JP2005171116A - Deterioration inhibitor for flavor or fragrance - Google Patents

Deterioration inhibitor for flavor or fragrance Download PDF

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JP2005171116A
JP2005171116A JP2003414370A JP2003414370A JP2005171116A JP 2005171116 A JP2005171116 A JP 2005171116A JP 2003414370 A JP2003414370 A JP 2003414370A JP 2003414370 A JP2003414370 A JP 2003414370A JP 2005171116 A JP2005171116 A JP 2005171116A
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flavor
fragrance
deterioration
tea
citral
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Susumu Kiyohara
進 清原
Toshio Ueno
寿夫 植野
Kenji Adachi
謙次 足立
Yuto Suzuki
佑人 鈴木
Hideki Masuda
秀樹 増田
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Ogawa and Co Ltd
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<P>PROBLEM TO BE SOLVED: To provide a deterioration inhibitor which can more effectively inhibit the deterioration of the flavor or the fragrance of foods, drinks or cosmetics that is caused by heat, light, or the like, in particular inhibit the production of off-flavor originated from citral than the conventional technique. <P>SOLUTION: The deterioration of the flavor/fragrance is inhibited by adding theaflavins which are red colorant components contained in a fermented tea into foods, drinks or cosmetics in an addition amount less than that of the conventional deterioration inhibitor. This deterioration inhibitor of the flavor or the fragrance exhibits in particular a significant effect of suppressing the production of p-cresol and p-methylacetophenone which are the off-flavor components originated from citral and is suitable to apply to foods, drinks or cosmetics having the flavor or the fragrance of a citrus note including citral. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

本発明は、飲料や食品あるいは歯磨き剤、口臭防止剤のような口腔衛生剤(以下併せて「経口組成物」と称する。)、香料、香粧品等に広く適用することができる香味又は香気の劣化抑制剤および香味劣化抑制方法に関するものである。   The present invention is a flavor or fragrance that can be widely applied to oral hygiene agents (hereinafter also referred to as “oral compositions”), flavorings, cosmetics, and the like, such as beverages, foods, toothpastes, and bad breath deodorants. The present invention relates to a deterioration inhibitor and a flavor deterioration suppressing method.

一般に飲料や食品等の味と匂いは食欲の増進や減退に大きく影響するため、その香味は各種栄養成分と同様に食生活において重要な要素と考えられる。また、化粧品や石けん、シャンプー等のトイレタリー製品に付された香気はその基材臭をマスクすると共に、使用者や周囲の人に快い感覚を与え、化粧品等における重要な要素となっている。しかしながら、飲食品、化粧品等の香味、香気成分は不安定なものが多く、酸素、光、熱等により徐々に劣化し、製造、流通、保存等の各段階で本来の香味、香気が消失したり、異味異臭(劣化臭)が発生することもよく知られている。   In general, the taste and smell of beverages and foods greatly affect the increase and decrease of appetite, and the flavor is considered to be an important factor in the diet as well as various nutritional components. In addition, the aroma attached to toiletries such as cosmetics, soap, and shampoo masks the base material odor and gives a pleasant sensation to the user and the surrounding people, which is an important factor in cosmetics. However, the flavor and fragrance components of foods and beverages and cosmetics are often unstable and gradually deteriorate due to oxygen, light, heat, etc., and the original flavor and fragrance disappear at each stage of production, distribution, storage, etc. It is also well known that off-flavor odor (deteriorated odor) occurs.

特に、シトラールはレモン様の匂いを有し、飲食品や化粧品等にシトラス調の香味、香気を付与する重要な成分であるが、加熱もしくは経時的に減少しオフフレーバーが生成することが知られている〔Peter Schieberle and Werner Grosch; J. Agric. Food Chem., Vol.36, 797-800(1988)〕。特に酸性条件下では製品中のシトラールは、製造、流通、保存期間中の各段階で減少し、環化、水和、異性化等の反応によりその構造が変化し、その結果フレッシュ感の低下を引き起こす。さらにはシトラール由来の生成物の酸化反応により非常に強い劣化臭原因物質であるp−メチルアセトフェノン及びp−クレゾールが生成することにより著しい製品の品質低下を招く。   In particular, citral has a lemon-like odor and is an important component that imparts a citrus-like flavor and aroma to foods and beverages, cosmetics, etc., but it is known that off-flavor is produced by heating or decreasing over time. [Peter Schieberle and Werner Grosch; J. Agric. Food Chem., Vol. 36, 797-800 (1988)]. In particular, under acidic conditions, citral in products decreases at each stage during production, distribution, and storage, and the structure changes due to reactions such as cyclization, hydration, and isomerization, resulting in a decrease in freshness. cause. Furthermore, p-methylacetophenone and p-cresol, which are very strong odor-causing substances, are produced by the oxidation reaction of the citral-derived product, resulting in a significant product quality degradation.

従来、こうした香味、香気の劣化を抑制するために、アスコルビン酸等各種の酸化防止剤や光劣化防止剤の添加が提唱されている(非特許文献1)。さらに、シトラールの劣化抑制に関しては茶ポリフェノールやロズマリン酸等を添加する方法が開示されている(特許文献1、2)。また、本発明者らもシトラールをはじめとする飲食品等の香味、香気の劣化抑制について研究を重ね、これまでにシソやペパーミント等の植物の抽出物や、カテキン類等の天然由来の成分を添加することによる香味、香気の劣化抑制方法を提案してきた(特許文献3〜13)。   Conventionally, the addition of various antioxidants such as ascorbic acid and photodegradation inhibitors has been proposed in order to suppress such flavor and fragrance degradation (Non-patent Document 1). Furthermore, methods for adding tea polyphenols, rosmarinic acid, and the like have been disclosed for suppressing deterioration of citral (Patent Documents 1 and 2). In addition, the present inventors have also conducted research on flavor and odor deterioration inhibition of citral and other foods and beverages, and so far have extracted plant extracts such as perilla and peppermint, and naturally derived ingredients such as catechins. A method for suppressing deterioration of flavor and aroma by adding them has been proposed (Patent Documents 3 to 13).

しかしながら、飲食品や化粧品等の香味、香気の劣化は、香味、香気成分自身が酸素、光、熱等により変化することに加え、飲食品や化粧品等に含まれる油脂、たんぱく質、糖類、アミノ酸類、有機酸類等の各成分の酸化、分解、異性化、重合等の数多くの反応も関与する複合的な要因により引き起こされるものである。このため上記従来技術を用いてもなお効果が不十分な場合があり、さらに効果の高い劣化抑制技術が求められていた。   However, the deterioration of flavor and aroma of foods and beverages and cosmetics, in addition to the fact that the flavor and aroma components themselves change due to oxygen, light, heat, etc., as well as fats and oils, proteins, sugars and amino acids contained in foods and beverages and cosmetics. It is caused by complex factors that involve many reactions such as oxidation, decomposition, isomerization, and polymerization of each component such as organic acids. For this reason, even if it uses the said prior art, an effect may still be inadequate, and the deterioration suppression technique with still higher effect was calculated | required.

「特許庁公報 周知・慣用技術集(香料)第1部」1999年1月29日 p141〜147"Patent Office Gazette of Known and Conventional Techniques (Fragrance) Part 1" January 29, 1999, p141-147 特開2003−96486号公報JP 2003-96486 A 特表2002−507887号公報Special Table 2002-50787 gazette 特開平9−227456号公報Japanese Patent Laid-Open No. 9-227456 特開平11−137224号公報JP-A-11-137224 特開平11−169148号公報JP-A-11-169148 特開2001−346558号公報JP 2001-346558 A 特開2002−244号公報Japanese Patent Laid-Open No. 2002-244 特開2002−180081号公報JP 2002-180081 A 特開2002−255778号公報JP 2002-255778 A 特開2002−330741号公報JP 2002-330741 A 特開2002−338990号公報JP 2002-338990 A 特開2003−82384号公報JP 2003-82384 A 特開2003−79335号公報JP 2003-79335 A

本発明が解決しようとする課題は、複雑な要因により引き起こされる飲食品や化粧品等の香味、香気の劣化に対し、従来技術よりもさらに効果の高い劣化抑制剤を提供することである。   The problem to be solved by the present invention is to provide a deterioration inhibitor that is more effective than the prior art for the deterioration of flavor and aroma of foods and beverages and cosmetics caused by complex factors.

本発明者らは、加熱によるシトラールの劣化とその抑制方法について詳細に検討した結果、紅茶に含まれるポリフェノールの一種であるテアフラビン類に、シトラール由来の非常に強い劣化臭原因物質であるp−クレゾール及びp−メチルアセトフェノンの生成抑制に顕著な効果を示すことを見出した。さらにシトラール以外の香味、香気の劣化抑制についてもテアフラビン類が顕著な効果を示すことを見出し、本発明を完成するに至った。   As a result of detailed studies on the deterioration of citral by heating and a method for suppressing the deterioration, p-cresol which is a very strong deterioration odor-causing substance derived from citral is added to theaflavins which are a kind of polyphenols contained in black tea. And a remarkable effect on the suppression of the production of p-methylacetophenone. Furthermore, the theaflavins have been found to have a remarkable effect on the suppression of flavor and aroma deterioration other than citral, and the present invention has been completed.

すなわち、本発明はテアフラビン類を有効成分とする香料、飲食品、香粧品等の香味又は香気の劣化抑制剤であり、さらに、香味又は香気がシトラールに基づくシトラス調香味又は香気であることを主な特徴とするものである。   That is, the present invention is a flavor or fragrance degradation inhibitor for flavors, foods and drinks, cosmetics, etc. containing theaflavins as an active ingredient, and the flavor or fragrance is a citrus flavor or fragrance based on citral. It is a characteristic.

本発明の劣化抑制剤を香料や飲食品等に添加することにより、熱や光による香味、香気の劣化を抑制することができる。特にシトラールの劣化に対しては顕著な効果を有し、シトラールに由来する劣化臭原因物質であるp−クレゾール及びp−メチルアセトフェノンの生成を抑制し、シトラス調のフレッシュな香味、香気を維持できる。   By adding the deterioration inhibitor of the present invention to a fragrance, a food or drink, etc., deterioration of flavor and aroma due to heat and light can be suppressed. In particular, it has a remarkable effect on the deterioration of citral, suppresses the generation of p-cresol and p-methylacetophenone, which are the cause of deterioration odor derived from citral, and can maintain a fresh citrus flavor and aroma. .

本発明に使用するテアフラビン類は、茶(Camellia sinensis)の葉の発酵過程でカテキン類から生成する赤色色素成分であり、テアフラビン、テアフラビン 3−o−ガレート、テアフラビン 3'−o−ガレート、テアフラビン 3,3'−ジ−o−ガレート等を含む。テアフラビン類は試薬として市販されているものをそのまま使用することができるが、茶葉から抽出物として得たものを使用することもできる。抽出に使用する茶葉は特に制限はないが、テアフラビン類を多く含む発酵茶又は半発酵茶の茶葉が好ましい。発酵茶とは茶の生葉を萎凋・揉捻後、自らの酸化酵素で完全に発酵させたものであり、半発酵茶とは生葉を萎凋・攪拌する際に、生葉のカテキン類などの一部を自らの酸化酵素で発酵(酸化)させたもので、発酵の程度が30〜70%のものをいう。テアフラビン類の抽出に用いる発酵茶として紅茶、プーアル茶等が挙げられ、半発酵茶としてウーロン茶等が挙げられるが、特に紅茶が好ましい。茶葉からテアフラビン類の抽出処理に使用する溶媒は水又は極性有機溶媒であり、有機溶媒は含水物であっても良い。極性有機溶媒としては、アルコール、アセトン、酢酸エチル等が上げられる。中でも人体への安全性と取扱性の観点から水またはエタノール、プロパノール、ブタノールのような炭素数2〜4の脂肪族アルコールが望ましい。特に水又はエタノール又はこれらの混合物が望ましい。
抽出に用いる溶媒の量は任意に選択できるが、一般には上記原材料1重量部に対し溶媒量2〜100重量部を使用する。
なお、抽出の前処理としてヘキサン等の非極性有機溶媒であらかじめ脱脂処理をし、後の抽出処理時に余分な脂質が抽出されるのを防止することもできる。またこの脱脂処理で結果的に脱臭等の精製ができる場合がある。また脱臭の目的で抽出前に水蒸気蒸留処理を施してもよい。
The theaflavins used in the present invention are red pigment components generated from catechins during the fermentation of tea (Camellia sinensis) leaves. , 3′-di-o-gallate and the like. As the theaflavins, those commercially available as reagents can be used as they are, but those obtained as an extract from tea leaves can also be used. The tea leaf used for extraction is not particularly limited, but tea leaves of fermented tea or semi-fermented tea containing a large amount of theaflavins are preferable. Fermented tea is a tea that has been fermented and twisted and then completely fermented with its own oxidase.Semi-fermented tea is a part of raw leaf catechins, etc. It is fermented (oxidized) with its own oxidase and has a degree of fermentation of 30 to 70%. Examples of fermented tea used for the extraction of theaflavins include black tea and puer tea, and examples of semi-fermented tea include oolong tea, with black tea being particularly preferred. The solvent used for the extraction of theaflavins from tea leaves is water or a polar organic solvent, and the organic solvent may be a hydrate. Examples of the polar organic solvent include alcohol, acetone, ethyl acetate and the like. Of these, water or an aliphatic alcohol having 2 to 4 carbon atoms such as ethanol, propanol, and butanol is desirable from the viewpoint of safety to the human body and handleability. Water or ethanol or a mixture thereof is particularly desirable.
The amount of the solvent used for the extraction can be arbitrarily selected, but generally 2 to 100 parts by weight of the solvent is used with respect to 1 part by weight of the raw material.
It should be noted that as a pretreatment for extraction, degreasing treatment can be performed in advance with a non-polar organic solvent such as hexane to prevent excess lipids from being extracted during the subsequent extraction treatment. Further, this degreasing treatment may result in purification such as deodorization. For the purpose of deodorization, steam distillation treatment may be performed before extraction.

