JP2006104229A - Flavoring composition - Google Patents
Flavoring composition 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
- 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 description 22
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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
- 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 description 16
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- CWVRJTMFETXNAD-GMZLATJGSA-N 5-Caffeoyl quinic acid 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-GMZLATJGSA-N 0.000 claims description 12
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- DSHJQVWTBAAJDN-SMKXDYDZSA-N 4-caffeoylquinic acid Natural products CO[C@@]1(C[C@@H](O)[C@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@H](O)C1)C(=O)O DSHJQVWTBAAJDN-SMKXDYDZSA-N 0.000 claims description 4
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- GYFFKZTYYAFCTR-LMRQPLJMSA-N cryptochlorogenic acid Natural products O[C@H]1C[C@@](O)(C[C@H](O)[C@H]1OC(=O)C=Cc2ccc(O)c(O)c2)C(=O)O GYFFKZTYYAFCTR-LMRQPLJMSA-N 0.000 claims description 4
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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
- 229940069765 bean extract Drugs 0.000 claims description 3
- 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
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- 239000000284 extract Substances 0.000 abstract description 38
- -1 quinic acid ester Chemical class 0.000 abstract description 16
- 239000000126 substance Substances 0.000 abstract description 13
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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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Landscapes
- Confectionery (AREA)
- Tea And Coffee (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
本発明は、メントールの香気香味を増強し、清涼感を向上させた嗜好性の高い香味料組成物に関する。 The present invention relates to a flavoring composition with high palatability that enhances the aroma and flavor of menthol and improves the refreshing feeling.
メントールはハッカ特有の清涼な香味を有し、チューインガム、キャンディ、錠菓、アイスクリーム、飲料などの飲食物に用いられる他、歯磨き、口中清涼剤、洗口剤などの口腔用組成物にも使用され、また、強い冷涼感を示すことから各種化粧料に使用されるなど、極めて有用性の高い香料である。メントールを使用した製品の最近の傾向としては、より強い清涼感、より強い刺激を求められてきている。そのため、メントールの含有率を上げた商品開発が行われているが、メントール含量が高くなると結晶化しやすくなるという点、メントール特有の苦味が生じてくるという点、などが問題となることが指摘されてきている。 Menthol has a refreshing flavor peculiar to mint and is used for foods and drinks such as chewing gum, candy, tablet confectionery, ice cream and beverages, as well as for oral compositions such as toothpaste, mouth refresher and mouthwash. Moreover, since it shows a strong cool feeling, it is a highly useful fragrance such as used in various cosmetics. As a recent trend of products using menthol, stronger refreshing feeling and stronger stimulation have been demanded. For this reason, product development with an increased menthol content has been carried out, but it has been pointed out that problems such as the fact that menthol content tends to crystallize and that menthol-specific bitterness occurs. It is coming.
メントールの清涼感を増強する方法としては、例えばメントールとスピラントールとの組合せ(特許文献1)、メントールとピラン型リナロールオキサイドとの組合せ(特許文献2)、メントールとソブレロールとの組合せ(特許文献3)、メントールと特定のケトン・アルコール・エーテル類との組合せ(特許文献4)、メントールと特定の含硫化合物との組合せ(特許文献5)、メントールと特定のラクトン類との組合せ(特許文献6)、メントールとスクラロースとの組合せ(特許文献7)、メントールと各種エステル香料との組合せ(特許文献8)などが提案されてきている。しかしながら、いずれの方法においても、メントールと組み合わせる素材自体が特有の香りや味を有しており、最終製品の香味に影響を与えることがあり、汎用性の高いものであるとはいえず、更なる開発が望まれていた。
解決しようとする課題は、メントールの清涼感などの香気香味が増強され、かつ、異味異臭などを感じさせない、優れた清涼性香味料が無いという点である。 The problem to be solved is that there is no excellent refreshing flavor that enhances the aroma and flavor of menthol, such as a refreshing sensation, and does not give off a strange odor.
上記課題を解決するために本発明者らは鋭意検討した結果、メントールとキナ酸誘導体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、また、当該キナ酸誘導体は強い香味を有せず、少量の添加でも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ということを見いだし、本発明を完成させた。すなわち本発明は、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であり、詳しくは、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前記香味料組成物であり、更に詳しくは、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前記香味料組成物であり、また、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前記香味料組成物であり、また、キナ酸誘導体が、コーヒー豆加水分解物由来であることを特徴とする前記香味料組成物であり、詳しくは、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前記香味料組成物であり、また、更にミント精油を含有することを特徴とする前記香味料組成物であり、また、前記香味料組成物を含有することを特徴とする飲食物であり、また、前記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である。 In order to solve the above problems, the present inventors diligently studied. As a result, the menthol refreshment was enhanced by combining menthol and a quinic acid derivative, and the quinic acid derivative did not have a strong flavor and a small amount In order to show the effect even when added, it was found that even when combined with menthol, no off-flavor was felt, and the present invention was completed. That is, the present invention is a flavoring composition comprising a quinic acid derivative and menthol. Specifically, the quinic acid derivative comprises quinic acid, a salt of quinic acid, 3-caffeoylquinic acid ( Chlorogenic acid), 1-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid or 4,5-di The flavor composition described above, wherein the flavor composition is caffeoylquinic acid or a mixture thereof, and more specifically, the quinic acid derivative is quinic acid or a salt of quinic acid. And the quinic acid derivative is derived from tea leaf extract, and the quinic acid derivative is derived from a coffee bean hydrolyzate. The flavor composition , And the details, the content of quinic acid derivative is a said flavoring composition characterized in that it is a 10 -4 to 1 parts by weight with respect to menthol 1 part by weight, it may further contain a mint essential oil It is the above-mentioned flavoring composition, and is a food or drink characterized by containing the flavoring composition, and also contains the flavoring composition. Composition.
本発明の香味料組成物は、メントール自体の香気香味を阻害することなく増強し、清涼感の発現性、拡散性、持続性を向上し、かつ、異味異臭を感じさせることが無く、優れた香味料組成物を提供する。本発明の香味料組成物は強い清涼感を与えることもできるし、また、通常のメントール使用量と比較して少ない量で同等の清涼感を与えることができ、結果としてメントールの苦味改善効果を示すことができる。 The flavor composition of the present invention is enhanced without inhibiting the fragrance flavor of menthol itself, improves the expression of coolness, diffusibility, and persistence, and does not give off a strange odor and is excellent. A flavoring composition is provided. The flavoring composition of the present invention can give a strong refreshing feeling, and can also give an equivalent refreshing feeling in a small amount compared to the amount of normal menthol used, resulting in an effect of improving the bitterness of menthol. Can show.
(1)キナ酸誘導体
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) Quinic acid derivative The quinic acid derivative used in the present invention is particularly limited as long as it has a quinic acid residue, that is, a 1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid residue. However, quinic acid, quinic acid salts (Na salt, K salt, etc.) and various quinic acid derivatives are used, and preferably quinic acid, quinic acid salts or quinic acid ester derivatives are used. Examples of quinic acid ester derivatives are preferably quinic acid and cinnamic acid or cinnamic acid derivatives. Examples of cinnamic acid derivatives include caffeic acid, ferulic acid, and coumaric acid. Specific examples include caffeoylquinic acids such as chlorogenic acid, dicaffeoylquinic acids, feruloylquinic acids, coumaroylquinic acids such as p-coumaroylquinic acid, and cinnamoylquinic acids such as trans-cinnamoylquinic acid. Acid, 1-, 4-, or 5-caffeoylquinic acid, 3,4-, 3,5- or 4,5-dicaffeoylquinic acid are preferred, especially chlorogenic acid (ie 3-caffeoylquinic acid) Is preferred. In the present invention, it is most preferably used in the form of a composition containing quinic acid as an active ingredient.
