WO2016072114A1 - Extrait de grains de café enrichi en lactones d'acide chlorogénique, et procédé de fabrication de celui-ci - Google Patents
Extrait de grains de café enrichi en lactones d'acide chlorogénique, et procédé de fabrication de celui-ci Download PDFInfo
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- WO2016072114A1 WO2016072114A1 PCT/JP2015/070760 JP2015070760W WO2016072114A1 WO 2016072114 A1 WO2016072114 A1 WO 2016072114A1 JP 2015070760 W JP2015070760 W JP 2015070760W WO 2016072114 A1 WO2016072114 A1 WO 2016072114A1
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- 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
- A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
- A23F5/48—Isolation or recuperation of coffee flavour or coffee oil
- A23F5/50—Isolation or recuperation of coffee flavour or coffee oil from coffee extract
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- the present invention relates to a method for producing a coffee bean extract containing an increased amount of chlorogenic acid lactones by using a coffee bean extract as a raw material and performing dehydration heating. More specifically, it is particularly useful for imparting or enhancing a refreshing bitter taste to foods and drinks obtained by dehydrating and heating the concentrate or dried product from raw or shallow roasted coffee bean extract. Further, the present invention relates to a method for producing a coffee bean extract containing an increased amount of chlorogenic acid lactones, a coffee bean extract obtained by the production method, and use thereof for food and drink.
- Coffee is the most popular favorite drink that is loved all over the world. In China and other countries where tea culture has been centered, the culture of fast food shops and coffee shops in Europe and the United States is rapidly growing along with economic growth. The demand is increasing rapidly.
- canned coffee beverages such as canned coffee, chilled-type coffee beverages, coffee beverages in plastic bottles, etc. that have developed uniquely in Japan as a response to consumers' desire to simply and anywhere coffee
- Many processed coffee products such as instant coffee, which are widely used in general households, are consumed.
- Non-patent Document 1 Chlorogenic acid lactones have been known for a long time, but since the above reports, they have been attracting much attention as a bitter component of coffee, and the production of extracts containing high concentrations of chlorogenic lactones from coffee extracts And a method for isolating chlorogenic acid lactones (Patent Document 1), an assay for bitterness using a receptor (Patent Document 2), and the like.
- chlorogenic acid lactones are bitter components of coffee, they do not necessarily contribute to the deliciousness of coffee, and methods for reducing chlorogenic acid lactones have been proposed.
- a method for reducing chlorogenic acid lactones for example, a method in which roasted coffee bean extract is treated with alkali to hydrolyze chlorogenic acid lactones to chlorogenic acids (Patent Document 3), the coffee extract is treated with liver esterase or the like.
- Patent Document 4 Method of decomposing by treating with enzyme; Method of adsorbing and removing with adsorbent such as activated carbon, polyvinylpolypyrrolidone, polystyrene-divinylbenzene, N, N′-methylenebis (methacrylamide); hexane, dichloromethane, diethyl ether, ethyl acetate, etc.
- Patent Document 5 A method of adsorbing and removing using specific activated carbon (Patent Document 6) has been proposed. That.
- chlorogenic acid lactones are hardly contained in the green coffee beans and increase during roasting, it is known that they decrease rather when roasting becomes deeper (non-patent document 2). .
- chlorogenic lactones are components that contribute to the bitterness of coffee, but it can be said that the influence on the taste of the overall taste in coffee was not necessarily clear.
- An object of the present invention is to provide a method for producing a coffee bean extract containing an increased amount of chlorogenic acid lactones, and a coffee bean obtained by the production method for imparting a clean and good bitterness to a coffee flavored food such as a coffee beverage To provide an extract.
- Another object of the present invention is to provide a coffee beverage and a coffee-flavored food / drink product to which the refreshing bitterness is imparted or enhanced by adding the coffee bean extract.
- chlorogenic acids In ordinary roasted coffee beans, both chlorogenic acids and chlorogenic acid lactones exist, and chlorogenic acids also have a bitter taste, but it is known that the bitterness is much weaker than chlorogenic acid lactones.
- Patent Document 1 chlorogenic acid lactones have been reported to be useful as a bitter component of coffee.
- Patent Documents 3 to 6 components to be reduced are described. There is also an evaluation.
- chlorogenic acid lactones confirmed the taste and confirmed the effect of addition to the coffee beverage (see [Example] described later).
- chlorogenic acid lactones are high-quality bitterness components of “freshly brewed coffee”, and with the addition of about 1 ppm to several ppm, it has the effect of changing to a refreshing aftertaste that is refreshing like regular coffee.
- the evaluation result that it is an important ingredient was obtained.
- the present inventors use raw or extremely shallow roasted coffee beans that are rich in chlorogenic acids as raw materials, and chlorogenic acid lactones contained in this coffee bean extract using some method.
- a coffee bean extract containing a high concentration and a high content of chlorogenic acid lactones could be obtained by converting it into sucrose.
- chlorogenic acid lactones tend to decrease by heating in a concentrated coffee extract as described in Patent Document 5.
- a coffee bean extract with a higher concentration or a coffee bean extract with moisture reduced to near dryness is heated while drying, the lactonization reaction of chlorogenic acids proceeds.
- the present inventors have found that chlorogenic acid lactones are remarkably increased. Moreover, it was confirmed that by adding the obtained processed product to a coffee beverage, not a bitter taste remaining on the tongue but a sharp and pleasant bitter taste increased, and the present invention was completed.
- the present invention provides the following. (1) (a) A step of extracting coffee beans with an aqueous solvent to obtain a concentrate of Bx50 ° or more of the coffee bean extract or a dried product having a water content of 1% by mass to 10% by mass of the coffee bean extract. And (b) a step of heating the concentrate or dried product obtained in the above step at 150 to 400 ° C. for 0.1 to 60 minutes while dehydrating by heating means, A method for producing a coffee bean extract with increased lactones. (2) The method for producing a coffee bean extract according to (1), wherein the coffee beans are green coffee beans or roasted coffee beans having an L value of 25 or more.
