JP6238349B2 - Wenzhou mandarin orange flavoring or fruit juice sensation improving agent for mandarin orange flavored foods, flavorings, foods and beverages or cosmetics to which it is added - Google Patents

Wenzhou mandarin orange flavoring or fruit juice sensation improving agent for mandarin orange flavored foods, flavorings, foods and beverages or cosmetics to which it is added Download PDF

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JP6238349B2
JP6238349B2 JP2013239714A JP2013239714A JP6238349B2 JP 6238349 B2 JP6238349 B2 JP 6238349B2 JP 2013239714 A JP2013239714 A JP 2013239714A JP 2013239714 A JP2013239714 A JP 2013239714A JP 6238349 B2 JP6238349 B2 JP 6238349B2
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mandarin orange
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達哉 児玉
達哉 児玉
亮介 市野澤
亮介 市野澤
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Soda Aromatic Co Ltd
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本発明は、温州みかんの香味特徴である温州みかんを特徴づける果汁感を向上させる果汁感向上剤に関するものである。さらにはそれを添加してなる果汁感の向上した、温州みかん香料又は温州みかんの香味を有する飲食品、温州みかん様香気を有する香粧品に関するものである。   The present invention relates to a fruit juice sensation improving agent that improves the fruit juice sensation that characterizes Wenzhou mandarin. Furthermore, the present invention relates to a food and drink product having a flavor of Satsuma mandarin orange or a scent of Satsuma mandarin, and a cosmetic product having a scent of Satsuma mandarin orange.

温州みかんは日本原産であり、日本国内においては多種多様な柑橘のなかでも最も一般に親しまれているものである。国内での温州みかんの生産は主として生食用であり、加工原料としての生産は僅かでしかない。近年では温州みかん加工品は輸入品に頼っている状態であるが、温州みかんの精油については市場における流通量が少ないのが実情である。そのため温州みかん香料を製造するにあたっては温州みかん精油を多用することができず、温州みかん香料は必ずしも温州みかんらしい香気又は香味を有しているとはいえない。 Satsuma mandarin is native to Japan and is the most popular among a wide variety of citrus fruits in Japan. The production of Wenzhou mandarin oranges in Japan is mainly for raw consumption, and production as a processing raw material is very small. In recent years, processed Wenzhou mandarin oranges are in a state of reliance on imported products. However, the actual amount of citrus essential oils in Wenzhou is small in the market. Therefore, when manufacturing Wenzhou mandarin orange fragrance, Unshu mandarin orange essential oil cannot be used extensively, and it cannot be said that Wenzhou mandarin orange fragrance necessarily has the fragrance or flavor of Unshiu orange.

一方、香料の製造に関しては天然物の香気成分分析の結果を参考とすることも多く、特に食品そのものの香気の再現を多く要求される食品用香料においては、食品の香気成分分析が盛んに行われている。柑橘系香料は食品用香料の重要な1分野であって、種々の柑橘について香料が製造されている。(特許文献1)温州みかんについても従来から香気成分分析が多く試みられているものの、その香気を特徴づける成分には分からないことが多く、個々の成分の香気強度を成分量に乗じてFDファクターを算出し各成分の香気寄与度を評価したり、光学異性体が存在する主要成分の光学純度を比較するなど様々な分析手法を用いて研究がなされている。(非特許文献1〜3)しかしながら、未だ温州みかんの香気を特徴付ける成分について充分には解明されていない。   On the other hand, for the production of fragrances, the results of analysis of fragrance components of natural products are often used as references. It has been broken. Citrus fragrance is an important field of food fragrance, and fragrances are produced for various citrus fruits. (Patent Document 1) Although many fragrance component analyzes have been tried for mandarin oranges in the past, the components that characterize the fragrance are often unknown, and the FD factor is obtained by multiplying the component amount by the fragrance intensity of each component. Researches have been made using various analytical methods such as calculating the fragrance contribution of each component and comparing the optical purity of the main component in which optical isomers exist. (Non-Patent Documents 1 to 3) However, the components that characterize the aroma of Wenzhou mandarin oranges have not been fully elucidated.