抽出処理方法としては、溶媒の種類、量等により種々の方法を採用することができる。例えば前記天然物を溶媒中に入れ、浸漬法又は加熱還流法で抽出することができる。なお浸漬法による場合は加熱条件下、室温又は冷却条件下のいずれであってもよい。
ついで、溶媒に不溶な残渣を除去して抽出液を得るが、残渣除去方法としては遠心分離、濾過、圧搾等の各種の固液分離手段を用いることができる。
Various extraction methods can be employed depending on the type and amount of the solvent. For example, the natural product can be put in a solvent and extracted by an immersion method or a heating reflux method. In the case of the immersion method, any of heating conditions, room temperature or cooling conditions may be used.
Subsequently, the residue insoluble in the solvent is removed to obtain an extract. As the residue removal method, various solid-liquid separation means such as centrifugation, filtration, and pressing can be used.

上記方法で得られた抽出物は、さらに脱色、脱臭等の精製処理により、テアフラビン類の含量を高めて劣化抑制剤として使用する。精製処理には活性炭、アルミナ、シリカゲルや多孔性のスチレン-ジビニルベンゼン共重合体からなる合成樹脂吸着剤やメタクリル酸エステル系多孔性重合樹脂やゲル型合成吸着剤などが使用できる。精製用の合成樹脂吸着剤としては例えば三菱化学株式会社製「ダイヤイオンHP−20(商品名)」「ダイヤイオンSP−70(商品名)」やオルガノ株式会社製「アンバーライトXAD−2(商品名)」、アマシャム ファルマシア バイオテク株式会社製「セファデックスLH−20(商品名)」などが使用できる。また、抽出物をタンナーゼ等の加水分解酵素を使用し精製することもでき、さらに酵素処理により得られた抽出物を活性炭や合成吸着樹脂、ゲル型合成吸着剤を使用して精製することもできる。また、以上の群から選ばれる1種または2種以上の処理を組み合わせてもよい。精製した抽出物中のテアフラビン類の含量は5質量%以上であることが望ましい。   The extract obtained by the above method is used as a deterioration inhibitor by further increasing the content of theaflavins by purification treatment such as decolorization and deodorization. For the purification treatment, activated carbon, alumina, silica gel, a synthetic resin adsorbent composed of a porous styrene-divinylbenzene copolymer, a methacrylic ester porous polymer resin, a gel type synthetic adsorbent, or the like can be used. Synthetic resin adsorbents for purification include, for example, “Diaion HP-20 (trade name)” “Diaion SP-70 (trade name)” manufactured by Mitsubishi Chemical Corporation and “Amberlite XAD-2 (product) manufactured by Organo Corporation. Name) ”,“ Sephadex LH-20 (trade name) ”manufactured by Amersham Pharmacia Biotech Co., Ltd. can be used. The extract can be purified using a hydrolase such as tannase, and the extract obtained by the enzyme treatment can be purified using activated carbon, a synthetic adsorption resin, or a gel type synthetic adsorbent. . Moreover, you may combine 1 type, or 2 or more types of processes chosen from the above group. The content of theaflavins in the purified extract is preferably 5% by mass or more.

市販のテアフラビン類又は上記のとおり得られた精製物は、そのまま劣化抑制剤として飲食品等に配合できるが、以下のように調製して使用することもできる。例えば、水、アルコール、グリセリン、プロピレングリコール等の(混合)溶剤に適当な濃度で溶解させて(具体的には、水/エタノール、水/エタノール/グリセリン、水/グリセリン等の混合溶剤)液剤とする。またはデキストリン、シュークロース、ペクチン、キチン等を加えることもでき、これらをさらに濃縮してペースト状とすることもできる。また、各溶液に賦形剤(デキストリン等)を添加し噴霧乾燥によりパウダー状にすることも可能である。さらに上記液剤を乳化剤とともに油脂等に添加して分散させることにより、油溶性の液剤とすることもでき、用途に応じて種々の剤形を採用することができる。   Commercially available theaflavins or purified products obtained as described above can be directly incorporated into foods and drinks as deterioration inhibitors, but can also be prepared and used as follows. For example, dissolved in an appropriate concentration in a (mixed) solvent such as water, alcohol, glycerin, propylene glycol (specifically, a mixed solvent of water / ethanol, water / ethanol / glycerin, water / glycerin, etc.) To do. Alternatively, dextrin, sucrose, pectin, chitin or the like can be added, and these can be further concentrated to form a paste. It is also possible to add an excipient (such as dextrin) to each solution and form a powder by spray drying. Furthermore, an oil-soluble liquid agent can be obtained by adding and dispersing the liquid agent together with an emulsifier in an oil or the like, and various dosage forms can be adopted depending on the application.

本発明の劣化抑制剤は香料、経口組成物、香粧品等の加工段階で適宜添加することができる。添加量については、使用する劣化抑制剤中のテアフラビン類の純度、あるいは添加対象の種類により異なるが、一般的に0.001〜100ppmの添加量が適当である。対象製品が経口組成物の場合には、本来の香味にほとんど影響を及ぼさせないという観点からは0.01〜30ppm、特に0.1〜10ppmが好ましい。   The deterioration inhibitor of the present invention can be appropriately added at the processing stage of fragrances, oral compositions, cosmetics and the like. The addition amount varies depending on the purity of theaflavins in the deterioration inhibitor to be used or the type of addition target, but an addition amount of 0.001 to 100 ppm is generally appropriate. When the target product is an oral composition, 0.01 to 30 ppm, particularly 0.1 to 10 ppm is preferable from the viewpoint of hardly affecting the original flavor.

また、本発明の劣化抑制剤と遷移金属イオンを併用して用いることもでき、特に人体への安全性の観点から鉄イオンが好ましい。鉄イオンの供給源としては特に制限はなく、金属鉄、鉄塩類、ヘム鉄等を使用することができる。具体的には塩化鉄、クエン酸鉄、グルコン酸鉄、乳酸鉄、ピロリン酸鉄、硫酸鉄、ヘム鉄等を挙げることができる。また、本発明の劣化抑制剤と一般に使用されているL−アスコルビン酸、緑茶抽出物、酵素処理ルチン、エンジュ抽出物、ぶどう種子抽出物、ローズマリー抽出物等の酸化防止剤やクエン酸、グルコン酸、酒石酸、フィチン酸、ピロリン酸、ポリリン酸等の金属封鎖剤と混合することも可能である。   Moreover, the deterioration inhibitor of this invention and a transition metal ion can also be used together, and especially iron ion is preferable from a viewpoint of the safety | security to a human body. There is no restriction | limiting in particular as a supply source of an iron ion, Metallic iron, iron salts, heme iron etc. can be used. Specific examples include iron chloride, iron citrate, iron gluconate, iron lactate, iron pyrophosphate, iron sulfate, and heme iron. Further, antioxidants such as L-ascorbic acid, green tea extract, enzyme-treated rutin, Enju extract, grape seed extract, rosemary extract and the like, which are generally used with the deterioration inhibitor of the present invention, citric acid, glucone, etc. It is also possible to mix with metal sequestering agents such as acid, tartaric acid, phytic acid, pyrophosphoric acid and polyphosphoric acid.

