JP2006104229A - 香味料組成物 - Google Patents
香味料組成物 Download PDFInfo
- Publication number
- JP2006104229A JP2006104229A JP2004288894A JP2004288894A JP2006104229A JP 2006104229 A JP2006104229 A JP 2006104229A JP 2004288894 A JP2004288894 A JP 2004288894A JP 2004288894 A JP2004288894 A JP 2004288894A JP 2006104229 A JP2006104229 A JP 2006104229A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- quinic acid
- menthol
- extract
- quinic
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims abstract description 78
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229940041616 menthol Drugs 0.000 claims abstract description 56
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims abstract description 49
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims abstract description 48
- 239000000796 flavoring agent Substances 0.000 claims abstract description 44
- 235000019634 flavors Nutrition 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract 6
- 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 description 24
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- 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 description 16
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- GWTUHAXUUFROTF-JUHZACGLSA-N 1-O-caffeoylquinic acid Chemical compound [C@H]1(C[C@@](C(=O)O)(C[C@@H](O)[C@@H]1O)OC(=O)/C=C/C1=CC=C(O)C(O)=C1)O GWTUHAXUUFROTF-JUHZACGLSA-N 0.000 claims description 3
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- UFCLZKMFXSILNL-PSEXTPKNSA-N Isochlorogenic acid b Chemical compound O([C@@H]1C[C@@](O)(C[C@H]([C@H]1OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)O)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 UFCLZKMFXSILNL-PSEXTPKNSA-N 0.000 claims description 3
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- GWTUHAXUUFROTF-UHFFFAOYSA-N pseudochlorogenic acid Natural products C1C(O)C(O)C(O)CC1(C(O)=O)OC(=O)C=CC1=CC=C(O)C(O)=C1 GWTUHAXUUFROTF-UHFFFAOYSA-N 0.000 claims description 3
