JPWO2020075820A1 - Fragrance composition - Google Patents

Abstract

An object of the present invention is to provide a flavor composition capable of enhancing a citrus-like flavor, and to provide a food or drink using the same, which has an enhanced citrus-like flavor. And / or a flavor composition for adding citrus-like foods and drinks, which comprises 2,7-decadienal. The fragrance composition may contain other fragrance components. Further, 2,6-decadienal is preferably 2E, 6Z-decadienal, and 2,7-decadienal is preferably 2E, 7Z-decadienal.

Description

The present invention relates to a perfume composition capable of imparting or enhancing a citrus-like flavor and its use.

Citrus fruits are popular with Japanese people because of their refreshing aroma and flavor. In addition to the flesh of citrus fruits being eaten, the juice is often used for flavoring foods, and essential oils obtained from citrus fruits are also used to impart citrus aromas and flavors to foods. Often.
Further, as a means for enhancing the citrus-like flavor, addition of essential oils and the like and addition of various compounds are known.

Here, 2,6-decadienal is described as an ingredient that can be contained in a fragrance or a flavor composition in International Publication No. 2017/100426, but the document relates to the aroma of 2,6-decadienal itself. There is no description or description of the effect this has on the fragrance composition. In addition, J. Food Sci., 1962, p90 describes that 2E, 6Z-decadienal has a scent of "green, plant-like, and like cucumber". In addition, 2,7-decadienal is described as an ingredient that can be contained in a fragrance or flavor composition in Pamphlet No. 2017/100426, but the document relates to the aroma of 2,7-decadienal itself. There is no description or description of the effect this has on the fragrance composition. In addition, J. Am. Oil Chem. Soc. (1981), 58 (6), p68 describes that 2E, 7E-decadienal has a fragrance that is "green, plant-like".

An object of the present invention is to provide a flavor composition capable of enhancing a citrus-like flavor, and to provide a food or drink in which the citrus-like flavor is enhanced by using the same.

As a result of diligent studies to solve the above-mentioned problems, the present inventors have decided to use 2,6-decadienal and / or 2,7-decadienal, which have never been used as a citrus-like fragrance component. Unexpectedly, he found that the citrus-like flavor could be enhanced, and completed the present invention.
That is, the present invention includes the following contents [1] to [7].
[1] A flavor composition for adding citrus-like foods and drinks, which comprises 2,6-decadienal and / or 2,7-decadienal.
[2] The flavor composition for adding citrus-like foods and drinks according to the above [1], wherein 2,6-decadienal is 2E, 6Z-decadienal.
[3] The flavor composition for adding citrus-like foods and drinks according to the above [1], wherein 2,7-decadienal is 2E,7Z-decadienal.
[4] A citrus-like food or drink, an oral composition, or a tobacco product containing the flavor composition for adding a citrus-like food or drink according to any one of the above [1] to [3].
[5] The step of adding the citrus-like food / drink-adding flavor composition according to any one of the above [1] to [3] to a citrus-like food / drink, an oral composition, or a tobacco product is included. A method for producing citrus-like foods and drinks, oral compositions, and tobacco products.
[6] The step of adding the flavor composition for adding citrus-like food or drink according to any one of the above [1] to [3] to a citrus-like food or drink, an oral composition, or a tobacco product is included. , Citrus-like Foods, Oral Compositions, or Tobacco Products to Add or Enhance Citrus Flavor.
[7] In the step of adding a citrus-like food / drink-adding flavor composition to a citrus-like food / drink, an oral composition, or a tobacco product, 2 in the citrus-like food / drink, an oral composition, or a tobacco product. , 6-Decadienal and / or 2,7-Decadienal concentration adjusted to 0.00001-10000 ppb with respect to the total mass of the citrus-like food or oral composition, or tobacco product, said [5] or said above. The method according to [6].

By adding the citrus-like food and drink addition flavor composition of the present invention to the citrus-like food and drink, oral composition, and tobacco product flavoring composition, the citrus flavor can be imparted or enhanced.

