JPH01132344A - Food and drink - Google Patents
Food and drinkInfo
- Publication number
- JPH01132344A JPH01132344A JP63264222A JP26422288A JPH01132344A JP H01132344 A JPH01132344 A JP H01132344A JP 63264222 A JP63264222 A JP 63264222A JP 26422288 A JP26422288 A JP 26422288A JP H01132344 A JPH01132344 A JP H01132344A
- Authority
- JP
- Japan
- Prior art keywords
- food
- natural products
- acid
- fading
- drink
- 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.)
- Granted
Links
- 235000013305 food Nutrition 0.000 title claims abstract description 17
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims abstract description 31
- 238000005562 fading Methods 0.000 claims abstract description 22
- 239000000049 pigment Substances 0.000 claims abstract description 20
- 235000001368 chlorogenic acid Nutrition 0.000 claims abstract description 17
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 claims abstract description 16
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims abstract description 16
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 claims abstract description 16
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 claims abstract description 16
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 claims abstract description 16
- 229940074393 chlorogenic acid Drugs 0.000 claims abstract description 16
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 claims abstract description 16
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000004883 caffeic acid Nutrition 0.000 claims abstract description 15
- 229940074360 caffeic acid Drugs 0.000 claims abstract description 15
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229930014626 natural product Natural products 0.000 claims abstract description 15
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 23
- 239000000203 mixture Substances 0.000 abstract description 12
- 239000003085 diluting agent Substances 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 229920000084 Gum arabic Polymers 0.000 abstract description 4
- 235000010489 acacia gum Nutrition 0.000 abstract description 4
- 239000000205 acacia gum Substances 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 4
- 239000002552 dosage form Substances 0.000 abstract description 3
- 239000000796 flavoring agent Substances 0.000 abstract description 2
- 235000019634 flavors Nutrition 0.000 abstract description 2
- 229930002877 anthocyanin Natural products 0.000 abstract 3
- 235000010208 anthocyanin Nutrition 0.000 abstract 3
- 239000004410 anthocyanin Substances 0.000 abstract 3
- 150000004636 anthocyanins Chemical class 0.000 abstract 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 241000978776 Senegalia senegal Species 0.000 abstract 1
- 230000004075 alteration Effects 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 235000013361 beverage Nutrition 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241000533293 Sesbania emerus Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 244000151637 Sambucus canadensis Species 0.000 description 2
- 235000018735 Sambucus canadensis Nutrition 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000007123 blue elder Nutrition 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000011850 desserts Nutrition 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 235000007124 elderberry Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000008995 european elder Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- -1 glycose Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JOSXFMSHEQLBHG-TZYSVLOISA-N (3R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enyl]-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound C(\C=C\C1=CC(O)=C(O)C=C1)[C@]1(CC(C[C@H](C1O)O)(C(=O)O)O)O JOSXFMSHEQLBHG-TZYSVLOISA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical group O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000005206 Hibiscus Nutrition 0.000 description 1
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 1
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 238000004649 discoloration prevention Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SDBVEUJRZKHWSH-VEELZWTKSA-M sodium (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate Chemical compound [Na+].OC1=CC=C(\C=C\C([O-])=O)C=C1O SDBVEUJRZKHWSH-VEELZWTKSA-M 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は、酸素、光などに対して不安定である点でその
利用上トラブルのあるアントンアニン系色素含有飲料物
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antonine-based pigment-containing beverage that is problematic in its use because it is unstable to oxygen, light, and the like.
更に詳しくは、本発明は、天然物から分離されたクロロ
ゲン酸及び/又は合成もしくは天然物から分離されたカ
フェー酸を有効成分とする退色防止剤を、アントンアニ
ン系色素含有飲料物中に含有することを特徴とする飲食
物に関する。More specifically, the present invention contains an antifading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid isolated from a synthetic or natural product as an active ingredient in a beverage containing an anthonaniline pigment. This invention relates to food and drink characterized by the following.
例えば、ブドウ果皮色素、ハイビスカス色素、エルダー
ベリー色素、ラズベリー色素、シソ色素その他の天然も
しくは合成アントンアニン系色素は、赤色乃至赤紫色系
色調を賦与する色素として、例えば、飲食物、化粧品、
保健・医薬品などの分野で利用され、とくに飲食物の着
色に広く利用されている。For example, grape skin pigments, hibiscus pigments, elderberry pigments, raspberry pigments, perilla pigments, and other natural or synthetic anthonanine pigments are used as pigments that impart red to reddish-purple hues, for example, in foods, drinks, cosmetics, etc.