本発明のキナ酸誘導体は、試薬として入手することもでき、単独で使用もできるが、2種以上組み合わせて使用することもできる。また、これらの化合物は天産品から抽出・精製することにより得ることができ、純粋なキナ酸誘導体物質として得ることもできるが、キナ酸誘導体混合物として得ることもできる。ある種の天然物抽出物には、抽出される成分の相乗作用により、純粋なキナ酸誘導体と同等以上の効果を示すものがあり、それらの例としては、茶葉(不発酵茶・半発酵茶・発酵茶)抽出物及びコーヒー豆加水分解物(塩基・酵素)抽出物などが挙げられる。 The quinic acid derivative of the present invention can be obtained as a reagent and can be used alone, but can also be used in combination of two or more. In addition, these compounds can be obtained by extraction and purification from natural products, and can be obtained as pure quinic acid derivative substances, but can also be obtained as quinic acid derivative mixtures. Some natural product extracts have effects equivalent to or better than pure quinic acid derivatives due to the synergistic action of the extracted components. Examples of these are tea leaves (non-fermented tea and semi-fermented tea). -Fermented tea) extract and coffee bean hydrolyzate (base / enzyme) extract.
(1)キナ酸を含む茶葉抽出物
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。
(1) Tea leaf extract containing quinic acid 1) Raw materials The raw tea leaves are buds, leaves and stems of camellia family tea tree (Camellia sinensis var.), And can be used regardless of cultivar or origin. Further, it may be raw or pretreated. Tea pretreatment methods include non-fermentation, semi-fermentation, and fermentation, and any treatment method may be used. Non-fermented tea includes green tea (sencha, gyokuro, kabusecha, bancha, tamago green tea, matcha tea, hojicha, etc.), semi-fermented tea includes oolong tea, baled tea, etc., and fermented tea includes black tea.
2)抽 出
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。
2) Extraction Extract the raw tea leaves using water and / or a polar organic solvent. Examples of the polar organic solvent include solvents such as methanol, ethanol, 2-propanol, and acetone. One or a mixture of two or more of these can be used, and if necessary, a mixed form with water, that is, an aqueous solution. Used in. The solvent used for extraction is preferably water or an aliphatic alcohol having 2 to 4 carbon atoms such as ethanol, propanol, or butanol, and most preferably water, ethanol, or a mixture thereof from the viewpoint of safety to the human body and handleability. Although the quantity of the solvent used for extraction can be selected arbitrarily, generally 1 to 30 times (weight) of tea leaves is used, preferably 5 to 20 times. The temperature and time of extraction can be arbitrarily determined and are not particularly limited, but are suitable at 10 to 100 ° C. for 1 to 12 hours, preferably 1 to 2 hours. The extract extracted from tea leaves, etc. can be used as a flavoring composition in combination with menthol after removing insoluble matter, but after the extract is concentrated as necessary, the following purification treatment should be performed. Thus, it is possible to obtain a flavor composition having a further refreshing feeling.
3)精 製
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。
3) Refinement By the purification process following the extraction process, colored substances, caffeine, catechins, polysaccharides, proteins, mineral components such as calcium, potassium, and sodium, and contaminants such as amino acids such as theanine are removed. A refreshing feeling is further enhanced. As described below, suitable purification methods include (A) treatment with an adsorbent, (B) treatment with a separation membrane, (C) insoluble matter treatment by adding an organic solvent, and (D) treatment with a cation exchange resin. Among them, (A) treatment with an adsorbent is preferable.
(A)吸着剤による処理
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。
(A) Treatment with adsorbent This is a purification method in which the extract obtained in the above step is brought into contact with an adsorbent such as a synthetic adsorbent or activated carbon. It is preferable that the adsorbent has a specific surface area of 300 to 600 m 2 / g and a pore diameter of 50 to 300 Å. The type of adsorbent is not particularly limited as long as it is a synthetic adsorbent. For example, “Diaion HP” (trade name, manufactured by Mitsubishi Chemical Corporation), which is a synthetic adsorbent of a styrene-divinylbenzene copolymer resin. And a synthetic adsorbent “Amberlite XAD-7” (trade name, manufactured by Organo Corporation) of acrylic ester resin. Either a batch method or a column method may be used as the method of contacting with these resins, but the column method is more common on a commercial production scale, and a preferable processing condition is a space velocity SV = 1.
(B)分離膜による処理
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。
(B) Treatment with a separation membrane This is a method of removing polysaccharides and proteins, which are macromolecules, by membrane (filtration) treatment and purifying them. Ultrafiltration membranes, reverse osmosis membranes, and dialysis membranes can be used as membrane types. .
(C)有機溶媒添加による不溶物処理
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。
(C) Insoluble matter treatment by addition of organic solvent This is a method of purifying by adding an organic solvent to the extract or its concentrated solution to remove the precipitated insoluble matter. Examples of the organic solvent to be added include methanol, ethanol, n-propanol, acetone, and the like, and ethanol is particularly preferable from the viewpoint of safety and handleability. Although the addition amount is not particularly limited, 0.1 to 10 parts by mass is used with respect to 1 part by mass of the extract or concentrate.
(D)陽イオン交換樹脂による処理
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)。
(D) Treatment with cation exchange resin This is a method of purifying an extract or concentrate by contacting with a cation exchange resin. From the viewpoint of adsorption capacity and strength, the matrix of the ion exchanger is preferably an organic synthetic polymer. The type of cation exchange resin is not particularly limited. For example, “Amberlite IRA-400” (manufactured by Organo Corporation, trade name) and “ Diaion SK1B "(trade name, manufactured by Mitsubishi Chemical Corporation).
より清涼感の高い香味料組成物を得るための最も好ましい精製方法としては、上記の吸着剤による処理を必須とし、更に分離膜による処理、有機溶媒添加による不溶物処理および陽イオン交換樹脂による処理から選択される1又は2以上の精製方法を組み合わせて併用する。精製工程で得られた液状組成物はそのままで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、減圧濃縮や凍結乾燥などにより溶媒を除去し、粉末状として使用するのが好ましい。 As the most preferable purification method for obtaining a flavor composition with a higher refreshing feeling, the treatment with the above-mentioned adsorbent is essential, the treatment with a separation membrane, the treatment with an insoluble matter by adding an organic solvent, and the treatment with a cation exchange resin. One or two or more purification methods selected from are used in combination. The liquid composition obtained in the purification step can be used as it is in combination with menthol as a flavoring composition, but it is preferable to use it as a powder after removing the solvent by vacuum concentration or freeze drying.
(2)キナ酸を含むコーヒー豆加水分解物
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。
(2) Coffee Bean Hydrolyzate Containing Quinic Acid 1) Raw Material As the raw material coffee beans, any beans can be used without being limited by the production varieties. Raw coffee beans contain a large amount of chlorogenic acids, but roasted coffee beans are hydrolyzed with chlorogenic acids during roasting to produce quinic acid. Therefore, when the raw material is roasted coffee beans, a flavoring composition combined with menthol can be obtained through the above-described extraction and purification process in the same manner as tea leaves.
コーヒー生豆などクロロゲン酸等のキナ酸誘導体が含まれる原材料の場合は、クロロゲン酸等を含む抽出物を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ができるが、キナ酸の清涼感増強効果がクロロゲン酸等より高いことから、クロロゲン酸等を加水分解してキナ酸を含む抽出物とするのが好ましい。また、加水分解により得られたキナ酸を含む抽出物から未反応のクロロゲン酸等を除去することにより、クロロゲン酸等に由来する苦味が除去された、更に清涼効果の高い香味料素材を得ることができる。この場合は、水及び/又は極性有機溶媒により抽出し、その後溶媒を除去して酵素又はアルカリにて加水分解したものを精製工程に付して香味料素材を得ることができる。 In the case of raw materials containing quinic acid derivatives such as chlorogenic acid such as green coffee beans, the extract containing chlorogenic acid can be used as it is as a flavoring composition in combination with menthol. Since an effect is higher than chlorogenic acid etc., it is preferable to hydrolyze chlorogenic acid etc. to make an extract containing quinic acid. Moreover, by removing unreacted chlorogenic acid and the like from the extract containing quinic acid obtained by hydrolysis, a bitter taste derived from chlorogenic acid and the like is removed, and a flavoring material having a higher cooling effect is obtained. Can do. In this case, it is possible to obtain a flavoring material by performing extraction with water and / or a polar organic solvent, then removing the solvent and hydrolyzing with an enzyme or alkali to a purification step.
2)抽出物の加水分解処理
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。
2) Hydrolysis treatment of extract When using green coffee beans, when hydrolyzing the extract obtained as chlorogenic acid, etc., after removing the insoluble matter, preferably through a concentration step, preferably It hydrolyzes using an enzyme or an alkali as follows.
