JP2002038187A - Method for modifying essential oil of plant belonging to genus mentha of family labiatae - Google Patents
Method for modifying essential oil of plant belonging to genus mentha of family labiataeInfo
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- JP2002038187A JP2002038187A JP2000228857A JP2000228857A JP2002038187A JP 2002038187 A JP2002038187 A JP 2002038187A JP 2000228857 A JP2000228857 A JP 2000228857A JP 2000228857 A JP2000228857 A JP 2000228857A JP 2002038187 A JP2002038187 A JP 2002038187A
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- essential oil
- modified
- flavor
- distillation
- mint
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Abstract
Description
【０００１】[0001]
【発明が属する技術分野】本発明は、チューインガム、
キャンディー、ゼリー、飲料等の食品、口中清涼剤、練
り歯磨、芳香剤、化粧品等の香粧品、医薬品、及びタバ
コ等に対して用いられるシソ科メンタ属植物精油におい
て、不快臭、不快味、苦味物質、雑草様臭、水分及び不
揮発性樹脂状着色物質を取り除き、コク味があり加熱劣
化臭が少ない自然な風味をもたらす改質方法に関する。TECHNICAL FIELD The present invention relates to a chewing gum,
Unpleasant odor, unpleasant taste, bitterness in menta plant essential oils used for foods such as candies, jellies, beverages, mouth fresheners, toothpastes, fragrances, cosmetics such as cosmetics, pharmaceuticals, and tobacco etc. The present invention relates to a modification method for removing a substance, a weed-like odor, moisture, and a nonvolatile resinous coloring substance, and providing a natural flavor having a rich taste and a little heat deterioration odor.
【０００２】[0002]
【従来の技術】ペパーミント油、スペアミント油等に代
表されるシソ科メンタ属植物の茎葉から採油されたミン
ト精油類（以下「ミント精油」という）は、かかる植物
乾燥物を原材料として、一般に水蒸気蒸留法によって採
油されている。その際、必然的に加熱された水蒸気に曝
されるため１００℃以上の熱履歴を受け、その結果、香
味成分等の品質低下を伴っている。また、採油時に大量
の水と接触するため、ミント精油は通常は０.８％を超
える水分を含有しており、香味料として製剤化する際の
濁りの原因ともなっている。水分については、通常の乾
燥処理によりその含有量を調整することは可能である。
しかし、たとえば硫酸マグネシウムのような乾燥剤によ
り水分を除去した場合に、水分とともに水溶性の有用な
香味成分（トップノート成分）が同時に除去されてしま
うという問題点がある。2. Description of the Related Art Mint essential oils (hereinafter referred to as "mint essential oils") obtained from the foliage of Menta genus plants of the Labiatae typified by peppermint oil, spearmint oil, etc. are generally obtained by steam-drying such plant dried materials as raw materials. It is oiled by law. At that time, since it is inevitably exposed to the heated steam, it receives a heat history of 100 ° C. or more, and as a result, the quality of flavor components and the like is reduced. In addition, mint essential oil usually contains more than 0.8% of water because it comes into contact with a large amount of water at the time of oil collection, which causes turbidity when it is formulated as a flavoring agent. The content of water can be adjusted by ordinary drying treatment.
However, when moisture is removed by a desiccant such as magnesium sulfate, for example, there is a problem that a water-soluble useful flavor component (top note component) is removed together with the moisture.
【０００３】そのため水蒸気蒸留法で得られたミント精
油の香味を改質する従来技術の主なものとして、(１)
ミント精油を、さらに、常圧又は減圧下に水蒸気蒸留
し、低沸点部分に存在する不快臭物質と高沸点ピッチを
除去する方法、(２) ミント精油を減圧下に単蒸留又は
精密蒸留し、低沸点部分に存在する不快臭物質と高沸点
ピッチを除去する方法が提案されている。さらに、上記
以外にもミント精油の香味を改質する種々の方法が提案
されているが、機能的には、分画、中和反応、吸着、抽
出、付加反応、酸化還元反応に分類され、それらの手段
は、ほとんどの場合、反応処理後に水蒸気蒸留や減圧蒸
留（精密蒸留又は単蒸留）による分離分画を必要とす
る。[0003] Therefore, as the main ones of the prior art for modifying the flavor of mint essential oil obtained by the steam distillation method, (1)
Mint essential oil is further subjected to steam distillation under normal pressure or reduced pressure to remove unpleasant odor substances and high boiling pitch present in a low boiling point portion, (2) simple distillation or precision distillation of mint essential oil under reduced pressure, A method has been proposed for removing unpleasant odor substances and high boiling point pitch present in a low boiling point portion. Furthermore, other than the above, various methods for modifying the flavor of mint essential oil have been proposed, but functionally, it is classified into fractionation, neutralization reaction, adsorption, extraction, addition reaction, and oxidation-reduction reaction, In most cases, these means require separation and fractionation by steam distillation or vacuum distillation (precision distillation or simple distillation) after the reaction treatment.
