WO2016072114A1 - Coffee bean extract containing increased amount of chlorogenic acid lactone and production method for same - Google Patents

Abstract

[Problem] To provide a production method for a coffee bean extract that contains an increased amount of chlorogenic acid lactone and that is for imparting a crisp and refreshing bitter flavor to a coffee-flavored foodstuff such as a coffee drink, and to provide a coffee bean extract that is obtained by said production method. [Solution] The present invention includes: (a) a step for performing an extraction on coffee beans in an aqueous solvent and obtaining a coffee bean extract liquid concentrate that is 50 °Bx or more or obtaining a coffee bean extract liquid dried material that has 1-10 mass% water content; and (b) a step for using a heating means to dehydrate and heat the concentrate or the dried material obtained in the previous step at 150℃-400℃ for 1-60 minutes. [Drawing] None.

Description

Coffee bean extract with increased chlorogenic acid lactones and process for producing the same

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.

In Japan, 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.

The taste of coffee is thought to be in the balance of rich aroma, richness and umami, but “bitterness” is considered to be an important factor as one of the factors that bring out deliciousness in the balance with richness and umami. Caffeine, chlorogenic acids, vinyl catechol oligomers, diketopiperazines, coffee melanoidins and the like are conventionally known as bitter components of coffee.

On the other hand, even if coffee is caffeine-less, it still has a bitter taste, so it was thought that there was an ingredient contributing to bitterness in addition to the above compound group. It has been reported that components that greatly contribute to the bitterness of coffee are chlorogenic acid lactones (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.

On the other hand, the bitter taste of coffee is generally not a good image, but there is an idea that it should be reduced rather. Although 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. As 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. 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 4), and a method of adjusting the coffee bean extract to pH 5.5 to 6.5 at a concentration of Bx10 to 40 ° and heating at 100 ° C. or more (Patent Document 5) A method of adsorbing and removing using specific activated carbon (Patent Document 6) has been proposed. That.

Moreover, although 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). .

Thus, it is known that 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.

Eur. Food Res. Technol. 2006, 222, 492-508 J. et al. Agric. Food Chem. , Vol. 54, no. 2,2006,374-381

Special table 2008-543336 gazette Special table 2009-501317 Japanese Patent Laid-Open No. 10-215771 JP 2008-541712 A JP 2012-125237 A JP 2014-168433 A

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.

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.

As described in Patent Document 1, chlorogenic acid lactones have been reported to be useful as a bitter component of coffee. On the other hand, as described in Patent Documents 3 to 6, components to be reduced are described. There is also an evaluation.

Therefore, the present inventors synthesized chlorogenic acid lactones, confirmed the taste and confirmed the effect of addition to the coffee beverage (see [Example] described later). As a result, 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.

However, a method of preparing chlorogenic acid lactones themselves by a synthetic method or a method of preparing them by isolating from a coffee extract is not practical in terms of complexity of work steps and cost.

Therefore, the present inventors conducted development studies on a method for obtaining a coffee bean extract in which chlorogenic acid lactones are increased. Raw coffee beans contain the most abundant chlorogenic acids but little chlorogenic lactones. As roasting of coffee beans progresses, chlorogenic acids decrease and chlorogenic acid lactones increase, but if roasting progresses too much, both chlorogenic acids and chlorogenic acid lactones may decrease. It is known (see Non-Patent Document 2).

Therefore, 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. We thought that a coffee bean extract containing a high concentration and a high content of chlorogenic acid lactones could be obtained by converting it into sucrose.

Usually, chlorogenic acid lactones tend to decrease by heating in a concentrated coffee extract as described in Patent Document 5. Surprisingly, however, when 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.

Thus, 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.
(3) The method for producing a coffee bean extract according to (1) or (2), wherein the heating means is at least one of superheated steam heating, hot air heating, far-infrared heating, microwave heating, or electric heater heating.
(4) A coffee bean extract obtained by the production method according to any one of (1) to (3).
(5) The mass ratio of 3,4-dicaffeoylquinic acid lactone content to 3,5-caffeoylquinic acid content (3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid) is 0. A coffee bean extract having an increased amount of chlorogenic acid lactones, having a mass ratio of the total amount of chlorogenic acids to the availability solid content of coffee beans of 0.1 to 0.8 or more.
(6) A coffee beverage containing the coffee bean extract according to (4) or (5).
(7) Instant coffee containing the coffee bean extract according to (4) or (5).
(8) A method for enhancing the bitterness of a coffee beverage by blending the coffee bean extract according to (4) or (5).
(9) A method for enhancing the bitterness of instant coffee by blending the coffee bean extract according to (4) or (5).