(A)酵素による加水分解
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。
(A) Hydrolysis by enzyme When the obtained extract is a water extract, it can be used as it is, and when it contains a water-soluble solvent, the amount of the water-soluble solvent can be reduced to 5% or less by concentration or the like, followed by enzyme treatment. desirable. For enzymatic degradation, tannase or chlorogenic acid esterase is used. The type of tannase that can be used is not particularly limited, and examples thereof include filamentous fungi such as Aspergillus, microorganisms such as yeast and bacteria, particularly tannase produced from the genus Aspergillus and Penicillium, and preferably the Aspergillus genus. Particularly preferably, tannase produced from Aspergillus oryze is used.
利用できるクロロゲン酸エステラーゼの種類についても特に限定されるものではなく、Aspergillus属、Penicillium属、Botrytis属などの糸状菌により産生されるもの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 japonicsやAspergillus nigerから産生されるクロロゲン酸エステラーゼが用いられる。これらの酵素は、キッコーマン株式会社より入手することもできる。また、これらの酵素は各種の固定化方法により固定化したものを使用することで、更に好便な効果を得ることも可能となる。酵素分解の条件は特に限定されるものではないが、好ましくは30〜50℃で1〜48時間、特に好ましくは35〜45℃で2〜24時間が適当である。 The type of chlorogenic acid esterase that can be used is not particularly limited, and examples thereof include those produced by filamentous fungi such as Aspergillus genus, Penicillium genus, Botrytis genus, preferably Aspergillus genus, particularly preferably Aspergillus. Chlorogenic acid esterase produced from japonics and Aspergillus niger is used. These enzymes can also be obtained from Kikkoman Corporation. In addition, it is possible to obtain a more convenient effect by using these enzymes immobilized by various immobilization methods. The conditions for enzymatic degradation are not particularly limited, but it is preferably 1 to 48 hours at 30 to 50 ° C, particularly preferably 2 to 24 hours at 35 to 45 ° C.
酵素分解物は不溶物を濾過除去後、精製工程に付されるが、精製方法としては好ましくは合成樹脂吸着剤に接触することにより、未反応のクロロゲン酸、副生成物のカフェー酸、或いはカフェイン等の夾雑物や苦味成分を除去することにより精製される。また、吸着剤は比表面積が300〜600m2/g、細孔径が50〜300オングストロームのものが好ましく、例えばスチレン−ジビニルベンゼン系合成吸着剤「ダイヤイオンHP」(三菱化学社製、商品名)などを使用でき、「ダイヤイオンHP−20」(三菱化学社製、商品名)が特に好ましい。これら陽イオン交換樹脂や合成樹脂吸着剤に接触させる方法はバッチ式、カラム式いずれでも良いが、商業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が挙げられる。 The enzyme degradation product is subjected to a purification step after removing insolubles by filtration. However, as a purification method, unreacted chlorogenic acid, by-product caffeic acid, or cafe is preferably obtained by contacting with a synthetic resin adsorbent. Refined by removing impurities such as in and bitter components. The adsorbent preferably has a specific surface area of 300 to 600 m 2 / g and a pore diameter of 50 to 300 angstroms. For example, a styrene-divinylbenzene synthetic adsorbent “Diaion HP” (trade name, manufactured by Mitsubishi Chemical Corporation) “Diaion HP-20” (trade name, manufactured by Mitsubishi Chemical Corporation) is particularly preferable. The method of contacting the cation exchange resin or synthetic resin adsorbent may be either a batch type or a column type, but the column type is more common on a commercial production scale, and the preferred processing condition is a space velocity SV = 1. It is done.
(B)アルカリによる加水分解
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。
(B) Hydrolysis with alkali When performing alkali hydrolysis, coffee beans are finely pulverized, an aqueous alkali solution is added thereto, and the mixture is heated and stirred at 60 to 90 ° C for 10 to 60 minutes. As the alkaline aqueous solution, an aqueous solution of calcium hydroxide, sodium hydroxide, sodium carbonate or the like is used, and calcium hydroxide is preferably used. After hydrolysis, the reaction solution is neutralized by adding an acid such as hydrochloric acid, sulfuric acid, succinic acid, or phosphoric acid.
中和処理した加水分解液をイオン交換膜電気透析装置にかけ、中和により生成した塩を除去する。脱塩は陰イオン交換膜分画分子量100〜300、好ましくは100相当膜を用いて行うのが望ましく、また、陽イオン交換膜は特に制限無く用いられる。 The neutralized hydrolyzed solution is applied to an ion exchange membrane electrodialyzer to remove salts generated by neutralization. Desalting is desirably performed using a membrane having an anion exchange membrane fraction molecular weight of 100 to 300, preferably 100, and a cation exchange membrane is not particularly limited.
上記の加水分解処理を行って得られた液状組成物は、そのままでメントールと組み合わせた香味料組成物として使用することもできるが、好ましくは減圧濃縮、凍結乾燥などにより水などの溶媒を除去し、粉末状として用いる。なお、こうした粉末状のキナ酸を含む茶葉抽出物中のキナ酸、単糖類の含有率はそれぞれ約5〜35質量%、1〜40質量%であり、一方、粉末状のキナ酸を含むコーヒー豆加水分解物中のキナ酸、単糖類の含有率はそれぞれ約30〜50質量%、20〜40質量%である。 The liquid composition obtained by performing the above hydrolysis treatment can be used as a flavoring composition in combination with menthol as it is, but preferably removes a solvent such as water by concentration under reduced pressure, lyophilization or the like. Used as a powder. The content of quinic acid and monosaccharide in the tea leaf extract containing powdered quinic acid is about 5 to 35% by mass and 1 to 40% by mass, respectively, while coffee containing powdered quinic acid is used. The content of quinic acid and monosaccharide in the bean hydrolyzate is about 30 to 50% by mass and 20 to 40% by mass, respectively.
本発明におけるキナ酸誘導体は、上記以外に各種天産物に含まれており、それらから抽出精製、或いは抽出加水分解精製などを行い入手することができる。それら天産物の例としては、オオムギ、サツマイモ、バレイショ、ヤムイモ、サトイモ、キャベツ、シュンギク、アーティチョーク、チコリー、ヒマワリ、ゴボウ、フキ、ナスビ、トマト、コウサイ、レンコン、ダイズ、ソラマメ、グアー、リンゴ、ナシ、モモ、セイヨウスモモ、ウメ、アンズ、セイヨウミザクラ、セイヨウスミザクラ、ビワ、オランダイチゴ、クロキイチゴ、ラズベリー、クランベリー、クロスグリ、アカスグリ、セイヨウスグリ、ブルーベリー、ツルコケモモ、コケモモ、アボカド、オリーブ、キウイフルーツ、パインアップル、アマダイダイ、カカオ、マテ、メース、アニス、フェネル、コリアンダー、キャラウェイ、スターアニスなどが挙げられる。 The quinic acid derivative in the present invention is contained in various natural products other than the above, and can be obtained by performing extraction purification or extraction hydrolysis purification from them. Examples of these natural products are barley, sweet potato, potato, yam, taro, cabbage, sengoku, artichoke, chicory, sunflower, burdock, burdock, eggplant, tomato, kosai, lotus root, soybean, broad bean, guar, apple, pear, Peach, Prunus, Ume, Apricot, Prunus apricot, Prunus apricot, Biwa, Dutch strawberry, Blackberry strawberry, Raspberry, Cranberry, Blackcurrant, Redcurrant, Bluecurrant, Blueberry, Cranberry, Cowberry, Avocado, Olive, Kiwifruit, Pineapple , Red sea bream, cacao, mate, mace, anise, fennel, coriander, caraway, star anise.
