The present invention, 3,7-dimethyl-2-methylene-6-octen-1-food products and food flavor compositions containing ol, especially excellent food or beverage and food flavoring composition citrus-like flavor was granted on things.
BACKGROUND
[0002]
　As used in the present invention 3,7-dimethyl-2-methylene-6-octen-1-ol is a known compound, for example, Flavour Fragr. J., (2004), 19, the 121-133 is it has been described as having odor Fresh citrus peel and Citrus odour with aliphatic aldehyde. Furthermore, the GB 1136345 A, floral, is described with rose-muguet odor. However, it is in these documents that can be utilized in cosmetics perfumes are disclosed, not at all mention of it to be used in the food and drink as a food flavoring material.
Summary of the Invention
[0003]
　An object of the present invention, 3,7-dimethyl-2 is methylene-6-octene-1, characterized in that blending all excellent flavor characteristics, especially citrus food or drink flavor is imparted and food to provide a perfume composition.
[0004]
　The present inventors have formulated a result of studies to solve the above problems, a 3,7-dimethyl-2-methylene-6-octen-1-ol represented by the following formula (1) as food flavoring materials by, it found that the resulting food or beverage and food flavor composition having excellent flavor, and completed the present invention.
[0005]
[Formula 1]

[0006]
　That is, the present invention includes the contents of the following [1] to [7].
[1] 3,7-dimethyl-2-methylene-6-octen-1-food products including all.
[2] food product according to the food or drink is acidic beverages [1].
[3] 3,7-dimethyl-2-methylene-6-octen-1-ol The containing 1 ppb ~ 1000 ppm (concentration) [1] or food product according to [2].
[4] The method used to flavoring substances as 3,7-dimethyl-2-methylene-6-octen-1-ol food products.
Use according to [4] [5] food and drink is acidic beverages.
[6] 3,7-dimethyl-2-methylene-6-octen-1-ol 1 ppb ~ 1000 ppm (concentration) Use according to the above [4] or [5] to be contained.
[7] 3,7-dimethyl-2-methylene-6-octen-1-food flavoring composition containing all.
DESCRIPTION OF THE INVENTION
[0007]
　3,7-dimethyl-2-methylene-6-octen-1-ol and food flavoring composition of the present invention can be imparted or enhanced flavor by blending it in food or drink, and other components mixing can be. Other perfume ingredients which may be mixed, usually synthetic fragrances of various used in the art, natural flavors, natural essential oils, and the like can be illustrated plant extracts, for example, "Patent Office, known-routine techniques Collection (perfume) part II food flavoring, P88-131, 2000 January 14, issued "natural are described in the essential oils, natural flavors, such as synthetic fragrances, and the like.
　This also 3,7-dimethyl-2-methylene-6-octen-1-ol, (3R) form and (3S) Body optically active form, as well as racemates are present, even those of any steric It can be used in the invention.
In food flavor composition of the present invention, 3,7-dimethyl-2-methylene-6-octen-1 content ol, since it may vary by other perfume components to be mixed flatly, usually, 0.0001% to 50% by weight, based on the food perfume composition, preferably from 0.001% to 10%, more preferably, to a concentration range of 0.01% to 5%. 3,7-dimethyl-2-methylene-6-octen-1 concentration-ol can not be obtained the effect of imparting or enhancing effect of the fragrance or flavor of the present invention with less than 0.0001%, at concentrations greater than 50% There may impair the overall balance of the perfume composition, which is not preferable.
[0008]
　Also, when adding 3,7-dimethyl-2-methylene-6-octen-1-ol in food or drink, 1 ppb ~ 5000 ppm based on the weight of food or beverage, preferably from 10 ppb ~ 1000 ppm, more preferably 100 ppb ~ it can be a concentration range of 100 ppm. 3,7-dimethyl-2-methylene-6-octen-1 concentration-ol can not be obtained the effect of imparting or enhancing effect of the fragrance or flavor of the present invention with less than 1 ppb, at concentrations exceeding 5000 ppm 3,7 too out strong floral feeling dimethyl-2-methylene-6-octen-1-ol is inherent, undesirable.
The food flavoring composition of the present invention containing 3,7-dimethyl-2-methylene-6-octen-1-ol, optionally commonly used, for example, water, a solvent such as ethanol; ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Hercolyn, medium chain fatty acid triglyceride may contain a fixative, such as medium-chain fatty acid diglyceride.
本発明の食品用香料組成物及び３，７－ジメチル－２－メチレン－６－オクテン－１－オールの添加によって、香味を付与することができる飲食品の具体例としては、例えば、炭酸飲料、果汁飲料、スポーツドリンク、乳酸菌飲料、発酵乳飲料、果実酒類等の酸性飲料、乳飲料類、ドリンク剤類、豆乳、茶飲料などの飲料類；アイスクリーム、アイスミルク、ラクトアイス、氷菓、ヨーグルト、プリンゼリー、デイリーデザートなどのデザート類；キャラメル、キャンディー、錠菓、クラッカー、ビスケット、クッキー、パイ、チョコレート、スナック、チューインガム、饅頭、羊羹などの菓子類；和風スープ、洋風スープ、中華スープなどのスープ類；パン類；ジャム類；風味調味料類；各種インスタント食品類などを挙げることができる。
飲食品への食品用香料組成物の添加量は、製品の種類や形態に応じて異なるが、通常、製品の重量を基準として０.００1～１０％、好ましくは０．０１～５％の濃度範囲である。
実施例
[0009]
　以下、実施例により本発明を詳細に説明するが、本発明はこれにより制限されるものではない。
[0010]
（実施例１）
　Flavour Fragr. J., (2004), 19, 121-133に記載の方法で製造した、（Ｓ）－３，７－ジメチル－２－メチレン－６－オクテン－１－オールを用いて、以下の表１に示す食品用香料組成物（レモンフレーバー）を調製した。表に記載した数値はすべて重量部を示す。
[0011]
[表1]