It is used in fields such as health care and medicine, and is especially widely used for coloring food and drinks.
このようなアントンアニン系色素は、酸素、光などに対
して不安定であることは良く知られており、また、水溶
液中でpHが低酸性側から中性に近づくに従って著るし
く不安定となり、退色乃至変色(本発明においては退色
と総称する)するトラブルのあることも知られている。It is well known that such anthonanine dyes are unstable to oxygen, light, etc., and they become significantly unstable in aqueous solutions as the pH approaches neutrality from low acidity. It is also known that there is a problem of fading or discoloration (generally referred to as discoloration in the present invention).
更に、アントンアニン系色素では、アスコルビン酸の存
在下では光のみならず熱に対しても著るしく不安定で退
色し易いことが知られている。Furthermore, it is known that in the presence of ascorbic acid, anthonanine dyes are extremely unstable not only to light but also to heat and are susceptible to fading.
従来、このようなアントンアニン系色素が有する不安定
性のトラブルを克服する目的で種々の安定化成分を配合
して安定化しようとする試みや提案がなされてきたが、
充分満足すべき効果が得られないのが実情である。In the past, attempts and proposals have been made to stabilize the antonine dyes by incorporating various stabilizing components in order to overcome the problem of instability that they have.
The reality is that a fully satisfactory effect cannot be obtained.
本発明者等は、このようなアントンアニン系色素の退色
のトラブルを克服できる退色防止剤の開発について研究
を行ってきた。The present inventors have conducted research on the development of an anti-fading agent that can overcome the problem of fading of anthonanine dyes.
その結果、天然物から分離されたクロロゲン酸及び/又
は合成もしくは天然物から分離されたカフェー酸がアン
トンアニン系色素の退色に対して、優れた防止効果を発
揮することを発見した。更に、アスコルビン酸の存在下
では光のみならず熱に対しても退色し易いアントンアニ
ン系色素の退色防止に際して、アスコルビン酸の存在下
でも優れた防止効果を発揮することを知った。又更に、
前述の如きこれら色素の利用される広い分野で退色防止
剤として有用であるが、とくにこれら色素を含有する飲
食物分野において好適に利用でき、飲食物に不都合な香
味変調を生ずることなしに、優れた退色防止効果を賦与
できる優れた防止剤であることがわかった。As a result, it has been discovered that chlorogenic acid isolated from natural products and/or caffeic acid isolated from synthetic or natural products exhibits an excellent preventive effect against fading of anthonanine pigments. Furthermore, it has been found that in the presence of ascorbic acid, an excellent preventive effect is exhibited even in the presence of ascorbic acid in preventing the fading of anthonanine pigments that are susceptible to fading not only by light but also by heat. Furthermore,
These pigments are useful as anti-fading agents in a wide range of fields where they are used, as mentioned above, but they are particularly suitable for use in the field of foods and beverages that contain these pigments, and can be used as an excellent anti-fading agent without causing any unfavorable flavor changes in foods or beverages. It was found that it is an excellent inhibitor that can provide a discoloration prevention effect.
従って、本発明の目的はアントンアニン系色素を含有す
る飲食物への利用を提供するにある。Therefore, an object of the present invention is to provide the use of anthonaniline pigments in foods and drinks containing them.
本発明の上記目的及び更に多くの他の目的ならびに利点
は、以下の記載から一層明らかとなるであろう。The above objects and many other objects and advantages of the present invention will become more apparent from the following description.
クロロゲン酸(3−カフエイルキナ酸)は、下記式
で表わすことのできる化合物であって、たとえばコーヒ
ー豆中にクロロゲン酸カリウムカフェインの形で含有さ
れ、微量にはタバコ葉、サツマイモ、ナシ葉、茶菓、リ
ンゴ果肉その他広く植物中に分布する。又、カフェー酸
(3,4−ジオキシケイ皮酸、3,4−ジオキシニラケ
イ酸は、下記式で表わすことのできる化合物であって、
コーヒータンニンの水酸化カリウムケン化物として単離
され、又、1878年T iemannらにより合成さ
れた。Chlorogenic acid (3-caffeylquinic acid) is a compound that can be represented by the following formula, and is contained, for example, in the form of potassium chlorogenic acid caffeine in coffee beans, and in trace amounts in tobacco leaves, sweet potatoes, pear leaves, and tea confectionery. , apple pulp and other plants are widely distributed. In addition, caffeic acid (3,4-dioxycinnamic acid, 3,4-dioxynillasilicic acid is a compound that can be represented by the following formula,
It was isolated as a saponified potassium hydroxide product of coffee tannin, and was also synthesized in 1878 by Tiemann et al.
針葉樹皮、タデ科植物、タバコなどに遊離状で存在する
が、クロロゲン酸としてコーヒー豆をはじめ広く分布す
る。クロロゲン酸からキナ酸部分を脱離させて得ること
もできる。本発明においてはこれらクロロゲン酸及び/
又はカフェー酸が利用され、本発明においては核酸の水
溶性塩酸を包含する呼称である。例えば、カフェー酸ナ
トリウム、カフェー酸カリウムの如き塩類を例示できる
。It exists in free form in coniferous bark, Polygonaceae, tobacco, etc., but is widely distributed as chlorogenic acid, including coffee beans. It can also be obtained by removing the quinic acid moiety from chlorogenic acid. In the present invention, these chlorogenic acids and/or
Alternatively, caffeic acid is used, and in the present invention, the name includes water-soluble hydrochloric acid of nucleic acids. For example, salts such as sodium caffeate and potassium caffeate can be exemplified.
本発明の退色防止剤に於ては、上述の如き天然物から分
離されたクロロゲン酸及び/又は合成もしくは天然物か
ら分離されたカフェー酸が有効成分である。本発明退色
防止剤は、これら有効成分の100%から成っていても
よいし、これら有効成分と適当な希釈剤もしくは担体と
の組成物の形態であってもよい。このような希釈剤もし
くは担体の例としては、アラビアガム、デキストリン、
グリコース、シュクロースなどの如き固体希釈剤もしく
は担体、水、エタノール、プロピレングリコール、グリ
セリン、界面活性剤、などの如き液体希釈剤もしくは担
体を例示することができる。In the antifading agent of the present invention, chlorogenic acid isolated from natural products as described above and/or caffeic acid isolated from synthetic or natural products are active ingredients. The antifading agent of the present invention may consist of 100% of these active ingredients, or may be in the form of a composition of these active ingredients and a suitable diluent or carrier. Examples of such diluents or carriers include gum arabic, dextrin,
Examples include solid diluents or carriers such as glycose, sucrose, etc., liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin, surfactants, and the like.
本発明の退色防止剤は、任意の剤形で利用してよく、例
えば、粉末状、顆粒状、液状、乳液状、ペースト状その
他適宜の剤形であることができる。The antifading agent of the present invention may be used in any desired dosage form, such as powder, granules, liquid, emulsion, paste, or other appropriate dosage forms.
更に、本発明の退色防止剤は、アントンアニン系色素と
の配合物の形態であってもよい。Further, the antifading agent of the present invention may be in the form of a blend with an anthonaniline dye.
例えば、アラビアガム、デキストリンなどを添加して粉
末状、顆粒状などの剤形で使用しても良く、また例えば
エタノール、プロピレングリフール、グリセリン、或い
はこれらの混合物に溶解して液状剤形として使用するこ
ともでき、更に例えばアラビアガムなどの天然ガム質、
或いは界面活性剤を添加して乳液状剤形として使用して
も良い。For example, it may be used in a powdered or granular form by adding gum arabic, dextrin, etc., or it may be used as a liquid form by dissolving it in, for example, ethanol, propylene glyfur, glycerin, or a mixture thereof. In addition, natural gums such as gum arabic,
Alternatively, it may be used as an emulsion by adding a surfactant.
本発明の天然物から分離されたクロロゲン酸及び/又は
合成もしくは天然物から分離されたカフェー酸を有効成
分とする上記退色防止剤を利用して、該退色防止剤をア
ントンアニン系色素含有飲食物中に含有することを特徴
とする飲食物を提供することができる。Utilizing the above-mentioned anti-fading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid isolated from a synthetic or natural product as an active ingredient, the anti-fading agent can be added to an anthonaniline pigment-containing food or drink. It is possible to provide a food or drink characterized by containing the following.
このような飲食品の例としては、無果汁飲料、果汁入飲
料、乳酸菌飲料、粉末飲料などの如き飲料類;アイスク
リーム、シャーベット、氷菓などの如き冷菓類ニブリン
、ゼリー、ババロア、ヨーグルトなどの如きデザート食
品類などを例示することができる。Examples of such foods and drinks include beverages such as non-fruit juice beverages, beverages with fruit juice, lactic acid bacteria beverages, powdered beverages, etc.; frozen desserts such as ice cream, sherbet, frozen desserts, etc.; Examples include dessert foods.