本発明のキナ酸誘導体はメントールに対してごく少量の添加でも効果を示すことができ、含有量が通常はメントール1質量部に対して10−5〜10質量部、好ましくは10−4〜1質量部、より好ましくは10−4〜10−1質量部、最も好ましくは10−3〜10−1質量部で用いられる。含有量が10−5質量部未満であれば添加効果が十分でない場合があり、含有量が10質量部を越えた場合は経済的に有利でないときがある。キナ酸誘導体はそれ自体強い香気香味を有せず、また、上記のように含有量も少なくて済むことから、メントールの香気香味に影響を与えることを抑えることができる。 The quinic acid derivative of the present invention can exhibit an effect even when added in a very small amount to menthol, and the content is usually 10 −5 to 10 parts by mass, preferably 10 −4 to 1 based on 1 part by mass of menthol. It is used in parts by mass, more preferably 10 −4 to 10 −1 parts by mass, and most preferably 10 −3 to 10 −1 parts by mass. If the content is less than 10 −5 parts by mass, the effect of addition may not be sufficient, and if the content exceeds 10 parts by mass, it may not be economically advantageous. The quinic acid derivative itself does not have a strong fragrance, and since the content thereof is small as described above, it is possible to suppress the influence of the menthol fragrance.
本発明で用いられるメントールは、メントールであれば特に限定されることはなく、あらゆる異性体もしくはその混合物を用いることができるが、通常はl−メントールが用いられる。メントールは化学的に合成されたものでも、植物の精油等から精製したものでも良く、また、メントールとミント精油とを組み合わせて好ましく用いることもできる。本発明で用いられるミント精油は、シソ科メンタ属植物の精油であれば特に限定されることはないが、好ましくはペパーミント(Mentha piperita L.)、スペアミント(Mentha spicata L.)、和種ハッカ(Mntha arvensis L.)が用いられ、これらは単独もしくは混合して用いることもできるが、特に好ましくはペパーミントの精油が用いられる。 The menthol used in the present invention is not particularly limited as long as it is menthol, and any isomer or a mixture thereof can be used, but usually 1-menthol is used. Menthol may be either chemically synthesized or purified from plant essential oil or the like, and menthol and mint essential oil may be preferably used in combination. The mint essential oil used in the present invention is not particularly limited as long as it is an essential oil of the Labiatae Menta plant, but is preferably peppermint (Mentha piperita L.), spearmint (Mentha spicata L.), Japanese mint ( Mntha arvensis L.) can be used, and these can be used alone or in combination, but peppermint essential oil is particularly preferably used.
本発明の香味料組成物は、チューインガム、キャンディ、錠菓、アイスクリーム、飲料などの飲食物、歯磨き、口中清涼剤、洗口剤などの口腔用組成物、煙草などに好ましく用いることができる。本発明の香味料組成物のこれら製品への添加率は、特に限定されることはないが、好ましくは0.001〜5質量%、特に好ましくは0.01〜3質量%、最も好ましくは0.03〜1質量%で用いられる。添加率が0.001質量%未満であれば添加効果が十分でないことがあり、添加率が5質量%を越えた場合は経済的に有利でないときがある。 The flavoring composition of the present invention can be preferably used for chewing gum, candy, tablet confectionery, ice cream, beverages such as beverages, oral compositions such as toothpaste, mouth fresheners, mouthwashes, and tobacco. The addition ratio of the flavoring composition of the present invention to these products is not particularly limited, but is preferably 0.001 to 5% by mass, particularly preferably 0.01 to 3% by mass, and most preferably 0. 0.03 to 1% by mass. If the addition rate is less than 0.001% by mass, the effect of addition may not be sufficient, and if the addition rate exceeds 5% by mass, it may not be economically advantageous.
本発明の香味料組成物には更に食品添加物、例えば甘味料、着色料、保存料、増粘安定剤、酸化防止剤、苦味料、酸味料、乳化剤、強化剤、製造用剤及び香料などを添加して各種製剤として用いることもできる。本発明で更に用いることのできる香料としては、例えばアセト酢酸エチル、アセトフェノン、アニスアルデヒド、α−アミルシンナムサルデヒド、アントラニル酸メチル、イオノン、イソオイゲノール、イソ吉草酸イソアミル、イソ吉草酸エチル、イソチオシアン酸アリル、イソチオシアン酸3−ブテニル、イソチオシアン酸4−ペンテニル、イソチオシアン酸ベンジル、イソチオシアン酸3−メチルチオプロピル、イソチオシアネート類、インドール及びその誘導体、γ−ウンデカラクトン、エステル類、エチルバニリン、エーテル類、オイゲノール、オクタノール、オクタナール、オクタン酸エチル、ギ酸イソアミル、ギ酸ゲラニル、ギ酸シトロネリル、ケイ皮酸、ケイ皮酸エチル、ケイ皮酸メチル、ケトン類、ゲラニオール、酢酸イソアミル、酢酸エチル、酢酸ゲラニル、酢酸シクロヘキシル、酢酸シトロネリル、酢酸シンナミル、酢酸テルピニル、酢酸フェネチル、酢酸ブチル、酢酸ベンジル、酢酸l−メンチル、酢酸リナリル、サリチル酸メチル、シクロヘキシルプロピオン酸アリル、シトラール、シトロネラール、シトロネロール、1,8−シネオール、脂肪酸類、脂肪族高級アルコール類、脂肪族高級アルデヒド類、脂肪族高級炭化水素類、シンナミルアルコール、シンナムアルデヒド、チオエーテル類、チオール類、デカナール、デカノール、デカン酸エチル、テルピネオール、リモネン、ピネン、ミルセン、タピノーレン、テルペン系炭化水素類、γ−ノナラクトン、バニリン、パラメチルアセトフェノン、ヒドロキシシトロネラール、ヒドロキシシトロネラールジメチルアセタール、ピペロナール、フェニル酢酸イソアミル、フェニル酢酸イソブチル、フェニル酢酸エチル、フェノールエーテル類、フェノール類、フルフラール及びその誘導体、プロピオン酸、プロピオン酸イソアミル、プロピオン酸エチル、プロピオン酸ベンジル、ヘキサン酸、ヘキサン酸アリル、ヘキサン酸エチル、ヘプタン酸エチル、l−ペリラアルデヒド、ベンジルアルコール、ベンズアルデヒド、芳香族アルコール類、芳香族アルデヒド類、d−ボルネオール、マルトール、N−メチルアントラニル酸メチル、メチルβ−ナフチルケトン、dl−メントール、酪酸、酪酸イソアミル、酪酸エチル、酪酸シクロヘキシル、酪酸ブチル、ラクトン類、リナロオール等の合成或いは天然由来の香料の他、オレンジ、レモン、ライム、グレープフルーツなどシトラス系精油類、アップル、バナナ、グレープ、メロン、ピーチ、パイナップル、ストロベリーなどフルーツ系の精油或いは回収フレーバー、ミルク、クリーム、バター、チーズ、ヨーグルトなど乳系の抽出香料、緑茶、ウーロン茶、紅茶、コーヒー、ココアなど嗜好品系の回収フレーバー、アサノミ、アサフェチダ、アジョワン、アニス、アンゼリカ、ウイキョウ、ウコン、オレガノ、オールスパイス、オレンジノピール、カショウ、カッシア、カモミール、カラシナ、カルダモン、カレーリーフ、カンゾウ、キャラウェー、クチナシ、クミン、クレソン、クローブ、ケシノミ、ケーパー、コショウ、ゴマ、コリアンダー、サッサフラス、サフラン、サボリー、サルビア、サンショウ、シナモン、シャロット、ジュニパーベリー、ショウガ、スターアニス、セイヨウワサビ、セロリー、ソーレル、タイム、タマネギ、タマリンド、タラゴン、チャイブ、ディル、トウガラシ、ナツメグ、ニガヨモギ、ニジェラ、ニンジン、ニンニク、バジル、パセリ、バニラ、パプリカ、ヒソップ、フェネグリーク、ホースラディッシュ、マジョラム、ミョウガ、ラベンダー、リンデン、レモングラス、レモンバーム、ローズ、ローズマリー、ローレル、ワサビなどから得られる香辛料抽出物、アイスランドモス、アカヤジオウ、アケビ、アサ、アサフェチダ、アジアンタム、アジョワン、アズキ、アスパラサスリネアリス、アップルミント、アーティチョーク、アニス、アボカド、アマチャ、アマチャズル、アミガサユリ、アミリス、アーモンド、アリタソウ、アルカンナ、アルテミシア、アルニカ、アルファルファ、アロエ、アンゴスツラ、アンゴラウィード、アンズ、アンズタケ、アンゼリカ、アンバー、アンバーグリス、アンブレット、イカ、イカリソウ、イグサ、イースト、イタドリ、イチゴ、イチジク、イチョウ、イノコヅチ、イランイラン、イワオウギ、インペラトリア、インモルテル、ウィンターグリーン、ウォータークレス、ウコギ、ウコン、ウスバサイシン、ウッドラフ、ウニ、ウメ、ウーロンチャ、エゴマ、エノキダケ、エビ、エビスグサ、エリゲロン、エルダー、エレウテロコック、エレカンペン、エレミ、エンゴサク、エンジュ、エンダイブ、欧州アザミ、オウレン、オオバコ、オカゼリ、オキアミ、オーク、オークモス、オケラ、オスマンサス、オポポナックス、オミナエシ、オモダカ、オランダセンニチ、オリガナム、オリス、オリバナム、オリーブ、オールスパイス、オレンジ、オレンジフラワー、カイ、カイニンソウ、カカオ、カキ、カサイ、カシューナッツ、カスカラ、カスカリラ、カストリウム、カタクリ、カツオブシ、カッシー、カッシャフィスチュラ、カテキュ、カニ、カーネーション、カノコソウ、カモミル、カヤプテ、カラシ、カラスウリ、カラスビシャク、ガラナ、カラムス、ガランガ、カーラント、カリッサ、カリン、カルダモン、ガルバナム、カレー、カワミドリ、カンゾウ、ガンビア、カンラン、キウィーフルーツ、キカイガラタケ、キキョウ、キク、キクラゲ、キササゲ、ギシギシ、キダチアロエ、キナ、キハダ、キバナオウギ、ギボウシ、ギムネマシルベスタ、キャットニップ、キャラウェイ、キャロップ、キュウリ、キラヤ、キンミズヒキ、グァバ、グァヤク、クコ、クサスギカズラ、クサボケ、クズ、クスノキ、クスノハガシワ、グーズベリー、クチナシ、クベバ、クマコケモモ、グミ、クミン、グラウンドアイビー、クララ、クラリセージ、クランベリー、クリ、クルミ、クリーム、グレインオブパラダイス、クレタディタニー、グレープフルーツ、クローバー、クローブ、クロモジ、クロレラ、クワ、クワッシャ、ケイパー、ゲットウ、ケード、ケブラコ、ゲルマンダー、ケンチュール、ケンポナシ、ゲンノショウコ、コウジ、コウダケ、コウチャ、コウホネ、コカ、コガネバナ、コクトウ、コクルイ、ココナッツ、ゴシュユ、コショウ、コスタス、コストマリー、コパイパ、コーヒー、コブシ、ゴボウ、ゴマ、コーラ、コリアンダー、コルツフート、ゴールデンロッド、コロンボ、コンサイ、コンズランゴ、コンフリー、サイプレス、魚、サクラ、サクランボ、ザクロ、サケカス、ササ、ササクサ、サーチ、サッサフラス、サフラン、サポジラ、サボテン、サラシナショウマ、サルサパリラ、サルシファイ、サルノコシカケ、サンザシ、サンシュユ、サンショウ、サンタハーブ、サンダラック、サンダルウッド、サンダルレッド、シイタケ、ジェネ、シダー、シトラス、シトロネラ、シヌス、シベット、シマルーバ、シメジ、シャクヤク、ジャスミン、ジャノヒゲ、ジャボランジ、シャロット、シュクシャ、ジュニパーベリー、ショウガ、ショウユ、ショウユカス、ジョウリュウシュ、ショウロ、シロタモギタケ、ジンセン、シンナモン、酢、スイカ、スイセン、スギ、スターアニス、スターフルーツ、スチラックス、スッポン、スッポンタケ、ズドラベッツ、スネークルート、スパイクナード、スプルース、スベリヒユ、スローベリー、セイボリー、セキショウ、セージ、ゼドアリー、セネガ、ゼラニウム、セロリー、センキュウ、センタウリア、センゲン、セントジョーンズウォルト、センナ、ソース、ダイオウ、ダイズ、タイム、タケノコ、タコ、タデ、ダバナ、タマゴ、タマゴタケ、タマネギ、タマリンド、ダミアナ、タモギタケ、タラゴン、タラノキ、タンジー、タンジェリン、タンポポ、チェリモラ、チェリーローレル、チェリーワイルド、チガヤ、チコリ、チーズ、チチタケ、チャイブ、チャービル、チャンパカ、チュベローズ、チョウセンゴミシ、チラータ、ツクシ、ツケモノ、ツタ、ツバキ、ツユクサ、ツリガネニンジン、ツルドクダミ、ディアタング、ティスル、ディタニー、ディル、デーツ、テンダイウヤク、テンマ、トウガラシ、トウキ、ドウショクブツタンパクシツ、ドウショクブツユ、トウミツ、トウモロコシ、ドクダミ、トチュウ、ドッググラス、トマト、ドラゴンブラッド、ドリアン、トリュフ、トルーバルサム、トンカ、ナギナタコウジュ、ナシ、ナスターシャム、ナッツ、ナットウ、ナツメ、ナツメグ、ナデシコ、ナメコ、ナラタケ、ニアウリ、ニュウサンキンバイヨウエキ、ニンジン、シンニク、ネズミモチ、ネットル、ネムノキ、ノットグラス、バイオレット、パイナップル、ハイビスカス、麦芽、ハコベ、バジル、ハス、ハスカップ、パースカップ、パセリ、バター、バターオイル、バターミルク、バーチ、ハチミツ、パチュリー、バックビーン、ハッコウシュ、ハッコウニュウ、ハッコウミエキ、パッションフルーツ、ハツタケ、バッファローベリー、ハトムギ、ハナスゲ、バナナ、バニラ、ハネーサックル、パパイヤ、バーベリー、ハマゴウ、ハマスゲ、ハマナス、ハマボウフウ、ハマメリス、バラ、パルマローザ、パンダナ、バンレイシ、ヒキオコシ、ヒシ、ピスタチオ、ヒソップ、ヒッコリー、ピーナッツ、ヒノキ、ヒバ、ピプシシワ、ヒメハギ、ヒヤシンス、ヒラタケ、ビワ、ビンロウ、フェイジョア、フェネグリーク、フェンネル、フジバカマ、フジモドキ、フスマ、フーゼルユ、プチグレイン、ブチュ、ブドウ、ブドウサケカス、フトモモ、ブナ、ブナハリタケ、ブラックキャラウェイ、ブラックベリー、プラム、ブリオニア、プリックリーアッシュ、プリムローズ、プルネラ、ブルーベリー、ブレッドフルーツ、ヘイ、ベイ、ヘーゼルナッツ、ベチバー、ベーテル、ベニバナ、ペニーロイヤル、ヘビ、ペピーノ、ペプトン、ベルガモット、ベルガモットミント、ペルーバルサム、ベルベナ、ベロニカ、ベンゾイン、ボアドローズ、ホアハウンド、ホウ、ホウキタケ、ホウショウ、ボウフウ、ホエイ、ホオノキ、ホースラディッシュ、ボタン、ホップ、ポピー、ポプラ、ポポー、ホホバ、ホヤ、ボルドー、ボロニア、マイタケ、マグウォルト、マシュマロー、マジョラム、マスティック、マソイ、マタタビ、マチコ、マツ、マツオウジ、マッシュルーム、マツタケ、マツブサ、マツホド、マテチャ、マメ、マリーゴールド、マルバダイオウ、マルメロ、マレイン、マロー、マンゴー、マンゴスチン、ミカン、ミシマサイコ、ミソ、ミツマタ、ミツロウ、ミート、ミモザ、ミョウガ、ミルク、ミルテ、ミルフォイル、ミルラ、ミロバラン、ムギチャ、ムスク、ムラサキ、メスキート、メドウスィート、メハジキ、メープル、メリッサ、メリロット、メロン、モウセンゴケ、モニリアバイヨウエキ、モミノキ、モモ、モロヘイヤ、ヤクチ、ヤマモモ、ユーカリ、ユキノシタ、ユズ、ユッカ、ユリ、ヨウサイ、ヨロイグサ、ライオンズフート、ライチ、ライフエバーラスティングフラワー、ライム、ライラック、ラカンカ、ラカンショウ、ラズベリー、ラタニア、ラディッシュ、ラブダナム、ラベンダー、ラングウォルト、ラングモス、ランブータン、リキュール、リーク、リツェア、リナロエ、リュウガン、リョウフンソウ、リョクチャ、リンゴ、リンデン、リンドウ、ルー、ルリジサ、レセダ、レモン、レモングラス、レンギョウ、レンゲ、レンブ、ローズマリー、ロベージ、ローレル、ロンゴザ、ワサビ、ワタフジウツギ、ワームウッド、ワームシード、ワラビ、ワレモコウなどから得られる天然香料、カレー、シチュー、デミグラスソースなど調理食品からの抽出フレーバー等天然香料が例示され、適宜選択して使用される。香料の添加量は特に限定されるものではないが、一般的には本発明の香味料組成物中、0.0001〜50質量%、好ましくは0.001〜30質量%、最も好ましくは0.01〜10質量%の添加量で用いられる。本発明の香味料組成物の使用形態は、そのまま或いは希釈した状態、乳化状態、更には粉化した様々な製剤の形で用いることができる。 The flavoring composition of the present invention further includes food additives such as sweeteners, coloring agents, preservatives, thickening stabilizers, antioxidants, bittering agents, acidulants, emulsifiers, reinforcing agents, manufacturing agents and flavoring agents. Can also be used as various preparations. Examples of the fragrance that can be further used in the present invention include ethyl acetoacetate, acetophenone, anisaldehyde, α-amylcinnamaldehyde, methyl anthranilate, ionone, isoeugenol, isoamyl isovalerate, ethyl isovalerate, isothiocyanic acid. Allyl, 3-butenyl isothiocyanate, 4-pentenyl isothiocyanate, benzyl isothiocyanate, 3-methylthiopropyl isothiocyanate, isothiocyanates, indole and its derivatives, γ-undecalactone, esters, ethyl vanillin, ethers, eugenol , Octanol, octanal, ethyl octoate, isoamyl formate, geranyl formate, citronellyl formate, cinnamic acid, ethyl cinnamate, methyl cinnamate, ketones, geraniol, isoacetate Mill, ethyl acetate, geranyl acetate, cyclohexyl acetate, citronellyl acetate, cinnamyl acetate, terpinyl acetate, phenethyl acetate, butyl acetate, benzyl acetate, l-menthyl acetate, linalyl acetate, methyl salicylate, allyl cyclohexylpropionate, citral, citronellal, citronellol 1,8-cineole, fatty acids, aliphatic higher alcohols, aliphatic higher aldehydes, aliphatic higher hydrocarbons, cinnamyl alcohol, cinnamaldehyde, thioethers, thiols, decanal, decanol, ethyl decanoate, Terpineol, limonene, pinene, myrcene, tapinolen, terpene hydrocarbons, γ-nonalactone, vanillin, paramethylacetophenone, hydroxycitronellal, hydroxycitronellal Methyl acetal, piperonal, isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, phenol ethers, phenols, furfural and its derivatives, propionic acid, isoamyl propionate, ethyl propionate, benzyl propionate, hexanoic acid, allyl hexanoate , Ethyl hexanoate, ethyl heptanoate, l-perilaldehyde, benzyl alcohol, benzaldehyde, aromatic alcohols, aromatic aldehydes, d-borneol, maltol, methyl N-methylanthranilate, methyl β-naphthyl ketone, dl- In addition to synthetic or naturally derived fragrances such as menthol, butyric acid, isoamyl butyrate, ethyl butyrate, cyclohexyl butyrate, butyl butyrate, lactones, linalool, orange, lemon, lime, Citrus essential oils such as rape fruit, fruit-based essential oils such as apple, banana, grape, melon, peach, pineapple, strawberry or recovered flavors, milk-based extract