本発明において香味とは、飲食品等の経口組成物の嗅覚で感じる香りと、口腔から鼻腔に抜けた部分で感じる風味を合わせたものをいう。香味には飲食品等の経口組成物が本来有している香味と、香料を添加することにより経口組成物に付与された香味の両方を含む。香気とは香粧品等に香料を添加することにより付された、主に嗅覚で感じる香りをいう。   In the present invention, the flavor refers to a combination of a scent felt by an olfactory sense of an oral composition such as a food and drink and a flavor felt at a portion from the oral cavity to the nasal cavity. The flavor includes both the flavor inherent to oral compositions such as food and drink and the flavor imparted to the oral composition by adding a fragrance. Aroma refers to a scent that is given to a cosmetic product or the like by adding a fragrance, and is felt mainly by the sense of smell.

本発明の劣化抑制剤は種々の香味・香気の劣化に有効であるが、好ましくはシトラス調の香味・香気の劣化に対して有効である。特にシトラールに基づく香味・香気の劣化に対しては有効で、シトラール由来の非常に強い劣化臭原因物質であるp−メチルアセトフェノン及びp−クレゾールの生成抑制に顕著な効果を有する。   The deterioration inhibitor of the present invention is effective for deterioration of various flavors and fragrances, but is preferably effective for deterioration of citrus flavor and fragrance. In particular, it is effective for the deterioration of flavor and aroma based on citral, and has a remarkable effect in suppressing the production of p-methylacetophenone and p-cresol, which are extremely strong odor-causing substances derived from citral.

本発明の劣化抑制剤は経口組成物、香料、香粧品等に特に制限なく使用できるが、具体例としては下記のものが挙げられる。
経口組成物の例としては、飲料、菓子類、油脂及び油脂加工食品、乳、乳製品、口腔衛生剤などが挙げられるが、より具体的には下記のものを挙げることができる。
飲料の例としては、コーヒー、紅茶、清涼飲料、乳酸菌飲料、無果汁飲料、果汁入り飲料、栄養ドリンクなどが挙げられ、特にシトラス系の炭酸飲料、果汁、果汁飲料、乳性飲料、茶飲料等に好適である。
菓子類の例としては、ゼリー、プリン、ババロア、キャンディー、ビスケット、クッキー、チョコレート、ケーキ類などが挙げられ、特にシトラール含有のヨーグルト、ゼリー、アイスクリーム等の冷菓、キャンディー、水飴、ガム等に好適である。
油脂及び油脂加工食品の例としては、食用油脂(動物性油脂、植物性油脂)、マーガリン、ショートニング、マヨネーズ、ドレッシング、ハードバターなど、さらに、即席(フライ)麺類、とうふの油揚(油揚、生揚、がんもどき)、揚かまぼこ、てんぷら、フライ、スナック類(ポテトチップス、揚あられ類、かりんとう、ドーナッツ)、調理冷凍食品(冷凍コロッケ、エビフライ等)などが挙げられる。
乳、乳製品等の例としては、乳として生乳、牛乳、加工乳等、乳製品としてクリーム、バター、バターオイル、濃縮ホエー、チーズ、アイスクリーム類、ヨーグルト、練乳、粉乳、濃縮乳等などが挙げられる。
口腔衛生剤の例としては、歯磨、うがい薬、口中清涼剤、口臭防止剤などが挙げられる。
香料の例としては、香料原料(精油、エッセンス、コンクリート、アブソリュート、エキストラクト、オレオレジン、レジノイド、回収フレーバー、炭酸ガス抽出精油、合成香料)およびそれらを含有する香料組成物などが挙げられ、特にシトラールを含有するシトラス系香料に好適である。
香粧品の例としては、香水、化粧品、洗剤、石鹸、シャンプー、リンス、入浴剤、芳香剤等が挙げられ、特にシトラールを含有するシトラス調の香りを有する香粧品に好適である。
(「特許庁公報 周知慣用技術集(香料)」参照)
The deterioration inhibitor of the present invention can be used for oral compositions, fragrances, cosmetics and the like without particular limitation, and specific examples thereof include the following.
Examples of oral compositions include beverages, confectionery, fats and oils and processed foods, milk, dairy products, oral hygiene agents, and more specifically, the following can be mentioned.
Examples of beverages include coffee, tea, soft drinks, lactic acid bacteria beverages, fruit juice beverages, fruit juice beverages, nutritional drinks, etc. Citrus carbonated beverages, fruit juices, fruit juice beverages, milk beverages, tea beverages, etc. It is suitable for.
Examples of confectionery include jelly, pudding, bavaria, candy, biscuits, cookies, chocolate, cakes, etc. Especially suitable for frozen confectionery such as citral-containing yogurt, jelly, ice cream, candy, chickenpox, gum, etc. It is.
Examples of fats and oils and processed foods include edible fats and oils (animal fats and oils, vegetable fats and oils), margarine, shortening, mayonnaise, dressing, hard butter, etc., and instant noodles and tofu fried (fried, fresh, Ganmodoki), fried kamaboko, tempura, fries, snacks (potato chips, fried potatoes, karinto, donuts), cooked frozen foods (frozen croquettes, fried shrimp, etc.).
Examples of milk, dairy products, etc. include raw milk, cow milk, processed milk, etc., milk as cream, butter, butter oil, concentrated whey, cheese, ice cream, yogurt, condensed milk, powdered milk, concentrated milk, etc. Can be mentioned.
Examples of oral hygiene agents include toothpastes, mouthwashes, mouth fresheners, bad breath odor prevention agents, and the like.
Examples of fragrances include fragrance raw materials (essential oils, essences, concrete, absolutes, extracts, oleoresin, resinoids, recovered flavors, carbon dioxide extracted essential oils, synthetic fragrances) and fragrance compositions containing them. Suitable for citrus fragrances containing citral.
Examples of cosmetics include perfumes, cosmetics, detergents, soaps, shampoos, rinses, bathing agents, fragrances and the like, and are particularly suitable for cosmetics having a citrus-like scent containing citral.
(Refer to “Patent Office Gazettes of Commonly Used Techniques (Fragrances)”)

以下に実施例を挙げて本発明を具体的に説明するが、本発明は実施例の記載に限定されるものではない。   EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.

試験例および実施例において単品試薬として以下のものを使用した。
1)テアフラビン類:
栗田工業(株)製「テアフラビン混合物(商品名)」を使用した。
2)エピガロカテキン:
栗田工業(株)製「(−)−エピガロカテキン(商品名)」を使用した。
3)エピガロカテキンガレート:
栗田工業(株)製「(−)−エピガロカテキンガレート(商品名)」を使用した。
4)エピカテキン:
栗田工業(株)製「(−)−エピカテキン(商品名)」を使用した。
5)L−アスコルビン酸:
ナカライテスク(株)製のL(+)−アスコルビン酸を使用した。
6)ルチン:
ナカライテスク(株)製のルチンを使用した。
7)クロロゲン酸:
和光純薬(株)製のクロロゲン酸を使用した。
In the test examples and examples, the following were used as single reagent.
1) Theaflavins:
“Theaflavin mixture (trade name)” manufactured by Kurita Kogyo Co., Ltd. was used.
2) Epigallocatechin:
“(−)-Epigallocatechin (trade name)” manufactured by Kurita Kogyo Co., Ltd. was used.
3) Epigallocatechin gallate:
“(−)-Epigallocatechin gallate (trade name)” manufactured by Kurita Kogyo Co., Ltd. was used.
4) Epicatechin:
“(−)-Epicatechin (trade name)” manufactured by Kurita Kogyo Co., Ltd. was used.
5) L-ascorbic acid:
L (+)-ascorbic acid manufactured by Nacalai Tesque was used.
6) Rutin:
Rutin manufactured by Nacalai Tesque was used.
7) Chlorogenic acid:
Chlorogenic acid manufactured by Wako Pure Chemical Industries, Ltd. was used.

