JP3863936B2 - Degradation preventive for food flavor - Google Patents
Degradation preventive for food flavor Download PDFInfo
- Publication number
- JP3863936B2 JP3863936B2 JP03934396A JP3934396A JP3863936B2 JP 3863936 B2 JP3863936 B2 JP 3863936B2 JP 03934396 A JP03934396 A JP 03934396A JP 3934396 A JP3934396 A JP 3934396A JP 3863936 B2 JP3863936 B2 JP 3863936B2
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- propenoic acid
- food flavor
- solution
- dihydroxyphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Description
【0001】
【発明の属する技術分野】
本発明は新規なプロペン酸エステルおよび該プロペン酸エステルからなる食品フレーバーの劣化防止剤に関する。
【0002】
【従来の技術】
食品の製造中および保存中におけるフレーバーの劣化は、ある程度避けがたいものであるが、その劣化をできるだけ防止することが重要な課題である。従来かかるフレーバーの劣化防止には一般的にL−アスコルビン酸あるいはBHTなどが用いられている。
【0003】
【発明が解決しようとする課題】
しかしながら、L−アスコルビン酸は食品によっては褐変を引き起こす場合があり、また、BHTのような合成添加物ではなく、天然由来の食品フレーバーの劣化防止剤が広く一般に求められている。
【0004】
【課題を解決するための手段】
本発明は式(I)
【化3】
(式中、
【化4】
は単結合または二重結合を示す)を有するプロペン酸エステルからなる。プロペン酸エステルの好ましい例としてはp−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステル、p−メンタ−1,8−ジエン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステルがあげられる。
【0005】
本発明はさらに上記プロペン酸エステルからなる食品フレーバーの劣化防止剤からなる。
前記式(I)を有するプロペン酸エステルは新規化合物であって、アオチリメンジソをメタノールや、エタノール等の溶剤で抽出することにより、あるいはカフェ酸をシソオールと反応させることによって得ることができる。
【0006】
本発明の劣化防止剤はプロペン酸エステルそのままでもよいし、適当な希釈剤もしくは担体との組成物の形であってもよい。希釈剤もしくは担体の例としては水、エタノール、プロピレングリコール、グリセリン、植物油脂、動物油脂、アラビアガム、デキストリン、シクロデキストリン、ソルビトール、キラヤ抽出物、ゼラチンなどを挙げることができ、これらを用いて液状、乳化状または粉末状の剤形とすることができる。
【0007】
本発明の劣化防止剤を適用するのに好ましい食品の例として、瓶、缶、紙容器等に充填される果汁飲料、無果汁飲料、アルコール飲料など、瓶、袋、プラスチック製容器で包装される漬物、佃煮などが挙げられる。特に、天然精油を利用したシトラス系のフレーバーを使用した飲料やシソ風味の食品のフレーバー劣化防止に有効である。劣化防止剤として用いる場合のプロペン酸エステルの量は、食品に対して0.00001〜0.1重量%程度、好ましくは0.0001〜0.02重量%程度である。
【0008】
【発明の実施の態様】
〔実施例〕
次に、実施例を示して本発明をさらに具体的に説明する。
実施例1
アオチリメンジソ〔Perilla frutescens Britton var. crispa(Thunb.)〕の乾燥地上部2.12kgのメタノール抽出物をヘキサンで抽出後、メタノール層に水を加え酢酸エチルで抽出し、酢酸エチル画分36.2gを得る。さらに酢酸エチル画分をシリカゲルカラムクロマトグラフィーおよびHPLCに供し、p−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステル13.7mgを得る。
【0009】
実施例2
カフェ酸(2.5g:13.9mmol)、シソオール(3.2g:20.9mmol)およびp−トルエンスルホン酸(1.32g)を、ベンゼン(60ml)−テトラヒドロフラン(55ml)混合溶液に溶解し、アルゴン存在下で30時間加熱還流する。この混合溶液に食塩水を加え、酢酸エチルで抽出する。有機層を飽和炭酸水素ナトリウム水溶液および食塩水で洗浄し、脱水後濃縮する。濃縮物をカラム(ODS)およびHPLCにて精製し、エーテル−ヘキサン混合溶液中で再結晶を行い150mgのp−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステルを得る。(収率3.4%)
スペクトルデータ:
MS(EI):M+316
1H−NMR(CD3OD:δppm)
7.56(1H,d,J=15.9Hz)、7.07(1H,d,J=2.0Hz)、6.98(1H,dd,J=8.3,2. 0Hz)、6.81(1H,d,J=8.3Hz)、6.29(1H,d,J=15.9Hz)、4.70(2H,m)、1.74( 1H,s)、4.02(2H,d,J=6.3Hz)、1.98-1.80(6H,m)、1.74(3H,s)、1.40-1.0 5(4H,m)
13C−NMR(CD3OD:δppm)
169.4、151.6、149.6、146.8、146.8、127.8、122.9、116.5、115.1、115.1、 108.8、70.5、46.7、38.5、32.3、30.8、21.1
【0010】
実施例3
アルコール飲料のモデル系としてシソ油0.0034重量部を水:エタノール=4:6の混合溶液100重量部に溶解し、シソ風味を有するシソ溶液を調製する。この溶液にp−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステルの所定量を添加溶解し、さらに酸素を溶液中に吹き込む。この溶液を透明ガラスビンに充填し密栓した後、紫外光(≦400nm;東芝“FL20BLB”×2+“FL20SE”×2)を16時間照射した。シソ溶液の劣化の度合いはHPLCを用い、ペリラアルデヒドの消長により評価した。結果を表1に示す。
【0011】
【表1】
【0012】
実施例4
アルコール飲料のモデル系としてシトラール0.0017重量部を水:エタノール=4:6の混合溶液100重量部に溶解し、レモン風味を有するレモン溶液を調製する。この溶液にp−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステルの所定量を添加溶解し、さらに酸素を溶液中に吹き込む。この溶液を透明ガラスビンに充填し密栓した後、紫外光(≦400nm;東芝“FL20BLB”×2+“FL20SE”×2)を16時間照射した。レモン溶液の劣化の度合いはHPLCを用い、シトラールの消長により評価した。結果を表2に示す。
【0013】
【表2】
【0014】
水で全量を1000mlとし、p−メンタ−8−エン−7−イル 3−(3,4−ジヒドロキシフェニル)−2−プロペン酸エステルの所定量を添加溶解する。この溶液を200ml容缶に充填し、65℃で10分間殺菌しレモン風味の焼酎を調製した。