- a coffee bean extract rich in coffee chlorogenic acid lactones can be produced from coffee beans by a simple method.
- the coffee bean extract of the present invention has a fresh and refreshing bitter taste.
- the bitterness quality and bitterness of the coffee beverage or instant coffee can be reduced.
- Cutting is greatly improved, and flavorful coffee drinks and instant coffee can be provided.
- FIG. 1 is a chart showing 1H-NMR measurement results of a mixture of 3-caffeoylquinic acid lactone (1) and 4-caffeoylquinic acid lactone (2) (Reference Example 1).
- FIG. 2 is a chart showing 1H-NMR measurement results of 3,4-dicaffeoylquinic acid lactone (3) (Reference Example 2).
- a method for obtaining a coffee bean extract containing an increased amount of chlorogenic acid lactones is a concentrate of Bx 50 ° or more of a coffee bean extract or a dried coffee bean extract having a water content of 1% by mass to 10% by mass.
- the product is heated at 150 to 400 ° C. for 0.1 to 60 minutes while dehydrating.
- the coffee bean extract refers to an extract obtained by extracting raw or roasted coffee beans with an aqueous solvent.
- any kind of Arabica, Riberica, Robusta, etc. may be used, and any coffee beans from Brazil, Colombia, Indonesia, etc. Can be used.
- the coffee beans one kind of beans may be used alone, or two or more kinds of blended beans may be used. These raw beans or raw beans roasted with a coffee roaster or the like can be used as raw materials.
- raw coffee beans rich in chlorogenic acids can be used as raw materials, but coffee beans roasted appropriately may be used.
- raw coffee beans are thought to contain abundant chlorogenic acids, which are raw materials for chlorogenic lactones, they have disadvantages such as high hardness of the beans, difficulty in grinding, and a unique flavor. Therefore, in order to eliminate these drawbacks, a method using roasted coffee beans as a raw material can be employed.
- the coffee beans can be roasted in a conventional manner using a coffee roaster or the like. For example, it can be roasted by putting green coffee beans inside a rotating drum and heating the rotating drum from below with a gas burner or the like while rotating and stirring.
- the degree of roasting of such coffee beans may be in any range, for example, the L value may be in the range of 14.5-60.
- the degree of roasting of such coffee beans is preferably in a range where the raw odor unique to green coffee beans disappears and the amount of chlorogenic acid does not substantially decrease relative to the green beans, and the L value is 25 to 60, preferably Can be exemplified by roasting to an L value of 40 to 55, more preferably an L value of 45 to 50.
- the L value is an index representing the degree of roasted coffee, and is a value obtained by measuring the lightness of the crushed coffee beans using a color difference meter. Black is represented by an L value of 0 and white is represented by an L value of 100. Therefore, the deeper the roasted coffee beans, the lower the value of the L value, and the shallower the coffee beans, the higher the value.
- the coffee beans used in the present invention are not preferable from the viewpoint that chlorogenic acids in the green beans are substantially reduced and chlorogenic acids are effectively used. .
- roasted beans with an L value of less than 25 may be preferred.
- the coffee beans are then pulverized and extracted using a continuous batch extraction device, drip-type extraction device, multi-function device with a stirrer, and other extraction devices, and filtered to obtain a coffee bean extract. Can do.
- a solvent for extracting a coffee extract from such green coffee beans or roasted coffee beans a solvent from which chlorogenic acids are sufficiently extracted is preferable, and an aqueous solvent can be mentioned.
- aqueous solvents include water or water-containing water-miscible organic solvents such as methanol, ethanol, 2-propanol, acetone, and water having a water content of 5% by mass or more, preferably about 5 to about 90% by mass.
- a water-containing water-miscible organic solvent such as methyl ethyl ketone can be exemplified.
- water or water-containing water-miscible organic solvents are usually used in an amount of about 2 to about 50 parts by weight with respect to 1 part by weight of roasted coffee beans and extracted at a temperature of about 20 ° C to about 100 ° C.
- a known extraction method such as batch extraction or continuous extraction using a column can be employed.
- the extract obtained by the above method is treated with, for example, a porous polymer resin and adsorbed on the resin, and then the resin is eluted with, for example, ethanol, and a coffee bean extract rich in chlorogenic acids You can also get
- the extract obtained by the above-described method is treated with, for example, a cation exchange resin, adsorbed and removed caffeine, neutralized the passing solution, and a caffeine-less coffee bean extract can be obtained. it can.
- the obtained coffee extract is substantially removed from the organic solvent by using various methods such as vacuum concentration, freeze concentration, and concentration using reverse osmosis membrane, and most of the water is also removed. And concentrate to Bx50 ° or more.
- the coffee bean extract or the concentrate of Bx 50 ° or more of the coffee bean extract is dried and powdered by various methods such as spray drying, vacuum drying, freeze drying, etc., so that the water content is 1% by mass or more. It can be set as 10 mass% or less dried material.
- the coffee bean extract has a name such as “coffee extract”, and various commercial products are distributed.
- a desired coffee extract can be marketed by specifying the type of beans and the degree of roasting.
- These coffee extracts can be used as a coffee bean extract in the present invention or a concentrate of Bx 50 ° or more of the coffee bean extract after appropriately adjusting the Brix value.
- commercially available instant coffee is basically prepared by the same production method as these coffee extracts and dried, and after adjusting the water content as appropriate, the water content of the coffee bean extract in the present invention is 1 mass. % To 10% by mass or less.
- the concentrate of Bx50 ° or more of the coffee bean extract or the dried product of the coffee bean extract having a water content of 1% by mass to 10% by mass is heated at 150 to 400 ° C. for 0.1 to 60%. Heat for a minute while dehydrating with heating means. By this heating, the concentrate or dried product is heated under dehydration conditions, so that chlorogenic acids contained in the concentrate or dried product are dehydrated and esterified in the molecule to produce chlorogenic acid lactones. To do.