According to the present invention, 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. By adding a trace amount of the coffee bean extract of the present invention to a coffee beverage or instant coffee, 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).

According to the present invention, 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. In this method, the product is heated at 150 to 400 ° C. for 0.1 to 60 minutes while dehydrating.

In the present invention, the coffee bean extract refers to an extract obtained by extracting raw or roasted coffee beans with an aqueous solvent.

There are no particular limitations on the variety and production area of the coffee beans used as the raw material, and any kind of Arabica, Riberica, Robusta, etc. may be used, and any coffee beans from Brazil, Colombia, Indonesia, etc. Can be used. In addition, as 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.

In the present invention, raw coffee beans rich in chlorogenic acids can be used as raw materials, but coffee beans roasted appropriately may be used. Although 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. However, 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.

For reference, the L value of roasted beans that are normally used for drinking is almost as shown below. Italian roast: 16-19, French roast: 19-21, Full city roast: 21-23, City roast: 23-25, High roast: 25-27, Medium roast: 27-29. Shallow roasting is less commonly used in normal drinking.

When roasted so that the L value is less than 25, 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. . However, when considering the overall flavor including taste other than bitterness, 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.

As 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. Examples of such 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.

These 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. For the extraction operation, a known extraction method such as batch extraction or continuous extraction using a column can be employed.

Further, for example, 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

Furthermore, for example, 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.

Further, 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.

In addition, 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.

Furthermore, the coffee bean extract has a name such as “coffee extract”, and various commercial products are distributed. Also, 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. Furthermore, 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.

Next, 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.

In the present invention, 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. In the heating conditions, the heating temperature may be 150 to 400 ° C., preferably 180 ° C. to 300 ° C., more preferably 200 to 250 ° C. In this heating start stage, the heated object, that is, the concentrate Alternatively, since the dried product contains moisture, the product temperature of the object to be heated is about 100 to 200 ° C. After the start of heating, 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. However, 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.

In the heating conditions (including dehydration conditions), the heating time may be 0.1 to 60 minutes, preferably 0.5 to 30 minutes, more preferably 2 to 15 minutes.

In the present invention, 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. For example, 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. When superheated steam is brought into contact with the concentrate or dried product by heating with superheated steam, it is brought into contact at approximately atmospheric pressure. That is, the heat treatment is performed by contacting with the superheated steam without any special pressurization or decompression. By heating under such conditions, heat is quickly transferred to the object to be heated, and the inside of the object to be heated is heated uniformly.

Commercially available 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. However, the present invention is not limited to these.

In particular, when used for experiments, a steam oven or water oven (registered trademark, manufactured by Sharp Corporation), which has been in the limelight and rapidly spread in recent years, as a commercial household cooker, specifically, A household cooker using superheated steam called Hercio (registered trademark, manufactured by Sharp Corporation) can also be used. These home cookers are efficient because they can be heated with superheated steam in a semi-enclosed space.

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 μm to 1000 μm 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 μm 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. 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. As 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.

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. In 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 μm 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. In the extruder treatment, 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. Here, at the moment when the heated and pressurized raw material is pushed out, a part of the high-pressure gaseous component expands by returning to atmospheric pressure, and may expand and solidify. As the extruder, a biaxial extruder EA-20 (manufactured by Suehiro EPM) or the like can be used.

In the present invention, as described above, 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.

Examples of the adsorbent 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- Nine types of feruloyl quinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid can be mentioned. Among these nine types, the most abundant one is 5-caffeoylquinic acid (about 35% by mass), and this content can represent the total amount of chlorogenic acids.

On the other hand, chlorogenic acid lactones are formed from chlorogenic acids by roasting green coffee beans. By various transfer reactions, 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. Among these chlorogenic lactones, 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).

In addition, when green coffee beans are roasted, 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.

For example, in the usual method, that is, the method of roasting green coffee 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. Whereas the ratio is about 0 to 0.003, when the raw coffee bean extract is heat-dehydrated and heat-treated according to the method of the present invention, 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.

Further, 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 (the total of the 9 types of chlorogenic acids) 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. As roasting or heating progresses, it is considered that the chlorogenic acid lactones once produced decrease with the decomposition of the chlorogenic acids. However, in the method of heating a coffee bean extract concentrate or the like at 150 to 400 ° C. for 0.1 to 60 minutes while dehydrating in accordance with the method of the present invention, the chlorogenic acids are added to the coffee bean extract before heat dehydration. The content does not decrease so much, and is a decrease of about 1/2 to 1/3 at most. Therefore, 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.