〔参考例〕紅茶葉50質量%エタノール水溶液抽出
紅茶葉50gに、50質量%エタノール水溶液500gを加え1時間加熱還流して抽出した。不溶物を濾過により除去した後、濾液を減圧濃縮、凍結乾燥し褐色の粉末(以下「紅茶抽出物」という)15.1g得た。この紅茶抽出物を以下の試験例1〜4で比較例として使用した。
[Reference Example] Extraction of 50% by weight ethanol aqueous solution of black tea leaf To 50g of black tea leaf, 500g of 50% by weight aqueous ethanol solution was added and extracted by heating under reflux for 1 hour. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure and freeze-dried to obtain 15.1 g of a brown powder (hereinafter referred to as “tea extract”). This black tea extract was used as a comparative example in the following Test Examples 1 to 4.

〔試験例1〕レモン風味飲料
上記劣化抑制剤をレモン風味飲料に添加し、p−クレゾール、p−メチルアセトフェノンの生成抑制効果を評価した。
砂糖100g、クエン酸1g、シトラールを含有するレモン香料1.5g及びテアフラビン混合物の1質量%/50質量%エタノール水溶液を表1の濃度になるよう適量添加し、精製水で全量を1000gに調整した。同様に比較例の酸化防止剤としてテアフラビン混合物に代えて、参考例の紅茶抽出物、エピガロカテキン、エピガロカテキンガレート、エピカテキン、L−アスコルビン酸、ルチン、クロロゲン酸(1質量%/50質量%エターノール水溶液)を添加した試料を調製した。この溶液を70℃にて10分間殺菌後、缶につめレモン風味飲料を作成した。50℃にて7日間、恒温槽中で保管した。各レモン風味飲料をジクロロメタンで抽出後、ガスクロマトグラフィーにてp−クレゾール及びp−メチルアセトフェノンの生成量を測定した。表1及び図1、図2にそれぞれの試料のp−クレゾール、p−メチルアセトフェノンの生成量を、無添加50℃、7日間保管品でのp−クレゾール、p−メチルアセトフェノンの生成量を100とした場合の相対値で表した。
[Test Example 1] Lemon-flavored beverage The above-described deterioration inhibitor was added to a lemon-flavored beverage, and the production inhibitory effect of p-cresol and p-methylacetophenone was evaluated.
An appropriate amount of 100 g of sugar, 1 g of citric acid, 1.5 g of lemon flavor containing citral and 1% by weight / 50% by weight ethanol aqueous solution of theaflavin mixture was added to the concentration shown in Table 1, and the total amount was adjusted to 1000 g with purified water. . Similarly, instead of theaflavin mixture as an antioxidant of the comparative example, the tea extract of the reference example, epigallocatechin, epigallocatechin gallate, epicatechin, L-ascorbic acid, rutin, chlorogenic acid (1 mass% / 50 mass) % Ethanol solution) was prepared. This solution was sterilized at 70 ° C. for 10 minutes and then packed in a can to prepare a lemon flavored beverage. It was stored in a thermostatic bath at 50 ° C. for 7 days. Each lemon flavored beverage was extracted with dichloromethane, and the amounts of p-cresol and p-methylacetophenone produced were measured by gas chromatography. Table 1 and FIGS. 1 and 2 show the amounts of p-cresol and p-methylacetophenone produced in each sample, and the amounts of p-cresol and p-methylacetophenone produced in a product stored at 50 ° C. for 7 days without addition. When expressed as a relative value.

Figure 2005171116
Figure 2005171116

表1及び図1、図2により、テアフラビン混合物からなる本発明の劣化抑制剤をレモン風味飲料に添加することにより、p−クレゾール及びp−メチルアセトフェノンの生成が強く抑制されることがわかった。その効果は紅茶抽出物、カテキン類、L−アスコルビン酸、ルチン、クロロゲン酸よりも高く、非常に少量の添加で十分な劣化防止効果を示した。   From Table 1, FIG. 1 and FIG. 2, it was found that the production of p-cresol and p-methylacetophenone was strongly suppressed by adding the deterioration inhibitor of the present invention comprising a theaflavin mixture to a lemon flavored beverage. The effect was higher than that of black tea extract, catechins, L-ascorbic acid, rutin, and chlorogenic acid, and showed a sufficient deterioration preventing effect with the addition of a very small amount.

〔試験例2〕 レモン風味飲料
試験例1のレモン風味飲料について、習熟したパネル10名を選んで官能評価を行った。対照レモン風味飲料として本発明の劣化抑制剤及び酸化防止剤無添加の冷蔵保管品(評価点:0)と、本発明の劣化抑制剤および酸化防止剤無添加の50℃、7日間保管品(評価点:4)を使用し、各レモン風味飲料の香味の劣化度合いを相対評価した。その結果は表2のとおりである。
なお、表2中の評価の点数は以下の基準で採点した各パネルの平均点である。
(採点基準)
異味、異臭*を非常に強く感じる:4点
異味、異臭*を強く感じる :3点
異味、異臭*を感じる :2点
異味、異臭*を若干感じる :1点
異味、異臭*を感じない :0点
p−クレゾール様(薬品臭)、p−メチルアセトフェノン様(桂皮様)の異臭
[Test Example 2] Lemon flavored drink For the lemon flavored drink of Test Example 1, ten experienced panelists were selected for sensory evaluation. As a reference lemon-flavored beverage, a refrigerated storage product with no addition of the deterioration inhibitor and antioxidant of the present invention (evaluation point: 0) and a product stored at 50 ° C. for 7 days without the deterioration inhibitor and antioxidant of the present invention (evaluated as 0 Evaluation point: 4) was used, and the degree of flavor deterioration of each lemon flavored beverage was relatively evaluated. The results are shown in Table 2.
In addition, the score of evaluation in Table 2 is an average score of each panel scored according to the following criteria.
(Scoring criteria)
Feels off-flavor, off-flavor * very strongly: 4 points Feel off-flavor, off-flavor * strongly: 3 points Feel off-flavor, off-flavor *: 2 points Feel off on off-flavor, off-flavor *: 1 point Don't feel off-flavor, off-flavor *: 0 P-cresol-like (chemical odor), p-methylacetophenone-like (cinnamon-like) off-flavor

Figure 2005171116
Figure 2005171116

表2から明らかなように、テアフラビン混合物からなる本発明の劣化抑制剤をレモン風味飲料に添加することにより、p−クレゾール様及びp−メチルアセトフェノン様の劣化臭の生成を強く抑制し、その効果は紅茶抽出物よりも高かった。一方、ルチン、クロロゲン酸、L−アスコルビン酸を添加してもp−クレゾール様及びp−メチルアセトフェノン様の劣化臭生成抑制効果はあまり認められなかった。   As is apparent from Table 2, by adding the deterioration inhibitor of the present invention consisting of a theaflavin mixture to a lemon flavored beverage, the production of p-cresol-like and p-methylacetophenone-like deteriorated odors is strongly suppressed, and its effect Was higher than black tea extract. On the other hand, even when rutin, chlorogenic acid, and L-ascorbic acid were added, the p-cresol-like and p-methylacetophenone-like deterioration odor formation inhibitory effects were not recognized so much.