- the concentrate or dried product is heated under the heating conditions and dehydrated with the heating. Therefore, the dehydrating conditions are the same as the heating conditions at 150 to 400 ° C. for 0.1 to 60 minutes.
- the heating temperature may be 150 to 400 ° C., preferably 180 ° C. to 300 ° C., more preferably 200 to 250 ° C.
- the heated object that is, the concentrate
- the product temperature of the object to be heated is about 100 to 200 ° C.
- the product temperature of the object to be heated rises and expands after a few minutes. This is because the whole object to be heated is heated and the water inside becomes steam and foams and tries to evaporate.
- the concentration of the object to be heated is high and the viscosity is also high, so it occurred in the entire inside of the object to be heated. This is because bubbles of water vapor inflate the entire object to be heated. This expansion is continued for several seconds to several minutes, and may be baked while maintaining the expanded form even after the evaporating water disappears, but may contract to form a plate shape. By this heat treatment, a dark brown fired product is obtained.
- the heating time may be 0.1 to 60 minutes, preferably 0.5 to 30 minutes, more preferably 2 to 15 minutes.
- the heating means for the concentrate of Bx50 ° or more of the coffee bean extract or the dried product of the coffee bean extract having a water content of 1% by mass to 10% by mass there is no particular limitation on the heating means for the concentrate of Bx50 ° or more of the coffee bean extract or the dried product of the coffee bean extract having a water content of 1% by mass to 10% by mass, and any method is adopted.
- superheated steam heating, hot air heating, far infrared heating, microwave heating, extruder heating and the like can be exemplified.
- Superheated steam heating is a method in which steam heated to a temperature higher than 100 ° C. is brought into contact with an object to be heated.
- steam heated to a temperature higher than 100 ° C. is brought into contact with an object to be heated.
- the heat treatment is performed by contacting with the superheated steam without any special pressurization or decompression.
- Superheated steam generators for commercial use include, for example, Genesis (manufactured by Nomura Engineering Co., Ltd.), DHF Super-Hi (registered trademark, Daiichi High Frequency Industrial Co., Ltd.), SV Roaster HOT-MAX (registered trademark, Manufactured by Nakanishi Seisakusho Co., Ltd.), QFB-5980C-3R (registered trademark, Naomoto Kogyo Co., Ltd.), super oven (Kiyomoto Seiko Co., Ltd.), etc.
- the present invention is not limited to these.
- Hot air heating is a method in which a gas such as air, nitrogen gas or carbon dioxide is heated using a heat source, and the heated gas and an object to be heated are brought into contact with each other in a container. It is commonly used when roasting green coffee beans and barley tea. Actually, an apparatus used for hot-air roasting of green coffee beans or barley tea can be used as it is.
- Far-infrared heating is a method in which an object to be heated is irradiated with electromagnetic waves (far-infrared rays) in the range of 3 ⁇ m to 1000 ⁇ m to directly heat the object to be heated.
- Far infrared rays are easily absorbed by ceramics, plastics, water, fibers, wood, humans, plants and animals, but transmit air and reflect metals.
- the molecules and crystals that make up the substance have their own vibrations.
- Substances that easily absorb far-infrared rays, such as water have a common vibration of 3 to 30 ⁇ m in common. Since the wavelength bands match, they resonate and activate the movement at the molecular level. This is called thermal vibration and raises the temperature of the irradiated material.
- far-infrared light When far-infrared light is absorbed by a substance, it is first converted into resonant vibration energy, which becomes thermal energy, and generates heat from itself. Therefore, when the concentrate of Bx50 ° or more of the coffee bean extract or the dried product of water of 1 to 10% by mass of the coffee bean extract in the present invention is irradiated, these temperatures rise.
- a method for generating far infrared rays it is utilized that far infrared rays are radiated from the surface of the heated ceramics or metal when ceramics or metal is heated using a heat source.
- an oven As the far infrared heating device, an oven, an oven toaster, an electric heater, an electric furnace, a far infrared roasting device for fresh coffee beans, etc. can be used as they are.
- the hot air heating when a gas is heated using a heat source, the surrounding devices (many of which are made of metal) are often heated, and the roasting device uses both far infrared rays and hot air. Many heating devices are also seen.
- Microwave heating is a method in which an object to be heated is irradiated with an electromagnetic wave (microwave) in a range of 100 ⁇ m to 1 m to directly heat the object to be heated.
- the non-communication ISM band is used for the microwave frequency used for heating, and it is standardized to 2.45 GHz (about 120 mm) in the international standard.
- the microwave heating is dielectric heating due to the interaction between the microwave and the substance, and the microwave is absorbed by the substance due to dielectric loss, and is heated when the energy becomes heat. Unlike heating by an external heat source, the effects of heat conduction and convection are almost negligible, and only specific substances can be selectively, rapidly and uniformly heated.
- a microwave oven can be used as an apparatus using microwave heating.
- An extruder is a screw-heat-pressure-extrusion molding machine, where multiple screws are entangled with each other and interfere with each other to generate physically high energy. It is an apparatus that can perform processing.
- Multi-axis extruders have been developed mainly in the food and plastic fields, and are widely used for food processing (cereals, protein, livestock meat, fish meat, etc.) and plastic injection molding.
- the raw material powder or high-viscosity fluid is fed into the equipment, the raw material is moved at a high temperature and high pressure while kneading the raw material with a screw, and further pressed against the extrusion surface (die surface). It is pushed out from the drilled hole.
- a part of the high-pressure gaseous component expands by returning to atmospheric pressure, and may expand and solidify.
- a biaxial extruder EA-20 manufactured by Suehiro EPM
- Suehiro EPM a biaxial extruder
- the coffee bean extract obtained by heating the coffee bean extract at 150 to 400 ° C. for 0.1 to 60 minutes while dehydrating is further dissolved in water and adsorbed.