特開2004−168936号公報JP 2004-168936 A

「柑橘果実の香り(2)―みかんの香気成分―」、香料、2012年、第254号、p.63-68"Scent of citrus fruit (2)-aroma component of mandarin orange", fragrance, 2012, No. 254, p.63-68 「Aroma Character Impact Compounds in Kinokuni Mandarin Orange(Citrus kinokuni) Compared with Satuma Mandarin Orange(Citrus unshiu)」、Bioscience Biotechnology Biochemistry、2010年、第74巻、第4号、p.90937-1-8“Aroma Character Impact Compounds in Kinokuni Mandarin Orange (Citrus kinokuni) Compared with Satuma Mandarin Orange (Citrus unshiu)”, Bioscience Biotechnology Biochemistry, 2010, 74, 4, p.90937-1-8 「ウンシュウミカン(Citrus unshiu Marc.)枝変わり品種の可否の精油成分」、2012年、第56回 香料・テルペンおよび精油化学に関する討論会 講演要旨集、p.243-245"Critus unshiu Marc. Essential oil component of whether or not branching varieties" 2012, 56th Symposium on Fragrance, Terpene and Essential Oil Chemistry, p.243-245

本発明の課題は、温州みかんの甘い果汁感を付与又は向上させるための方法、具体的には温州みかんの果汁感を向上させるための組成物を提供することである。   An object of the present invention is to provide a method for imparting or improving the sweet fruit juice sensation of Satsuma mandarin, specifically, a composition for improving the fruit juice sensation of Satsuma mandarin.

本発明者らは前記課題を解決するために温州みかんらしい甘い果汁感を向上させる成分を特定するために、本出願人の所有する特許第4618530号の評価方法及び装置を用いて温州みかんの精油成分の分析と評価を行った。その結果、FDファクターが高くない成分中に、温州みかんの甘い果汁感に寄与する成分が存在することを見いだし、飲食品への添加試験を繰り返すことによって本発明を完成するに至った。   In order to solve the above-mentioned problems, the present inventors use the evaluation method and apparatus of Japanese Patent No. 4618530 owned by the present applicant in order to identify ingredients that improve the sweet fruit juice-like taste of Wenzhou oranges. Components were analyzed and evaluated. As a result, the present inventors have found that a component contributing to the sweet fruit sensation of Satsuma mandarin is present in components having a low FD factor, and the present invention has been completed by repeating the addition test to food and drink.

すなわち、本発明はβ−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンから選択される1種以上からなる温州みかん香料又は温州みかん風味飲食品の果汁感向上剤であり、前記化合物群から選ばれる1種以上を特定量添加してなる温州みかん様香気又は香味を有する香料、飲食品又は香粧品である。   That is, the present invention relates to a mandarin orange fragrance comprising one or more selected from β-ionone, methyl salicylate, 1-p-menthen-9-ol, 1-p-menten-9-yl acetate, sabinene and p-cymene. Alternatively, it is a fruit juice sensation improver for Unshu mandarin orange flavored foods and drinks, a fragrance, a food or drink or a cosmetic product having a mandarin orange-like fragrance or flavor obtained by adding a specific amount of one or more selected from the above compound group.

本発明の温州みかん香料又は温州みかん風味飲食品の果汁感向上剤を用いることにより、従来表現が困難であった温州みかんらしい甘さを含む果汁感を有する温州みかん香料、または温州みかんを想起させるより嗜好性の高い温州みかん風味を有する飲食品を製造することができる。さらには、本発明の温州みかん香料又は温州みかん風味飲食品の果汁感向上剤を用いた温州みかん香料を香粧品用香料に応用することも可能であり、それら香粧品用香料を添加してより嗜好性の高い温州みかん様の香気を有する香粧品を製造することもできる。 By using the fruit juice sensation enhancer of the present invention Unshu mandarin fragrance or Unshu mandarin orange flavored food and drink, we recall the Unshu mandarin fragrance or Unshu mandarin orange having a fruit juice sensation that includes the sweetness of Unshu mandarin orange, which was difficult to express in the past. It is possible to produce a food or drink having a more tasteful Wenzhou mandarin flavor. Even more, with the mandarin flavoring or mandarin flavor mandarin flavor with food or drink juice feeling improver of the present invention it is also possible to apply the perfume for cosmetics, by adding them cosmetics perfume It is also possible to produce a cosmetic product having a taste of Wenzhou mandarin orange with high palatability.

