JPH02265433A - Preparation of natural bitter substance - Google Patents
Preparation of natural bitter substanceInfo
- Publication number
- JPH02265433A JPH02265433A JP1083963A JP8396389A JPH02265433A JP H02265433 A JPH02265433 A JP H02265433A JP 1083963 A JP1083963 A JP 1083963A JP 8396389 A JP8396389 A JP 8396389A JP H02265433 A JPH02265433 A JP H02265433A
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- water
- bitter
- coffee
- extract
- 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
- 239000000126 substance Substances 0.000 title claims abstract description 35
- 235000013353 coffee beverage Nutrition 0.000 claims abstract description 26
- 235000016213 coffee Nutrition 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000284 extract Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000243 solution Substances 0.000 abstract description 3
- 239000000839 emulsion Substances 0.000 abstract description 2
- 239000006072 paste Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000006188 syrup Substances 0.000 abstract description 2
- 235000020357 syrup Nutrition 0.000 abstract description 2
- 235000019658 bitter taste Nutrition 0.000 description 18
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 238000000605 extraction Methods 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 6
- 229960001948 caffeine Drugs 0.000 description 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 6
- 241000533293 Sesbania emerus Species 0.000 description 5
- 235000021539 instant coffee Nutrition 0.000 description 5
- 235000013361 beverage Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019629 palatability Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- -1 uracil compound Chemical class 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- VHLJDTBGULNCGF-UHFFFAOYSA-N Limonin Natural products CC1(C)OC2CC(=O)OCC23C4CCC5(C)C(CC(=O)C6OC56C4(C)C(=O)CC13)c7cocc7 VHLJDTBGULNCGF-UHFFFAOYSA-N 0.000 description 1
- OLHLJBVALXTBSQ-UHFFFAOYSA-N Lupulone Natural products CC(C)CC(=O)C1C(=O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O OLHLJBVALXTBSQ-UHFFFAOYSA-N 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPVSVIXDXMNGGN-UHFFFAOYSA-N beta-bitter acid Natural products CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O WPVSVIXDXMNGGN-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- YDAFVJGIRJZGKB-UHFFFAOYSA-N hulupone Chemical compound CC(C)CC(=O)C1=C(O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O YDAFVJGIRJZGKB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- KBDSLGBFQAGHBE-MSGMIQHVSA-N limonin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@@H]2[C@]34COC(=O)C[C@@H]3OC2(C)C)C=COC=1 KBDSLGBFQAGHBE-MSGMIQHVSA-N 0.000 description 1
- 235000020094 liqueur Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Landscapes
- Compounds Of Unknown Constitution (AREA)
- Tea And Coffee (AREA)
- Jellies, Jams, And Syrups (AREA)
- Seasonings (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、飲食品、医薬品その他の広い分野において利
用可能な、嫌みのない天然の苦味物質の製法に間し、更
に詳しくは、焙煎コーヒーの水抽出物に、水混和性有機
溶媒を添加し、生成する不溶性物質を除去して有機溶媒
可溶部を採取する方法において、該有機溶媒の濃度が４
０！量％以上となるように処理することを特徴とする天
然苦味物質の製法に関する。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a method for producing a natural bitter substance that is not unpleasant and can be used in a wide range of fields such as food and beverages, pharmaceuticals, etc. A method in which a water-miscible organic solvent is added to a water extract of coffee, the resulting insoluble substances are removed, and the organic solvent-soluble portion is collected, and the concentration of the organic solvent is 4.
0! % or more.
（従来の技術）
飲食品における苦味という感覚は一般的にはあまり好ま
れるものではないが、一方では、例えばビール、コーヒ
ー ビタードリンク、ある種のスパイス等にみられるよ
うにほろ苦味を身上とする飲食品もある。そしてこれら
の飲食品に特徴的な苦味を呈する物質として、アルカロ
イド、テルペン、配糖体、アミノ酸、ペプチド、ニトロ
化合物など多くの物質が知られている。(Prior art) Although the sensation of bitterness in food and beverages is generally not well-liked, on the other hand, there are people who experience bitterness as seen in beer, coffee bitter drinks, certain spices, etc. There are also food and drinks. Many substances, such as alkaloids, terpenes, glycosides, amino acids, peptides, and nitro compounds, are known to cause the characteristic bitter taste of these foods and drinks.