- UFCLZKMFXSILNL-BBLPPJRLSA-N (-) 4,5-dicaffeoylquinic acid Natural products OC=1C=C(C=CC=1O)C=CC(=O)O[C@@H]1C[C@@](C[C@H]([C@H]1OC(C=CC1=CC(=C(C=C1)O)O)=O)O)(C(=O)O)O UFCLZKMFXSILNL-BBLPPJRLSA-N 0.000 claims description 2
- KRZBCHWVBQOTNZ-PSEXTPKNSA-N 3,5-di-O-caffeoyl quinic acid Chemical compound O([C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N 0.000 claims description 2
- MVCIFQBXXSMTQD-UHFFFAOYSA-N 3,5-dicaffeoylquinic acid Natural products Cc1ccc(C=CC(=O)OC2CC(O)(CC(OC(=O)C=Cc3ccc(O)c(O)c3)C2O)C(=O)O)cc1C MVCIFQBXXSMTQD-UHFFFAOYSA-N 0.000 claims description 2
- UFCLZKMFXSILNL-UHFFFAOYSA-N NSC 649410 Natural products C=1C=C(O)C(O)=CC=1C=CC(=O)OC1C(O)CC(O)(C(O)=O)CC1OC(=O)C=CC1=CC=C(O)C(O)=C1 UFCLZKMFXSILNL-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000284 extract Substances 0.000 abstract description 38
- -1 quinic acid ester Chemical class 0.000 abstract description 16
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- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 52
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Abstract
【解決手段】 メントールと、キナ酸、キナ酸の塩又はキナ酸エステル誘導体或いはそれらを含有する天然物抽出物を組み合わせることにより、メントールの清涼感が増強される。また、当該キナ酸誘導体類はそれ自体強い香味を有せず、少量の添加で効果を示すためメントールと組み合わせても異味異臭を感じない。
【選択図】 なし
Description
本発明で用いられるキナ酸誘導体は、キナ酸残基、すなわち1,3,4,5−テトラヒドロキシシクロヘキサン−1−カルボン酸残基を有していれば特に限定されることはなく、キナ酸、キナ酸の塩(Na塩、K塩など)、各種キナ酸誘導体が用いられるが、好ましくはキナ酸、キナ酸の塩又はキナ酸エステル誘導体が挙げられる。キナ酸エステル誘導体の例としては、キナ酸と桂皮酸又は桂皮酸誘導体のエステルが好ましく、桂皮酸誘導体としてはカフェー酸、フェルラ酸、クマル酸等を挙げることができる。具体的にはクロロゲン酸等のカフェオイルキナ酸類、ジカフェオイルキナ酸類、フェルロイルキナ酸類、p−クマロイルキナ酸等のクマロイルキナ酸類、trans−シンナモイルキナ酸等のシンナモイルキナ酸類等を挙げることができるが、クロロゲン酸、1−、4−、又は5−カフェオイルキナ酸、3,4−、3,5−又は4,5−ジカフェオイルキナ酸が好ましく、特にクロロゲン酸(すなわち3−カフェオイルキナ酸)が好ましい。本発明においては、最も好ましくはキナ酸を有効成分とする組成物の形で用いられる。
1)原材料
原材料の茶葉は、ツバキ科茶の樹(Camellia sinensis var.) の芽、葉、茎であり、品種、産地を問わず使用することができ、また、生であっても、前処理を施したものであってもよい。茶の前処理方法としては不発酵、半発酵、発酵があるが、いずれの処理方法によるものでもよい。不発酵茶としては緑茶(煎茶、玉露、かぶせ茶、番茶、玉緑茶、抹茶、ほうじ茶等)、半発酵茶としてはウーロン茶、包種茶等、発酵茶としては紅茶が挙げられる。