flavors such as milk, cream, butter, cheese, yogurt, green tea, oolong tea, Collection flavors such as tea, coffee, cocoa, asanomi, asafetida, ajowan, anise, angelica, fennel, turmeric, oregano, allspice, orange nopeel, pepper, cassia, chamomile, mustard, cardamom, curry leaf, licorice, Caraway, gardenia, cumin, watercress, clove, poppy flea, caper, pepper, sesame, coriander, sassafras, saffron, savory, salvia, salamander, cinnamon, charlotte, juju Parberry, Ginger, Star anise, Horseradish, Celery, Sorrel, Thyme, Onion, Tamarind, Tarragon, Chives, Dill, Pepper, Nutmeg, Mugwort, Nigera, Carrot, Garlic, Basil, Parsley, Vanilla, Paprika, Hisop Spice extract from horseradish, marjoram, ginger, lavender, linden, lemongrass, lemon balm, rose, rosemary, laurel, horseradish, etc., Iceland moss, red gecko, akebi, Asa, Asafetida, Asian Tam, Ajowan, Azuki , Asparagus Linea Alice, Apple Mint, Artichoke, Anise, Avocado, Achacha, Amazazuru, Amigasailuri, Amiris, Almond, Aritasou, Arcanna , Artemisia, Arnica, Alfalfa, Aloe, Angostura, Angola Weed, Apricot, Apricot, Angelica, Amber, Ambergris, Amblet, Squid, Epimedium, Rabbit, East, Japanese Knotweed, Strawberry, Fig, Ginkgo, Wildflower , Imperatoria, Inmortel, Wintergreen, Watercress, Ukogi, Turmeric, Usbasaishin, Woodruff, Sea Urchin, Ume, Oolongcha, Egoma, Enokitake, Shrimp, Shrimp, Eligeron, Elder, Eletrocock, Elecanpen, Eremi, Engosaku, Enju, Endive, European Thistle, Auren, Plantain, Okazeri, Krill, Oak, Oak Moss, Okera, Ottomanthus, Opoponax, Ominaeshi, Omoda , Dutch Sennici, Origanum, Oris, Olivenum, Olive, Allspice, Orange, Orange Flower, Kai, Kainou, Cacao, Oyster, Kasai, Cashew Nut, Cascala, Cascarilla, Castrium, Katakuri, Cutlet Obsi, Cassie, Cassia Fistula, Catech, Crab, carnation, valerian, camomil, kayapte, mustard, crow crisp, galana, calamus, galanga, currant, carissa, karin, cardamom, galvanum, curry, kawamidori, licorice, ganbia, kanran, kiwifruit, kikaigaraki, kikugaraki , Jellyfish, catalpa, bark, aloe vera, kina, yellowfin, yellow-headed eagle, hosta, gymnema sylvestre, catnip, carawe , Carop, cucumber, kiraya, goldfish, guava, guayak, wolfberry, peony, peony, kudu, camphor, camphor, gooseberry, gardenia, kubeba, bearberry, gummy, cumin, ground ivy, clara, cranberry, cranberry, cranberry Cream, Grain of Paradise, Cretadi Tanny, Grapefruit, Clover, Clove, Chromoji, Chlorella, Mulberry, Washer, Caper, Ghetto, Cade, Kebraco, Gelmander, Kentul, Kemponashi, Gennoshoko, Kouji, Kodatake, Kocha, Kohone, Coca, Cognevana, Kokuto, Kokului, Coconut, Goshuyu, Pepper, Costas, Costmary, Copaipa, Coffee, Kobushi, Burdock, Sesame, Cola, Co Leander, Coltsfoot, Golden Rod, Colombo, Consai, Cons Lango, Comfrey, Cypress, Fish, Sakura, Cherry, Pomegranate, Salmon Cass, Sasa, Sasakusa, Search, Sassafras, Saffron, Sapodilla, Cactus, Sarasarashouma, Sarsaparilla, Salsify, Sarnos , Hawthorn, sanshuyu, salamander, santa herb, sandalack, sandalwood, sandal red, shiitake, gene, cedar, citrus, citronella, sinus, civet, simarouba, shimeji, peonies, jasmine, janohige, jaborangi, charlotte, shukusha, Juniper berry, ginger, ginger, ginger, ginger rush, ginger, shirotamogitake, ginseng, cinnamon, vinegar, watermelon, narcissus Japanese cedar, star anise, star fruit, stylax, suppon, suptake bamboo, zudrabets, snake root, spikenard, spruce, purslane, slow berry, savory, pepper, sage, zedary, senega, geranium, celery, senkyu, centauria, sengen, cent Joneswold, Senna, Sauce, Diou, Soybean, Thyme, Bamboo shoot, Octopus, Tade, Davana, Tamago, Bamboo shoot, Onion, Tamarind, Damiana, Tamamotake, Tarragon, Taranki, Tansy, Tangerine, Dandelion, Cherimora, Cherry Laurel, Cherry Wild , Chigaya, Chicory, Cheese, Chichitake, Chives, Chervil, Champaca, Tuberose, Datura, Cirata, Tsukushi, Tsukumono, Ivy Camellia, camellia, garlic, tsurudakudanami, diatang, tissuru, ditany, dill, dates, tendaiyaku, tenma, capsicum, cypress, cornflower, corn, dragonfly, tomato dragon, doggrass, tomato dragon, doggrass Durian, truffle, trout balsam, tonka, naginata koju, pear, naster sham, nuts, natto, jujube, nutmeg, nadesico, sea cucumber, aratake, niari, nusankinbaiyoueki, carrot, garlic, mud mochi, nettle, nemugrass, knotgrass , Violet, pineapple, hibiscus, malt, chickweed, basil, lotus, lotus cup, perth cup, parsley, butter, butter oil, buttermilk , Birch, honey, patchouli, buck bean, hakkoshu, hakkounyu, hakkoumieki, passion fruit, bonito, buffalo berry, pearl barley, chanterelle, banana, vanilla, honeysuckle, papaya, barberry, clam, hamasuge, hamanasu, hamafou , Palmarosa, Pandana, Van Reishi, Hikikoshi, Hishi, Pistachio, Hyssop, Hickory, Peanut, Hinoki, Hiba, Pipsisiwa, Himehagi, Hyacinth, Oyster Mushroom, Biwa, Binlaw, Feijoa, Fenegreek, Fennel, Fujibakafu, Fujimadokifu Grain, butch, grape, grape salmon, peach, beech, beech tree, black caraway, blackberry, plum, brio A, Prickly Ash, Primrose, Prunella, Blueberry, Breadfruit, Hay, Bay, Hazelnut, Vetiver, Bethel, Safflower, Penny Royal, Snake, Pepino, Peptone, Bergamot, Bergamot Mint, Peruvian Sam, Verbena, Veronica, Benzoin , Boad Rose, Hoa Hound, Hou, Bakitake, Hawsho, Bow Fu, Whey, Hoonoki, Horseradish, Button, Hop, Poppy, Poplar, Popau, Jojoba, Joya, Bordeaux, Boronia, Maitake, Magtake, Marshmallow, Marjoram, Mastic, Masoyi, Matatabi, Machiko, Pine, Matsuouji, Mushroom, Matsutake, Matsubusa, Matsuhodo, Matecha, Beans, Marigold, Marbadio, Quince, Malein