また、飲食品等に苦味を賦与することを目的とした苦味
料に関する提案も多くなされている。Furthermore, many proposals have been made regarding bittering agents for the purpose of imparting bitterness to foods and drinks.
例えば、苦味を有する特定のウラシル化合物を含有する
苦味料（特開昭６０−６６９５３号公報）；２． ６．
ｔ−ｅ″−テトラクロロ−２，６゜１− ６−−テ
トラデオキシマンノシユークロースからなる苦味賦与剤
（特開昭５５−９２８６９号公報）； リモニン（ｌｌ
ｍｏｎｉｎＬ ノミリン（ｎ ｏｍ ｉ １ ｉ ｎ
Ｌ ナリンジン（ｎａｌｉ−ｎｇｉｎ）を飲食品に添
加するフレーバー等の改善法（米国特許第４４７９９７
２号明細書）； シュークロース・ジー、 トリー、及
びテトラ−ベンゾ エ − ） にｕｃｒｏｓｅ
ｄｉ ＋、 ｔｒｉ −ａｎｄｔｅ
ｔｒａ−ｂｅｎｚｏａｔｅ）を飲食品の苦味物質とて利
用する提案（英国特許第４８２５１号明細書〉；植物起
海のシナロビクリン（Ｃ−ｙｎａｒｏｐｉｃｒ １ｎｅ
）をキニンの代わりにビターレモン等の飲料の苦味剤と
して添加する提案（***特許第２６５４１８４号明編書
）；テオブロミン（ｔｈｅｏｂｒｏｍｉｎｅ）と苦味を
有するジペブタイド、例えばシクロフェニルアラニルフ
ェニルアラニン（ｃｙｃ Ｉ ｏｐｈｅｎｙ １−ａｌ
ａｎｙｌｐｈｅｎｙｌａｌａｎｉｎｅＬシクロフェニル
アラニルバリン（ｃｙｃ １ｏｐｈ−ｅｎｙｌａｌａｎ
ｙｌｖａｌｌｎｅ）等を飲食品に添加してビターノート
を与える提案（西郷特許第２４４５６７４号明細書）；
ホップから抽出されたルブロン（ｌｕｐｕｌｏｎｅ）
を酸化して得られるフルポン（ｈｕｌｕｐｏｎｅ）をビ
ールの苦味成分とする提案（***特許第２３４８０５８
号明細書）等々の多数の提案がある。For example, a bittering agent containing a specific uracil compound having a bitter taste (Japanese Unexamined Patent Publication No. 60-66953);2. 6.
Bitterness imparting agent consisting of t-e''-tetrachloro-2,6゜1-6-tetradeoxymannosucrose (Japanese Unexamined Patent Publication No. 1983-92869); Limonin (ll
moninL moninL
Method for improving flavor, etc. by adding L nali-ngin to food and drink products (US Patent No. 447997)
(Specification No. 2);
di +, tri -andte
Proposal to use C-benzoate as a bitter substance in foods and drinks (UK Patent No. 48251);
) as a bittering agent for beverages such as bitter lemon instead of quinine (West German Patent No. 2654184); Theobromine and dipebutide having a bitter taste, such as cyclophenylalanylphenylalanine (cyc I opheny 1) -al
anyylphenylalanineL cyclophenylalanine
Proposal to add bitter notes to foods and drinks (Saigo Patent No. 2445674);
Lupulone extracted from hops
A proposal to use hulupone, which is obtained by oxidizing
There are many proposals such as
〈発明が解決しようとする’３Ｂ＞
上記した如き従来の提案は、（１）何れも食品添加物と
しての安全性の問題或いは！Ａ製方法が煩雑である、（
２）それ自体生理活性があり使用上の制約がある、（３
）水に対する溶解性が劣る等の多くの欠点があり必ずし
も満足できるものではない。<The '3B's that the invention seeks to solve> The conventional proposals as mentioned above are either (1) a problem of safety as a food additive or! A manufacturing method is complicated (
2) It is physiologically active and has restrictions on use; (3)
) It has many drawbacks such as poor solubility in water, and is not necessarily satisfactory.