本発明は、β−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンから選択される1種以上からなる温州みかん香料又は温州みかん風味飲食品の果汁感向上剤であり、さらにはそれらを含有してなる温州みかん香料、温州みかん風味を有する飲食品又は温州みかん様香気を有する香粧品である。本発明の有効成分であるβ−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンは、最終的に消費される製品に以下の濃度で添加することにより温州みかんらしい甘さのある果汁感を向上させる。なお、以下の数値範囲は温州みかん果汁100%の香気成分量に対する添加量を上限とするものであり、温州みかん果汁又は温州みかん香料の香気成分量が少ないときは、それに応じて添加量を減じることで全体の香気を調整することができ、一般的に最終的に消費される製品への添加量が以下の数値範囲になるよう調整することで、通常の温州みかん香料又は温州みかん風味の飲食品の温州みかんらしい果汁感の向上を達成することができる。 The present invention relates to a mandarin orange fragrance comprising one or more selected from β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene, p-cymene, or It is a fruit juice sensation improver for Wenzhou mandarin-flavored foods and drinks, and further includes Wenzhou mandarin orange fragrances, foods and drinks with Wenzhou mandarin flavors, and cosmetics having Wenzhou mandarin orange-like aromas. Β-ionone, methyl salicylate, 1-p-menthen-9-ol, 1-p-menten-9-yl acetate, sabinene and p-cymene, which are the active ingredients of the present invention, are finally consumed products. Add the following concentrations to improve the sweetness of Satsuma mandarin orange sweetness. The following numerical range is the upper limit of the amount of fragrance component of 100% Wenzhou mandarin orange juice. When the amount of fragrance component of Wenzhou mandarin orange juice or mandarin orange fragrance is small, the amount of addition is reduced accordingly. The overall aroma can be adjusted by adjusting the amount of addition to the products that are generally finally consumed within the following numerical range. It can achieve an improvement in the fruit juice quality of the product.

(a)β−イオノン:0.03〜8.0ppm
(b)サリチル酸メチル:0.003〜0.5ppm
(c)1−p−メンテン−9−オール:0.001〜0.2ppm
(d)1−p−メンテン−9−イルアセテート:0.02〜5.0ppm
(e)サビネン:0.1〜15.0ppm
(f)p−サイメン:0.03〜8.0ppm
(a) β-ionone: 0.03 to 8.0 ppm
(b) Methyl salicylate: 0.003-0.5 ppm
(c) 1-p-Menten-9-ol: 0.001 to 0.2 ppm
(d) 1-p-Menten-9-yl acetate: 0.02 to 5.0 ppm
(e) Sabinene: 0.1 to 15.0 ppm
(f) p-cymene: 0.03-8.0 ppm

本発明の前記有効成分はそれ自体の香気が柑橘の香気とは異なるため、本発明の果汁感向上剤のみでは温州みかん様の香気は形成しない。したがって、本発明の果汁感向上剤は最終的に消費される製品の段階において、温州みかん果汁、温州みかん果皮油、温州みかん香料の少なくとも1種との共存が必須である。また、上記の数値範囲を超えて添加するとそれぞれの化合物自体の香気が感じられるようになり、飲食品全体としての風味を損なうおそれがある。また、上記数値範囲の下限値を下まわると温州みかん様の甘さのある果汁感が充分に向上されず、嗜好性の点で未添加のものと差違がなくなる。 Since the active ingredient of the present invention has an aroma different from that of citrus, the fruit juice sensation enhancer of the present invention alone does not form a citrus-like fragrance. Therefore, juice feeling improver of the present invention at the stage of the product to be finally consumed, mandarin orange juice, mandarin peel oil, it is essential coexistence with at least one mandarin flavor. Moreover, when it adds exceeding said numerical range, the fragrance of each compound itself will be felt, and there exists a possibility of impairing the flavor as the whole food-drinks. Moreover, if the lower limit of the above numerical range is not reached, the sweet fruit juice feeling of Satsuma mandarin is not sufficiently improved, and there is no difference from the unadded one in terms of palatability.

本発明の果汁感向上剤は、β−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンの1種以上であれば効果を発揮するが、2種以上を組み合わせた方がより天然の温州みかん果汁に近い香気特性が得られるため好ましい。本発明の化合物群を2種以上組み合わせる場合は、前記の最終的に消費される製品中に添加される量を考慮して比率を決定する。 The fruit juice improving agent of the present invention is effective if it is one or more of β-ionone, methyl salicylate, 1-p-menthen-9-ol, 1-p-menten-9-yl acetate, sabinene, and p-cymene. exhibits, but preferred for odor properties closer to natural mandarin juice prefer a combination of two or more can be obtained. When combining two or more compounds of the present invention, the ratio is determined in consideration of the amount added to the final consumed product.