【０００４】また、水蒸気蒸留工程を経る方法では水の
存在下、ミント精油を高温加熱するため水分子の付加反
応がおこり、テルピネオール（４−Terpineol）等が生
成し自然な風味を損なう傾向があるとともに、種々の化
合物が酸化、重合反応を起こしその結果、着色物質が生
成する。また、水分量の調整を行うことはできない。[0004] In the method of passing through a steam distillation step, mint essential oil is heated at a high temperature in the presence of water, so that an addition reaction of water molecules occurs, and terpineol (4-Terpineol) or the like is formed, which tends to impair the natural flavor. At the same time, various compounds undergo oxidation and polymerization reactions, and as a result, a colored substance is generated. In addition, the amount of water cannot be adjusted.
【０００５】また、減圧蒸留工程を経る方法では、ミン
ト精油中の成分が蒸留中の高温加熱によって、シメン
（ｐ−Cymene）等の炭化水素化合物が生成されたり、種
々の化合物が酸化、重合反応を起こすことにより加熱臭
が発生し、得られる改質ミント精油の風味に著しい悪影
響を及ぼすことになる。また、減圧単蒸留では着色物質
の混入を防ぐことが困難であり、無色透明な改質ミント
精油を得ることができない。さらに減圧精密蒸留の場合
は、高沸点留分、例えば、ビリジフロロール（Viridifl
orol）に代表される香味に好影響を与える成分の回収が
困難であり、呈味が弱く、コク味の少ないミント油にな
るといった欠点がある。[0005] In the method of passing through a vacuum distillation step, components in the mint essential oil are heated at a high temperature during the distillation to produce hydrocarbon compounds such as p-Cymene, or various compounds are oxidized and polymerized. Causes a heated odor, which has a significant adverse effect on the flavor of the resulting modified mint essential oil. In addition, it is difficult to prevent colored substances from being mixed in the simple distillation under reduced pressure, and a colorless and transparent modified mint essential oil cannot be obtained. Furthermore, in the case of vacuum precision distillation, a high-boiling fraction, for example, Viridiflor
orol), which has the drawback that it is difficult to recover components that have a favorable effect on the flavor, and the mint oil has a weak taste and a low body taste.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、水蒸
気蒸留法によってシソ科メンタ属植物から採油されたミ
ント精油を違和感なく食品、香粧品及び医薬品に使用す
る目的で、その香味を改質しようとするものである。詳
しくは、これらミント精油について不快臭、不快味、苦
味物質、雑草様臭、水分及び不揮発性の樹脂状着色物質
を取り除き、より冷涼で自然な風味と香気を有し、酸化
による劣化や加熱劣化が少なく、製造コスト的に安価で
簡便な改質方法、並びに改質された精油及び当該改質精
油を含有する食品を提供することである。SUMMARY OF THE INVENTION It is an object of the present invention to improve the flavor of mint essential oil obtained from a Labiatae plant by the steam distillation method without any discomfort for use in foods, cosmetics and pharmaceuticals. What you want to do. More specifically, these mint essential oils remove unpleasant odors, unpleasant odors, bitter substances, weed-like odors, moisture and non-volatile resinous coloring substances, and have a cooler, more natural flavor and aroma, and deterioration due to oxidation and heat deterioration. It is an object of the present invention to provide a simple and low-cost reforming method which is inexpensive in production cost, and a modified essential oil and a food containing the modified essential oil.
【０００７】[0007]
【課題を解決するための手段】前記課題を解決するた
め、本発明者らは鋭意検討した結果、ミント精油をさら
に分子蒸留に付することにより優れた性質のミント精油
を簡便に得られることを見出し、本発明を完成させた。Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have made intensive studies and as a result, have found that mint essential oil having excellent properties can be easily obtained by further subjecting mint essential oil to molecular distillation. Heading, the present invention has been completed.