- Chlorogenic acid lactones can also be concentrated by adsorbing to the agent.
- adsorbent examples include known adsorbents such as polyamide, nylon powder, polyvinyl pyrrolidone, polyvinyl polypyrrolidone, casein, zein, Amberlite (registered trademark) XAD, and polymers having an amide group. Then, chlorogenic acid lactones are adsorbed on the adsorbent by column or batch treatment, and chlorogenic acid lactones are desorbed with an organic solvent such as ethanol, acetone, ethyl acetate, and the organic solvent is removed. Similar to the coffee bean extract of the present invention, it can be used for food and drink as a refined coffee bean extract rich in varieties.
- the coffee bean extract of the present invention thus obtained has a mass ratio of the content of 3,4-dicaffeoylquinic acid lactone to the content of 5-caffeoylquinic acid (3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid) is 0.01 or more, preferably 0.02 or more, more preferably 0.03 or more.
- the main chlorogenic acids of green coffee beans are 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid, 5-
- feruloyl quinic acid 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid
- 5-caffeoylquinic acid about 35% by mass
- this content can represent the total amount of chlorogenic acids.
- chlorogenic acid lactones are formed from chlorogenic acids by roasting green coffee beans.
- chlorogenic acid lactones include 3-caffeoylquinic acid lactone and 4-caffeoylquinic acid.
- a large amount of lactone and 3,4-dicaffeoylquinic acid lactone are produced.
- 3,4-dicaffeoylquinic acid lactone is particularly strong in bitterness, and is about 1/4 of the bitterness of 3-caffeoylquinic acid lactone or 4-caffeoylquinic acid lactone. It has a threshold value (see Non-Patent Document 1).
- the amount of 3,4-dicaffeoylquinic acid lactone is not so high, but when the coffee bean extract is heated according to the method of the present invention, An extremely large amount of 3,4-dicaffeoylquinic acid lactone is produced compared to roasting green beans.
- the mass of the content of 3,4-dicaffeoylquinic acid lactone relative to the content of 5-caffeoylquinic acid varies depending on the degree of roasting.
- the ratio is about 0 to 0.003
- the above-mentioned mass ratio is 0.01 or more, preferably 0.02 or more. More preferably, it shows a very high value of 0.03 or more. This is higher than ordinary coffee beverages, commercially available coffee extracts, commercially available instant coffee, and the like, and as a result, the product of the present invention has a good bitterness peculiar to coffee.
- the coffee bean extract of the present invention obtained as described above has a mass ratio of the total amount of chlorogenic acids to the availability solid content derived from coffee beans of 0.1 to 0.8, preferably 0.2 to 0.7. More preferably, it is 0.3 to 0.6.
- the content of chlorogenic acids in green coffee beans is about 5 to 10% by mass, but decreases as roasting of coffee beans proceeds and deep roasting (for example, L value) In 16.5), it will decrease to about 1/20 with respect to unroasted green beans.
- L value deep roasting
- the chlorogenic acid lactones once produced decrease with the decomposition of the chlorogenic acids.
- a coffee bean extract concentrate or the like at 150 to 400 ° C.
- the coffee bean extract of the present invention is a normal roasted coffee bean (L value), particularly when a raw coffee bean or a concentrated concentrate of roasted coffee beans having an L value of 25 or more is used as a raw material. Compared with the extract from 25 or less), it contains more chlorogenic acids.
- the coffee bean extract of the present invention is used as it is, or pulverized into a powder, or dissolved in an edible solvent such as water, ethanol, glycerin, instant coffee, coffee beverage, coffee-containing milk beverage, coffee jelly, It can be used in a wide range of foods and beverages with a variety of coffee flavors such as coffee cookies, coffee chocolate, coffee pudding, coffee bavaria, coffee cake, etc. It is possible to enhance.
- FIG. 1 shows a chart (400 MHz, CD 3 OD) showing 1H-NMR measurement results of Reference Product 1.
- Reference Example 2 Synthesis of 3,4-dicaffeoylquinic acid lactone (reference product 2) Agric. Food Chem. , Vol. According to the method described in 58, 2010, 3720-3728, 3,4-dicaffeoylquinic acid lactone (3) (reference product 2) represented by the following structural formula was synthesized as a standard product.
- a chart (400 MHz, CD 3 OD) showing the results of 1H-NMR measurement of Reference Product 2 is shown in FIG.
- Reference example 3 (confirmation of taste) Sensory evaluation was performed by five panelists who were well trained by dissolving 100 ppm of Reference Product 1 or Reference Product 2 in water. The average evaluation results were as follows. According to the description in Non-Patent Document 1, the bitterness threshold value of each compound is as follows. 3-caffeoylquinic acid lactone: 13.4 ppm, 4-caffeoylquinic acid lactone: 12.1 ppm, 3,4-dicaffeoylquinic acid lactone: 4.8 ppm (sensory evaluation) Reference product 1: 3 (and 4) -caffeoylquinic acid lactone: Astringency irritation is felt, but bitterness is weak. The bitterness is good. Reference product 2: 3,4-dicaffeoylquinic acid lactone: Clear bitterness, clean, and good bitterness.
- Reference Example 4 (Experiment to add standard product to beverage)
- the reference product 1 or reference product 2 is added to a commercially available black coffee beverage in a plastic bottle so as to have the concentration shown in Table 1 and dissolved, and sensory evaluation is performed by 5 panelists who are well trained immediately after dissolution. It was.
- the evaluation criteria are very good with respect to the strength of bitterness, lack of bitterness, low taste, coffee richness and regular coffee feeling when the additive-free product (control) is set as the standard (0 points): 10 points , Very good: 8 points, good: 6 points, slightly good: 4 points, slightly good: 2 points, extremely bad: -10 points, very bad: -8 points, bad: -6 points, slightly bad: Sensory evaluation was performed as -4 points, slightly bad: -2 points. The average score is shown in Table 1.