本発明の退色防止剤の添加量は、適宜な退色防止量を選
択できるが、クロロゲン酸及び/又はカフェー酸として
、例えば、約0.001〜約0.5重量%程度、更には
約0.O1〜約0.1重量%程度の範囲を好ましくは例
示できる。The amount of the anti-fading agent of the present invention to be added can be selected to be an appropriate anti-fading amount, but for example, about 0.001 to about 0.5% by weight, more preferably about 0.001 to about 0.5% by weight, as chlorogenic acid and/or caffeic acid. A preferable example is a range of O1 to about 0.1% by weight.
本発明で利用するクロロゲン酸及び/又はカフェー酸は
市場で入手可能であるが、天然物に由来するクロロゲン
酸及び/又はカフェー酸は、必らずしも純品である必要
はなく、例えば下記の如くして得ることができる。The chlorogenic acid and/or caffeic acid used in the present invention are commercially available, but the chlorogenic acid and/or caffeic acid derived from natural products do not necessarily have to be pure products, such as the following: It can be obtained as follows.
粉砕したコーヒー生豆に、例えば約0.5乃至約20倍
重量のエタノールもしくは含水エタノールを添加して、
たとえば約60℃乃至約100℃で、たとえば約1時間
乃至約10時間加熱する。For example, by adding about 0.5 to about 20 times the weight of ethanol or water-containing ethanol to the ground coffee beans,
For example, heating at about 60° C. to about 100° C., for example, for about 1 hour to about 10 hours.
冷却後、不溶性固形分を分離、除去して得られる抽出液
に、塩酸濃度がたとえば約3〜lO%になるように塩酸
を添加して、たとえば約50°c−100°Cで、たと
えば約30分乃至約5時間加熱撹拌する。次いで濃縮後
、該濃縮溶液をたとえば多孔性重合樹脂で処理して該樹
脂に吸着させ、次いで該樹脂をたとえばエタノールで溶
出処理して、クロロゲン酸及び/又はカフェー酸を得る
ことができる。After cooling, hydrochloric acid is added to the extract obtained by separating and removing insoluble solids so that the concentration of hydrochloric acid is, for example, about 3 to 10%, and the mixture is heated at, for example, about 50°C to 100°C, for example, about Heat and stir for 30 minutes to about 5 hours. After concentration, the concentrated solution can then be treated with, for example, a porous polymeric resin to adsorb onto the resin, and then the resin can be eluted with, for example, ethanol to obtain chlorogenic acid and/or caffeic acid.
以下、実施例により、本発明防止剤含有飲食物の調製及
び退色防止効果などについて、更に詳しく例示する。Hereinafter, the preparation of the food and drink containing the inhibitor of the present invention and the effect of preventing fading will be illustrated in more detail with reference to Examples.
実施例1
コーヒー生豆300gをコーヒーミルにて粉砕し、この
粉砕物に5倍重量の70%エタノール水溶液を加えて、
90℃、2時間撹拌加熱した。冷却後不溶性固形分を除
去して、抽出液1.loogを得た。次いでこれに35
%塩酸180gを加えて、抽出液中の塩酸濃度が約5%
になるように調整し、70°O,1時間撹拌加熱した。Example 1 300 g of green coffee beans were ground in a coffee mill, and 5 times the weight of a 70% aqueous ethanol solution was added to the ground product.
The mixture was stirred and heated at 90°C for 2 hours. After cooling, insoluble solids were removed and extract 1. I got loog. Then 35 to this
Add 180g of hydrochloric acid to reduce the concentration of hydrochloric acid in the extract to approximately 5%.
The mixture was stirred and heated at 70°O for 1 hour.
冷却後減圧下で300gになるまで濃縮し、得られた濃
縮液=7−
に20%水酸化ナトリウムを添加してpH11以上に調
整し、次いで塩化メチレン600gを加えて充分撹拌混
合した。水相を分離し、これに10%塩酸を加えてpH
を6〜7に調整し、このpH調整液をダイヤイオンHP
−20樹脂500ccを充てんしたカラム中に徐々に流
した。次いで樹脂を充分水洗した後95%エタノール3
00gを流して樹脂にi着した物質を溶出させ、得られ
た溶液を減圧濃縮後、乾燥してクロロゲン酸及びカフェ
ー酸の混合物的12gを得た。After cooling, the mixture was concentrated under reduced pressure to 300 g, and 20% sodium hydroxide was added to the resulting concentrated solution (7-) to adjust the pH to 11 or higher. Then, 600 g of methylene chloride was added and the mixture was thoroughly stirred and mixed. Separate the aqueous phase and add 10% hydrochloric acid to adjust the pH.
Adjust the pH to 6 to 7, and add this pH adjustment solution to Diaion HP.