Hereinafter, the present invention will be described in detail.
The flavor composition for adding citrus-like foods and drinks of the present invention contains 2,6-decadienal and / or 2,7-decadienal. The flavor composition for adding citrus-like foods and drinks in the present invention can be added as it is to citrus-like foods and drinks in a very small amount to enhance the citrus-like flavor and / or to impart a new spread to the citrus-like flavor. it can. When the flavor composition for adding citrus-like foods and drinks in the present invention contains 2,6-decadienal and / or 2,7-decazienal and other flavor components, the flavor composition is blended in a trace amount in the food and drink. It is also possible to impart or enhance a citrus-like flavor to foods and drinks (not necessarily citrus-like foods and drinks). Examples of other flavor components that can be mixed include various synthetic flavors, natural flavors, natural essential oils, plant extracts, and the like. For example, "Patent Agency Gazette, Well-known and Conventional Techniques (Fragrance) Part II Food Fragrances" , P88-131, issued on January 14, 2000 ”, such as natural essential oils, natural fragrances, and synthetic fragrances.

The content of 2,6-decadienal or 2,7-decadienal in the flavor composition for adding citrus-like foods and drinks of the present invention is 0.00001 to 10,000 ppm, preferably 0.0001 to 0.0001, respectively, based on the mass of the flavor composition. The concentration range can be 1000 ppm, more preferably 0.001 to 100 ppm.

When 2,6-decadienal and / or 2,7-decadienal are added to foods and drinks in order to enhance aroma and flavor, they are 0.00001 to 10000 ppb, preferably 0, respectively, based on the total mass of the foods and drinks. The concentration range can be .0001 to 1000 ppb, more preferably 0.001 to 100 ppb.

In the citrus-like food and drink addition fragrance composition of the present invention containing 2,6-decadienal and / or 2,7-decadienal, a solvent such as water, ethanol, etc., which is usually used as necessary; It can contain a fixative such as ethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium chain fatty acid triglyceride, and medium chain fatty acid diglyceride.
By adding the flavor composition for adding citrus-like foods and drinks containing 2,6-decadienal and / or 2,7-decadienal of the present invention, the citrus flavor of citrus-like foods and drinks can be enhanced.

Specific examples of foods and drinks that can impart or enhance the citrus flavor by adding the scent composition for adding citrus-like foods and drinks of the present invention include, for example, carbonated drinks, soft drinks, fruit juice drinks, dairy drinks, and the like. Beverages such as lactic acid bacteria beverages, drinks, soy milk, tea beverages; alcoholic beverages such as chewy, cocktail drinks, sparkling liquor, fruit liquor, confectionery liquor; ice cream, ice milk, lacto ice, ice cream, yogurt, pudding, Desserts such as jelly and daily desserts; confectioneries such as caramel, candy, locks, crackers, biscuits, cookies, pies, chocolates, snacks and chewing gum; soups such as Japanese-style soup and Western-style soup; jams; flavor seasonings Kind; various instant beverages; various instant foods and the like. Among these, beverages or alcoholic beverages are preferable.

The amount of the citrus-like flavoring composition added to food and drink varies depending on the type and form of the product, but is usually 0.001% based on the mass of the food and drink before adding the flavoring composition. The concentration range can be from 10% by mass, preferably 0.01 to 5% by mass.

Examples of the oral composition that can be flavored and flavored by adding the citrus-like food and drink additive flavor composition of the present invention include dentifrices, oral cleansers, mouthwashes, troches, chewing gums and the like. Can be done. The amount of the fragrance composition added to the oral composition varies depending on the type and form of the product, but is usually 0.01 to 5% by mass, more preferably 0.01 to 5% by mass, based on the total mass of the oral composition. It can be 0.1 to 3% by mass.

Examples of tobacco products that can be scented and flavored by adding the citrus-like food and drink flavoring composition of the present invention include cigarettes and electronic cigarettes. The amount of the perfume composition added to the tobacco product varies depending on the type and form of the product, but is preferably 0.00001 to 90% by mass, more preferably 0, based on the total mass of the tobacco leaf portion, for example. It can be .0001 to 50% by mass.

Although there are a plurality of cis-trans isomers in 2,6-decadienal or 2,7-decadienal used in the present invention, any isomer and a mixture of isomers can be used. Among these, the (2E) form is preferable, and the (2E, 6Z) and (2E, 7Z) forms are more preferable because the citrus-like flavor can be enhanced more naturally.