〔試験例3〕 レモンティー
紅茶葉4.2g、アスコルビン酸0.2gを70℃のお湯300gに加え、3分間抽出した。ろ過により茶葉を取り除き、得られたろ液を10℃以下に冷却後、ろ紙ろ過した。この溶液に60gの砂糖と0.25gのクエン酸、シトラールを含有するレモン香料1g及びテアフラビン混合物の1質量%/50質量%エタノール水溶液を表3の濃度になるよう適量添加し、精製水で全量を1000gに調整した。同様に比較例の酸化防止剤としてテアフラビン混合物に代えて紅茶抽出物(1質量%/50質量%エタノール水溶液)を同濃度添加した試料を調製した。この溶液を70℃にて10分間殺菌後、缶につめレモンティーを作成した。60℃にて7日間、恒温槽中で保管した。習熟したパネル10名を選んで官能評価を行った。対照レモンティーとしてテアフラビン混合物及び紅茶抽出物無添加の冷蔵保管品(評価点:0)と、テアフラビン混合物および酸化防止剤無添加の60℃、7日間保管品(評価点:4)を使用し、各レモンティーの香味の劣化度合いを相対評価した。その結果は表3のとおりである。
なお、表3中の評価の点数は以下の基準で採点した各パネルの平均点である。
(採点基準)
異味、異臭*を非常に強く感じる:4点
異味、異臭*を強く感じる :3点
異味、異臭*を感じる :2点
異味、異臭*を若干感じる :1点
異味、異臭*を感じない :0点
* 薬品臭、ムレ臭
[Test Example 3] Lemon tea 4.2 g of black tea leaf and 0.2 g of ascorbic acid were added to 300 g of hot water at 70 ° C. and extracted for 3 minutes. The tea leaves were removed by filtration, and the obtained filtrate was cooled to 10 ° C. or lower and filtered through filter paper. Add appropriate amount of 1g / 50% by weight ethanol solution of 60g sugar, 0.25g citric acid, lemon flavor containing citral and 1% by weight / 50% by weight ethanol solution of theaflavin mixture to this solution. Was adjusted to 1000 g. Similarly, instead of the theaflavin mixture as a comparative antioxidant, a sample was prepared by adding the same concentration of black tea extract (1 mass% / 50 mass% ethanol aqueous solution). This solution was sterilized at 70 ° C. for 10 minutes and then put into a can to make lemon tea. It was stored in a thermostatic bath at 60 ° C. for 7 days. Ten experienced panelists were selected for sensory evaluation. As a control lemon tea, use a refrigerated storage product without addition of theaflavin mixture and black tea extract (evaluation point: 0) and a product stored at 60 ° C. without addition of theaflavin mixture and antioxidant (evaluation point: 4), The degree of deterioration of the flavor of each lemon tea was relatively evaluated. The results are shown in Table 3.
In addition, the score of evaluation in Table 3 is an average score of each panel scored according to the following criteria.
(Scoring criteria)
Feels off-flavor, off-flavor * very strongly: 4 points Feel off-flavor, off-flavor * strongly: 3 points Feel off-flavor, off-flavor *: 2 points Feel off on off-flavor, off-flavor *: 1 point Don't feel off-flavor, off-flavor *: 0 point
* Chemical odor, stuffy odor

Figure 2005171116
Figure 2005171116

表3から明らかなように、テアフラビン混合物からなる本発明の劣化抑制剤をレモンティーに添加することにより、異味、異臭の発生を強く抑制し、その効果は紅茶抽出物よりも高かった。   As is apparent from Table 3, the addition of the deterioration inhibitor of the present invention consisting of the theaflavin mixture to lemon tea strongly suppressed the occurrence of off-flavors and off-flavors, and the effect was higher than that of the black tea extract.

〔試験例4〕100%オレンジ飲料
バレンシアオレンジ5倍濃縮果汁40gに蒸留水160gを添加し混合し、100%オレンジ飲料を調製した。これをそのまま缶につめたもの(無添加品)と、テアフラビン混合物、紅茶抽出物、L−アスコルビン酸、クロロゲン酸を5ppmずつ添加したものをそれぞれ缶に詰め、70℃、10分間殺菌した後、それぞれ40℃の恒温槽に入れ2週間保管した。習熟した10名のパネルを選んで官能評価を行った。そして、この場合、香味の変化のない対照サンプルとして無添加の100%オレンジ飲料を5℃で2週間保管したものを使用し、香味の変化(劣化)度合いを評価した。その結果は表4のとおりである。なお、表4中の評価の点数は、試験例2と同様の基準で採点した各パネルの平均点である。また、採点基準中の異味、異臭とは特に「イモ臭」、「スパイス様の匂い」を指す。
Test Example 4 100% Orange Beverage 160 g of distilled water was added to and mixed with 40 g of Valencia Orange 5-fold concentrated fruit juice to prepare a 100% orange beverage. After filling this in a can (without additives) and theaflavin mixture, black tea extract, L-ascorbic acid, and chlorogenic acid added at 5 ppm each, each can was sterilized at 70 ° C. for 10 minutes, Each was placed in a constant temperature bath at 40 ° C. and stored for 2 weeks. Sensory evaluation was performed by selecting 10 experienced panels. In this case, a non-added 100% orange beverage stored at 5 ° C. for 2 weeks was used as a control sample having no change in flavor, and the change (deterioration) in flavor was evaluated. The results are shown in Table 4. In addition, the score of evaluation in Table 4 is the average score of each panel scored on the same basis as in Test Example 2. Also, the off-flavors and off-flavors in the scoring standards refer to “potato odor” and “spice-like odor” in particular.

Figure 2005171116
Figure 2005171116

表4に示されるように、無添加及び紅茶抽出物、クロロゲン酸、L−アスコルビン酸添加のものに比べ、テアフラビン混合物からなる本発明の劣化抑制剤を100%オレンジ飲料に添加したものは香味劣化抑制効果が高いことがわかった。   As shown in Table 4, the addition of the deterioration inhibitor of the present invention consisting of a theaflavin mixture to a 100% orange beverage compared to the additive-free and black tea extract, chlorogenic acid, and L-ascorbic acid added flavor deterioration It was found that the inhibitory effect was high.