Next, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the following examples, “%” represents “% by mass” unless otherwise specified.

Reference Example 1 Synthesis of 3 (and 4) -caffeoylquinic acid lactone (mixture: Reference product 1) Agric. Food Chem. , Vol. According to the method described in 58, 2010, 3720-3728, 3-caffeoylquinic acid lactone (1) represented by the following structural formula was synthesized.
By 1H-NMR (400 MHz, CD3OD) measurement and two-dimensional NMR measurement of the obtained synthetic product, it was confirmed that the main component of the synthetic product was a caffeoyl group bonded to the 3-position of quinic acid lactone. It was also confirmed that a portion of 3-caffeoylquinic acid lactone (1) was transferred to 4-caffeoylquinic acid lactone (2) over time in heavy methanol.
It was considered that 3-caffeoylquinic acid lactone easily undergoes an acyl group transfer reaction in a proton solvent such as alcohol or water to produce 4-caffeoylquinic acid lactone. Therefore, the present invention treats 3 (and 4) -caffeoylquinic acid lactone (mixture) as a standard product (reference product 1). 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.

As shown in Table 1, when the reference product 1 or the reference product 2 was added to the black coffee beverage, both had the effect of imparting or enhancing bitterness to the black coffee beverage, and the bitterness quality remained on the tongue. It was not a bitter taste, but a pleasant bitter taste with good sharpness. The quality of this bitterness is a bitter taste that does not interfere with the “sweet finish” that is characteristic of coffee's original deliciousness, that is, a so-called “first taste”. Addition to the black coffee beverage has the effect of changing the quality of bitterness and making it difficult to feel miscellaneous taste, and as a result, the regular coffee feeling is increased, and it is thought that it has the effect of increasing the original taste of coffee. .
In addition, the effect of enhancing the bitterness by the addition of Reference product 1 or Reference product 2 is that 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. These effects were sufficiently felt even when 1 ppm was added to both Reference Sample 1 and Reference Sample 2.

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. When 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. 1 was precoated with 50 g of diatomaceous earth. Suction filtration was performed with a Nutsche fitted with 26 (210 mm) filter paper to obtain 5300 g of filtrate (pH 5.6, chlorogenic acid 1.4%, caffeine 0.4%). To this filtrate, 58 g of a 10% aqueous sodium hydroxide solution was added to adjust to a pH 10 solution. This solution was passed through a column packed with 200 ml of the synthetic adsorption resin (SP-207) at SV = 2.5, and the obtained passing solution was continuously applied to a column packed with 200 ml of the cation exchange resin (SK-116). 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%).
Subsequently, 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.). As a result, 190.3 g (reference product 3: moisture 3.1%, chlorogenic acids 55.98%, caffeine 13.89%) was obtained.

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. Then, the column was fed from the upper part to the lower part to obtain about 2100 g of extract (required time: about 3 hours). Each of the obtained extracts was cooled to 20 ° C., and then pre-coated with 50 g of diatomaceous earth. Suction filtered through a Nutsche equipped with a 26 (210 mm) filter paper to obtain a filtrate, then concentrated under reduced pressure to Bx70 ° using a rotary evaporator, and the concentrate (coffee bean extract) was vacuum dried and shown in Table 3. A non-roasted (raw) or roasted (L value) coffee beans (raw or roasted) concentrated dry extract (water content of about 3%) was obtained (comparative products 1-9).

(Analysis of the product of the present invention)
According to the analysis method shown below, caffeine, chlorogenic acids (3-caffeoylquinic acid, 5-caffeoylquinic acid, 4-caffeoylquinic acid, 3-feroline were used for Reference product 3 and Invention products 1 to 3. Roylquinic acid, 5-feruloylquinic acid, 4-ferloylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid), chlorogen The content of acid lactones (3 (and 4) -caffeoylquinic acid lactone (mixture), 3,4-dicaffeoylquinic acid lactone) was measured. The analysis results are shown in Table 4.

As shown in Table 4, 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.

On the other hand, 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). Among the chlorogenic acids, 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.

In contrast, 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. Of the total acid content, 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. As a result, in the products 1 to 3 of the present invention, 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.

