g of granulated sugar, and a solution prepared by dissolving 0.6 g of sucrose palmitic acid ester obtained in Examples or Comparative Examples and 3 g of polyglycerol fatty acid ester in warm water at 60 ° C. were added, and pH 6. After adjusting to 9, water was further added to bring the total amount to 1000 g to obtain a coffee mix. The weight-adjusted coffee mix was homogenized at a pressure of 15 MPa at a temperature of 65 to 75 ° C. using a high-pressure homogenizer, filled in a can and retort sterilized at 121 ° C. for 30 minutes. The pH of the coffee mix after sterilization was 6.6.
  • Test Example 2-3 Hot water extraction (extraction efficiency 25%) was performed using 50 g of roasted coffee beans with an L value of 22 to obtain 400 g of a Bx3.0 coffee extract. To this was added 200 g of milk, 60 g of granulated sugar, and a solution prepared by dissolving 0.5 g of sucrose palmitic acid ester obtained in Examples or Comparative Examples and 3 g of succinic monoglyceride in warm water at 60 ° C., and a pH of 6.8 with sodium bicarbonate. After adjustment, water was further added to make the total amount 1000 g to obtain a coffee mix. The weight-adjusted coffee mix was homogenized at a pressure of 15 MPa at a temperature of 65 to 75 ° C. using a high-pressure homogenizer, and then subjected to UHT heat sterilization treatment at 140 ° C. for 30 seconds and aseptically filled into a PET bottle container. The pH of the coffee mix after sterilization was 6.6.
  • Test Example 2-4 In 200 g of black tea extract (Bx1.0), 250 g of milk, 30 g of fresh cream, 60 g of granulated sugar, and 0.5 g of sucrose palmitate obtained in Examples or Comparative Examples and 3 g of monoglyceride are dissolved in 60 ° C. warm water. The solution was added and adjusted to pH 7.0 with sodium citrate, and then water was added to make the total amount 1000 g to obtain a black tea mix. The black tea mix whose weight was adjusted was homogenized at a pressure of 15 MPa at a temperature of 65 to 75 ° C. using a high-pressure homogenizer, and then subjected to UHT heat sterilization treatment at 140 ° C. for 30 seconds and aseptically filled into a PET bottle container. The pH of the black tea mix after sterilization was 6.7.
  • Test Example 2-5 10 g of cocoa powder (fat content 12%) is added and dispersed in 55 ° C. warm water, and then 60 g of granulated sugar, 200 g of milk, and 1 g of sucrose palmitate obtained in Examples or Comparative Examples in 60 ° C. of warm water. A solution in which 4 g of microcrystalline cellulose and 0.1 g of carrageenan were dissolved was added, and water was further added to make the total amount 1000 g to obtain a cocoa mix. The weight-adjusted cocoa mix was pre-emulsified with a high-speed stirrer at a temperature of 65 to 75 ° C. Next, the solution was homogenized at a temperature of 65 to 75 ° C. at a pressure of 15 MPa using a high-pressure homogenizer, filled in a can container, and retort sterilized at 121 ° C. for 60 minutes.
  • Example 2-1 and Examples 2-1 and 2-2 show that Examples 2-1 and 2-2 irradiated with microwaves are excellent in flavor.
  • the best result was obtained in Example 2-1 in which ultrasonic waves were irradiated. Even if the reaction mixture is purified in the same manner, it is presumed that there are few heat-degraded components that cause off-flavors by using microwaves.
  • the present invention provides a practical germination inhibitor that exerts an excellent germination-inhibiting action (bacteriostatic action) against heat-resistant spore-forming bacteria and causes little problems in flavor.
  • the present invention can provide a food and drink with excellent taste that is stable against deterioration due to microorganisms and has no flavor modulation by the bacteriostatic method using the bacteriostatic agent.
  • the present invention is useful in the field of beverages such as foods and drinks, particularly coffee, black tea, green tea, cocoa, matcha tea, soy milk, soups (corn soup, consommé soup, vegetable soup, etc.) and milk shakes.

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Abstract

L'invention concerne un inhibiteur de germination pour des bactéries sporulées thermophiles, qui comprend un ester d'acide gras de saccharose, l'acide palmitique représentant 90 % en moles ou plus des acides gras constitutifs dans l'ester d'acide gras de saccharose. La présente invention permet d'obtenir un inhibiteur de germination utile dans la pratique qui présente une excellente activité d'inhibition de la germination (une activité bactériostatique) contre les bactéries sporulées thermophiles et affecte rarement un arôme. La présente invention permet également d'obtenir un aliment ou une boisson qui est produit(e) par un procédé de stérilisation utilisant l'agent de stérilisation, est stable à la corruption par des micro-organismes, ne subit pas de modification de son arôme et a un excellent goût. Par conséquent, la présente invention constitue une importante contribution pour les industries. La présente invention est utile dans le domaine des aliments et des boissons, en particulier des boissons comprenant du café, du thé noir, du thé vert, du cacao, du thé vert en poudre, du lait de soja, des soupes (par ex. soupe de maïs, consommé, soupe de légumes) et des milkshakes.
PCT/JP2016/067732 2015-07-21 2016-06-15 Inhibiteur de germination pour bactéries sporulées thermophiles, et procédé de production d'ester d'acide gras de saccharose WO2017013966A1 (fr)

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JP2015-143988 2015-07-21
JP2015143988A JP2017025015A (ja) 2015-07-21 2015-07-21 ショ糖脂肪酸エステルの製造方法
JP2015-225341 2015-11-18
JP2015225341A JP5996761B1 (ja) 2015-11-18 2015-11-18 耐熱性芽胞形成細菌の発芽抑制剤

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CN112218541A (zh) * 2018-06-08 2021-01-12 三菱化学食品株式会社 饮料、乳化油脂组合物和乳化剂组合物

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JP2004242670A (ja) * 2003-01-20 2004-09-02 Mitsubishi Chemicals Corp 乳化安定剤およびこれを含有する乳飲料
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CN112218541A (zh) * 2018-06-08 2021-01-12 三菱化学食品株式会社 饮料、乳化油脂组合物和乳化剂组合物
JP2020022408A (ja) * 2018-08-08 2020-02-13 青葉化成株式会社 茹卵用保存剤、保存剤漬け茹卵および保存性茹卵製造方法

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