Examples of citrus fruits having a citrus-like aroma / flavor imparted or enhanced in the present invention include grapefruit, orange, lemon, lime, yuzu, blood orange, bitter orange, tangerine, mandarin orange, mandarin orange, sweet summer, amanatsu, hassaku, and pomelo. Cabos, citrus, hebes, bergamot, sweetie (orobronco) and the like are preferred, but are not limited to the citrus fruits described herein.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.
[measuring equipment]
The analytical instruments used in the examples are as follows.
NMR measuring device: AVANCE III 500 (BRUKER BIO SPIN KK: manufactured by Bruker-Biospin)
Gas chromatograph mass spectrometer: GCMS-QP2010 (manufactured by Shimadzu Corporation)
Gas Chromatograph-Orbitrap Mass Spectrometer: TRACE1310 (GC) + Active GC (Mass Spectrometer) (manufactured by Thermo Fisher Scientific)
High Performance Liquid Chromatograph Pump: LC-20A (manufactured by Shimadzu Corporation)
Detector: SPD-M20A (manufactured by GL Sciences)
Separation column: YMC-TriartC18 ExRS (manufactured by YMC)

(Synthesis Example 1) Synthesis of 2,6-decadienal 4.79 g (0.03 mol) of 4Z-octenal, 10.04 g (0.033 mol) of (triphenylphosphoranylidene) acetaldehyde and acetonitrile (300 ml) were added for 20 hours. Refluxed. After cooling, 100 ml of hexane was extracted 3 times. The combined hexane solution is concentrated and then distilled under reduced pressure (bp38 ° C./1 torr) to obtain 1.42 g of 2E, 6Z-decadienal (GC purity 94.7%, yield 31.1%, 6Z / 6E = 91). / 9) was obtained.

Subsequently, purification was performed by high performance liquid chromatography (eluent; water: acetonitrile = 75: 25 (volume ratio)), and (2E, 6Z) -decagenal (GC purity 100%) and (2E, 6E) -decagenal (2E, 6E) GC purity 100%) was obtained.

<(2E, 6Z) -Physical data of Decadienal>
^{1 1} H NMR (500 MHz, (CD ₃ ) ₂ CO) δ:
9.38 (1H, d, J = 7.8Hz), 6.85 (1H, dt, J = 15.6Hz, 6.8Hz), 5.97 (1H, ddt, J = 15.6Hz, 7. 8Hz, 1.4Hz), 5.31 (1H, dt, J = 11.0Hz, 6.7Hz), 5.27 (1H, dt, J = 11.0Hz, 6.7Hz), 2.29 (2H) , Td, J = 7.0Hz, 6.8Hz), 2.16 (2H, td, J = 7.0Hz, 6.7Hz), 1.91 (2H, dt, J = 7.4Hz, 6.7Hz) ), 1.25 (2H, sext., J = 7.4Hz), 0.77 (3H, t, J = 7.4Hz)
¹³ C NMR (125 MHz, (CD ₃ ) ₂ CO) δ:
193.18, 157.68, 133.01, 130.67, 128.02, 32.33, 28.93, 25.33, 22.47, 13.06
HRMS (EI ⁺ ): calcd C ₁₀ H ₁₆ O (M ⁺ ) 152.1196; found, 152.196

<(2E, 6E) -Physical data of Decadienal>
^{1 1} H NMR (500 MHz, (CD ₃ ) ₂ CO) δ:
9.38 (1H, d, J = 8.0Hz), 6.84 (1H, dt, J = 15.5Hz, 7.0Hz), 5.95 (1H, ddt, J = 15.5Hz, 8.5Hz). 0Hz, 1.5Hz), 5.37 (1H, dt, J = 15.5Hz, 6.0Hz), 5.32 (1H, dt, J = 15.5Hz, 6.0Hz), 2.29 (2H) , Qd, J = 7.0Hz, 1.5Hz), 2.09 (2H, td, J = 7.0Hz, 6.0Hz), 1.82-1.86 (2H, m), 1.24 ( 2H, sext., J = 7.5Hz), 0.74 (3H, t, J = 7.5Hz)
¹³ C NMR (125 MHz, (CD ₃ ) ₂ CO) δ:
193.15, 157.72, 132.93, 131.18, 128.57, 34.23, 32.18, 30.49, 22.22, 12, 78
HRMS (EI ⁺ ): calcd C ₁₀ H ₁₆ O (M ⁺ ) 152.1196; found, 152.197