[0012]
(Test Example 1)
　was compared with Table panelists -5 people well-trained resulting food flavor composition 1, the five all natural fruit juice feeling is not in Comparative Example 1 rather Example 1 been granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0013]
(Test Example 2)
　The food flavoring composition 0.1% vehicles in commercial lemon flavored beverage Kaguwashi well was evaluated flavor with panelists -5 people trained, five everyone of Example 1 who added perfume composition is a natural fruit juice feeling accompanied by voluminous is applied, it responded that much better. It was the same when using the (R) form and racemic.
[0014]
(Example
　2) (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was 5ppm added to a commercial lemon flavored beverage, rated the flavor well panelists -5 people trained When the, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 who were added all natural fruit juice feeling accompanied by voluminous is given, much better I answered there. It was the same when using the (R) form and racemic.
[0015]
(Example 3)
　was less food fragrance composition shown in Table 2 (grapefruit flavor) was prepared. The numerical values set forth in the table show all parts.
[0016]
[Table 2]

[0017]
(Test Example 3)
　was compared with Table panelists -5 people who are well trained resulting food flavor composition 2, the five all natural fruit juice feeling is not in Comparative Examples 2 towards the Example 3 been granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0018]
(Test Example 4)
　of a commercially available this food flavoring composition 0.1% vehicle in drinking grapefruit flavor Kaguwashi well was evaluated flavor with panelists -5 people trained, five everyone of Example 3 who added perfume composition is a natural fruit juice feeling accompanied by voluminous is applied, it responded that much better. It was the same when using the (R) form and racemic.
[0019]
(Example
　4) (S)-3,7 dimethyl-2-methylene-6-octen-1-ol was 2ppm added to a commercially available grapefruit flavor sports drinks, well flavored with panelists -5 people trained were evaluated, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 who were added all natural fruit juice feeling accompanied by voluminous is given, much better and it was answered that. It was the same when using the (R) form and racemic.
[0020]
(Example 5)
　was less food fragrance composition shown in Table 3 (orange flavor) was prepared. The numerical values set forth in the table show all parts.
[0021]
[table 3]

[0022]
(Test Example 5)
　was compared with panelists -5 people well-trained resulting food flavor composition Table 3, the natural sweet juice sense not to five everyone Example 5 Comparative Example 3 been granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0023]
(Test Example 6)
　The food flavoring composition 0.1% vehicle to a commercial orange flavored beverage Kaguwashi well was evaluated flavor with panelists -5 people trained, five everyone of Example 5 who added perfume composition is naturally sweet juice sensation accompanied by a sense volume is imparted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0024]
(Example
　6) (S)-3,7-dimethyl-2-methylene-6-octen-1-ol was 2ppm added to a commercial orange flavored beverage, rated the flavor well panelists -5 people trained When the, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 who were added all natural sweet juice feeling accompanied by voluminous is given, much better and it was answered that. It was the same when using the (R) form and racemic.
[0025]
(Example 7)
　were the following food fragrance composition shown in Table 4 (banana flavor) was prepared. The numerical values set forth in the table show all parts.
[0026]
[Table 4]