[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.
(1) Quantification method of chlorogenic acids 5-Caffeoylquinic acid is used as a standard substance, and the chromatogram peaks of analytical samples obtained by high performance liquid chromatography (HPLC) under the following operating conditions are shown for each retention time. The group was assigned to 9 types of chlorogenic acids, and the concentration (% by mass) of chlorogenic acids was determined from the peak area value.
Apparatus: Waters HPLC system
Column: Waters Symmetry C18, 5 μm, 4.6 × 250 mm
Detector: Waters 2487 dual λ 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 μl
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. Membrane filter (GL chromatodisc 25A, pore size 0.45 μm, GL Sciences ( )) And filtered for analysis.
Retention time of chlorogenic acids (9 kinds of chlorogenic acids): 3-caffeoylquinic acid (7.9 minutes), 5-caffeoylquinic acid (15.9 minutes), 4-caffeoylquinic acid (18.7 minutes) ), 3-feruloylquinic acid (15.5 minutes), 5-feruloylquinic acid (30.8 minutes), 4-feruloylquinic acid (31.2 minutes), 3,4-dicaffeoylquinic acid (41.6 minutes), 3,5-dicaffeoylquinic acid (43.0 minutes), 4,5-dicaffeoylquinic acid (49.3 minutes)
(2) Caffeine quantification method Caffeine quantitative analysis was performed simultaneously with chlorogenic acids. That is, it was carried out simultaneously in the same manner as in the case of chlorogenic acids except that ultraviolet absorption (measurement of absorbance): 270 nm and caffeine was used as the standard substance under the quantification conditions of the chlorogenic acids.
Caffeine retention time: 18.2 minutes (3) Method for confirming and quantifying chlorogenic acid lactones The quantitative analysis of chlorogenic acid lactones was performed simultaneously with the chlorogenic acids. That is, it carried out at the same time by the same method as in the case of chlorogenic acids under the quantification conditions of the chlorogenic acids. Chlorogenic acid lactones were confirmed by LC-MS / MS under the following conditions.
Using 3 (and 4) -caffeoylquinic acid lactone: m / z = 337 in scan and single ion observation mode, this was confirmed by comparison with a standard product.
3,4-dicaffeoylquinic acid lactone: The mass transition reactions of m / z = 497 → 335 and 497 → 161 were used in the multi-reaction observation mode, and confirmed by comparison with a standard product.
Retention time of chlorogenic lactones: 3-monocaffeoylquinic acid lactone (29.6 minutes), 4-monocaffeoylquinic acid lactone (31.7 minutes), 3,4-dicaffeoylquinic acid lactone (55 .4 minutes). However, as described above, 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).

(Analysis of comparative products)
Based on the above analysis method, for comparative products 1 to 9, caffeine, chlorogenic acids (nine types described above), chlorogenic acid lactones (3 (and 4) -caffeoylquinic acid lactone (mixture), 3,4-di The content of caffeoylquinic acid lactone) was measured. The analysis results are shown in Table 5.

As shown in Table 5, the water extract of unroasted (raw) coffee beans (Comparative product 1) contained about 38% chlorogenic acids, but almost no chlorogenic acid lactones. . On the other hand, in 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.

In coffee beans with low roasting strength (between raw and L value around 25), chlorogenic lactones tend to be generated or increased as roasting strength progresses, but 3 (and 4) -cafe oil The quinic acid lactone had an L value of 27.5, and the 3,4-dicaffeoylquinic acid lactone had an L value of 40 and the highest content. However, all chlorogenic lactones tended to decrease as roasting deepened further. In comparative products 1 to 9, the content of 3 (and 4) -caffeoylquinic acid lactone is 0.12 (raw) to 2.23 (L value 27.5)%, 3,4-dicaffeoylquinic acid Lactone was 0.000 (raw and L value 16.5) to 0.023 (L value 40)%.

As described above, 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. -Regarding the mass ratio of the content of chlorogenic lactones to the content of caffeoylquinic acid, 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.

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), when the dried coffee bean extracted dry powder was dehydrated and heat-treated, the chlorogenic acids were hardly decreased within the range of the conditions of Example 1 (except for the present product 3) In this case, 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. In particular, it is observed that 3,4-dicaffeoylquinic acid lactone is produced in large amounts (see Table 4).

On the other hand, when the coffee beans themselves are roasted and extracted and then not subjected to dehydration heat treatment (Comparative Example 1: Comparative products 1 to 9), 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. When the roasting is further deepened and the roasting is 25 or less in the L value, the chlorogenic acids are greatly reduced (1/2 to 1/4 of the raw beans at the L value of 20 to 25), and at the same time, 3 (and 4 ) -Caffeoylquinic acid lactone and 3,4-dicaffeoylquinic acid lactone both decrease significantly. When roasting deepens further (L values 17.5 and 16.5), the mass ratio of the content of 3 (and 4) -caffeoylquinic acid lactone to the content of 5-caffeoylquinic acid is high. However, the content (absolute amount) of 3 (and 4) -caffeoylquinic acid lactone in the extract itself is smaller than the amount of the heat-treated product of the raw coffee bean extracted dry powder.