(Synthesis Example 2) Synthesis of 2,7-decadienal 5.79 g (0.03 mol) of 5Z-octenal, 10.04 g (0.033 mol) of (triphenylphosphoranylidene) acetaldehyde and acetonitrile (300 ml) were added for 20 hours. Refluxed. After cooling, 100 ml of hexane was extracted 3 times. The combined hexane solution is concentrated and then distilled under reduced pressure (bp38 ° C./1 torr) to obtain 1.39 g of 2E, 7Z-decadienal (GC purity 91.3%, yield 30.5%, 7Z / 7E = 96). / 4) was obtained.

Subsequently, purification was performed by high performance liquid chromatography (eluent; water: acetonitrile = 75: 25 (volume ratio)), and (2E, 7Z) -decagenal (GC purity 100%) and (2E, 7E) -decagenal (2E, 7E) GC purity 100%) was obtained.

<(2E, 7Z) -Physical data of Decadienal>
^{1 1} H NMR (500 MHz, (CD ₃ ) ₂ CO) δ:
9.52 (1H, d, J = 7.8Hz), 6.99 (1H, dt, J = 15.6Hz, 6.9Hz), 6.09 (1H, ddt, J = 15.6Hz, 7. 8Hz, 1.5Hz), 5.40 (1H, dtt, J = 10.8Hz, 7.1Hz, 1.4Hz), 5.34 (1H, dtt, J = 10.8Hz, 7.1Hz, 1. 4Hz), 2.38 (2H, tdd, J = 7.2Hz, 6.9Hz, 1.5Hz), 2.11 (2H, tdd, J = 7.3Hz, 7.1Hz, 1.4Hz), 2 .04 (2H, tt, J = 7.3Hz, 7.2Hz), 1.59 (2H, td, J = 7.5Hz, 7.1Hz) 0.94 (3H, t, J = 7.5Hz)
¹³ C NMR (125 MHz, (CD ₃ ) ₂ CO) δ:
194.89, 159.86, 134.54, 133.66, 129.72, 33.40, 29.34, 27.78, 21.74, 15.25
HRMS (EI ⁺ ): calcd C ₁₀ H ₁₆ O (M ⁺ ) 152.1196; found, 152.197

<(2E, 7E) -Physical data of Decadienal>
^{1 1} H NMR (500 MHz, (CD ₃ ) ₂ CO) δ:
9.52 (1H, d, J = 7.9Hz), 6.99 (1H, dt, J = 15.6Hz, 6.9Hz), 6.09 (1H, ddt, J = 15.6Hz, 7. 9Hz, 1.4Hz), 5.50 (1H, dtt, J = 15.2Hz, 6.3Hz, 1.2Hz), 5.42 (1H, dtt, J = 15.2Hz, 6.6Hz, 1. 1Hz), 2.36 (2H, dtd, J = 7.8Hz, 6.9Hz, 1.4Hz), 2.03-2.07 (2H, m), 1.99 (2H, qdd, J = 7) .4Hz, 6.3Hz, 1.1Hz), 1.59 (2H, tt, J = 7.8Hz, 7.3Hz), 0.95 (3H, t, J = 7.4Hz)
¹³ C NMR (125 MHz, (CD ₃ ) ₂ CO) δ:
194.89, 159.93, 134.53, 134.20, 129.89, 33.28, 33.26, 29.21, 26.87, 14.92
HRMS (EI ⁺ ): calcd C ₁₀ H ₁₆ O (M ⁺ ) 152.1196; found, 152.197

(Examples 1 to 4) Grapefruit flavor composition Using (2,6) -decagenal and (2,7) -decazienal produced by the methods described in Synthesis Examples 1 and 2, a grapefruit flavor composition according to the following formulation. (A-1) to (A-4) were prepared.
<Example 1> Fragrance composition (A-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Grapefruit oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 2> Fragrance composition (A-2) formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0001
Grapefruit oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 3> The same as the fragrance composition (A-1) formulation except that (2E, 6E) -decagenal was used instead of the fragrance composition (A-3) formulation (2E, 6Z) -decagenal.
<Example 4> The same as the fragrance composition (A-2) formulation, except that the fragrance composition (A-4) formulation (2E, 7Z) -decazienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 1)
As Comparative Example 1, a grapefruit flavor composition (B) was prepared according to the following formulation.
<Comparative Example 1> Fragrance Composition (B) Formulation (Ingredients) (Parts by Mass)
Grapefruit oil (cold press) 50.0
Ethanol Residual 1000.0

