Patent Application
20200154747
The present invention relates to a food and/or beverage and a food flavoring composition comprising 3,7-dimethyl-2-methylene-6-octen-1-ol and in particular to a food and/or beverage and a food flavoring composition to which an excellent citrus-like flavor is imparted.
3,7-Dimethyl-2-methylene-6-octen-1-ol used in the present invention is a known compound, and is described as having fragrance of fresh citrus peel and citrus odour with aliphatic aldehyde in Flavour Fragr. J., (2004), 19, 121-133. Meanwhile, GB 1136345 A states that 3,7-dimethyl-2-methylene-6-octen-1-ol has floral, rose-muguet odor. However, these literatures disclose that 3,7-dimethyl-2-methylene-6-octen-1-ol can be used as a fragrance for perfumes and/or cosmetics, but do not state anything about use of it as a food flavoring ingredient in foods and/or beverages.
An object of the present invention is to provide a food and/or beverage and a food flavoring composition which comprises 3,7-dimethyl-2-methylene-6-octen-1-ol and to which an excellent flavor property, in particular, a citrus flavor is imparted.
As a result of study for achieving the above object, the present inventors have found that a food and/or beverage and a food flavoring composition having an excellent flavor can be obtained when 3,7-dimethyl-2-methylene-6-octen-1-ol expressed by the following formula (1) is added as a food flavoring ingredient, and therefore have completed the present invention.
That is, the present invention comprises the following [1] to[7].
3,7-Dimethyl-2-methylene-6-octen-1-ol and the food flavoring composition of the present invention can be directly added to foods and beverages to impart or enhance a flavor, or also can be mixed with other ingredients. The other flavoring ingredients that can be mixed include various kinds of ingredients commonly used in this field, such as synthetic flavors, natural flavors, natural essential oils, and plant extracts, and are, for example, natural essential oils, natural flavors, synthetic flavors and so on described in “Official Gazette of Japan Patent Office, Collection of Well-known Prior Arts (Flavor and/or Fragrance), Chapter II Food Flavor, pp. 88-131, issued on Jan. 14, 2000”.
In addition, as 3,7-dimethyl-2-methylene-6-octen-1-ol, there are (3R) and (3S) optically active isomers and a racemate, any of which can be used in the present invention.
The content of 3,7-dimethyl-2-methylene-6-octen-1-ol in the food flavoring composition of the present invention varies depending on other flavoring ingredients mixed and cannot be mentioned unconditionally, but may be usually at a concentration range of 0.0001% to 50%, preferably 0.001% to 10%, and more preferably 0.01% to 5% with respect to the weight of the food flavoring composition. When the concentration of 3,7-dimethyl-2-methylene-6-octen-1-ol is less than 0.0001%, the effect of imparting or enhancing aroma and flavor of the present invention cannot be obtained. Meanwhile, when the concentration exceeds 50%, 3,7-dimethyl-2-methylene-6-octen-1-ol may impair the balance of the flavoring composition as a whole. Both cases are unfavorable.
Moreover, when 3,7-dimethyl-2-methylene-6-octen-1-ol is added to a food or beverage, the concentration range may be 1 ppb to 5000 ppm, preferably 10 ppb to 1000 ppm, and more preferably 100 ppb to 100 ppm with respect to the weight of the food or beverage. When the concentration of 3,7-dimethyl-2-methylene-6-octen-1-ol is less than 1 ppb, the effect of imparting or enhancing aroma and flavor of the present invention cannot be obtained. Meanwhile, when the concentration exceeds 5000 ppm, the floral scent inherent to 3,7-dimethyl-2-methylene-6-octen-1-ol may be felt too strong. Both cases are also unfavorable.
The food flavoring composition of the present invention comprising 3,7-dimethyl-2-methylene-6-octen-1-ol may contain generally-used ingredients as needed, for example, a solvent such as water or ethanol, and a fixative such as ethylene glycol, propylene glycol, dipropylene glycol, hexylglycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercoline, medium-chain fatty acid triglyceride, or medium-chain fatty acid diglyceride.
Specific examples of the foods and beverages to which the flavor can be imparted by addition of either of the food flavoring composition and 3,7-dimethyl-2-methylene-6-octen-1-ol of the present invention include: acidic beverages such as carbonated beverage, fruit juice beverage, sports drink, lactic acid bacteria beverage, fermented beverage, and alcoholic fruit drink; beverages such as dairy beverage, energy drink, soy milk, and tea beverage; desserts such as ice cream, ice milk, mellorine, sorbet, yogurt, pudding and jelly, and daily dessert; confectionery products such as caramel, candy, tablet, cracker, biscuit, cookie, pie, chocolate, snack food, chewing gum, steamed bean-jam bun, and Yokan; soups such as Japanese style soup, Western style soup, and Chinese style soup; bread; jam; flavor seasonings; various instant foods; and so on.
The amount of the food flavoring composition added to a food and/or beverage varies depending on the kind or form of a product, but may be usually at a concentration range of 0.001 to 10% and preferably 0.01 to 5% with respect to the weight of the product.
Hereinafter, the present invention will be described in detail by using Examples, but the present invention should not be limited to these Examples.