本発明はこれら従来提案の欠点を解決した、入手容易な
天然原料から簡便な手段によって、安価で且つ安全性の
高い天然の苦味物質を工業的に有利に安定供給すること
を目的とする。The purpose of the present invention is to overcome the drawbacks of these conventional proposals and provide an industrially advantageous and stable supply of inexpensive and highly safe natural bitter substances by simple means from readily available natural raw materials.
（ｒｌ、題を解決するための手段）
浅炒り、中炒り等の萱通の焙煎コーヒーの主要な苦味成
分がカフェインであることはよく知られている。コーヒ
ーの苦味は焙煎度により強くなり、例えば、イタリアン
、フレンチ、ブラシリアローストのような深炒りコーヒ
ー豆は非常に強い苦味を冑している。これらの苦味物質
の化学構成はまだ不明であり、これを飲食品の苦味賦与
剤として利用することは未だ知られていない。(rl, means to solve the problem) It is well known that the main bitter component of Kayadori roasted coffee, such as light roast and medium roast, is caffeine. The bitterness of coffee becomes stronger depending on the degree of roasting; for example, deeply roasted coffee beans such as Italian, French, and Brasilia roasts have a very strong bitterness. The chemical composition of these bitter substances is still unknown, and it is not yet known that they can be used as bitter taste imparting agents for foods and drinks.
本発明者らはこれらの知見に基づいて、焙煎コーヒーか
ら天然の苦味物質を製造する方法を検討し、先に、焙煎
コーヒー抽出液をスチレン−ジビニルベンゼン系又はメ
タアクリル酸エステル系合成多孔性樹脂吸着剤処理した
際に吸着された成分が極めて強い苦味を有し、しかもそ
の苦味は嫌みがなく嗜好性に優れ、汎用性のある非常に
優れた苦味物質であることを見出した。更に、焙煎コー
ヒーを常法によって水抽出し、得られた抽出液を、前記
合成吸着性樹脂で処理する前に、予め限外濾過処理する
と着色物質及び不溶性の高分子物質を分画することがで
き、次いで限外濾過液を合成吸着性樹脂で処理し、吸着
された成分を含水水混和性有機溶媒で溶出せしめること
により、−層純度が高く且つ強い苦味物質が得られるこ
とを見出して特許出願した（特願昭６３−１５６１３４
２）。Based on these findings, the present inventors investigated a method for producing a natural bitter substance from roasted coffee, and first, the roasted coffee extract was processed into a styrene-divinylbenzene-based or methacrylic acid ester-based synthetic porous material. It has been found that the components adsorbed when treated with a synthetic resin adsorbent have an extremely strong bitter taste, and that the bitter taste is not unpleasant and has excellent palatability, making it an extremely versatile bitter substance. Furthermore, roasted coffee is extracted with water by a conventional method, and the resulting extract is subjected to ultrafiltration in advance before being treated with the synthetic adsorptive resin to fractionate colored substances and insoluble polymer substances. We have discovered that by treating the ultrafiltrate with a synthetic adsorptive resin and eluting the adsorbed components with a water-containing water-miscible organic solvent, a highly bitter substance with high layer purity can be obtained. Patent application filed (Patent application 156134/1986)
2).
しかしながら上記出ＩＩ発明は、限外濾過、樹脂吸着処
理等の煩雑な工程を要するため、更に簡便な製法を開発
すべく検討した。However, since the above-mentioned invention of Exemplar II requires complicated steps such as ultrafiltration and resin adsorption treatment, studies were conducted to develop a simpler manufacturing method.
その結果、焙煎コーヒーの水抽出物に、水混和性有機溶
媒を添加し、生成する不溶性物質を除去して有機溶媒可
溶部を採取する方法において、該有機溶媒の濃度が４０
重量％以上となるように処理することにより、上記出願
発明に劣らない優れた嗜好性と持続性のある強い苦味物
質が得られることを見いだし本発明を完成した。As a result, in a method in which a water-miscible organic solvent is added to an aqueous extract of roasted coffee, the resulting insoluble substances are removed, and the organic solvent-soluble portion is collected, the concentration of the organic solvent is 40%.
The present invention has been completed based on the discovery that by processing the bitter substance so that the content is at least % by weight, it is possible to obtain a strongly bitter substance with excellent palatability and durability comparable to that of the above-mentioned invention.
以下、本発明の具体的な内容について説明する。Hereinafter, the specific content of the present invention will be explained.