原材料の茶葉を水及び/又は極性有機溶媒を用いて抽出する。極性有機溶媒としてはメタノール、エタノール、2−プロパノール、アセトン等の溶媒が例示され、これらの1種又は2種以上の混合物を用いることができ、必要に応じて水との混合形態すなわち水溶液の形で使用される。抽出に用いる溶媒は人体への安全性と取扱性の観点から水又はエタノール、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く、特に水又はエタノール又はこれらの混合物が最も望ましい。抽出に用いる溶媒の量は任意に選択できるが、一般には茶葉の1〜30倍量(重量)が用いられ、好ましくは5〜20倍量が用いられる。抽出の温度及び時間は任意に定めることができ、特に限定されるものではないが、10〜100℃にて1〜12時間、好ましくは1〜2時間が適当である。茶葉等から抽出した抽出液は不溶物を除去した後、そのままメントールと組み合わせて香味料組成物として使用することもできるが、抽出液を必要に応じて濃縮した後、下記の精製処理を行うことにより、更に清涼感に優れた香味料組成物を得ることができる。
前記抽出処理に続く精製処理により、着色物質、カフェイン、カテキン類、多糖類、たんぱく質、カルシウム、カリウム、ナトリウム等のミネラル成分、テアニン等のアミノ酸類等の夾雑物が除去され、清涼感が更に高められる。好適な精製方法としては、以下に述べるように、(A)吸着剤による処理、(B)分離膜による処理、(C)有機溶媒添加による不溶物処理および(D)陽イオン交換樹脂による処理、を挙げることができ、中でも(A)吸着剤による処理が好ましい。
前記工程で得られた抽出液を、合成吸着剤又は活性炭のような吸着剤に接触させる精製方法である。吸着剤の比表面積が300〜600m2/g、細孔径が50〜300オングストロームのものが好適である。吸着剤の種類としては、合成吸着剤であれば特に限定されるものではなく、例えばスチレン−ジビニルベンゼン共重合体系樹脂の合成吸着剤である「ダイヤイオンHP」(三菱化学社製、商品名)やアクリル酸エステル系樹脂の合成吸着剤「アンバーライトXAD−7」(オルガノ社製、商品名)などが挙げられる。これら樹脂に接触させる方法はバッチ式、カラム式のいずれでも良いが、商業的生産規模ではカラム方式の方が一般的で、好ましい処理条件としては空間速度SV=1を挙げることができる。
膜(濾過)処理により高分子である多糖類およびたんぱく質を除去して精製する方法であり、膜の種類としては限外濾過膜、逆浸透膜、透析膜を利用できる。
抽出液又はその濃縮液に有機溶媒を添加して、析出する不溶物を除去することにより精製する方法である。添加する有機溶媒は、メタノール、エタノール、n−プロパノール、アセトン等が例示され、中でも安全性と取扱性の点からエタノールが好適である。添加量は特に限定されるものではないが抽出液又は濃縮液1質量部に対して0.1〜10質量部が用いられる。
抽出液又は濃縮液を陽イオン交換樹脂に接触することにより精製する方法である。吸着能力、強度の観点からイオン交換体のマトリックスが有機合成ポリマーのものが好ましい。陽イオン交換樹脂の種類は特に限定されるものではないが、例えば好適なものとしてスチレン系樹脂でスルホン酸基を交換基とする「アンバーライトIRA−400」(オルガノ社製、商品名)や「ダイヤイオンSK1B」などが挙げられる(三菱化学社製、商品名)。
1)原材料
原材料のコーヒー豆は、産地品種により制限されることなく任意の豆を用いることができる。生のコーヒー豆にはクロロゲン酸類が多量に含まれているが、焙煎したコーヒー豆には焙煎時にクロロゲン酸類が加水分解されてキナ酸が生じている。従って、原材料が焙煎したコーヒー豆である場合は、茶葉と同様に前述の抽出精製工程を経て、メントールと組み合わせた香味料組成物とすることができる。
コーヒー生豆を用いる場合、クロロゲン酸等として得られた抽出液を加水分解する際は、不溶物を除去した後、必要に応じて濃縮工程を経て、好適には以下のように酵素又はアルカリを用いて加水分解する。
得られた抽出液が水抽出液の場合はそのまま、水溶性溶媒を含む場合は濃縮等により水溶性溶媒の量を5%以下にした後、酵素処理を行うことが望ましい。酵素分解にはタンナーゼ又はクロロゲン酸エステラーゼが用いられる。利用できるタンナーゼの種類としては特に限定されるものではなく、麹菌などの糸状菌、酵母、細菌などの微生物、特にAspergillus属やPenicillium属から産生されるタンナーゼを挙げることができるが、好ましくはAspergillus属、特に好ましくはAspergillus oryzeから産生されるタンナーゼが用いられる。
アルカリ加水分解を行う場合は、コーヒー豆を微粉砕し、これにアルカリ水溶液を加えて60〜90℃で10〜60分間加熱攪拌する。アルカリ水溶液としては、水酸化カルシウム、水酸化ナトリウム、炭酸ナトリウムなどの水溶液が用いられ、好ましくは水酸化カルシウムが用いられる。加水分解後、反応液に、塩酸、硫酸、蓚酸、リン酸などの酸を加えて中和処理する。