(Sensory test 1)
When 0.1% of each of the above grapefruit flavoring compositions (A-1), (A-2) and (B) was added to water and a sensory test was conducted by 6 specialized panelists, the above grapefruit flavoring composition ( All of them said that A-1) and (A-2) were significantly superior to the fragrance composition (B) in that they were given a citrus sandy flesh, juice, and freshness. It pointed out. The grapefruit flavor compositions (A-3) and (A-4) also showed the same results as the grapefruit flavor compositions (A-1) and (A-2).

(Example 5) Addition to a commercially available grapefruit juice beverage 0.1 ppb of (2E, 6Z) -decazienal was added to a commercially available grapefruit juice beverage.
(Example 6) Addition to a commercially available grapefruit juice beverage 0.1 ppb of (2E, 6E) -decazienal was added to a commercially available grapefruit juice beverage.

(Sensory test 2)
When a sensory test was conducted by 6 specialized panelists, all of Examples 5 and 6 were given a fresher fruit juice feeling and a natural fruity feeling as compared with the commercially available grapefruit juice beverage, and all of them were significantly superior. It pointed out.

(Example 7) Addition to a commercially available grapefruit juice beverage 0.1 ppb of (2E, 7Z) -decazienal was added to a commercially available grapefruit juice beverage.
(Example 8) Addition to a commercially available grapefruit juice beverage 0.1 ppb of (2E, 7E) -decazienal was added to a commercially available grapefruit juice beverage.

(Sensory test 3)
When a sensory test was conducted by 6 specialized panelists, all of Examples 7 and 8 were given a fresher fruit juice feeling and a natural fruity feeling as compared with the commercially available grapefruit juice beverage, and all of them were significantly superior. It pointed out.

(Examples 9 to 12) Grapefruit flavor composition Grapefruit flavor compositions (C-1) to (C-4) were prepared according to the following formulations.
<Example 9> Fragrance composition (C-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Nootkatone 2.0
Octanal 0.3
Decanal 0.2
Dodecanal 0.1
Linalool 0.8
Cis-3-hexenol 0.5
Ethanol Residual 1000.0

<Example 10> Fragrance composition (C-2) formulation (ingredients) (parts by mass)

(2E, 7Z) -Decadienal 0.0001
Nootkatone 2.0
Octanal 0.3
Decanal 0.2
Dodecanal 0.1
Linalool 0.8
Cis-3-hexenol 0.5
Ethanol Residual 1000.0

<Example 11> The same as the fragrance composition (C-1) formulation, except that the fragrance composition (C-3) formulation (2E, 6Z) -decadienal was used instead of (2E, 6E) -decagenal.
<Example 12> The same as the fragrance composition (C-2) formulation, except that the fragrance composition (C-4) formulation (2E, 7Z) -decadienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 2)
As Comparative Example 2, a grapefruit flavor composition (D) was prepared according to the following formulation.
<Comparative Example 2> Fragrance Composition (D) Formulation (Ingredients) (Parts by Mass)
Nootkatone 2.0
Octanal 0.3
Decanal 0.2
Dodecanal 0.1
Linalool 0.8
Cis-3-hexenol 0.5
Ethanol Residual 1000.0

(Sensory test 4)
When 0.1% of each of the above grapefruit flavor compositions (C-1), (C-2) and (D) was added to water and a sensory test was conducted by 6 specialized panelists, the flavor composition (C-) was performed. All pointed out that 1) and (C-2) were significantly superior to the fragrance composition (D) in that they were given a citrus-like fruit flesh, juice, and freshness. The grapefruit flavor compositions (C-3) and (C-4) also showed the same results as the grapefruit flavor compositions (C-1) and (C-2).