本発明において利用することのできるコーヒーとしては
、通常飲用に供されている例えば、アラビカ種、ロブス
タ種などのあらゆる種類のコーヒー豆を常法によって約
２００〜約２５０℃で焙煎した焙煎コーヒーを挙げるこ
とができる。焙煎の程度は特に限定されるものではない
が、やや深炒り処理したコーヒー豆を好適に利用するこ
とができる。また、焙煎コーヒー豆は、そのまま粉砕し
て利用することができるが、予め水Ｍ気蒸留或いは不活
性ガス等によって揮発性の香気成分を回収した残渣であ
ってもよく、この残渣も本発明の焙煎コーヒーに包含さ
れる。The coffee that can be used in the present invention includes roasted coffee obtained by roasting all kinds of coffee beans, such as Arabica and Robusta, by a conventional method at about 200 to about 250°C. can be mentioned. Although the degree of roasting is not particularly limited, slightly deeply roasted coffee beans can be suitably used. Further, roasted coffee beans can be used by pulverizing them as they are, but they can also be used as a residue from which volatile aroma components have been recovered by water vapor distillation or inert gas, and this residue can also be used in the present invention. Included in roasted coffee.
抽出操作としては、上記のごとき焙煎粉砕コーヒー豆１
重量部に対し、約２〜５０１量部、好ましくは約２〜１
０重量部の水を加え、温度約２０〜約９５℃、好ましく
は約８０〜９５℃で約１０分〜１２０分間抽出を行う、
抽出操作はバッチ式又は複数のカラムによる連続式の何
れの方法も採用することができる。For the extraction operation, roasted and ground coffee beans as described above 1
About 2 to 501 parts by weight, preferably about 2 to 1 part by weight
Adding 0 parts by weight of water and performing extraction at a temperature of about 20 to about 95°C, preferably about 80 to 95°C, for about 10 to 120 minutes.
The extraction operation can be carried out either batchwise or continuously using a plurality of columns.
抽出終了後、カラム抽出の場合は一般的にはそのまま、
またバッチ式の場合は遠心分離、濾過などの手段により
コーヒー粕と抽出液を分離することにより、本発明で利
用する焙煎コーヒー水抽出物を得ることができる。得ら
れた抽出液はそのまま利用することもできるが、一般的
には有機溶媒処理に使用する溶媒量を節約するために、
ｍ縮物叉は乾燥物とするのが好ましい、濃縮物とする場
合には、例えば、減圧条件下に水を回収して可溶性固形
分濃度Ｂｒ１ｘ（以下Ｂｘとすることがある）約５０〜
７５″″ 好ましくは、Ｂｘ約６０〜７０°程度まで濃
縮する。After the extraction is complete, in the case of column extraction, generally
In the case of a batch method, the roasted coffee water extract used in the present invention can be obtained by separating coffee grounds and extract by means such as centrifugation or filtration. The obtained extract can be used as is, but in general, in order to save the amount of solvent used for organic solvent treatment,
It is preferable to use a condensate or a dried product. In the case of a concentrate, for example, water is collected under reduced pressure conditions and the soluble solids concentration Br1x (hereinafter referred to as Bx) is about 50 to
75″″ Preferably, Bx is concentrated to approximately 60 to 70°.
また、上記の操作によって得られる焙煎コーヒーの水抽
出物に代えて、市販の粉末状、顆粒状のインスタントコ
ーヒーまたは濃縮コーヒーエキス、濃縮冷凍コーヒーエ
キス等を利用することもできる。Furthermore, instead of the aqueous extract of roasted coffee obtained by the above procedure, commercially available powdered or granular instant coffee, concentrated coffee extract, concentrated frozen coffee extract, etc. can also be used.
さらに、本発明に利用できる水混和性有機溶媒としては
、例えば、メタノール、エタノール、イソプロピルアル
コール、アセトン及びメチルエチルケトン等を挙げるこ
とができる。Furthermore, examples of water-miscible organic solvents that can be used in the present invention include methanol, ethanol, isopropyl alcohol, acetone, and methyl ethyl ketone.