On the other hand, 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.

From the above, when the dry coffee powder extracted from fresh coffee beans is 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.

It has been confirmed in Reference Example 3 that 3,4-dicaffeoylquinic acid lactone greatly contributes to the refreshing bitterness of coffee as described above. The mass ratio of 3,4-dicaffeoylquinic acid lactone content to acid content (3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid) was made clear from chlorogenic acid lactones. It was thought that it could be used as an index of ability to impart bitterness.

[Sensory evaluation] Addition to beverage In the same manner as in Reference Example 4, 0.01% by mass (100 ppm) of Reference Product 3, Invention Products 1 to 3 or Comparative Products 1 to 9 was added to a commercially available black coffee beverage in a plastic bottle. ) Added and dissolved, and immediately after dissolution, sensory evaluation was performed by five well-trained panelists. 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.

As shown in Table 6, after the coffee beans were roasted and the extract was obtained, 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. On the other hand, 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.

Regarding the relationship between the dehydration heating temperature and sensory evaluation, between 200 and 250 ° C., the bitterness, little taste, coffee richness and regular coffee feeling were most favorable at 230 ° C. On the other hand, the bitterness was strongest at 250 ° C. In general, 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. In the case of the products 1 to 3 of the present invention in which the green coffee bean extract is dehydrated and heated, 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 value of 3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid is thought to greatly contribute to the sharp bitterness as described above, but after roasting coffee beans and obtaining an extract In comparison products 1 to 9 which were not subjected to dehydration heat treatment, the value was less than 0.0023, whereas in products 1 to 3 of the present invention in which fresh coffee bean extract was dehydrated and heated, the value was larger than 0.0247. The difference between them was more than 10 times.

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). As described above, 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.

In addition, in the roasting of coffee beans and the heat treatment of coffee bean extract, as roasting and heating proceed, the content of chlorogenic acids (the above nine types) in the coffee beans tends to decrease. In addition, 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. Therefore, it is considered that 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.

As shown in Table 7, the extract of coffee beans not subjected to dehydration heat treatment (no dehydration heat treatment of the extract, comparative products 1 to 4) 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. On the other hand, 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.
As described above, among the chlorogenic lactones, the component that contributes to a refreshing bitterness is 3,4-dicaffeoylquinic acid lactone, and 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.

On the other hand, considering the products 4 to 7 of the present invention obtained by subjecting the comparative products 1 to 4 to dehydration and heat treatment at 230 ° C. for 4 minutes, 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). On the other hand, 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. However, 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.

From these results, it was considered that 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.

[Sensory evaluation] Addition experiment to instant coffee 10 ppm each of comparative products 1 to 4 or products 4 to 7 of the present invention may be added to commercially available instant coffee (100% roasted coffee bean extract, spray dried product). Mixed.
Each instant coffee was dissolved in 1% by weight of water and immediately subjected to sensory evaluation by five well-trained panelists. 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.

As shown in Table 8, the instant coffee to which the extract of roasted coffee beans was not heat-treated (Comparative products 1 to 4) had almost no influence on the flavor regardless of the degree of roasting. . On the other hand, 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.
In the present invention 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.

Claims (9)

(A) extracting coffee beans with an aqueous solvent and obtaining a Bx50 ° or higher concentrate 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;
(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 containing an increased amount of chlorogenic lactones. The method for producing a coffee bean extract according to claim 1, wherein the coffee beans are green coffee beans or roasted coffee beans having an L value of 25 or more. The method for producing a coffee bean extract according to claim 1 or 2, wherein the heating means is at least one of superheated steam heating, hot air heating, far-infrared heating, microwave heating and extruder heating. A coffee bean extract containing an increased amount of chlorogenic acid lactones, obtained by the production method according to any one of claims 1 to 3. The mass ratio of 3,4-dicaffeoylquinic acid lactone content to 3,5-caffeoylquinic acid content (3,4-dicaffeoylquinic acid lactone / 5-caffeoylquinic acid) is 0.01 or more. A coffee bean extract having an increased amount of chlorogenic acid lactones, wherein the mass ratio of the total amount of chlorogenic acids to the available solid content derived from coffee beans is 0.1 to 0.8. A coffee beverage containing the coffee bean extract according to claim 4 or 5. Instant coffee blended with the coffee bean extract according to claim 4 or 5. A method for enhancing the bitterness of a coffee beverage by blending the coffee bean extract according to claim 4 or 5. A method for enhancing the bitterness of instant coffee by blending the coffee bean extract according to claim 4 or 5.

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