〔実施例1〕口腔洗浄剤
下記処方量で配合し口腔洗浄剤を作成した。
エタノール 15.00g
グリセリン 10.00g
ポリオキシエチレン 2.00g
サッカリンナトリウム 0.15g
安息香酸ナトリウム 0.05g
香料 0.30g
リン酸二水素ナトリウム 0.10g
着色剤 0.20g
テアフラビン混合物の
1質量%/50質量%エタノール水溶液 0.01g
精製水 72.10g
[Example 1] Oral Cleaner An oral cleanser was prepared by blending in the following prescribed amounts.
Ethanol 15.00g
Glycerin 10.00g
Polyoxyethylene 2.00g
Saccharin sodium 0.15g
Sodium benzoate 0.05g
Fragrance 0.30g
Sodium dihydrogen phosphate 0.10g
Colorant 0.20g
0.01 g ethanol solution of 1% by mass / 50% by mass of theaflavin mixture
72.10 g of purified water

〔実施例2〕マーガリン
ショートニング55g、コーン油15g、30%ベータカロチン液0.1g、レシチン0.2g及び乳化剤0.3gを混合し、湯煎にて溶解し、80℃、10分間殺菌した(1)。蒸留水27.9g、食塩0.5g、脱脂粉乳1g及びテアフラビン混合物の1重量%/50重量%エタノール水溶液0.01gを混合し、湯煎にて85℃まで加熱した(2)。(1)、(2)をそれぞれ50〜60℃まで冷却した後、混合し、氷水にて冷却しながらディスパーを用いて1500rpmにて5分間撹拌した。ゴムベラで全体をよく練りながら、水にて10℃まで冷却した。このものを容器に移し、一晩冷蔵庫で熟成させてマーガリンを完成した。
[Example 2] 55 g of margarine shortening, 15 g of corn oil, 0.1 g of 30% beta carotene solution, 0.2 g of lecithin and 0.3 g of an emulsifier were mixed, dissolved in a hot water bath and sterilized at 80 ° C. for 10 minutes (1 ). Distilled water (27.9 g), sodium chloride (0.5 g), skim milk powder (1 g) and 1 g / 50 wt% ethanol aqueous solution of theaflavin mixture (0.01 g) were mixed and heated to 85 ° C. in a hot water bath (2). (1) and (2) were each cooled to 50 to 60 ° C., mixed, and stirred for 5 minutes at 1500 rpm using a disper while cooling with ice water. While thoroughly kneading the whole with a rubber spatula, it was cooled to 10 ° C. with water. This was transferred to a container and aged overnight in a refrigerator to complete the margarine.

〔実施例3〕抹茶プリン
牛乳500gと蒸留水を混合し、湯煎にて40℃まで加熱した(1)。蒸留水に抹茶5g、砂糖100g、乳化剤10g及びテアフラビン混合物の1重量%/50重量%エタノール水溶液0.01gを分散した(2)。(1)、(2)を混合し、80℃、15分殺菌した。このものをお湯で100gに重量調整した後、クリアミックスを用いて乳化した。香料0.03gを添加し、さらに撹拌した後、容器に移し抹茶プリンを完成した。
[Example 3] Matcha pudding 500 g of milk and distilled water were mixed and heated to 40 ° C in a hot water bath (1). In distilled water, 5 g of Matcha, 100 g of sugar, 10 g of emulsifier, and 0.01 g of a 1 wt% / 50 wt% ethanol aqueous solution of theaflavin mixture were dispersed (2). (1) and (2) were mixed and sterilized at 80 ° C. for 15 minutes. The weight of this product was adjusted to 100 g with hot water, and then emulsified using a clear mix. After adding 0.03 g of fragrance and further stirring, it was transferred to a container to complete the matcha pudding.

〔実施例4〕ミルクティー
紅茶葉8gを、少量の重曹を添加した蒸留水200gにて80℃、5分間熱水抽出した。茶葉をろ過し、得られたろ液に、蒸留水800g、グラニュー糖70g、牛乳120g及び乳化剤0.3gを添加し乳化した。香料0.5g及びテアフラビン混合物の1重量%水溶液0.15gを添加し、スチール容器に充填後、123℃、20分間殺菌しミルクティーを完成した。
Example 4 Milk Tea 8 g of black tea leaf was extracted with 200 g of distilled water to which a small amount of sodium bicarbonate was added at 80 ° C. for 5 minutes. The tea leaves were filtered, and the obtained filtrate was emulsified by adding 800 g of distilled water, 70 g of granulated sugar, 120 g of milk and 0.3 g of an emulsifier. After adding 0.5 g of a fragrance and 0.15 g of a 1% by weight aqueous solution of the theaflavin mixture, the mixture was filled in a steel container and sterilized at 123 ° C. for 20 minutes to complete a milk tea.

〔実施例5〕アイスクリーム
砂糖15g及び乳化安定剤0.6gを混合した(1)。蒸留水66.1gに脱脂粉乳8.4g、テアフラビン混合物の0.1重量%/50重量%エタノール水溶液0.05g及びトコフェロール(イーミックス P−20)0.2gを分散した(2)。(2)を40℃まで加熱し、(1)を添加し、攪拌しながら、85℃まで加熱した。このものに無塩バター9.6gを添加し、85℃、15分間殺菌した。ホモミキサーを用いて10000rpmにて5分間撹拌した。このものを5℃まで冷却し、12時間冷蔵庫で保管した。香料0.2gを添加し、30分間フリージングし、カップに充填後、−20℃に冷却してアイスクリームを完成した。
[Example 5] Ice cream 15 g of sugar and 0.6 g of an emulsion stabilizer were mixed (1). 8.4 g of skim milk powder, 0.05 g of a 0.1% by weight / 50% by weight ethanol aqueous solution of the theaflavin mixture and 0.2 g of tocopherol (Emix P-20) were dispersed in 66.1 g of distilled water (2). (2) was heated to 40 ° C., (1) was added and heated to 85 ° C. with stirring. To this, 9.6 g of unsalted butter was added and sterilized at 85 ° C. for 15 minutes. The mixture was stirred for 5 minutes at 10,000 rpm using a homomixer. This was cooled to 5 ° C. and stored in the refrigerator for 12 hours. 0.2g of fragrance was added, frozen for 30 minutes, filled into a cup, and then cooled to -20 ° C to complete an ice cream.

〔実施例6〕殺菌乳酸菌飲料
蒸留水80g及び発酵乳原液(全固形分54%、無脂乳固形分4%)20gを混合した。このものにレモン香料0.1g及びテアフラビン混合物の0.1重量%/50重量%エタノール水溶液を0.05g添加し、ガラス容器に充填後、70℃、10分間殺菌し殺菌乳酸菌飲料を完成した。
[Example 6] Bactericidal lactic acid bacteria beverage 80 g of distilled water and 20 g of a fermented milk stock solution (total solid content 54%, non-fat milk solid content 4%) were mixed. To this, 0.1 g of lemon flavor and 0.05 g of 0.1% by weight / 50% by weight ethanol aqueous solution of theaflavin mixture were added, filled in a glass container, and sterilized at 70 ° C. for 10 minutes to complete a sterilized lactic acid bacteria beverage.