本発明のコーヒー苦味物質の採取方法としては、前記の
焙煎コーヒー水抽出物を、溶媒濃度４０重量％以上、即
ち含水量６０重量％以下の水混和性有機溶媒で抽出処理
すればよい、溶媒濃度が４０重量％以下の場合には苦味
物質以外の夾雑物の溶出を伴うので好ましくない。As a method for collecting coffee bitter substances of the present invention, the above-mentioned roasted coffee water extract may be extracted with a water-miscible organic solvent having a solvent concentration of 40% by weight or more, that is, a water content of 60% by weight or less. If the concentration is less than 40% by weight, impurities other than bitter substances will be eluted, which is not preferable.
抽出処理は、例えば、Ｂｘ５０〜７０”のｌＩ縮物１重
量部に対して、上記水混和性有機溶媒的０．４０〜１０
重量部、好ましくは、約１〜６重量部を加え、約５０〜
９０℃、好ましくは、約７０〜８０℃の温度にて約１０
分〜６０分、好ましくは、約３０分程度攪拌して苦味物
質を含水有機溶媒で抽出する。In the extraction process, for example, 0.40 to 10% of the water-miscible organic solvent is added to 1 part by weight of the II condensate of Bx50 to 70''.
parts by weight, preferably about 1 to 6 parts by weight, and about 50 to 6 parts by weight.
at a temperature of about 90°C, preferably about 70-80°C.
The mixture is stirred for 60 minutes to 60 minutes, preferably about 30 minutes, and bitter substances are extracted with a water-containing organic solvent.
抽出終了後、冷却して静置し、デカンテーション等によ
り有機溶媒不溶部を除去し、上澄液を分離する。得られ
た分離液は、エタノールのごとき可食性溶媒を用いた場
合にはそのまま苦味物質溶液として利用することができ
るが、一般的には常圧叉は減圧条件下に溶媒を除去し、
Ｂｘ７０°程度まで濃縮することにより本発明の天然苦
味物質を得ることができる。After the extraction is completed, the mixture is cooled and allowed to stand, the organic solvent insoluble portion is removed by decantation, etc., and the supernatant liquid is separated. The obtained separated liquid can be used as it is as a bitter substance solution if an edible solvent such as ethanol is used, but generally the solvent is removed under normal or reduced pressure conditions.
The natural bitter substance of the present invention can be obtained by concentrating to about Bx70°.
本発明の天然苦味物質は、用途に応じて任意の形態を選
択することができ、例えば、上記のごとき溶液状のほか
ペースト状、シロップ状、乳濁液状とすることができ、
更に所望により適宜の賦形剤、滑沢剤、担持剤を用いて
粉末状、顆粒状、叉は錠剤などの形態とすることができ
る。The natural bitter substance of the present invention can be in any form depending on the intended use; for example, in addition to the above-mentioned solution form, it can also be in the form of a paste, syrup, emulsion,
Furthermore, if desired, it can be made into a powder, granule, or tablet form by using appropriate excipients, lubricants, and carriers.
以下、実施例により本発明の好ましい態様を更に具体的
に説明する。Hereinafter, preferred embodiments of the present invention will be explained in more detail with reference to Examples.
（実施例）
実施例１
■コーヒーの水抽出
容量３１にのジャケット付きガラスカラムに、焙煎粉砕
コーヒー８００ｇを仕込み、蒸気で湿潤させた後、約９
５℃の熱水２８００ｇを用いて抽出し、Ｂｚ１２°のエ
キス１８２０ｇを得た。(Example) Example 1 ■ 800 g of roasted and ground coffee was charged into a jacketed glass column with a coffee water extraction capacity of 31, and after moistening with steam, about 9
Extraction was performed using 2800 g of 5°C hot water to obtain 1820 g of Bz 12° extract.
１００メツシユの濾布で濾過後減圧濃縮し、Ｂｘ７０°
の濃縮液３００ｇ（カフェイン含量４．７２％）を得た
。After filtering with a 100-mesh filter cloth, concentrate under reduced pressure, Bx70°
300 g of concentrated liquid (caffeine content 4.72%) was obtained.
■苦味物質の抽出
上記Ｂｘ７０＠の濃縮液１００ｇにに９２Ｉｌ量％エタ
ノール１５０ｇを添加しくアルコール濃度的５６％）、
？＋５−８０℃で３０分攪拌し、苦味物質を抽出した。■ Extraction of Bitter Substances Add 150 g of 92Il% ethanol to 100 g of the above Bx70@ concentrate (alcohol concentration: 56%),
? The mixture was stirred at +5-80°C for 30 minutes to extract bitter substances.