- Reference product 2 (3,4-dicaffeoylquinic acid lactone) is better than Reference product 1 (3 (and 4) -Caffeoylquina.
- the reference product 2 was particularly effective in enhancing the richness of coffee.
- Reference Example 5 Fill the column with 1000 g of ground coffee beans (Indonesian Robusta seeds) into a column (column inner diameter 7 cm, length 25 cm, 200 g coffee beans per bottle, 5 connected) and soft water heated to 95 ° C.
- the extract extracted from the upper part of the column at a flow rate of 2500 ml / hr and extracted from the lower part of the column is continuously sent to the upper part of the next column, and the final extract is extracted from the fifth column.
- the liquid was below Bx1.0 °
- extraction was completed (required time: about 3 hours), and 5300 g (chlorogenic acids 1.4%) of Bx6.0 ° extract was obtained.
- the resulting extract was cooled to 20 ° C., and then No.
- the solution was passed through to remove sodium ions, and further pressed to obtain 7789 g of coffee bean extract (Bx 2.4 °, pH 4.2, chlorogenic acids 1.3%, caffeine 0.34%). Subsequently, the obtained coffee bean extract was concentrated under reduced pressure to Bx70 ° using a rotary evaporator, and 267.1 g of the concentrate of the coffee bean extract (Bx70 °, pH 4.1, chlorogenic acids 40.2%, cafe In 9.9%).
- this concentrated liquid is spray-dried at a hot air inlet temperature of 150 ° C., a discharged air temperature of 80 ° C., and an atomizer rotation speed of 20000 rpm using a mobile minor type spray dryer (manufactured by Niro Japan Co., Ltd.).
- a mobile minor type spray dryer manufactured by Niro Japan Co., Ltd.
- Example 1 (heating of dry coffee bean powder extracted from purified chlorogenic acids)
- the reference product 3 (10 g) was placed on a stainless steel tray and heated at the heating temperature and heating time shown in Table 2 using the water oven function of a superheated steam cooker (Sharp, Hercio (registered trademark) AX-GX2). Under conditions, dehydration heat treatment was performed to obtain a brown fired product. At this time, expansion of the reference product 3 occurred about 2 minutes after the start of heating, and after that, the baking progressed while expanding and changed to brownish brown with heating. Further, depending on the heating conditions, after the firing proceeded in an expanded state for several minutes, it contracted, and then a plate-like fired product such as a brown thin cocoon was obtained. The obtained fired product was pulverized with a mill to obtain a powder (Products 1 to 3 of the present invention).
- Comparative Example 1 Hot water extracted dry powder of coffee beans with various roasting degrees
- Roasted coffee beans (Indonesian Robusta) (Probat Company sample roaster used / city gas)
- L value 40 L value 30, L value 27.5, L value 25, L value 22.5, L Roasted coffee beans with a value of 20, L value of 17.5 and L value of 16.5 were prepared.
- the above-mentioned green coffee beans and roasted coffee beans are pulverized in a coffee mill, and 200 g of the pulverized product is packed in a column (column inner diameter 7 cm, length 25 cm), and soft water heated to 95 ° C. is supplied at a flow rate of 500 ml / hr.
- the raw coffee bean extracted dry powder of Reference product 3 (a type obtained by purifying chlorogenic acids) contains about 56% chlorogenic acids and about 14% caffeine, but 3 (and 4) -Caffeoylquinic acid lactone was very small, 0.17%, and 3,4-dicaffeoylquinic acid lactone was 0.002%, containing only a trace amount.
- the content of caffeine is within the range of 14 to 15% in the products 1 to 3 of the present invention obtained by heating the reference product 3 that is an extract from green coffee beans at 200 ° C. or higher. Compared with the reference product 3 It was shown that caffeine is stable to heating.
- chlorogenic acids decreased as the strength of dehydration and heating conditions of the products 1 to 3 of the present invention increased, and decreased to 20.43% when heated at 250 ° C. for 5 minutes (product 3 of the present invention).
- the content of 5-caffeoylquinic acid which is the most abundant, is about 35% of all chlorogenic acids in any heated product (the products of the present invention 1 to 3). It was considered to be an index representing the content of.
- 3 (and 4) -caffeoylquinic acid lactone and 3,4-dicaffeoylquinic acid lactone increased most at the heating temperature of 230 ° C. (Product 2 of the present invention), and products 1 to 3 of the present invention.
- the content of 3 (and 4) -caffeoylquinic acid lactone in the heat-treated product is 2.37 to 3.93%, and 3,4-dicaffeoylquinic acid lactone is 0.26 to 0.55% Met.
- the mass ratio of the content of chlorogenic acid lactones to the content of chlorogenic acids, which are the main components of coffee, is considered to be greatly related to the degree of contribution of chlorogenic acid lactones as a sharp bitter component.
- the mass ratio of the content of the chlorogenic acid lactone to the content of 5-caffeoylquinic acid which is the highest and contained in a certain amount, is suitable for the bitter taste of chlorogenic acid lactone.
- the degree of contribution could be judged. Therefore, the mass ratio of the contents of 3 (and 4) -caffeoylquinic acid lactone and 3,4-dicaffeoylquinic acid lactone to the content of 5-caffeoylquinic acid was calculated.
- the values of 3 (and 4) -caffeoylquinic acid lactone / 5-caffeoylquinic acid were 0.13-0.37, 3,4-dicaffeoylquinic acid.
- the value of lactone / 5-caffeoylquinic acid was 0.025 to 0.039.
- chlorogenic acids [Analysis of chlorogenic acids, caffeine and chlorogenic acid lactones]
- the aforementioned chlorogenic acids (3-caffeoylquinic acid, 5-caffeoylquinic acid, 4-caffeoylquinic acid, 3-feruloylquinic acid, 5-feruloylquinic acid, 4-feruloylquinic acid, 3, 4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid), caffeine and chlorogenic lactones (3 (and 4) -caffeoylquinic acid lactone, 3 , 4-dicaffeoylquinic acid lactone) is analyzed as follows.
