JP2021000032A - Method for producing aromatic liquid and aromatic liquid - Google Patents

Abstract

To provide a convenient production method for an aromatic liquid having a green aroma.SOLUTION: A method for producing an aromatic liquid includes the steps of: heating the yeast dried in advance, in aqueous liquid to produce a C6-10 linear saturated aliphatic aldehyde; and recovering the linear saturated aliphatic aldehyde.SELECTED DRAWING: None

Description

The present invention relates to an aromatic liquid, and more particularly to an aromatic liquid having a green aroma.

Aoba aldehyde (that is, unsaturated aldehyde (2E) -hexenal) is known as a component that produces an aroma generally called a green scent (Non-Patent Documents 1 and 2). This green leaf aldehyde is contained in vegetables and fruits as a component constituting a "grass-like" or "leaf-like" aroma in the aroma of food.

Among the characteristic scents recognized in high-quality Scotch whiskey, there is a "green" scent, which is a major classification of aroma (innermost) in the flavor wheel used to specifically express the aroma of whiskey. "Green / Grassy" is described as the ring), and "Herbal, Leafy" is described as the middle classification (intermediate ring) (Non-Patent Document 3). ..

Non-Patent Document 4 describes E, Z-2,6-nonenal, as a result of analyzing malt whiskey using multidimensional gas chromatography-mass spectrometer / orfactometry (MDGC-MS-O). It is described that E-2-nonenal, 1-octen-3-ol, 4-heptene-1-ol and nonane-2-ol contribute to the green aroma.

Whiskey does not contain green leaf aldehyde. Nevertheless, there are products that feature a green scent. Green leaf aldehydes are characterized by a refreshing green scent, while the sensual "green scent" of whiskey has a fresh or dry grassy scent. The mechanism by which green scent is produced in whiskey has not been elucidated.

Patent Document 1 relates to a product having a green scent, a method for obtaining the product, and an alcoholic beverage containing the same. Patent Document 1 describes a method for obtaining a product having a green scent, which is characterized by allowing lipoxygenase to act on unsaturated fatty acids in a medium, the product, and an alcoholic beverage containing the same. In Patent Document 1, a sensory test was actually performed on whiskey and shochu by adding a solution having a green scent. As a result, when the flavor changes the taste of distilled liquor and a green scent is felt, it is said to have an advantage in that the taste is sweet and the taste is improved.

However, the method for producing a product having a green aroma in Patent Document 1 requires complicated work such as preparing an appropriate medium, preparing aspergillus as an enzyme source, pre-culturing, and performing an enzyme reaction. .. Therefore, the production efficiency of products with green aroma is very low and the cost of implementation is high.

In Patent Document 1, whiskey and shochu having a green scent are produced by adding the produced green scented distillate to commercially available shochu or shochu. That is, the product having a green aroma of Patent Document 1 is used as a fragrance. On the other hand, distilled liquors such as whiskey are often prohibited from using additives such as flavors during their production (Non-Patent Document 3). As described above, the product having the green aroma of Patent Document 1 has a narrow application target and is not practical.

As for whiskey, it has not yet been clarified how to manufacture it to enhance its green aroma.

Japanese Unexamined Patent Publication No. 2005-21055

Akikazu Hatanaka, "Scent of Plant Origin", FFI Journal, No. 168, 1996, pp. 5-22 Akikazu Hatanaka, "After the 5th Anniversary Symposium" Why Humans Are Refreshed by the Green Scent! ", FFI Journal, No. 198, 2002, pp. 45-55. Charles W. Bamforce and Robert E. Ward, "The Oxford Handbook of Food Fermentations", Oxford University Press, 2014, pp. 238-241 Akira Wanikawa et al., "Identification of green note compounds in malt whiskey using multimetric gas chromatography", Flavor Fragr. J. , 2002, No. 17, pp. 207-211

The present invention solves the above-mentioned conventional problems, and an object of the present invention is to provide a method for producing an aromatic liquid having a green aroma, which is easy to operate and has excellent practicality.

The present inventors have discovered that a linear saturated aliphatic aldehyde, particularly a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms, contributes to the green aroma of whiskey, and is particularly convenient and particularly in whiskey production. We have found a highly practical method for adding green scent.

The present invention is a step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by heating a pre-dried yeast in an aqueous solution; and a step of recovering the linear saturated aliphatic aldehyde;
Provided is a method for producing an aromatic liquid including.

In one embodiment, heating of the yeast is carried out in a substantially anoxic environment.

In one embodiment, heating of the yeast is carried out by distilling an aqueous solution containing the yeast.