[0027]
(Test Example 7)
　was compared with panelists -5 people well-trained resulting food flavor composition in Table 4, is natural and fresh juice sense not to five everyone Example 7 Comparative Example 4 been granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0028]
(Test Example 8)
　The food flavoring composition 0.1% vehicle to the banana flavored milk drinks Kaguwashi was evaluated for flavor well panelists -5 people trained, five everyone Example 7 fresh fruit juice feeling of a natural person who was added to the perfume composition is given of, replied that much better. It was the same when using the (R) form and racemic.
[0029]
(Example
　8) (S)-3,7 dimethyl-2-methylene-6-octen-1-ol was 1ppm added to the banana flavored milk drinks, well flavored with panelists -5 people trained were evaluated, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 fresh juice feeling natural better with the addition of all is given and answered much better did. It was the same when using the (R) form and racemic.
[0030]
(Example 9)
　was less food fragrance composition shown in Table 5 (cider flavor) was prepared. The numerical values set forth in the table show all parts.
[0031]
[table 5]

[0032]
(Test Example 9)
　was compared with panelists -5 people well-trained resulting food flavor composition in Table 5, the fresh sweetness five everyone not found in Comparative Example 5 In Example 9 been granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0033]
(Test Example 10)
　0.1% vehicle Kaguwashi Commercially available carbonated water the food flavor composition may was evaluated flavor with panelists -5 people trained, perfume composition of Example 9 is five All thing has the better the the fresh sweetness of a natural added, responded that much better. It was the same when using the (R) form and racemic.
[0034]
(Example
　10) (S)-3,7 dimethyl-2-methylene-6-octen-1-ol was 2ppm added to carbonated beverages of commercial cider flavor, well flavored with panelists -5 people trained were evaluated, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 fresh sweet natural better with the addition of all is given and answered much better did. It was the same when using the (R) form and racemic.
[0035]
(Example 11)
　was less food perfume composition according to Table 6 (ginger ale flavor) was prepared. The numerical values set forth in the table show all parts.
[0036]
[Table 6]

[0037]
(Test Example 11)
　was compared with panelists -5 people well-trained resulting food flavor composition in Table 6, natural and fresh ginger sense not to Comparative Example 6, five everyone Example 11 There is granted, the respondents said that much better. It was the same when using the (R) form and racemic.
[0038]
(Test Example 12)
　The food flavoring composition 0.1% vehicle to a commercially available carbonated water Kaguwashi well was evaluated flavor with panelists -5 people trained, perfume composition of Example 11 is five All who added things have ginger specific freshness, responded that much better. It was the same when using the (R) form and racemic.
[0039]
(Example
　12) 3 ppm was added (S)-3,7-dimethyl-2-methylene-6-octen-1-ol compound to a commercially available ginger ale flavor carbonated beverage, well panelists -5 people trained evaluation of the flavor, five everyone (S)-3,7-dimethyl-2-methylene-6-octen-1 who were added all is enhanced fresh ginger feeling and have much better I answered. It was the same when using the (R) form and racemic.
[0040]
(Example 13)
　was as follows food flavor compositions of Table 7 (lemon flavor) was prepared. The numerical values set forth in the table show all parts.
[0041]
[Table 7]

[0042]
(Test Example 13)
　The food grade fragrance composition in chewing gum base material shown in Table 8 below 1% vehicle Kaguwashi was evaluated for flavor well panelists -5 people trained, five everyone Example 13 towards the addition of perfume composition is a natural fruit juice feeling accompanied by voluminous is applied, it responded that much better. It was the same when using the (R) form and racemic.
[0043]
[Table 8]

[0044]
(Test Example 14)
　Table 7 0.2% food grade flavoring composition candy base material shown in Table 9 below vehicles Kaguwashi was evaluated for flavor well panelists -5 people trained, five all There is granted natural juice sense who was added perfume composition is accompanied by sweetness of example 13, responded that much better. It was the same when using the (R) form and racemic.
[0045]
[Table 9]

WE claims

[Requested item 1]
3,7-dimethyl-2-methylene-6-octen-1-food products including all.
[Requested item 2]
Food product according to claim 1 foods and drinks is acidic beverages.
[Requested item 3]
3,7-dimethyl-2-methylene-6-octen-1 food and drink according to claim 1 or 2 containing 1 ppb ~ 5000 ppm ol.
[Requested item 4]
Using the flavoring substances as 3,7-dimethyl-2-methylene-6-octen-1-ol food products.
[Requested item 5]
Use according to claim 4 food or drink is acidic beverages.
[Requested item 6]
Use according to claim 4 or 5 is contained 3,7-dimethyl-2-methylene-6-octen-1-ol in 1 ppb ~ 5000 ppm.
[Requested item 7]
3,7-dimethyl-2-methylene-6-octen-1-food flavoring composition containing all.