- Apparatus Waters HPLC system Column: Waters Symmetry C18, 5 ⁇ m, 4.6 ⁇ 250 mm Detector: Waters 2487 dual ⁇ absorbance detector Eluent A: 10 mM citric acid (80 V / V%) / methanol (20 V / V%) Eluent B: Methanol gradient condition Time Eluent A Eluent B 0.0 minutes 100% 0% 19.0 minutes 100% 0% 25.0 minutes 80% 20% 35.0 minutes 80% 20% 50.0 minutes 60% 40% 60.0 minutes 60% 40% 61.0 minutes 100% 0% 70.0 minutes 100% 0% Flow rate: 1.0 ml / min Column oven set temperature: 30 ° C Detection: UV absorption (measurement of absorbance): 325 nm Analytical sample injection volume: 10 ⁇ l Preparation of analytical sample: About 0.02 g of a sample (in the case of coffee extract powder) was precisely weighed and then made up to 10 mL with eluent A.
- 3-caffeoylquinic acid lactone easily undergoes an acyl group transfer reaction in a proton solvent such as alcohol or water to form 4-caffeoylquinic acid lactone. 3 (and 4) -caffeoylquinic acid lactone (mixture).
- the water extract of unroasted (raw) coffee beans contained about 38% chlorogenic acids, but almost no chlorogenic acid lactones. .
- comparative products 2 to 9 as the roasting strength of coffee beans progresses, especially when the L value is 25 or less, chlorogenic acids decrease to less than 20%, and when the L value is 20 or less, it becomes less than 10%. In No. 5, only a very small amount of 1.97% remained.
- the mass ratio of the content of chlorogenic acid lactones to the content of 5-caffeoylquinic acid is considered to determine the degree of contribution of chlorogenic acid lactones to the sharp bitterness.
- the value of 3 (and 4)-caffeoylquinic acid lactone / 5-caffeoylquinic acid in Comparative products 1 to 9 was 0.01 to 0.79, and the value of 3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid was 0 to 0.0023.
- Example 1 Extraction of dried coffee beans from dried coffee (Example 1: Invention products 1 to 3) and extraction after roasting of coffee beans in advance, followed by no dehydration (No comparison)
- Example 1 Comparing the comparative products 1 to 9
- the chlorogenic acids were hardly decreased within the range of the conditions of Example 1 (except for the present product 3)
- about 2/3 or more of the chlorogenic acid content of the reference product 3 remains), and chlorogenic acid lactones are produced in a large amount.
- 3,4-dicaffeoylquinic acid lactone is produced in large amounts (see Table 4).
- chlorogenic acids are used in shallow roasting (L value of 25 or more). Chlorogenic acid lactones, in particular 3 (and 4) -caffeoylquinic acid lactone, are produced slightly more, but 3,4-dicaffeoylquinic acid lactone is less produced.
- the mass ratio of 3,4-dicaffeoylchlorogenic acid lactone content to 5-caffeoylquinic acid content is 0.0023 (L value 30) when roasted coffee beans.
- Comparative product 3 which was only a small value of about 1/11 of 0.025 (product 1 of the present invention), which is the minimum value when the dried coffee bean-extracted dry powder was dehydrated and heat-treated.
- Example 1 the present invention products 1 to 3
- the raw coffee beans or the coffee beans themselves are roasted and extracted, and then dehydrated.
- the amount of 3,4-dicaffeoylquinic acid lactone produced is larger than when no heat treatment is performed (Comparative Example 1: Comparative products 1 to 9).
- the mass ratio of the content of 1,4-dicaffeoylquinic acid lactone was found to be high.
- the evaluation criteria are very good with respect to the strength of bitterness, lack of bitterness, low taste, coffee richness and regular coffee feeling when the additive-free product (control) is set as the standard (0 points): 10 points , Very good: 8 points, good: 6 points, slightly good: 4 points, slightly good: 2 points, extremely bad: -10 points, very bad: -8 points, bad: -6 points, slightly bad: Sensory evaluation was performed as -4 points, slightly bad: -2 points. The average score is shown in Table 6.
- the coffee beverages to which comparative products 1 to 9 which were not subjected to dehydration heat treatment were added had a strong bitterness, but the bitterness was lost.
- the regular coffee sensation was rather reduced, and the richness increased, but the miscellaneous taste also increased at the same time. This tendency was conspicuous as coffee beans roasted deeper.
- the coffee beverages to which the present invention products 1 to 3 obtained by dehydrating the raw coffee bean extract are added have enhanced bitterness, reduced bitterness, reduced taste, increased coffee richness, and regular coffee. The feeling increased.
- the bitterness intensity of coffee itself is known to increase as roasting progresses, but this is thought to be due to an increase in bitterness components other than chlorogenic lactones such as vinyl catechol oligomers.
- the bitterness intensity is increased at the dehydration heating temperature of 250 ° C. due to an increase in bitterness components other than chlorogenic lactones such as vinyl catechol oligomers. It seems to have strengthened.
- the flavor tendency of the coffee beverages to which the products 1 to 3 of the present invention are added is similar to the flavor change when chlorogenic acid lactones, particularly 3,4-dicaffeoylquinic acid lactone is added (Reference Example 1).
- the value of 3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid is considered to be an index of the bitterness-imparting effect of the present invention. It is recognized that a greater bitterness-imparting effect of the present invention is obtained as the value increases to 0.020 or more, preferably 0.030 or more, more preferably 0.035 or more.
- the content of chlorogenic acids (the above nine types) in the coffee beans tends to decrease.
- the mass ratio of the total amount of chlorogenic acids to the available solid content of coffee beans in the extract will also be reduced.