Mallow, Mango, Mangosteen, Mikan, Mishima Psycho, Miso, Mitsumata, Beeswax, Meat, Mimosa, Myoga, Milk, Milte, Milfoil, Myrrh, Milobaran, Mugica, Musk, Murasaki, Mesquite, Meadowito, Maple, Melissa, Merilot , Melon, moss, monalia, peach, peach, moroheiya, yakchi, bayberry, eucalyptus, yukinoshita, yuzu, yucca, lily, wild rhinoceros, yorogusa, lion's foot, lychee, life everlasting flower, lime, lilac, lakanka, Lacanshaw, Raspberry, Latania, Radish, Lovedanum, Lavender, Langwald, Langmoth, Rambutan, Liqueur, Leak, Lyzea, Linaroe, Longan, Ryofunso, Ryokucha, apple, linden, gentian, roux, borage, reseda, lemon, lemongrass, forsythia, lotus, renbu, rosemary, lobe, laurel, longoza, horseradish, slater, wormwood, wormwood, bracken, bracken Natural flavors obtained from the above, natural flavors such as curry, stew, demiglace sauce and other flavors extracted from cooked foods are exemplified and used as appropriate. The amount of the fragrance added is not particularly limited, but is generally 0.0001 to 50% by mass, preferably 0.001 to 30% by mass, and most preferably 0.001 to 30% by mass in the flavor composition of the present invention. It is used in an addition amount of 01 to 10% by mass. The flavoring composition of the present invention can be used as it is or in a diluted state, an emulsified state, and various powdered preparations.
[製造例1](キナ酸含有緑茶抽出物)
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。
[Production Example 1] (Quinic acid-containing green tea extract)
To 100 g of green tea leaves, 2,000 g of distilled water was added and stirred at 60 ° C. for 1 hour. After cooling to 40 ° C., the tea leaves and insolubles were separated using a centrifugal filter, and the separated solution was filtered through Celite to obtain 1,780 g of an extract. The extract was concentrated under reduced pressure at a liquid temperature of 50 ° C. until the liquid volume reached 300 g. After adding 360 g of 95% ethanol to 300 g of this concentrated liquid, the resulting insoluble matter was cooled to 10 ° C. and filtered through Celite to obtain 593 g of a filtrate. Further, 12 g of activated carbon was added to the filtrate, stirred for 30 minutes, filtered through Celite, and the filtrate was freeze-dried to obtain 2.2 g of a green tea extract containing quinic acid. As a result of analysis using HPLC, the components contained in the green tea extract were quinic acid 7.6%, glucose 0.76%, fructose 0.81%, sucrose 7.95%, theanine 3.16 by mass ratio. %Met.
[製造例2](キナ酸含有紅茶抽出物)
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。
[Production Example 2] (Quinic acid-containing black tea extract)
2,000 g of distilled water was added to 100 g of black tea leaves and heated to reflux for 1 hour. After cooling, solid-liquid separation was performed with a centrifugal filter to obtain 1,920 g of filtrate. 5 g of activated carbon was added to the filtrate, and 500 ml of a synthetic adsorbent (“Diaion HP-20” (trade name) manufactured by Mitsubishi Chemical Corporation) was added, followed by stirring for 1 hour. Thereafter, the synthetic adsorbent was removed by filtration to obtain 1,890 g of a filtrate. 1,890 g of the filtrate was applied to a column packed with 1,000 ml of a cation exchange resin (“Diaion SK1B” (trade name) manufactured by Mitsubishi Chemical Corporation) and fed at a space velocity of SV = 1. The passing liquid was filtered through an ultrafiltration membrane (“NTU-2120” manufactured by Nitto Denko Corporation). By lyophilizing 1,810 g of the obtained filtrate, 5.9 g of black tea extract containing quinic acid was obtained. As a result of analysis using HPLC, the components contained in the black tea extract are in a mass ratio of 17.0% quinic acid, 19.7% glucose, 15.1% fructose, 2.2% sucrose, 7.6% theanine. Met.
[製造例3](クロロゲン酸等を含有するコーヒー生豆抽出物)
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。
[Production Example 3] (raw coffee bean extract containing chlorogenic acid)
After pulverizing 300 g of green coffee beans, 1,500 ml of 70% aqueous ethanol solution was added, and the mixture was stirred and heated at 90 ° C. for 2 hours. After cooling, insoluble solids were removed to obtain 1,100 ml of extract. The extract was concentrated under reduced pressure to remove ethanol, and then added with 180 g of 35% hydrochloric acid to adjust the concentration of hydrochloric acid in the extract to about 5%, followed by stirring and heating at 70 ° C. for 1 hour. did. After cooling, the mixture was concentrated under reduced pressure to 300 g, neutralized by adding 20% sodium hydroxide to the resulting concentrated solution, and then 600 g of methylene chloride was added and thoroughly mixed and stirred. After the aqueous layer was separated, it was led to a column packed with 500 ml of Diaion HP-20 resin (trade name, manufactured by Mitsubishi Chemical Corporation). Next, the resin was thoroughly washed with water, and chlorogenic acids were eluted with 750 g of 95% aqueous ethanol. The obtained eluate was concentrated under reduced pressure and dried to obtain 27 g of green coffee bean extract containing chlorogenic acid and the like.