【0015】
【発明の効果】
本発明のプロペン酸エステルを添加することにより、食品フレーバーの劣化を有効に防止することが出来る。特に、天然精油を利用したシトラス系のフレーバーを使用した飲料や、シソ風味の食品のフレーバー劣化防止に有効である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel propenoic acid ester and a food flavor deterioration inhibitor comprising the propenoic acid ester.
[0002]
[Prior art]
Degradation of flavor during the production and storage of food is unavoidable to some extent, but it is an important issue to prevent the degradation as much as possible. Conventionally, L-ascorbic acid, BHT, or the like is generally used to prevent such flavor deterioration.
[0003]
[Problems to be solved by the invention]
However, L-ascorbic acid may cause browning depending on foods, and there is a general demand for a deterioration inhibitor of naturally occurring food flavor, not a synthetic additive such as BHT.
[0004]
[Means for Solving the Problems]
The present invention is a compound of formula (I)
[Chemical 3]
(Where
[Formula 4]
Is a propenoic acid ester having a single bond or a double bond). Preferable examples of propenoic acid ester include p -menta-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2-propenoic acid ester, p -menta-1,8-dien-7-yl 3 -(3,4-dihydroxyphenyl) -2-propenoic acid ester.
[0005]
The present invention further comprises a food flavor deterioration preventing agent comprising the above propenoic acid ester.
The propenoic acid ester having the formula (I) is a novel compound, and can be obtained by extracting aothylmendiso with a solvent such as methanol or ethanol, or by reacting caffeic acid with cisool.
[0006]
The deterioration preventing agent of the present invention may be a propenoic acid ester as it is, or may be in the form of a composition with an appropriate diluent or carrier. Examples of diluents or carriers include water, ethanol, propylene glycol, glycerin, vegetable oils, animal oils, gum arabic, dextrin, cyclodextrin, sorbitol, quilla extract, gelatin and the like. The dosage form can be emulsified or powdered.
[0007]
Examples of preferred foods to which the deterioration preventing agent of the present invention is applied include fruit juice beverages, fruit juice beverages, alcoholic beverages, etc. filled in bottles, cans, paper containers, etc., which are packaged in bottles, bags, plastic containers. Examples include pickles and boiled sardines. In particular, it is effective in preventing flavor deterioration of beverages using citrus flavors using natural essential oils and perilla flavored foods. When used as a deterioration inhibitor, the amount of propenoic acid ester is about 0.0001 to 0.1% by weight, preferably about 0.0001 to 0.02% by weight, based on food.
[0008]
BEST MODE FOR CARRYING OUT THE INVENTION
〔Example〕
Next, the present invention will be described more specifically with reference to examples.
Example 1
After extracting 2.12 kg of methanol extract from dry ground part of Perilla frutescens Britton var. Crispa (Thunb.) With hexane, water was added to the methanol layer and extracted with ethyl acetate, and 36.2 g of ethyl acetate fraction was extracted. obtain. Further, the ethyl acetate fraction is subjected to silica gel column chromatography and HPLC to obtain 13.7 mg of p -mentha-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2-propenoate.