In one form, the aqueous solution that heats the yeast is mash.

In one form, the yeast is contained in the mash after fermentation.

In one form, the fragrance is an alcoholic beverage.

In one form, the fragrance is a distilled liquor.

The present invention also provides an aromatic liquid produced by the method for producing an aromatic liquid according to any one of the above.

The present invention also provides an aromatic liquid having a green aroma containing 1-hexanal, 1-heptanal and 1-nonanal.

In one form, the green aroma of the aromatic solution further contains 1-octanal and 1-decanal.

Further, the present invention is a step of incorporating yeast into mash after fermentation;
A step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by distilling the yeast-containing sardine; and a step of recovering the linear saturated aliphatic aldehyde;
Provided is a method for producing distilled liquor including.

Further, the present invention is a step of incorporating yeast into mash after fermentation;
A step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by distilling a yeast-containing 醪; and a step of recovering the linear saturated aliphatic aldehyde;
Provided is a method for increasing the green aroma of distilled liquor including.

In one form, the yeast has undergone freezing.

The method for producing an aromatic liquid having a green aroma of the present invention can be incorporated into a general manufacturing process for distilled liquor, and is easy to operate. Further, in the method of the present invention, an aromatic liquid having a green aroma can be produced as a spice or as a distilled liquor. Therefore, the present invention has a wide range of applications and is excellent in practicality.

In the method of the present invention, a predetermined lipid peroxide is thermally decomposed to produce a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms. It suffices if any one of the linear saturated aliphatic aldehydes having 6 to 10 carbon atoms is produced. In a preferred embodiment, all linear saturated aliphatic aldehydes having 6, 7 and 9 carbon atoms are produced. In a more preferred form, all linear saturated aliphatic aldehydes with 6-9 carbon atoms are produced. In a more preferred form, all linear saturated aliphatic aldehydes having 6 to 10 carbon atoms are produced.

The linear saturated aliphatic aldehyde having 6 to 10 carbon atoms is preferably 1-hexanal, 1-heptanal, 1-octanal, 1-nonanal and 1-decanal, respectively. At least one aldehyde selected from the group consisting of 1-hexanal, 1-heptanal, 1-octanal, 1-nonanal and 1-decanal may be hereinafter referred to as "green aldehyde".

Yeast, regardless of its type, has many unsaturated fatty acids in the cells. Unsaturated fatty acids are easily converted to lipid peroxides upon contact with oxygen. Therefore, yeast can be used as a raw material for the method of the invention, i.e., as a source of lipid peroxide. In addition, yeast decomposition products obtained by decomposing yeast cells can also be used as a source of lipid peroxide. Specific examples of the yeast decomposition product include a residue obtained by extracting an extract from yeast cells, a yeast cell wall which is a dried product thereof, and the like.

The yeast that can be used in the method of the present invention is not particularly limited as long as it has an unsaturated fatty acid in the cells. Examples of such yeasts include Candida yeasts, Pichia yeasts, and Cliveromies yeasts. Among these yeasts, those used as beer yeast, whiskey yeast, and wine yeast are preferable, and ale beer yeast and whiskey yeast having a high content of unsaturated fatty acids are particularly preferable.

The yeast and yeast degradation products are preferably pre-dried. Drying of yeast and the like is preferably carried out in an environment in which oxygen is present. When dried, the unsaturated fatty acids in the yeast cells come into contact with oxygen and change into lipid peroxides. As a result, the amount of lipid peroxide contained in yeast increases. Drying of yeast is carried out until the yeast is substantially free of water.

Examples of the yeast drying method include natural drying such as sun drying and shade drying, warm air drying, cold air drying, vacuum drying and artificial drying such as freeze vacuum drying. In consideration of drying efficiency, artificial drying is preferably used. The type of artificial drying is not particularly limited, but hot air drying, freeze drying, spray drying, and drum drying are usually used. These are industrially commonly used drying methods, and it is easy to prepare the equipment and optimize the conditions. Of these, the preferred drying methods are freeze-drying and spray-drying.

It is considered that the yeast once dried becomes a brittle block, the affinity for a liquid such as water is improved, and the lipid peroxide contained in the yeast is easily dissolved in the aqueous liquid. Furthermore, freezing yeast before drying promotes the destruction of yeast cell membranes, which is effective for increasing green aroma. From this point of view, an example of a preferable drying method is freeze-drying.