- the mass ratio of the total amount of chlorogenic acids to the availability solid content derived from coffee beans is considered to be an indicator that chlorogenic acids are not excessively decomposed or reduced by heating, but this mass ratio is 0.1 for comparative products 7-9. Is less than As roasting or heating progresses, it is considered that the chlorogenic acid lactones once produced decrease with the decomposition of the chlorogenic acids.
- this mass ratio value needs to be high to some extent, and the range thereof is usually 0.1 to 0.8, preferably 0.2 to 0.7, based on the results shown in Table 6. More preferably, it was considered to be within the range of 0.3 to 0.6.
- Example 2 Comparative products 1 to 4 used in Comparative Example 1 were each placed on a 10 g stainless steel tray, and 230 ° C., using the water oven function of a superheated steam cooker (manufactured by Sharp Corporation, Hercio (registered trademark) AX-GX2). A dehydrated heat treatment was performed for 4 minutes to obtain a brown fired product. At this time, expansion of the comparative products 1 to 4 occurred about 2 minutes after the start of the dehydration heat treatment, and then the firing proceeded with the expansion, and the color changed to brown near black with heating. The obtained fired product was pulverized with a mill to obtain a powder (Products 4 to 7 of the present invention). The products 4 to 7 of the present invention were analyzed for chlorogenic acids, caffeine and chlorogenic acid lactones by the same method as described above. The results are shown in Table 7.
- the extract of coffee beans not subjected to dehydration heat treatment contains about 38% of chlorogenic acids in the raw coffee bean extract. It was confirmed that although roasting with an L value of 40 hardly decreased, the L value gradually decreased as roasting progressed to 30, 27.5. On the other hand, in Comparative products 1 to 4, among the chlorogenic lactones, 3 (and 4) -caffeoylquinic acid lactone is hardly contained in the raw coffee bean extract (Comparative product 1), but an L value of 27 Up to .5 roasting was observed to increase as roasting progressed.
- 3,4-dicaffeoylquinic acid lactone is hardly contained in the raw coffee bean extract (Comparative product 1), but most in roasting with L value 40 (Comparative product 2). It was observed that it decreased as roasting progressed.
- the component that contributes to a refreshing bitterness is 3,4-dicaffeoylquinic acid lactone
- the roasting degree of coffee beans for beverages is so-called Taking into account that the roasting degree said to be “drinking” is an L value of 25 or less, roasted beans deeply roasted to an L value of 25 or less have a refreshing bitterness, that is, 3,4-dicaffe oil. From the viewpoint of containing a large amount of quinic acid lactone, it was considered not necessarily advantageous.
- the chlorogenic acids are about 30 in the dehydrated and heat-treated product of the raw coffee bean extract (product 4 of the present invention). %, But gradually decreased as roasted coffee beans became deeper (L value decreased to 30, 27.5).
- chlorogenic acid lactones were increased by dehydration heat treatment of the extract, and were particularly abundant in the products 4 and 5 of the present invention using raw or roasted beans having an L value of 40.
- the amount of chlorogenic lactones did not increase so much even when the coffee beans were deeply roasted (L value 30, 27.5). This was thought to be because chlorogenic acids had already decreased due to roasting of the coffee beans themselves, and the potential to produce chlorogenic acid lactones was reduced.
- the coffee beans used as the raw material of the coffee extract to be used in the present invention are preferably green coffee beans or roasted coffee beans having an L value of about 25 or more. Since the L value of green coffee beans is approximately 60, the L value of roasted (or unroasted) coffee beans used in the present invention is 25 to 60, preferably L value 40 to 55, more preferably The L value was considered to be 45-50.
- the evaluation criteria are very good with respect to the strength of bitterness, lack of bitterness, low taste, coffee richness and regular coffee feeling when the additive-free product (control) is set as the standard (0 points): 10 points , Very good: 8 points, good: 6 points, slightly good: 4 points, slightly good: 2 points, extremely bad: -10 points, very bad: -8 points, bad: -6 points, slightly bad: Sensory evaluation was performed as -4 points, slightly bad: -2 points. The average points are shown in Table 8.
- the instant coffee to which the extract of roasted coffee beans was not heat-treated had almost no influence on the flavor regardless of the degree of roasting.
- the coffee beverages to which the present invention products 4 to 7 obtained by heating the coffee bean extracts of the comparative products are added have enhanced bitterness, reduced bitterness and reduced taste, and further reduced the richness of coffee.
- the regular coffee feeling increased and a very delicious effect was recognized.
- products 4 to 7 the content of 3,4-dicaffeoylquinic acid lactone relative to the content of 5-caffeoylquinic acid (3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid)
- the mass ratio is extremely large compared to the comparative products 1 to 4, and this value is considered to be a clear index of bitterness.
- the bitterness and miscellaneous taste decreased, and the richness of coffee and regular coffee increased.