緑茶葉100gに蒸留水2,000gを加え、60℃で一時間攪拌した。40℃まで冷却後、遠心濾過器を用いて茶葉及び不溶物を分離後、分離液をセライト濾過し、1,780gの抽出液を得た。その抽出液を減圧下、液温50℃で液量が300gになるまで濃縮した。この濃縮液300gに95%エタノール360gを加えた後、10℃まで冷却し生じた不溶物をセライト濾過し、濾液593gを得た。さらにその濾液に活性炭12gを加え、30分間攪拌後セライト濾過し、濾液を凍結乾燥することによりキナ酸を含有する緑茶抽出物2.2gを得た。HPLCを用いて分析した結果、緑茶抽出物に含まれる成分は、質量比で、キナ酸7.6%、グルコース0.76%、フルクトース0.81%、スクロース7.95%、テアニン3.16%であった。
紅茶葉100gに蒸留水2,000gを加え、1時間加熱還流した。冷却後、遠心濾過器で固液分離し、濾液1,920gを得た。その濾液に活性炭5gを加え、合成吸着剤(三菱化学社製「ダイヤイオンHP−20」(商品名))500mlを添加し、1時間攪拌した。その後濾過により合成吸着剤を除去し、濾液1,890gを得た。濾液1,890gを陽イオン交換樹脂(三菱化学社製「ダイヤイオンSK1B」(商品名))1,000mlを充填したカラムに供し、空間速度SV=1で送液した。通過液は限外濾過膜(日東電工社製「NTU−2120」)により濾過した。得られた濾液1,810gを凍結乾燥することにより、キナ酸を含有する紅茶抽出物5.9gを得た。HPLCを用いて分析した結果、紅茶抽出物に含まれる成分は質量比で、キナ酸17.0%、グルコース19.7%、フルクトース15.1%、スクロース2.2%、テアニン7.6%であった。
コーヒー生豆300gを微粉砕した後、70%エタノール水溶液1,500mlを加え、90℃で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1,100mlを得た。この抽出液を減圧下で濃縮してエタノールを除去した後、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℃で1時間撹拌加熱した。冷却後、減圧下で300gになるまで濃縮し、得られた濃縮液に20%水酸化ナトリウムを添加して中和し、次いで塩化メチレン600gを加えて充分混合撹拌した。水層を分離した後、ダイヤイオンHP−20樹脂(三菱化学社製、商品名)500mlを充填したカラムに通導した。次いで該樹脂を充分に水洗した後、95%エタノール水溶液750gでクロロゲン酸類を溶出させた。得られた溶出液を減圧濃縮後、乾燥してクロロゲン酸等を含有するコーヒー生豆抽出物27gを得た。
コーヒー生豆500gを微粉砕した後、70%エタノール水溶液5,000mlを加え、2時間加熱還流した。冷却後、遠心濾過器で固液分離し、濾過液をエタノール含量5%以下まで減圧濃縮し、クロロゲン酸エステラーゼ(キッコーマン社製)1,000単位を加え40℃で3時間攪拌した。処理液を、遠心分離により不溶物を取り除き、合成吸着剤(三菱化学社製「ダイヤイオンHP−20」(商品名))1,000mlを充填したカラムに通導し、溶出してきた液を凍結乾燥することにより、キナ酸を含有するコーヒー生豆加水分解抽出物26.6gを得た。HPLCを用いて分析した結果、コーヒー生豆加水分解抽出物中の成分は質量比で、キナ酸32%、グルコース16%、フルクトース15%であった。なお、クロロゲン酸エステラーゼの1単位は30℃の水中において3−カフェオイルキナ酸を1分間に1マイクロモル加水分解する酵素量である。
コーヒー生豆100gを微粉砕した後、水酸化カルシウム30gと水1,000mlを加え、80℃で30分間加熱攪拌した。室温まで冷却後、固液分離して水溶液を得た。希塩酸を加えてpHを3に調整した後、活性炭脱色を行った。不溶物を濾過にて除去し、濾液を得た。この濾液をイオン交換膜電気透析装置(陽イオン交換膜分画分子量:300、陰イオン交換膜分画分子量:100)にて脱塩処理した後、減圧濃縮し、凍結乾燥することにより、キナ酸含有コーヒー生豆加水分解物9gを得た。HPLCを用いて分析した結果、コーヒー生豆加水分解物中の成分は質量比で、キナ酸35%、庶糖25%、単糖類11%、灰分9%であった。
クランベリー濃縮果汁600gを希釈し、ポーラスポリマー樹脂XAD−2(オルガノ株式会社製)600mlを用いて脱色後、さらに活性炭で脱色、セライト濾過を経て、濾液2,800gを得た。この濾液を、イオン交換膜電気透析装置(陽イオン交換膜分画分子量:300、陰イオン交換膜分画分子量:300)を用いて透析し、塩廃液側に濃縮液を得た。これを、キナ酸濃度が2%、エタノール濃度が20%になるようにエタノール水溶液で希釈し、キナ酸含有クランベリー抽出物560gを得た。HPLCを用いて分析した結果、クランベリー抽出物中の成分は質量比で、キナ酸35%、クエン酸30%、リンゴ酸35%であった。