Food flavoring compositions (lemon flavor) specified below in Table 1 were prepared. (S)-3,7-dimethyl-2-methylene-6-octen-1-ol used herein was produced in accordance with the method described in Flavour Fragr. J., (2004), 19, 121-133. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 1 were compared by five well-trained panelists. All the five panelists answered that Example 1 was remarkably superior because a natural fruit juice-like flavor which was not obtained by Comparative Example 1 was imparted by Example 1. The same result was also obtained when the (R) isomer and the racemate were used.
Each of the food flavoring compositions was added for flavoring at 0.1% to a commercially available lemon-flavored beverage and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 1 was remarkably superior because a natural fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 5 ppm to a commercially available lemon-flavored beverage and the flavor of the resultant beverage was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because a natural fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (grapefruit flavor) specified below in Table 2 were prepared. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 2 were compared by five well-trained panelists. All the five panelists answered that Example 3 was remarkably superior because a natural fruit juice-like flavor which was not obtained by
Comparative Example 2 was imparted by Example 3. The same result was also obtained when the (R) isomer and the racemate were used.
Each of these food flavoring compositions was added for flavoring at 0.1% to a commercially available grapefruit-flavored beverage and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 3 was remarkably superior because a natural fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 2 ppm to a commercially available grapefruit-flavored sports drink and the flavor of the resultant drink was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the drink supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because a natural fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (orange flavor) specified below in Table 3 were prepared. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 3 were compared by five well-trained panelists. All the five panelists answered that Example 5 was remarkably superior because a natural sweet fruit juice-like flavor which was not obtained by Comparative Example 3 was imparted by Example 5. The same result was also obtained when the (R) isomer and the racemate were used.
Each of these food flavoring compositions was added for flavoring at 0.1% to a commercially available orange-flavored beverage and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 5 was remarkably superior because a natural sweet fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 2 ppm to a commercially available orange-flavored beverage and the flavor of the resultant beverage was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because a natural sweet fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (banana flavor) specified below in Table 4 were prepared. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 4 were compared by five well-trained panelists. All the five panelists answered that Example 7 was remarkably superior because a natural fresh fruit juice-like flavor which was not obtained by Comparative Example 4 was imparted by Example 7. The same result was also obtained when the (R) isomer and the racemate were used.
Each of these food flavoring compositions was added for flavoring at 0.1% to a commercially available banana-flavored dairy beverage and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 7 was remarkably superior because a natural fresh fruit juice-like flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 1 ppm to a commercially available banana-flavored dairy beverage and the flavor of the resultant beverage was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because a natural fresh fruit juice-like flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (lemon lime flavor) specified below in Table 5 were prepared. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 5 were compared by five well-trained panelists. All the five panelists answered that Example 9 was remarkably superior because fresh sweetness which was not obtained by Comparative Example 5 was imparted by Example 9. The same result was also obtained when the
(R) isomer and the racemate were used.
Each of these food flavoring compositions was added for flavoring at 0.1% to commercially available carbonated water and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 9 was remarkably superior because it had natural fresh sweetness. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 2 ppm to a commercially available lemon lime-flavored carbonated beverage and the flavor of the resultant beverage was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because natural fresh sweetness was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (ginger ale flavor) specified below in Table 6 were prepared. All the numeric values in Table are of parts by weight.
The food flavoring compositions obtained according to Table 6 were compared by five well-trained panelists. All the five panelists answered that Example 11 was remarkably superior because a natural fresh ginger flavor which was not obtained by Comparative Example 6 was imparted by Example 11. The same result was also obtained when the (R) isomer and the racemate were used.
Each of these food flavoring compositions was added for flavoring at 0.1% to commercially available carbonated water and the flavors of the resultant beverages were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with the flavoring composition of Example 11 was remarkably superior because it had ginger-like freshness. The same result was also obtained when the (R) isomer and the racemate were used.
(S)-3,7-dimethyl-2-methylene-6-octen-1-ol was added at 3 ppm to a commercially available carbonated beverage with a ginger ale flavor and the flavor of the resultant beverage was evaluated by five well-trained panelists. All the five panelists answered that the flavor of the beverage supplemented with (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was remarkably superior because the fresh ginger flavor was enhanced. The same result was also obtained when the (R) isomer and the racemate were used.
Food flavoring compositions (lemon flavor) specified below in Table 7 were prepared. All the numeric values in Table are of parts by weight.
Each of these food flavoring compositions was added for flavoring at 1% to a chewing gum base specified below in Table 8 and the flavors of the resultant gums were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the gum supplemented with the flavoring composition of Example 13 was remarkably superior because a natural fruit juice-like and voluminous flavor was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
Each of the food flavoring compositions in Table 7 was added for flavoring at 0.2% to a candy base specified below in Table 9 and the flavors of the resultant candies were evaluated by five well-trained panelists. All the five panelists answered that the flavor of the candy supplemented with the flavoring composition of Example 13 was remarkably superior because a natural fruit juice-like flavor with sweetness was imparted. The same result was also obtained when the (R) isomer and the racemate were used.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2017-146168 | Jul 2017 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2018/028263 | 7/27/2018 | WO | 00 |