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Abstract
L'invention fournit un procédé de fabrication d'un extrait de grains de café enrichi en lactones d'acide chlorogénique, et un extrait de grains de café obtenu à l'aide de ce procédé destiné à conférer à un produit alimentaire au goût de café, tel qu'une boisson au café, ou similaire, une amertume clair et rafraichissante. Le procédé de l'invention inclut : (a) une étape au cours de laquelle des grains de café sont soumis à une extraction à l'aide d'un solvant aqueux pour obtenir un concentré présentant un liquide d'extraction de grains de café supérieur ou égal à B×50°, ou une matière sèche qui présente une humidité du liquide d'extraction de grains de café supérieure ou égale à 1% en masse et inférieure ou égale à 10% en masse; et (b) une étape au cours de laquelle le concentré ou la matière sèche obtenu(e) lors de la précédente étape, est déshydraté(e) et chauffé(e) simultanément par un moyen de chauffage entre 150 et 400°C et pendant 0,1 à 60 minutes
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016557466A JP6381055B2 (ja) | 2014-11-05 | 2015-07-22 | クロロゲン酸ラクトン類の増加したコーヒー豆抽出物およびその製造方法 |
| CN201580058542.7A CN107072233A (zh) | 2014-11-05 | 2015-07-22 | 增加了绿原酸内酯类的咖啡豆提取物及其制造方法 |
| TW104136177A TWI678158B (zh) | 2014-11-05 | 2015-11-03 | 增加綠原酸內酯類之咖啡豆萃取物及其製造方法 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014-225261 | 2014-11-05 | ||
| JP2014225261 | 2014-11-05 | ||
| JPPCT/JP2015/067961 | 2015-06-23 | ||
| PCT/JP2015/067961 WO2016072111A1 (fr) | 2014-11-05 | 2015-06-23 | Agent conférant, renforçant ou modifiant le goût pour boisson ou aliment au café |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2016072114A1 true WO2016072114A1 (fr) | 2016-05-12 |
Family
ID=55908844
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2015/067961 Ceased WO2016072111A1 (fr) | 2014-11-05 | 2015-06-23 | Agent conférant, renforçant ou modifiant le goût pour boisson ou aliment au café |
| PCT/JP2015/070760 Ceased WO2016072114A1 (fr) | 2014-11-05 | 2015-07-22 | Extrait de grains de café enrichi en lactones d'acide chlorogénique, et procédé de fabrication de celui-ci |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2015/067961 Ceased WO2016072111A1 (fr) | 2014-11-05 | 2015-06-23 | Agent conférant, renforçant ou modifiant le goût pour boisson ou aliment au café |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JP6338228B2 (fr) |
| CN (2) | CN107072234A (fr) |
| TW (2) | TWI678158B (fr) |
| WO (2) | WO2016072111A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019062848A (ja) * | 2017-10-03 | 2019-04-25 | サントリーホールディングス株式会社 | クロロゲン酸ラクトン類を含む容器詰めコーヒー飲料 |
| JP2019156780A (ja) * | 2018-03-14 | 2019-09-19 | 味の素株式会社 | キサンチンオキシダーゼ阻害剤 |
| JP2020130036A (ja) * | 2019-02-19 | 2020-08-31 | 雪印メグミルク株式会社 | インスタントコーヒー類の製造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020196630A1 (fr) * | 2019-03-27 | 2020-10-01 | 株式会社カネカ | Boisson lactée contenant du café et son procédé de fabrication |
| CN112640981B (zh) * | 2020-12-03 | 2023-11-10 | 东莞波顿香料有限公司 | 咖啡热处理液、提取液及其制备方法和应用 |
| GB2601759B (en) * | 2020-12-08 | 2023-04-26 | Douwe Egberts Bv | A method of producing a coffee product |
| CN114521605A (zh) * | 2022-02-17 | 2022-05-24 | 德宏芸茶屋咖啡有限公司 | 一种降低咖啡豆中咖啡因含量的方法 |
| CN115381130B (zh) * | 2022-08-19 | 2024-09-10 | 深圳萨特瓦生物科技有限公司 | 咖啡精制物及其制备方法、应用和电子烟烟油 |
| TWI892758B (zh) * | 2024-07-19 | 2025-08-01 | 陳百修 | 咖啡烘焙方法 |
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| JP2009219488A (ja) * | 2008-02-20 | 2009-10-01 | Unicafe Inc | コーヒーカラメルと、コーヒーカラメル入り食品、及びコーヒーカラメルの製造方法 |
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| TWI469737B (zh) * | 2005-01-28 | 2015-01-21 | Suntory Beverage & Food Ltd | Can be processed into high green base of coffee beans method |
| US20060286238A1 (en) * | 2005-06-20 | 2006-12-21 | The Procter & Gamble Company | Processes for isolating bitter quinides for use in food and beverage products |
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2015
- 2015-06-23 CN CN201580058731.4A patent/CN107072234A/zh not_active Withdrawn
- 2015-06-23 WO PCT/JP2015/067961 patent/WO2016072111A1/fr not_active Ceased
- 2015-06-23 JP JP2016557464A patent/JP6338228B2/ja active Active
- 2015-07-22 WO PCT/JP2015/070760 patent/WO2016072114A1/fr not_active Ceased
- 2015-07-22 CN CN201580058542.7A patent/CN107072233A/zh active Pending
- 2015-07-22 JP JP2016557466A patent/JP6381055B2/ja active Active
- 2015-11-03 TW TW104136177A patent/TWI678158B/zh active
- 2015-11-03 TW TW104136175A patent/TWI677289B/zh active
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| JP2000093085A (ja) * | 1998-09-09 | 2000-04-04 | Kraft Foods Inc | 増強したフレ―バ―及び色を有するソルブルコ―ヒ―並びにその製造方法 |
| JP2009219488A (ja) * | 2008-02-20 | 2009-10-01 | Unicafe Inc | コーヒーカラメルと、コーヒーカラメル入り食品、及びコーヒーカラメルの製造方法 |
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| JP2019062848A (ja) * | 2017-10-03 | 2019-04-25 | サントリーホールディングス株式会社 | クロロゲン酸ラクトン類を含む容器詰めコーヒー飲料 |
| JP2019156780A (ja) * | 2018-03-14 | 2019-09-19 | 味の素株式会社 | キサンチンオキシダーゼ阻害剤 |
| JP2020130036A (ja) * | 2019-02-19 | 2020-08-31 | 雪印メグミルク株式会社 | インスタントコーヒー類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107072234A (zh) | 2017-08-18 |
| TWI677289B (zh) | 2019-11-21 |
| JP6381055B2 (ja) | 2018-08-29 |
| TWI678158B (zh) | 2019-12-01 |
| CN107072233A (zh) | 2017-08-18 |
| WO2016072111A1 (fr) | 2016-05-12 |
| TW201618674A (zh) | 2016-06-01 |
| JP6338228B2 (ja) | 2018-06-06 |
| JPWO2016072111A1 (ja) | 2017-05-25 |
| TW201616974A (zh) | 2016-05-16 |
| JPWO2016072114A1 (ja) | 2017-05-18 |
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