上澄の含水アルコール相１２４ｇを分離採取し、減圧濃
縮して、Ｂｘ７０°の本発明天然苦味物質４２ｇを得た
（カフェイン含量７．９９％）。124 g of the supernatant hydroalcoholic phase was separated and collected and concentrated under reduced pressure to obtain 42 g of the natural bitter substance of the present invention with Bx 70° (caffeine content 7.99%).
実施例２〜５
市販のスプレードライ−インスタントコーヒー（カフェ
イン含量３．４９％）１００ｇに実施例２（５０重量％
エタノール、以下同じ）、実施例３（６０％）、実施例
４（８０％）及び実施例６（９０％）のエタノールをそ
れぞれ５００をｇ加え、７５〜８０℃で３０分間攪拌し
、冷却後生成した不溶部を濾紙濾過して除き、アルコー
ル濃度の異なる抽出液４品を１！Ｒ１！シた。この濾液
を減圧濃縮し、Ｂｘ７０°の濃縮物を調製した。その結
果を表１に示した。Examples 2 to 5 Example 2 (50% by weight) was added to 100 g of commercially available spray-dried instant coffee (caffeine content 3.49%).
Add 500 g of each of the ethanols of Example 3 (60%), Example 4 (80%), and Example 6 (90%), stir at 75 to 80°C for 30 minutes, and cool. The generated insoluble portion was removed by filter paper, and 4 extracts with different alcohol concentrations were prepared in 1! R1! Shita. This filtrate was concentrated under reduced pressure to prepare a Bx70° concentrate. The results are shown in Table 1.
表 １
※インスタントコーヒー希釈液（Ｂｘ７０＠）表１の結
果から明らかな如く、アルコール濃度が高くなるにした
がって収率は低下するが、カフェイン含量が高くなる傾
向にあり、また苦味もアルコール濃度に比例して強くな
った。実施例２〜実施例６によって得られた濃縮物は何
れもこくのある好ましい苦味を有していた。これに対し
て、それぞれのカフェイン濃度に合わせた水溶液は、刺
激及び嫌みのある苦味であった。Table 1 *Instant coffee diluted liquid (Bx70@) As is clear from the results in Table 1, as the alcohol concentration increases, the yield decreases, but the caffeine content tends to increase, and the bitterness also increases with the alcohol concentration. became proportionally stronger. The concentrates obtained in Examples 2 to 6 all had a rich and desirable bitter taste. In contrast, aqueous solutions tailored to each caffeine concentration had an irritating and unpleasant bitter taste.
比較例１
実施例１の■で得られたＢｘ７０°のＳ縮液１００ｇに
９２重量％エタノール６０ｇを添加しくアルコール濃度
約３４．５％）、７５−８０℃で３０分攪拌し、苦味物
質の抽出を行なったところ全て可溶化し、不溶物は生成
せず結果的に苦味物質は抽出できなかった。Comparative Example 1 60 g of 92% ethanol (alcohol concentration: approximately 34.5%) was added to 100 g of the Bx70° S condensate obtained in Example 1 (■), and the mixture was stirred at 75-80°C for 30 minutes to remove bitter substances. When extracted, all the substances were solubilized, no insoluble matter was produced, and as a result, no bitter substance could be extracted.
比較例２
市販のスプレードライ・インスタントコーヒー１００ｇ
に３５重量％エタノール５００ｇを加え、７５−８０℃
で３０分間攪拌し冷却したところ不溶物は殆ど生成せず
可溶化し、苦味物質は抽出できなかった。Comparative Example 2 Commercially available spray-dried instant coffee 100g
Add 500 g of 35 wt% ethanol to 75-80℃
When the mixture was stirred for 30 minutes and cooled, almost no insoluble substances were formed and the mixture was solubilized, and no bitter substances could be extracted.