[製造例4](キナ酸含有コーヒー生豆加水分解物抽出物)
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。
[Production Example 4] (Quinic acid-containing green coffee bean hydrolyzate extract)
After pulverizing 500 g of green coffee beans, 5,000 ml of 70% ethanol aqueous solution was added and heated to reflux for 2 hours. After cooling, solid-liquid separation was performed with a centrifugal filter, and the filtrate was concentrated under reduced pressure to an ethanol content of 5% or less, 1,000 units of chlorogenic acid esterase (manufactured by Kikkoman) were added, and the mixture was stirred at 40 ° C. for 3 hours. The insoluble matter is removed by centrifugation, the treatment liquid is passed through a column filled with 1,000 ml of a synthetic adsorbent (“Diaion HP-20” (trade name) manufactured by Mitsubishi Chemical Corporation), and the eluted liquid is frozen. By drying, 26.6 g of a green coffee bean hydrolyzed extract containing quinic acid was obtained. As a result of analysis using HPLC, the components in the green coffee bean hydrolyzed extract were quinic acid 32%, glucose 16%, and fructose 15% in mass ratio. One unit of chlorogenic acid esterase is the amount of enzyme that hydrolyzes 3-caffeoylquinic acid by 1 micromole per minute in water at 30 ° C.
[製造例5](キナ酸含有コーヒー生豆加水分解物)
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。
[Production Example 5] (Quinic acid-containing green coffee bean hydrolyzate)
After crushing 100 g of green coffee beans, 30 g of calcium hydroxide and 1,000 ml of water were added, and the mixture was heated and stirred at 80 ° C. for 30 minutes. After cooling to room temperature, solid-liquid separation was performed to obtain an aqueous solution. After adjusting the pH to 3 by adding dilute hydrochloric acid, the activated carbon was decolorized. Insoluble matter was removed by filtration to obtain a filtrate. The filtrate was desalted with an ion exchange membrane electrodialyzer (cation exchange membrane fraction molecular weight: 300, anion exchange membrane fraction molecular weight: 100), concentrated under reduced pressure, and lyophilized to obtain quinic acid. 9 g of a green coffee bean hydrolyzate was obtained. As a result of analysis using HPLC, the components in the green coffee bean hydrolyzate were 35% quinic acid, 25% sucrose, 11% monosaccharide, and 9% ash.
[製造例6](キナ酸含有クランベリー抽出物)
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。
[Production Example 6] (Cranberry extract containing quinic acid)
Cranberry concentrated fruit juice (600 g) was diluted and decolorized using 600 ml of porous polymer resin XAD-2 (manufactured by Organo Corp.). The filtrate was dialyzed using an ion exchange membrane electrodialyzer (cation exchange membrane fraction molecular weight: 300, anion exchange membrane fraction molecular weight: 300) to obtain a concentrate on the salt waste side. This was diluted with an aqueous ethanol solution so that the quinic acid concentration was 2% and the ethanol concentration was 20% to obtain 560 g of a quinic acid-containing cranberry extract. As a result of analysis using HPLC, the components in the cranberry extract were 35% quinic acid, 30% citric acid, and 35% malic acid.
[試験例1]
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。
[Test Example 1]
In a 100 ppm aqueous solution of menthol, sucralose (manufactured by Saneigen FFI Co., Ltd., trade name) 1 ppm, quinic acid (reagent manufactured by Nacalai Tesque) 1 ppm, chlorogenic acid (manufactured by Wako Pure Chemical Industries, Ltd.) as a quinic acid derivative And the extract obtained in the above production example were added so as to correspond to about 1 ppm as quinic acid, and sensory evaluation of refreshing feeling and flavor was performed by 20 panelists. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. The average value of the evaluation results and the evaluation comments are shown in Table 1.
[製造例7]
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。
[Production Example 7]
A fragrance composition (hereinafter referred to as “mint fragrance”) comprising 40 parts of l-menthol, 35 parts of peppermint oil and 25 parts of ethanol was prepared.
[試験例2]
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。
[Test Example 2]
Into 200ppm aqueous solution of mint flavor, sucralose (manufactured by Saneigen FFI Co., Ltd., trade name) 1ppm, quinic acid (reagent made by Nacalai Tesque) 1ppm, chlorogenic acid (Wako Pure Chemical Industries, Ltd.) as quinic acid derivative Reagents manufactured) 1.8 ppm and the extract obtained in the above production example were added so as to correspond to about 1 ppm as quinic acid, and a panel of 20 persons performed sensory evaluation of refreshing feeling and flavor. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. Table 2 shows the average value of the evaluation results and the evaluation comments.
以上の結果から、キナ酸、キナ酸誘導体及びキナ酸類を含有する抽出物のいずれにおいてもメントールの清涼感を増強し、拡散性及び持続性を付与し、かつ、メントール本来の風味を阻害しないことが確認された。 From the above results, in any of the extracts containing quinic acid, quinic acid derivatives and quinic acids, enhance the sensation of menthol, impart diffusibility and sustainability, and do not inhibit the original flavor of menthol. Was confirmed.
[実施例1](キャンディ)
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。
[Example 1] (Candy)
Bx. 70 maltitol syrup was cooked to 185 ° C., rapidly cooled to 155 ° C., added with a mixture of menthol and the extract of Production Example 4 and homogenized and molded to prepare the candy of the present invention. Menthol was added so that the final amount was 0.5% by mass, and the extract of Production Example 4 was added so that the amount of quinic acid was 1 ppm. The sensory evaluation of the flavor was performed by 10 expert panelists. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. Table 3 shows the average evaluation results and the evaluation comments.
[実施例2](チューインガム)
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。
[Example 2] (chewing gum)
Gum base, sugar, glucose and corn syrup are mixed, and 1% by mass of mint flavor and the extract of Production Example 4 are added so that the amount of quinic acid is 1 ppm, and about 50 using a high shear mixer according to a conventional method. The mixture was cooled at 0 ° C., and after cooling, it was press-molded with a roller to prepare a sheet gum of the present invention that would be 3 g per sheet. The sensory evaluation of the flavor was performed by 10 expert panelists. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. Table 4 shows the average value of the evaluation results and the evaluation comments.
[実施例3](粉末香料)
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。
[Example 3] (powder flavor)
30 parts of gum arabic and 50 parts of DE10 dextrin were heated and dissolved in 150 parts of water, and after cooling, 20 parts of menthol was added and emulsified, and spray drying was performed with a spray dryer to prepare a menthol powder flavor. This was made into an additive-free product. Similarly, a product obtained by adding the extract of Production Example 4 to 0.005 part of quinic acid before emulsification was prepared, and this product was used as an additive product. The prepared menthol powder flavor was added to 0.5% of the powdered sugar and stirred well, and this was eaten as it was, and the sensory evaluation of the flavor was performed by 10 professional panelists. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. Table 5 shows the average value of the evaluation results and the evaluation comments.
[実施例4](錠菓)
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。
[Example 4] (Tablets)
A menthol tablet was prepared by adding 1.0% of sucrose fatty acid ester as a lubricant and each powdered fragrance prepared in Example 3 to sorbitol, and tableting at a tableting pressure of 1 t. The sensory evaluation of the flavor was performed by 10 expert panelists. The evaluation score was 4 points for the additive-free product, 7 points when the refreshing feeling was very strong, and 1 point when the refreshing feeling was weakened. Table 6 shows the average value of the evaluation results and the evaluation comments.
本発明の香味料組成物は、メントール自体の香気香味を阻害することなく増強し、清涼感の発現性、拡散性、持続性を向上し、かつ、異味異臭を感じさせることが無く、優れた香味料組成物を提供する。本発明の香味料組成物は強い清涼感・刺激を与えることもできるし、また、通常のメントール使用量と比較して少ない量で同等の清涼感を与えることができ、結果としてメントールの苦味改善効果を示すことができる。 The flavor composition of the present invention is enhanced without inhibiting the fragrance flavor of menthol itself, improves the expression of coolness, diffusibility, and persistence, and does not give off a strange odor and is excellent. A flavoring composition is provided. The flavoring composition of the present invention can give a strong refreshing feeling and irritation, and can give the same refreshing feeling in a smaller amount compared to the normal amount of menthol, resulting in improvement of the bitterness of menthol. The effect can be shown.
Claims (9)
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