メントールの100ppm水溶液に、それぞれにスクラロース(三栄源エフ・エフ・アイ社製、商品名)1ppm、キナ酸(ナカライテスク社製の試薬)1ppm、キナ酸誘導体としてクロロゲン酸(和光純薬工業社製の試薬)1.8ppm、および上記製造例で得られた抽出物をキナ酸として約1ppm相当となるように加え、パネル20名にて清涼感と香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表1に示した。
l−メントール40部、ペパーミント油35部、エタノール25部からなる香料組成物(以後「ミント香料」という)を調製した。
ミント香料の200ppm水溶液に、それぞれにスクラロース(三栄源エフ・エフ・アイ社製、商品名)1ppm、キナ酸(ナカライテスク社製の試薬)1ppm、キナ酸誘導体としてクロロゲン酸(和光純薬工業社製の試薬)1.8ppm、および上記製造例で得られた抽出物をキナ酸として約1ppm相当となるように加え、パネル20名にて清涼感と香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表2に示した。
Bx.70のマルチトールシロップを185℃まで炊き上げ、155℃まで急冷後、メントール及び製造例4の抽出物の混合物を添加して攪拌均一化し、成型して本発明のキャンディを作成した。メントールは仕上がり時0.5質量%、製造例4の抽出物はキナ酸量1ppmとなるよう添加した。これを専門パネラー10名にて香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表3に示した。
ガムベース、砂糖、ブドウ糖、コーンシロップを混合し、これにミント香料を1質量%及び製造例4の抽出物をキナ酸量1ppmとなるよう添加し、常法に従って高剪断型ミキサーを用いて約50℃で混和し、冷却後ローラーにより圧展成形し、1枚3gとなる本発明の板ガムを調製した。これを専門パネラー10名にて香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表4に示した。
水150部にアラビアガム30部、DE10のデキストリン50部を加温溶解し、冷却後メントール20部を添加して乳化し、スプレードライヤーにて噴霧乾燥を行ってメントール粉末香料を調製した。これを無添加品とし、同様に乳化前に製造例4の抽出物をキナ酸0.005部となるよう添加したものを作成し、これを添加品とした。調製したメントール粉末香料を、粉糖に0.5%添加してよく攪拌し、これをそのまま食して、専門パネラー10名にて香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表5に示した。
ソルビトールに滑択剤としてのショ糖脂肪酸エステル及び実施例3で調製した各粉末香料を1.0%添加し、打錠圧1tにて打錠してメントールタブレットを調製した。これを専門パネラー10名にて香味の官能評価を行った。評価点は、無添加品を4点とし、非常に清涼感が強くなった場合を7点、逆に清涼感が弱くなった場合を1点とした7段階評価試験をブラインドで行った。評価結果の平均値及び評価のコメントを表6に示した。
Claims (9)
- キナ酸誘導体と、メントールとを含有することを特徴とする香味料組成物。
- キナ酸誘導体が、キナ酸、キナ酸の塩、3−カフェオイルキナ酸(クロロゲン酸)、1−カフェオイルキナ酸、4−カフェオイルキナ酸、5−カフェオイルキナ酸、3,4−ジカフェオイルキナ酸、3,5−ジカフェオイルキナ酸又は4,5−ジカフェオイルキナ酸或いはこれらの混合物であることを特徴とする請求項1記載の香味料組成物。
- キナ酸誘導体が、キナ酸又はキナ酸の塩であることを特徴とする請求項1記載の香味料組成物。
- キナ酸誘導体が、茶葉抽出物由来であることを特徴とする請求項1乃至請求項3のいずれかの項に記載の香味料組成物。
- キナ酸誘導体が、コーヒー豆抽出物の加水分解物由来であることを特徴とする請求項1乃至請求項3のいずれかの項に記載の香味料組成物。
- キナ酸誘導体の含有量が、メントール1質量部に対して10−4〜1質量部であることを特徴とする請求項1乃至請求項5のいずれかの項に記載の香味料組成物。
- 更にミント精油を含有することを特徴とする請求項1乃至請求項6のいずれかの項に記載の香味料組成物。
- 請求項1乃至請求項7のいずれかの項に記載の香味料組成物を含有することを特徴とする飲食物。
- 請求項1乃至請求項7のいずれかの項に記載の香味料組成物を含有することを特徴とする口腔用組成物。
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