（発明の効果）
本発明によって得られる苦味物質は、日常飲用に供され
ているコーヒーを原料とするため、極めて安全で且つ全
く嫌みのない好ましい苦味を呈し、苦味を要求されるあ
らゆる用途に回答制約を受けることなしに利用すること
ができる。殊にコーヒー飲料、コーヒーゼリー等に好適
に利用することができるほか、例えば、ビール、ベネデ
ィクトリキュール、ワイン、レモネード、トニックウォ
ーター スポーツドリンク等の飲料類； インスタント
コーヒー ビターチョコレート、スナック類等に苦味賦
与剤として配合することがでＩＪる。また医薬品、工業
用薬品、植物種子等に苦味を賦与して非食用或いは忌避
剤として利用することもできる。(Effects of the Invention) The bitter substance obtained by the present invention is made from coffee that is consumed on a daily basis, so it exhibits a pleasant bitter taste that is extremely safe and has no unpleasant taste, and is suitable for all applications that require bitter taste. It can be used without any restrictions. In particular, it can be suitably used in coffee drinks, coffee jelly, etc., and also as a bittering agent for beverages such as beer, Benedictine liqueur, wine, lemonade, tonic water, sports drinks, etc.; instant coffee, bitter chocolate, snacks, etc. It can be blended as IJ. It can also be used as non-edible or repellent agents by imparting bitterness to pharmaceuticals, industrial chemicals, plant seeds, etc.
本発明によって得られる苦味物質の、上記の如き各用途
における添加量は、目的に応じて適宜任意に選択するこ
とができるが、例えば、飲食品に添加する場合には、−
船釣には飲食品の重量に基づいて、約０．０２〜約１０
％の如き添加量を例示することができる。The amount of the bitter substance obtained by the present invention added in each of the above uses can be arbitrarily selected depending on the purpose.
For boat fishing, approximately 0.02 to approximately 10
The amount added may be exemplified as %.
特許出願人 長谷川香料株式会社Patent applicant: Hasegawa Fragrance Co., Ltd.
Claims (1)
、生成する不溶性物質を除去して有機溶媒可溶部を採取
する方法において、該有機溶媒の濃度が４０重量％以上
となるように処理することを特徴とする特徴とする天然
苦味物質の製法。A method in which a water-miscible organic solvent is added to a water extract of roasted coffee, the resulting insoluble substances are removed, and the organic solvent-soluble portion is collected, such that the concentration of the organic solvent is 40% by weight or more. A method for producing a natural bitter substance characterized by processing it into
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1083963A JP2559070B2 (en) | 1989-04-04 | 1989-04-04 | Natural bitter substance manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1083963A JP2559070B2 (en) | 1989-04-04 | 1989-04-04 | Natural bitter substance manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02265433A true JPH02265433A (en) | 1990-10-30 |
| JP2559070B2 JP2559070B2 (en) | 1996-11-27 |
Family
ID=13817210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1083963A Expired - Lifetime JP2559070B2 (en) | 1989-04-04 | 1989-04-04 | Natural bitter substance manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2559070B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08191664A (en) * | 1995-01-12 | 1996-07-30 | Yoshihide Hagiwara | Production of new coffee extract |
| JP2007259726A (en) * | 2006-03-28 | 2007-10-11 | Kao Corp | Method for producing chlorogenic acid-containing material |
| EP1893034B1 (en) * | 2005-06-20 | 2012-05-23 | The Folgers Coffee Company | Processes for isolating bitter compounds for use in food and beverage products |
-
1989
- 1989-04-04 JP JP1083963A patent/JP2559070B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08191664A (en) * | 1995-01-12 | 1996-07-30 | Yoshihide Hagiwara | Production of new coffee extract |
| EP1893034B1 (en) * | 2005-06-20 | 2012-05-23 | The Folgers Coffee Company | Processes for isolating bitter compounds for use in food and beverage products |
| JP2007259726A (en) * | 2006-03-28 | 2007-10-11 | Kao Corp | Method for producing chlorogenic acid-containing material |
| WO2007122796A1 (en) | 2006-03-28 | 2007-11-01 | Kao Corporation | Method for production of chlorogenic acid-containing material |
| EP2000034A2 (en) * | 2006-03-28 | 2008-12-10 | Kao Corporation | Method for production of chlorogenic acid-containing material |
| EP2000034A4 (en) * | 2006-03-28 | 2011-08-24 | Kao Corp | Method for production of chlorogenic acid-containing material |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2559070B2 (en) | 1996-11-27 |
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