(Examples 13 to 16) Orange fragrance compositions Orange fragrance compositions (E-1) to (E-4) were prepared according to the following formulations.
<Example 13> Fragrance composition (E-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Orange oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 14> Perfume composition (E-2) formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0001
Orange oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 15> The same as the fragrance composition (E-1) formulation except that (2E, 6E) -decagenal was used instead of the fragrance composition (E-3) formulation (2E, 6Z) -decagenal.
<Example 16> The same as the fragrance composition (E-2) formulation, except that the fragrance composition (E-4) formulation (2E, 7Z) -decazienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 3)
As Comparative Example 3, an orange fragrance composition (F) was prepared according to the following formulation.
<Comparative Example 3> Fragrance Composition (F) Formulation (Ingredients) (Parts by Mass)
Orange oil (cold press) 50.0
Ethanol Residual 1000.0

(Sensory test 5)
When 0.1% of each of the orange food flavor compositions (E-1), (E-2) and (F) was added to water and a sensory test was conducted by 6 specialized panelists, the flavor composition (E) All pointed out that -1) and (E-2) are far superior to the fragrance composition (F) in that they have enhanced citrus sand-like flesh, juice, and freshness. did. The orange flavoring compositions (E-3) and (E-4) also showed the same results as the grapefruit flavoring compositions (E-1) and (E-2).

(Example 17) Addition to a commercially available orange juice beverage 0.1 ppb of (2E, 6Z) -decadienal was added to a commercially available orange juice beverage.
(Example 18) Addition to a commercially available orange juice beverage 0.1 ppb of (2E, 6E) -decadienal was added to a commercially available orange juice beverage.

(Sensory test 6)
When a sensory test was conducted by 6 specialized panelists, both Examples 17 and 18 were remarkably superior in that the citrus sandy flesh, juice, and freshness were enhanced as compared with the commercially available orange juice beverage. Everyone pointed out that.

(Example 19) Addition to a commercially available orange juice beverage 0.1 ppb of (2E, 7Z) -decadienal was added to a commercially available orange juice beverage.
(Example 20) Addition to a commercially available orange juice beverage 0.1 ppb of (2E, 7E) -decadienal was added to a commercially available orange juice beverage.

(Sensory test 7)
When a sensory test was conducted by 6 specialized panelists, both Examples 19 and 20 had a citrus sandy flesh, juice, and freshness enhanced as compared with the commercially available orange juice beverage, and were significantly superior. Everyone pointed out that.

(Examples 21 to 24) Orange fragrance compositions Orange fragrance compositions (G-1) to (G-4) were prepared according to the following formulations.
<Example 21> Fragrance composition (G-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Ethyl butyrate 0.5
Octanal 1.0
Nonanal 0.1
Decanal 0.5
Linalool 2.0
Ethanol Residual 1000.0

<Example 22> Fragrance composition (G-2) formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0001
Ethyl butyrate 0.5
Octanal 1.0
Nonanal 0.1
Decanal 0.5
Linalool 2.0
Ethanol Residual 1000.0

<Example 23> The same as the fragrance composition (G-1) formulation, except that (2E, 6E) -decagenal was used instead of the fragrance composition (G-3) formulation (2E, 6Z) -decagenal.
<Example 24> The same as the fragrance composition (G-2) formulation, except that the fragrance composition (G-4) formulation (2E, 7Z) -decadienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 4)
As Comparative Example 4, an orange fragrance composition (H) was prepared according to the following formulation.
<Comparative Example 4> Fragrance Composition (H) Formulation (Ingredients) (Parts by Mass)
Ethyl butyrate 0.5
Octanal 1.0
Nonanal 0.1
Decanal 0.5
Linalool 2.0
Ethanol Residual 1000.0

(Sensory test 8)
When 0.1% of each of the orange fragrance compositions (G-1), (G-2) and (H) was added to water and a sensory test was conducted by 6 specialized panelists, the fragrance composition (G-1) was performed. ) And (G-2) were given a fresher fruit juice feeling and a natural fruity feeling than the perfume composition (H), and all pointed out that they were far superior. The orange flavoring compositions (G-3) and (G-4) also showed the same results as the orange flavoring compositions (G-1) and (G-2).

(Examples 25 to 28) Lemon flavor compositions Lemon flavor compositions (I-1) and (I-2) were prepared according to the following formulations.
<Example 25> Fragrance composition (I-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Lemon oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 26> Fragrance composition (I-2) Formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0001
Lemon oil (cold press) 50.0
Ethanol Residual 1000.0

<Example 27> The same as the fragrance composition (I-1) formulation, except that the fragrance composition (I-3) formulation (2E, 6Z) -decadienal was used instead of (2E, 6E) -decagenal.
<Example 28> The same as the fragrance composition (I-2) formulation, except that the fragrance composition (I-4) formulation (2E, 7Z) -decazienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 5)
As Comparative Example 5, a lemon flavor composition (J) was prepared according to the following formulation.