本発明の有効成分であるβ−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンは、いずれも公知の化合物であるため公知の方法によって製造することができる。   Since β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene and p-cymene, which are active ingredients of the present invention, are all known compounds. It can be produced by a known method.

本発明の果汁感向上剤又はそれを含有してなる香料は、温州みかん風味を有する飲食品であればいずれであっても使用することができる。例えば、果実飲料、果汁入り飲料、野菜ジュース、発泡性飲料、濃縮ジュース、凍結ジュース、スポーツドリンク、栄養ドリンク、その他の機能性ドリンク、フレーバードティー、乳飲料、乳酸菌飲料、豆乳類等の飲料一般、ヨーグルト、ゼリー、ムース、デザート類、アイスクリーム、ラクトアイス、アイスミルク、シャーベット等の冷菓並びに氷菓、ケーキ、クッキー、ビスケット、パイ、煎餅、その他の米菓等といった洋菓子及び和菓子を含む焼菓子や蒸菓子等の菓子類、パン、スナック類、チューインガム、ハードキャンディ、ソフトキャンディー、ゼリービーンズ、グミ、錠菓等を含む糖菓一般、クリーム、果実フレーバーソース、みかんジャムやマーマレード、甘味料、シロップ、缶詰、冷凍食品などが挙げられ、口腔衛生製品としては、口内清涼剤、うがい剤、歯磨き等の医薬品部外品、シロップ剤等の医薬品を挙げることができる。 The fruit juice sensation improving agent of the present invention or the fragrance containing the same can be used as long as it is a food or drink product having a mandarin orange flavor. For example, beverages such as fruit drinks, fruit juice drinks, vegetable juices, effervescent drinks, concentrated juices, frozen juices, sports drinks, nutrition drinks, other functional drinks, flavored teas, milk drinks, lactic acid bacteria drinks, soy milk, etc. Baked confectionery and steamed confectionery including yogurt, jelly, mousse, desserts, ice cream, lacto ice, ice milk, sorbet, etc. Confectionery such as confectionery, bread, snacks, chewing gum, hard candy, soft candy, jelly beans, gummi, tablet confectionery etc. in general, cream, fruit flavor sauce, mandarin jam and marmalade, sweetener, syrup, canned food, Oral hygiene products such as frozen foods Is to, mouth fresheners, mouthwashes, toothpastes, such as pharmaceuticals, quasi-drugs, and can be given drugs such as syrup.

また、本発明の果汁感向上剤又はそれを含有してなる香料は、香粧品用香料への応用も可能であり、温州みかん様香気を有する香粧品であればいずれであっても使用することができる。具体的な用途としては、例えば、香水、コロン、オードトワレ、化粧水、基礎化粧料、シャンプー、リンス、ヘアトリートメント剤、整髪料、洗顔剤、身体洗浄剤、食器用洗剤、洗濯用洗剤、柔軟剤、清掃用品、芳香剤、消臭剤、線香、インセンス、皮膚外用剤、インク、匂い付き文具、玩具などを挙げることができる。 In addition, the fruit juice sensation improving agent of the present invention or the fragrance containing the same can be applied to a fragrance for cosmetics, and any cosmetic product having a mandarin orange-like fragrance should be used. Can do. Specific applications include, for example, perfume, colon, eau de toilette, lotion, basic cosmetics, shampoo, rinse, hair treatment agent, hair conditioner, facial cleanser, body cleaner, dish detergent, laundry detergent, softener , Cleaning supplies, fragrances, deodorants, incense sticks, incense, external preparations for skin, ink, scented stationery, toys and the like.

本願発明の果汁感向上剤又はそれを含有してなる香料は、使用時の利便性のため適宜溶剤などで希釈されてもよい。希釈に用いる溶剤などは香料組成物に常用されるものであれば特に制限はない。また、香気又は香味に悪影響のない範囲であれば香料以外の成分として常用される他の添加物を加えた組成物としてもよい。さらに、本発明の香料においては香料一般に適用される製剤化技術の適用も可能であり、粉末化、カプセル化など情報により所望の形態に調整することもできる。   The fruit juice feeling improving agent of the present invention or a fragrance containing the same may be appropriately diluted with a solvent or the like for convenience during use. The solvent used for dilution is not particularly limited as long as it is commonly used in perfume compositions. Moreover, it is good also as a composition which added the other additive normally used as components other than a fragrance | flavor, if it is a range which does not have a bad influence on aroma or flavor. Furthermore, in the fragrance | flavor of this invention, the formulation technique applied to a fragrance | flavor generally can also be applied, and it can also adjust to a desired form with information, such as pulverization and encapsulation.