The dried yeast is preferably stored in an environment in the presence of oxygen. As a result, the content of lipid peroxide is further increased. The storage period is appropriately adjusted in consideration of the degree to which the content of lipid peroxide increases. When the product is stored in a normal temperature environment, the storage period is, for example, about 5 days or more, preferably about 10 to 300 days, and more preferably about 20 to 100 days.

The dried yeast is contained in an aqueous solution and heated. As an example of the means for incorporating the dried yeast into the aqueous solution, there is a means for adding the yeast to the aqueous solution. The amount of yeast used is appropriately determined in consideration of the degree of green aroma produced. Generally, it is 0.01 to 15 parts by weight, preferably 0.02 to 5.0 parts by weight, and more preferably 0.03 to 1.0 parts by weight with respect to 100 parts by weight of the aqueous liquid.

An aqueous solution is a substance that contains water and exhibits fluidity. The aqueous solution blocks yeast from oxygen and functions as a medium for transferring heat to yeast. The aqueous solution may be water, an aqueous solution, or an inhomogeneous mixture containing solids. The aqueous solution may contain alcohol. When the yeast is heated in an aqueous solution, the lipid peroxide is heated in an oxygen-free environment, which improves the efficiency of the decomposition reaction.

The heating temperature is sufficient as long as the lipid peroxide decomposes. The heating temperature is preferably the temperature up to the boiling point of the aqueous solution. From the viewpoint of decomposition efficiency, the heating temperature is preferably 70 ° C. or higher, more preferably 80 to 110 ° C., and even more preferably 90 to 100 ° C. when heated at normal pressure. When heating under reduced pressure, it is desirable to heat at 40 to 70 ° C. The heating of yeast may be carried out by distilling an aqueous liquid containing yeast.

For example, when the fragrance liquid is distilled liquor, mash can be used as the aqueous liquid. Specific examples of the distilled liquor, which is an aromatic liquid, include whiskey, shochu, brandy, and spirits such as gin, vodka, and rum. The distilled liquor, which is an aromatic liquid, is particularly preferably whiskey. Among the characteristic scents found in high-quality Scotch whiskey is the "green" scent, which makes the green scent useful for the production of highly palatable whiskey.

Moromi is an intermediate raw material for alcoholic beverages made by fermenting starch raw material, jiuqu, water, and yeast. The mash containing the dried yeast is preferably in a fermented state. When dried yeast is contained in unfermented mash, the amount of lipid peroxide may decrease due to the metabolic action of yeast.

In this case, the yeast contained in the fermented mash may be undried or dried. If the yeast contained in the mash has lipid peroxide, it is effective for increasing the green aroma of distilled liquor. The amount of yeast used is the same as described above.

Distillation of mash containing yeast may be carried out under the conditions normally used for distilling mash when producing distilled liquor. When the distilled liquor is malt whiskey, the distillation of mash, that is, the initial distillation, is usually carried out by maintaining the distillation temperature for 5 to 8 hours, although it depends on the capacity of the container. The distillation temperature of mash is generally 70 to 100 ° C.

In the distillation step, the air in the distiller is discharged to the outside of the system by the heated steam, and the distillation process becomes substantially oxygen-free.

The thermal decomposition of the lipid peroxide produces a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms, and further heating in an anoxic environment enhances the production of the linear saturated aliphatic aldehyde. The produced linear saturated aliphatic aldehyde having 6 to 10 carbon atoms is volatile and may be released from the aqueous solution. In such a case, the released linear saturated aliphatic aldehyde having 6 to 10 carbon atoms is brought into contact with a medium for dissolving them, dissolved and recovered. Water, an aqueous alcohol solution, or the like is used as a medium for dissolving the linear saturated aliphatic aldehyde having 6 to 10 carbon atoms. When the aqueous liquid is distilled, the linear saturated aliphatic aldehyde having 6 to 10 carbon atoms is recovered in a state of being contained in the reflux liquid.

The solution in which the recovered linear saturated aliphatic aldehyde having 6 to 10 carbon atoms is dissolved is an aromatic liquid having a green scent. The fragrance is used as is, or adjusted to a concentration that gives a more suitable green aroma, for example as a distilled liquor or flavor. The distilled liquor of the present invention can be used alone or appropriately mixed with liquors to produce a distilled liquor having a green scent, an alcoholic beverage, or the like. The distilled liquor of the present invention has an enhanced green aroma. The fragrance of the present invention can be appropriately mixed with predetermined components such as drinking water, sweeteners, alcohols, pigments, and carbonic acids to produce soft drinks and alcoholic beverages having a green scent.