<Comparative Example 5> Fragrance Composition (J) Formulation (Ingredients) (Parts by Mass)
Lemon oil (cold press) 50.0
Ethanol Residual 1000.0

(Sensory test 9)
Lemon fragrance composition (I-1), (I-2) and (J) were added to water at 0.1% each, and a sensory test was conducted by 6 specialized panelists. As a result, the fragrance composition (I-1) ) And (I-2) are far superior to the fragrance composition (J) in that the fresh fruit juice reminiscent of sliced lemon is enhanced. The lemon flavor compositions (I-3) and (I-4) also showed similar results to the grapefruit flavor compositions (I-1) and (I-2).

(Example 29) Addition to a commercially available lemon juice beverage 0.1 ppb of (2E, 6Z) -decazienal was added to a commercially available lemon juice beverage.
(Example 30) Addition to a commercially available lemon juice beverage 0.1 ppb of (2E, 6E) -decadienal was added to a commercially available lemon juice beverage.

(Sensory test 10)
When a sensory test was conducted by 6 specialized panelists, all of them pointed out that both Examples 29 and 30 had a stronger natural peeling feeling and fruitiness as compared with the commercially available lemon juice beverage, and were significantly superior.

(Example 31) Addition to a commercially available lemon juice beverage 0.1 ppb of (2E, 7Z) -decazienal was added to a commercially available lemon juice beverage.
(Example 32) Addition to a commercially available lemon juice beverage 0.1 ppb of (2E, 7E) -decadienal was added to a commercially available lemon juice beverage.

(Sensory test 11)
When a sensory test was conducted by six specialized panelists, all of them pointed out that both Examples 31 and 32 had a stronger natural peeling feeling and fruitiness as compared with the commercially available lemon juice beverage, and were significantly superior.

(Examples 33 to 36) Lemon flavor compositions Lemon flavor compositions (K-1) and (K-2) were prepared according to the following formulations.
<Example 33> Fragrance composition (K-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0001
Citral 3.0
α-Tarpineol 1.0
Geraniol 0.5
Geranyl acetate 0.5
Neryl acetate 0.5
Ethanol Residual 1000.0

<Example 34> Fragrance composition (K-2) formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0001
Citral 3.0
α-Tarpineol 1.0
Geraniol 0.5
Geranyl acetate 0.5
Neryl acetate 0.5
Ethanol Residual 1000.0

<Example 35> The same as the fragrance composition (K-1) formulation, except that the fragrance composition (G-3) formulation (2E, 6Z) -decadienal was used instead of (2E, 6E) -decagenal.
<Example 36> The same as the fragrance composition (K-2) formulation, except that (2E, 7E) -decagenal was used instead of the fragrance composition (G-4) formulation (2E, 7Z) -decagenal.

(Comparative Example 6)
As Comparative Example 6, an orange fragrance composition (L) was prepared according to the following formulation.
<Comparative Example 6> Fragrance Composition (L) Formulation (Ingredients) (Parts by Mass)
Citral 3.0
α-Tarpineol 1.0
Geraniol 0.5
Geranyl acetate 0.5
Neryl acetate 0.5
Ethanol Residual 1000.0

(Sensory test 12)
Lemon flavor composition (K-1), (K-2) and (L) were added to water at 0.1% each, and a sensory test was conducted by 6 specialized panelists. As a result, the flavor composition (K-1) was subjected to a sensory test. ) And (K-2) were given a fresher fruit juice sensation reminiscent of sliced lemon than the perfume composition (L), and all pointed out that they were far superior. The lemon flavor compositions (K-3) and (K-4) also showed the same results as the lemon flavor compositions (K-1) and (K-2).

(Examples 37 to 40) Evaluation of fragrance of toothpaste Grapefruit-like fragrance compositions for toothpaste (M-1) and (M-2) were prepared according to the following formulations.