[0009]
Example 2
Caffeic acid (2.5 g: 13.9 mmol), Sisool (3.2 g: 20.9 mmol) and p-toluenesulfonic acid (1.32 g) were dissolved in a mixed solution of benzene (60 ml) -tetrahydrofuran (55 ml), Heat to reflux for 30 hours in the presence of argon. To this mixed solution is added brine and extracted with ethyl acetate. The organic layer is washed with a saturated aqueous sodium bicarbonate solution and brine, dehydrated and concentrated. The concentrate was purified by column (ODS) and HPLC, recrystallized in a mixed solution of ether-hexane and 150 mg of p -menta-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2. -Propenoic acid ester is obtained. (Yield 3.4%)
Spectral data:
MS (EI): M + 316
1 H-NMR (CD 3 OD: δ ppm)
7.56 (1H, d, J = 15.9Hz), 7.07 (1H, d, J = 2.0Hz), 6.98 (1H, dd, J = 8.3,2. 0Hz), 6.81 (1H, d, J = 8.3Hz) , 6.29 (1H, d, J = 15.9Hz), 4.70 (2H, m), 1.74 (1H, s), 4.02 (2H, d, J = 6.3Hz), 1.98-1.80 (6H, m), 1.74 ( 3H, s), 1.40-1.0 5 (4H, m)
13 C-NMR (CD 3 OD: δ ppm)
169.4, 151.6, 149.6, 146.8, 146.8, 127.8, 122.9, 116.5, 115.1, 115.1, 108.8, 70.5, 46.7, 38.5, 32.3, 30.8, 21.1
[0010]
Example 3
As a model system for alcoholic beverages, 0.0003 part by weight of perilla oil is dissolved in 100 parts by weight of a mixed solution of water: ethanol = 4: 6 to prepare a perilla flavored perilla solution. A predetermined amount of p -menta-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2-propenoate is added and dissolved in this solution, and oxygen is blown into the solution. This solution was filled in a transparent glass bottle and sealed, and then irradiated with ultraviolet light (≦ 400 nm; Toshiba “FL20BLB” × 2 + “FL20SE” × 2) for 16 hours. The degree of deterioration of the perilla solution was evaluated by the change of perilaldehyde using HPLC. The results are shown in Table 1.
[0011]
[Table 1]
[0012]
Example 4
As a model system of an alcoholic beverage, 0.0019 parts by weight of citral is dissolved in 100 parts by weight of a mixed solution of water: ethanol = 4: 6 to prepare a lemon solution having a lemon flavor. A predetermined amount of p -menta-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2-propenoate is added and dissolved in this solution, and oxygen is blown into the solution. This solution was filled in a transparent glass bottle and sealed, and then irradiated with ultraviolet light (≦ 400 nm; Toshiba “FL20BLB” × 2 + “FL20SE” × 2) for 16 hours. The degree of deterioration of the lemon solution was evaluated by HPLC using citral. The results are shown in Table 2.
[0013]
[Table 2]
[0014]
The total amount is made up to 1000 ml with water, and a predetermined amount of p -menta-8-en-7-yl 3- (3,4-dihydroxyphenyl) -2-propenoate is added and dissolved. This solution was filled into a 200 ml can and sterilized at 65 ° C. for 10 minutes to prepare a lemon-flavored shochu.
[0015]
【The invention's effect】
By adding the propenoic acid ester of the present invention, deterioration of food flavor can be effectively prevented. In particular, it is effective for preventing flavor deterioration of beverages using citrus flavors using natural essential oils and perilla flavored foods.
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03934396A JP3863936B2 (en) | 1996-02-27 | 1996-02-27 | Degradation preventive for food flavor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03934396A JP3863936B2 (en) | 1996-02-27 | 1996-02-27 | Degradation preventive for food flavor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH09227456A JPH09227456A (en) | 1997-09-02 |
JP3863936B2 true JP3863936B2 (en) | 2006-12-27 |
Family
ID=12550448
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP03934396A Expired - Lifetime JP3863936B2 (en) | 1996-02-27 | 1996-02-27 | Degradation preventive for food flavor |
Country Status (1)
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JP (1) | JP3863936B2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69836328T2 (en) * | 1997-06-23 | 2007-05-31 | Naturex Inc. | STORAGE-STABLE, CITRUSAROMATISED COMPOSITIONS CONTAINING PLANT EXTRACTS |
JP4291988B2 (en) * | 2002-09-30 | 2009-07-08 | 小川香料株式会社 | Method for suppressing deterioration odor generation of citral or citral-containing products |
US9028886B2 (en) | 2007-07-13 | 2015-05-12 | Ogawa & Co., Ltd. | Degradation inhibitor for flavor or aroma |
JP7305297B2 (en) * | 2017-10-31 | 2023-07-10 | サッポロビール株式会社 | Alcoholic beverage and method for improving flavor of alcoholic beverage |
-
1996
- 1996-02-27 JP JP03934396A patent/JP3863936B2/en not_active Expired - Lifetime
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Publication number | Publication date |
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JPH09227456A (en) | 1997-09-02 |
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