-20 resin was gradually poured into a column filled with 500 cc. Next, after washing the resin thoroughly with water, 95% ethanol 3
The substance adhering to the resin was eluted by flowing 00 g of the resin, and the resulting solution was concentrated under reduced pressure and dried to obtain 12 g of a mixture of chlorogenic acid and caffeic acid.
実施例2〜5
ブドウ果皮色素をpH3の酒石酸ソーダ緩衝液にて希釈
してODo、54に調整した。次いでこの色素水溶液に
本発明による退色防止剤を添加して、無色透明の100
mffびんに入れ、6時間日光照射して色素残存率を測
定した。その結果を法衣に示した。本発明による退色防
止剤は、アンドシアン色素に対して著しい退色防止効果
を示すことが分った。Examples 2 to 5 Grape skin pigments were diluted with a pH 3 sodium tartrate buffer to adjust the ODo to 54. Next, the anti-fading agent according to the present invention is added to this dye aqueous solution to obtain a colorless and transparent 100%
It was placed in an mff bottle, exposed to sunlight for 6 hours, and the dye residual rate was measured. The results were shown on the robe. It has been found that the anti-fading agent according to the present invention exhibits a remarkable anti-fading effect on andocyan dyes.
8一 実施例6 エルダベリー色素水溶液(OD 350/g) l 。81 Example 6 Elderberry dye aqueous solution (OD 350/g) 1.
Og、砂糖120g、酒石酸0.2gsクエン酸1゜2
g、 ビタミンCI 、Ogの混合物に水を加えてHと
する。これにカフェー酸0.2!5g添加して200m
Q透明びんに入れ、6時間日光照射して色素残存率を測
定したところ85%であった。一方退色防止剤を添加し
なかった対照品の色素残存率は55%であった。Og, sugar 120g, tartaric acid 0.2gs citric acid 1゜2
Add water to a mixture of g, vitamin CI, and Og to obtain H. Add 0.2!5g of caffeic acid to this and make 200m
When placed in a Q transparent bottle and exposed to sunlight for 6 hours, the dye residual rate was measured and found to be 85%. On the other hand, the dye residual rate of the control product to which no anti-fading agent was added was 55%.
Claims (1)
もしくは天然物から分離されたカフエー酸を有効成分と
する退色防止剤を、アントンアニン系色素含有飲食物中
に含有することを特徴とする飲食物。1. A food or drink characterized by containing an anti-fading agent containing chlorogenic acid isolated from a natural product and/or caffeic acid separated from a synthetic or natural product as an active ingredient in an anthonaniline pigment-containing food or drink. thing.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63264222A JPH01132344A (en) | 1988-10-21 | 1988-10-21 | Food and drink |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63264222A JPH01132344A (en) | 1988-10-21 | 1988-10-21 | Food and drink |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56162799A Division JPS5865761A (en) | 1981-10-14 | 1981-10-14 | Fading inhibitor for coloring matter and utilization thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01132344A true JPH01132344A (en) | 1989-05-24 |
JPH0333298B2 JPH0333298B2 (en) | 1991-05-16 |
Family
ID=17400194
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63264222A Granted JPH01132344A (en) | 1988-10-21 | 1988-10-21 | Food and drink |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01132344A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002233330A (en) * | 2001-02-08 | 2002-08-20 | Sanei Gen Ffi Inc | Discoloring inhibitor |
WO2007096643A1 (en) * | 2006-02-23 | 2007-08-30 | Med-Eq As | Tea |
CN102835649A (en) * | 2012-01-18 | 2012-12-26 | 天津天康源生物技术有限公司 | Gardenia yellow pigment colour retention agent and preparation method thereof |
CN105199425A (en) * | 2015-10-12 | 2015-12-30 | 南京农业大学 | Extraction method of cyanidin |
-
1988
- 1988-10-21 JP JP63264222A patent/JPH01132344A/en active Granted
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002233330A (en) * | 2001-02-08 | 2002-08-20 | Sanei Gen Ffi Inc | Discoloring inhibitor |
WO2007096643A1 (en) * | 2006-02-23 | 2007-08-30 | Med-Eq As | Tea |
CN102835649A (en) * | 2012-01-18 | 2012-12-26 | 天津天康源生物技术有限公司 | Gardenia yellow pigment colour retention agent and preparation method thereof |
CN105199425A (en) * | 2015-10-12 | 2015-12-30 | 南京农业大学 | Extraction method of cyanidin |
Also Published As
Publication number | Publication date |
---|---|
JPH0333298B2 (en) | 1991-05-16 |
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