<Example 1>
(Manufacturing method of hot air dried yeast)
Frozen ale beer waste yeast was obtained and thawed at room temperature. The thawed yeast was dried with hot air under the conditions shown in Table 1.

[Table 1]

<Example 2>
(Manufacturing method of freeze-dried yeast)
Frozen ale beer waste yeast was obtained and thawed at room temperature. The thawed yeast was placed on a sample table and frozen at −25 ° C. to −40 ° C., and then the water content was sublimated at 4.6 mmHg or less and 40 to 50 ° C. to dry the frozen yeast. Then, the freeze-dried yeast was heated under the conditions shown in Table 2.

[Table 2]

<Example 3>
(Manufacturing method of spray-dried yeast)
Frozen ale beer waste yeast was obtained and thawed at room temperature. The thawed yeast was spray-dried under the conditions shown in Table 3. After spray-drying, only A-SD-5 and A-AD-8 were heated by a fluidized bed granulator under the conditions shown in Table 3.

[Table 3]

<Example 4>
(Manufacturing method of spray-dried yeast)
Frozen ale beer waste yeast was obtained and thawed at room temperature. The thawed yeast was heated at 70 ° C. for 2 hours and spray-dried at 150 ° C. Heating after spray drying was performed only on W-SD-6 to 8. The types of processing are shown in Table 4.

(Details of processing performed during drying)
(1) Heating: High-pressure homogenization (35MPa)
(2) Heating: Air injection (1L / min)
(3) Heating: Copper contact (stir in a container containing a copper wire with a diameter of 0.3 mm x 15 m)
(4) Air injection during spray drying (flow rate 15 to 20 L / hr)
(5) Heating: Incubator treatment (99 ° C ± 1 ° C)
(6) Heating: Fluidized bed granulator (Freund FL-5 equivalent machine)

[Table 4]

<Example 5>
(Drum dry yeast production method)
Frozen ale beer waste yeast was obtained and thawed at room temperature. The thawed yeast was placed in a drum dryer and dried under the conditions shown in Table 5.

[Table 5]

<Example 6>
(Analysis method of lipid peroxide)
A Lipid Hydroperoxide (LPO) Assay Kit manufactured by Cayman Chemical Company, which is a color-developing enzyme method reagent kit, was used. Ethyl acetate / methanol = 9/1 was used as the extraction solvent.

(Amount of lipid peroxide)
The amount of lipid peroxide in the samples prepared in Examples 1 to 5 was analyzed. The untreated yeast is yeast obtained by thawing frozen ale beer waste yeast at room temperature and not being dried.

[Table 6]

(Change in the amount of lipid peroxide over time)
The time course of the amount of lipid peroxide when the samples prepared in Examples 1 to 5 were stored at room temperature was confirmed.

[Table 7]

[Table 8]

<Example 7>
(Distillation test with model solution)
To 4 L of an ethanol solution of 8% alcohol, 12 g (0.3% of the liquid weight) of the dried yeast prepared in Examples 1 to 5 was added, and the whole amount was distilled twice with a 5 L volume distiller to obtain the obtained product. The green aldehyde concentration (1-hexanal, 1-heptanal, 1-octanal, 1-nonanal, 1-decanal) of the distillate was analyzed. The results are shown in Table 9.

(1-hexanal analysis method)
(1) Sample collection 2.5 ml of ultrapure water and 0.5 ml of distillate were collected in a headspace vial, 75 μL of 63% EtOH water and 50 μl of internal standard solution (1-pentanal 2 ppm) were added and used for measurement.
The standard solution (STD) (1-hexanal 1.64ppm) is used after mixing with 2.5 ml of ultrapure water and 0.5 ml of 63% EtOH water. To prepare a calibration curve, add 25 μl, 50 μl, and 75 μl. I prepared it.

(2) Analytical condition device: Agilent HS7697A, GC6890N, MS5973
Headspace condition: Loop size 3ml
Temperature (oven 60 ° C, loop 80 ° C, transfer line 120 ° C)
Vial equilibration time 10 min
Loop equilibration time 0.01 min
Injection time 1min
Injection conditions: pulsed split (20: 1), 250 kPa, gas saver 30 ml / min (2 min)
Injection temperature: 150 ℃
Column: VF-WAXms (Varian) 1 μm × 0.25 mm I.D. × 30 m
Column flow rate: 1.2 ml / min (He, constant flow mode)
Heating conditions: 40 ° C (10 min) → 10 ° C / min → 240 ° C (1 min)
MS conditions: Temperature (transfer line 230 ° C, ion source 230 ° C, quadrupole 150 ° C)

[Table 9]