β−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンを温州みかんとオレンジのストレートジュースに添加して専門パネルによる官能評価により香味の変化を確認した。また、温州みかんの精油成分中でFDファクターの高い化合物の内、リナロールとデカナールについても同様に添加試験を行い温州みかんらしい果汁感の増強に関する効果を比較した。結果を表1に示す。   β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene and p-cymene are added to Wenzhou oranges and orange straight juice and subjected to sensory evaluation by a specialized panel. The change in flavor was confirmed. In addition, among the compounds with high FD factor among the essential oil components of mandarin orange, linalool and decanal were also subjected to the same addition test to compare the effects on the enhancement of fruit juice sensation that seems to be mandarin orange. The results are shown in Table 1.

Figure 0006238349
Figure 0006238349

試験の結果、本願発明のβ−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンは温州みかんジュースに添加した場合、特定の濃度範囲内であれば温州みかんらしい果汁感を増加させた。これに対して、同様にオレンジジュースに添加した場合は、温州みかんらしい香味は発現せず、場合によってはオレンジの香味とは異なる好調を増加させた。以上より、本発明のβ−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンから選択される1種以上からなる、温州みかん香料又は温州みかん風味飲食品の果汁感向上剤は、温州みかんの香味を有するものに添加したときに、特定の濃度範囲で温州みかんの果汁感を特異的に向上させる効果を有していることが確認された。   As a result of the test, β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene and p-cymene of the present invention are specified when added to Unshu orange juice. If it is within the concentration range, the fruit juice sensation of Unshu orange was increased. On the other hand, when it was added to orange juice in the same manner, it did not develop a savory flavor of Wenzhou, and in some cases increased its favorable performance different from that of orange. As described above, Wenzhou, which comprises one or more selected from β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene, and p-cymene according to the present invention. The fruit juice enhancer of mandarin orange flavor or Unshu mandarin flavored food and drink has the effect of specifically improving the citrus juice taste of Unshu in a specific concentration range when added to those having the flavor of Unshu mandarin orange It was confirmed.

Claims (2)

β−イオノン、サリチル酸メチル、1−p−メンテン−9−オール、1−p−メンテン−9−イルアセテート、サビネン、p−サイメンから選択される1種以上からなる、温州みかん香料又は温州みかん風味を有する飲食品の果汁感向上剤。 β-ionone, methyl salicylate, 1-p-menten-9-ol, 1-p-menten-9-yl acetate, sabinene, p-cymene A fruit juice improving agent for foods and drinks. 化合物(a)〜(e)の1種以上を含有し、飲食品又は香粧品への(a)〜(e)の添加濃度がそれぞれ以下の濃度となるよう使用されるために、飲食品又は香粧品への香料添加量を加味して(a)〜(e)の添加量を調整されてなる、温州みかん香料(ただし温州ミカン果皮油を含むもの、及び、温州ミカン果汁を含むものを除く)。
(a)β−イオノン:0.03〜8.0ppm
(b)サリチル酸メチル:0.003〜0.5ppm
(c)1−p−メンテン−9−オール:0.001〜0.2ppm
(d)1−p−メンテン−9−イルアセテート:0.02〜5.0ppm
(e)p−サイメン:0.03〜8.0ppm
Compound (a) containing one or more ~ (e), to the addition concentration of the food products or cosmetics (a) ~ (e) are used so that the following concentrations, respectively, food and drink or Wenzhou mandarin orange fragrances (excluding those containing Satsuma mandarin peel oil and those containing Satsuma mandarin fruit juice ), which are adjusted by adding the amount of fragrance added to cosmetics (a) to (e). ).
(a) β-ionone: 0.03 to 8.0 ppm
(b) Methyl salicylate: 0.003-0.5 ppm
(c) 1-p-Menten-9-ol: 0.001 to 0.2 ppm
(d) 1-p-Menten-9-yl acetate: 0.02 to 5.0 ppm
(e) p-cymene: 0.03-8.0 ppm
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