〔実施例7〕100%アップル飲料
蒸留水160g及びアップル5倍濃縮混濁果汁40gを混合した。このものにテアフラビン混合物の1重量%/50重量%エタノール水溶液を0.01g添加し、スチール容器に充填後、70℃、10分間殺菌し100%アップル飲料を完成した。
[Example 7] 100% apple beverage 160 g of distilled water and 40 g of apple 5-fold concentrated turbid juice were mixed. To this, 0.01 g of a 1% / 50% by weight ethanol solution of the theaflavin mixture was added, filled into a steel container, and then sterilized at 70 ° C. for 10 minutes to complete a 100% apple beverage.

〔実施例8〕コロン
下記処方量で配合しコロンを作成した。
エタノール 90.0g
水 6.9g
レモン香料 3.0g
テアフラビン混合物の
0.1質量%/50質量%エタノール水溶液 0.1g
[Example 8] Colon A colon was prepared by blending in the following prescribed amount.
Ethanol 90.0g
6.9g of water
Lemon flavor 3.0g
0.1 g / 50 wt% aqueous ethanol solution of theaflavin mixture 0.1 g

本発明の香味又は香気の劣化抑制剤は、従来から飲食に供されてきた茶に由来するテアフラビン類を有効成分とし、安全性が高く、少ない添加量で熱や光による香味、香気の劣化を抑制することができ、特にシトラールの劣化に対しては顕著な効果を有しているので、飲食品や化粧品等に幅広く利用可能である。   The flavor or fragrance degradation inhibitor of the present invention comprises theaflavins derived from tea that has been conventionally used for eating and drinking as an active ingredient, is highly safe, and reduces the flavor and fragrance due to heat and light with a small addition amount. Since it has a remarkable effect on the deterioration of citral, in particular, it can be widely used for foods and drinks and cosmetics.

試験例1におけるp−クレゾールの生成量を表したグラフである。2 is a graph showing the amount of p-cresol produced in Test Example 1. FIG. 試験例1におけるp−メチルアセトフェノンの生成量を表したグラフである。3 is a graph showing the amount of p-methylacetophenone produced in Test Example 1. FIG.

Claims (15)

テアフラビン類を有効成分とする香味又は香気の劣化抑制剤。 A flavor or fragrance degradation inhibitor comprising theaflavins as active ingredients. テアフラビン類が茶(カメリア シネンシス)の葉から水、極性有機溶媒又はこれらの混合物で抽出されたテアフラビン類である請求項1記載の香味又は香気の劣化抑制剤。 The flavor or fragrance degradation inhibitor according to claim 1, wherein the theaflavins are theaflavins extracted from tea (camellia sinensis) leaves with water, a polar organic solvent or a mixture thereof. 茶の葉が発酵茶又は半発酵茶の茶葉である請求項2記載の香味又は香気の劣化抑制剤。 The flavor or fragrance degradation inhibitor according to claim 2, wherein the tea leaves are tea leaves of fermented tea or semi-fermented tea. 香味又は香気がシトラス調である請求項1〜3のいずれかの項に記載の香味又は香気の劣化抑制剤。 The flavor or fragrance has a citrus tone, The flavor or fragrance degradation inhibitor according to any one of claims 1 to 3. 香味又は香気がシトラールに基づくものである請求項1〜4のいずれかの項に記載の香味又は香気の劣化抑制剤。 The flavor or fragrance degradation inhibitor according to any one of claims 1 to 4, wherein the flavor or fragrance is based on citral. 請求項1〜5のいずれかの項に記載の香味又は香気の劣化抑制剤を含有することを特徴とする香料。 A flavor comprising the flavor or fragrance deterioration inhibitor according to any one of claims 1 to 5. 請求項1〜5のいずれかの項に記載の香味又は香気の劣化抑制剤を含有することを特徴とする経口組成物。 An oral composition comprising the flavor or fragrance degradation inhibitor according to any one of claims 1 to 5. 請求項6記載の香料を含有することを特徴とする経口組成物。 An oral composition comprising the fragrance according to claim 6. 請求項1〜5のいずれかの項に記載の香味又は香気の劣化抑制剤を含有することを特徴とする香粧品。 A cosmetic comprising the flavor or fragrance deterioration inhibitor according to any one of claims 1 to 5. 請求項6記載の香料を含有することを特徴とする香粧品。 A cosmetic comprising the fragrance according to claim 6. 請求項1〜5のいずれかの項に記載の香味又は香気の劣化抑制剤を添加することによる香料、経口組成物又は香粧品の香味又は香気の劣化抑制方法。 A method for inhibiting deterioration of flavor or fragrance of a fragrance, oral composition or cosmetic by adding the flavor or fragrance deterioration inhibitor according to any one of claims 1 to 5. 香味又は香気がシトラス調である請求項11記載の香味又は香気の劣化抑制方法。 The method for inhibiting deterioration of flavor or fragrance according to claim 11, wherein the flavor or fragrance is citrus. 香味又は香気がシトラールに基づくものである請求項11又は12記載の香味又は香気の劣化抑制方法。 The method for inhibiting deterioration of flavor or fragrance according to claim 11 or 12, wherein the flavor or fragrance is based on citral. 熱又は光による劣化臭の生成を抑制することを特徴とする請求項13記載の香味又は香気の劣化抑制方法。 14. The method for suppressing deterioration of flavor or fragrance according to claim 13, wherein the generation of a deteriorated odor due to heat or light is suppressed. 劣化臭がp−クレゾール又はp−メチルアセトフェノンによる劣化臭である請求項14記載の香味又は香気の劣化抑制方法。 The method for inhibiting deterioration of flavor or fragrance according to claim 14, wherein the deterioration odor is a deterioration odor caused by p-cresol or p-methylacetophenone.
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JP2007039610A (en) * 2005-08-05 2007-02-15 Asahi Breweries Ltd Method for suppressing deterioration of lemon flavor and beverage containing the same flavor
WO2009011271A1 (en) 2007-07-13 2009-01-22 Ogawa & Co., Ltd. Degradation inhibitor for flavor or aroma
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JP2010200659A (en) * 2009-03-03 2010-09-16 Ogawa & Co Ltd Flavor deterioration inhibitor
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JP2003096486A (en) * 2001-09-27 2003-04-03 T Hasegawa Co Ltd Citrus flavor composition with less flavor deterioration
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Cited By (10)

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Publication number Priority date Publication date Assignee Title
JP2006306844A (en) * 2005-03-31 2006-11-09 Kobayashi Pharmaceut Co Ltd Oral hygiene composition
JP2007039610A (en) * 2005-08-05 2007-02-15 Asahi Breweries Ltd Method for suppressing deterioration of lemon flavor and beverage containing the same flavor
JP2009533361A (en) * 2006-04-13 2009-09-17 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング Use of flavonoids
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JP2010200659A (en) * 2009-03-03 2010-09-16 Ogawa & Co Ltd Flavor deterioration inhibitor
CN104568534A (en) * 2013-10-28 2015-04-29 云南天士力帝泊洱生物茶集团有限公司 Determination method for taste quality and aroma quality of Pu-Er ripe tea
JP6652690B1 (en) * 2019-08-01 2020-02-26 小川香料株式会社 Flavor or flavor deterioration inhibitor containing theanaphthoquinones as active ingredient
WO2021019763A1 (en) * 2019-08-01 2021-02-04 小川香料株式会社 Scent/flavor deterioration inhibitor containing theanaphthoquinone as active ingredient

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