(1-heptanal, 1-octanal, 1-nonanal, 1-decanal analysis method)
(1) Collect 5 ml of the pretreatment distillate in a 50 ml centrifuge tube, add 20 μl of IS (Octanal-d16 100 ppm), and add 20 ml of ultrapure water to dilute.
The standard solution (STD) (50 ppm for each component) is used after mixing with 20 ml of ultrapure water, 5 ml of 63% EtOH water, and 20 μl of IS, but 3 types of 10 μl, 20 μl, and 30 μl are added to prepare a calibration curve. ..
These test solutions are loaded on a solid-phase column (Oasis HLB 3cc, 60 mg manufactured by Waters) conditioned with ethyl acetate, methanol, and ultrapure water, and passed through at about 1 drop / sec. After passing the test solution, wash with 10 ml of ultrapure water and suck and dry for about 5 minutes. After drying, remove the solid phase, wash the flow path with acetone, dry it, set a dehydration cartridge (GL Science Inertsep Slim-J DRY), attach the adsorbed solid phase on it, and quantify with 6 ml of ethyl acetate. Dissolve in a test tube. The eluate is concentrated to 0.5 ml or less by nitrogen purging, and the volume is adjusted to 1 ml with ethyl acetate and subjected to GC / MS.

(2) Analytical condition device: Agilent GC6890N, MS5973
Injection conditions: pulsed split (20: 1), 250kPa, gas saver 20ml / min (2min)
Temperature 210 ° C, injection volume 1 μl
Column: Inert Pure WAX (GL Science) 0.25 μm × 0.25 mm I.D. × 30 m
Column flow rate: 1.2 ml / min (He, constant flow mode)
Heating conditions: 40 ° C (3min) → 8 ° C / min → 120 ° C (2min) → 12 ° C / min → 230 ° C (10min)
MS conditions: Temperature (transfer line 230 ° C, ion source 230 ° C, quadrupole 150 ° C)

[Table 10]

[Table 11]

<Example 8>
(Manufacturing method of distilled liquor)
10 g of whiskey yeast (Distiller's yeast) was added to 4 L of wort having a specific gravity of 1.060, fermentation was started at 23 ° C, controlled to a maximum temperature of 32 ° C, and fermented for 3 days. After adding 12 g of the dried yeast prepared in Examples 1 to 5 to the fermented nonanal, the whole amount was distilled twice in a 5 L volume distiller, and the green aldehyde concentration (1-) of the obtained distillate was obtained. Hexanal, 1-heptanal, 1-octanal, 1-nonanal, 1-decanal) were analyzed.

[Table 12]

(Sensory evaluation of whiskey)
The sensory evaluation of the produced distilled liquor was carried out by seven specialized panels of distilled liquor. The evaluation score was the average of 5 of the 7 panels, excluding the upper and lower ones.

[Table 13]

[Table 14]

[Table 15]

Claims (12)

A step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by heating a pre-dried yeast in an aqueous solution; and a step of recovering the linear saturated aliphatic aldehyde;
A method for producing an aromatic liquid including. The method for producing an aromatic liquid according to claim 1, wherein heating of the yeast is performed in a substantially oxygen-free environment. The method for producing an aromatic liquid according to claim 1 or 2, wherein the heating of the yeast is performed by distilling an aqueous liquid containing yeast. The method for producing an aromatic liquid according to any one of claims 1 to 3, wherein the aqueous liquid for heating the yeast is mash. The method for producing an aromatic liquid according to claim 4, wherein the yeast is contained in the mash after fermentation. The method for producing an aromatic liquid according to any one of claims 1 to 5, wherein the aromatic liquid is an alcoholic beverage. The method for producing an aromatic liquid according to any one of claims 1 to 6, wherein the aromatic liquid is distilled liquor. An aromatic liquid produced by the method for producing an aromatic liquid according to any one of claims 1 to 7. An aromatic liquid having a green aroma containing 1-hexanal, 1-heptanal and 1-nonanal. The aromatic liquid having a green aroma according to claim 9, further containing 1-octanal and 1-decanal. The process of adding yeast to the mash after fermentation;
A step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by distilling a yeast-containing 醪; and a step of recovering the linear saturated aliphatic aldehyde;
A method for producing distilled liquor including. The process of adding yeast to the mash after fermentation;
A step of producing a linear saturated aliphatic aldehyde having 6 to 10 carbon atoms by distilling a yeast-containing 醪; and a step of recovering the linear saturated aliphatic aldehyde;
A method of increasing the green aroma of distilled liquor, including.