<Example 37> Fragrance composition (M-1) formulation (ingredients) (parts by mass)
(2E, 6Z) -Decadienal 0.0002
L-Menthol 400.0
Peppermint oil 150.0
Grapefruit oil (cold press) 100.0
Mineral oil 100.0
Anethole 60.0
Eucalyptus 20.0
Ethanol Residual 1000.0

<Example 38> Fragrance composition (M-2) formulation (ingredients) (parts by mass)
(2E, 7Z) -Decadienal 0.0002
L-Menthol 400.0
Peppermint oil 150.0
Grapefruit oil (cold press) 100.0
Mineral oil 100.0
Anethole 60.0
Eucalyptus 20.0
Ethanol Residual 1000.0

<Example 39> The same as the fragrance composition (M-1) formulation, except that (2E, 6E) -decagenal was used instead of the fragrance composition (M-3) formulation (2E, 6Z) -decagenal.
<Example 40> The same as the fragrance composition (M-2) formulation, except that the fragrance composition (M-4) formulation (2E, 7Z) -decadienal was used instead of (2E, 7E) -decagenal.

(Comparative Example 7)
As Comparative Example 7, a grapefruit-like fragrance composition (M) for toothpaste was prepared according to the following formulation.
<Comparative Example 7> Fragrance composition (M) formulation (ingredients) (parts by mass)
L-Menthol 400.0
Peppermint oil 150.0
Grapefruit oil (cold press) 100.0
Mineral oil 100.0
Anethole 60.0
Eucalyptus 20.0
Ethanol Residual 1000.0

The prescription of the toothpaste base material is as follows.
(Component) (Mass part)
Calcium carbonate 400.0
Silicate anhydride 16.5
Sorbitol (70%) 240.0
Sodium lauryl sulfate 13.0
Sodium Carboxymethyl Cellulose 12.5
Carrageenan 3.0
Sodium benzoate 4.0
Saccharin sodium 1.5
Purified water 259.5
Propylene glycol (PG) 40.0
990.0 in total

(Sensory test 13)
Using the fragrance composition and the toothpaste base material obtained in Examples 37 and 38 and Comparative Example 7, the following toothpastes (N), (O) and (P) were prepared and sensory evaluation was performed.
(N) Toothpaste base material 990 g + fragrance composition M-1 10 g
(O) Toothpaste base material 990 g + fragrance composition M-2 10 g
(P) Toothpaste base material 990 g + fragrance composition M 10 g
When a sensory test was conducted on these by three specialized panelists, the toothpaste (N) and (O) using the fragrance composition (M-1) and (M-2) were the fragrance composition (M). All pointed out that it is much better than the toothpaste (P) that uses the above, because it gives a real fruity feeling and a fresh fruity juice feeling. The fragrance compositions (M-3) and (M-4) also showed the same results as the fragrance compositions (M-1) and (M-2).

Claims (7)

A flavor composition for adding citrus-like foods and drinks, which comprises 2,6-decadienal and / or 2,7-decadienal. The perfume composition for adding citrus-like food or drink according to claim 1, wherein the 2,6-decadienal is 2E, 6Z-decadienal. The perfume composition for adding citrus-like foods and drinks according to claim 1, wherein the 2,7-decadienal is 2E,7Z-decadienal. A citrus-like food or drink, an oral composition, or a tobacco product containing the citrus-like food or drink additive flavor composition according to any one of claims 1 to 3. The perfume composition for adding a citrus-like food or drink according to any one of claims 1 to 3 is added to a citrus-like food or drink, an oral composition, or a tobacco product. A method for producing citrus-like foods and drinks, oral compositions, and tobacco products. A citrus-like food or drink, which comprises a step of adding the flavor composition for adding a citrus-like food or drink according to any one of claims 1 to 3 to a citrus-like food or drink, an oral composition, or a tobacco product. A method of imparting or enhancing a citrus flavor to an oral composition or a tobacco product. In the process of adding a citrus-like food / drink-adding flavor composition to a citrus-like food / drink, an oral composition, or a tobacco product, 2,6-in the citrus-like food / drink, an oral composition, or a tobacco product. 5. The claim 5 or 6, wherein the decadienal and / or 2,7-decadienal concentration is adjusted to 0.00001-10000 ppb with respect to the total mass of the citrus-like food or drink, oral composition, or tobacco product. the method of.