【０００８】すなわち、本発明は、水蒸気蒸留法で採油
されたシソ科メンタ属植物精油をさらに分子蒸留するこ
とを特徴とするシソ科メンタ属植物精油の改質方法であ
り、好適には０.００１〜１０.０mmHgの圧力、４０〜１
００℃の温度、処理液を０.０５〜５.０mm厚の薄膜状、
且つ０.１〜５.０秒間の加熱時間で蒸発させるものであ
る改質方法である。また、本発明は、前記方法で改質さ
れたシソ科メンタ属植物精油である。さらに、本発明
は、上記方法によって改質されたシソ科メンタ属植物精
油を含有する食品、香粧品、医薬品又はタバコである。[0008] That is, the present invention is a method for improving the essential oil of a Labiatae menta plant, wherein the essential oil of a Labiatae menta plant obtained by steam distillation is further subjected to molecular distillation. 001 to 10.0 mmHg pressure, 40 to 1
At a temperature of 00 ° C., a processing liquid of 0.05 to 5.0 mm
In addition, this is a reforming method in which evaporation is performed with a heating time of 0.1 to 5.0 seconds. The present invention is also an essential oil of a Labiatae genus plant modified by the above method. Furthermore, the present invention is a food, a cosmetic, a medicament or a tobacco containing the essential oil of a Labiatae menta plant modified by the above method.
【０００９】[0009]
【発明の実施の形態】以下、本発明をさらに詳細に説明
する。本発明で改質に付されるミント精油は、シソ科メ
ンタ属植物から水蒸気蒸留法で採油されたものであれば
特に限定されるものではない。採油の対象となるシソ科
メンタ属植物としては、ミズハッカ（Mentha aquatica
L.）、セイヨウハッカ（Mentha piperita L）、ペニロ
イアルハッカ（Menthapulegium L）、マルバハッカ（Me
ntha rotundifolia (L.) Huds）、オランダハッカ（Men
tha spicata L）、ベルガモットハッカ（Mentha citrat
a (Ehrh.) Briq.）及びこれらの変種等が例示され、好
ましくはセイヨウハッカ（Mentha piperita L）、オラ
ンダハッカ（Mentha spicata L）が用いられる。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail. The mint essential oil to be modified in the present invention is not particularly limited as long as it is obtained by steam distillation from a Menta plant of the Labiatae family. Mentha aquatica (Mentha aquatica) includes
L.), mint (Mentha piperita L), peniroyal mint (Menthapulegium L), malba mint (Me
ntha rotundifolia (L.) Huds), Dutch mint (Men
tha spicata L), Bergamot mint (Mentha citrat)
a (Ehrh.) Briq.) and their variants, and the like. Preferably, common mint (Mentha piperita L) and Dutch mint (Mentha spicata L) are used.
【００１０】本発明で適用される分子蒸留とは、高真空
条件下での蒸留であって、蒸発した分子が他の分子と衝
突を起こさず冷却面へ到達して凝縮するような蒸留によ
る精製方法を言い、使用される装置或いは器具について
は、かかる精製方法が適用できる装置等であればその種
類は問わない。実生産に供される装置であって入手可能
なものとしては、一般的に回分式又は連続式分子蒸留装
置があり、形式により流下薄膜式分子蒸留装置、遠心薄
膜式分子蒸留装置に分類される。これらの装置の中でも
安定した薄膜状態を形成できる観点から遠心薄膜式分子
蒸留装置、特に連続式遠心薄膜式分子蒸留装置を使用す
ることが好ましい。The molecular distillation applied in the present invention is a distillation under a high vacuum condition, and is a purification by distillation in which evaporated molecules reach a cooling surface without causing collision with other molecules and are condensed. It refers to a method, and the type of apparatus or equipment used is not particularly limited as long as the apparatus or the like to which such a purification method can be applied. There are generally batch-type or continuous-type molecular distillation apparatuses that are available for actual production, and are classified into falling-film type molecular distillation apparatuses and centrifugal-film type molecular distillation apparatuses according to the type. . Among these apparatuses, it is preferable to use a centrifugal thin film molecular distillation apparatus, particularly a continuous centrifugal thin film molecular distillation apparatus, from the viewpoint of forming a stable thin film state.
【００１１】なお、遠心薄膜式分子蒸留装置を使用し、
同一原料を３回に分けて分子蒸留に付することにより、
収率８０〜９０％の高収率で改質精油を得ることができ
る。すなわち、１回目の分子蒸留（温度６０℃の、圧力
２〜３mmHg）で５％の改質精油を得、２回目の分子蒸留
（８０℃、２〜３mmHg）で７０％の改質精油を得、さら
に３回目の分子蒸留（１００℃、０.１〜１mmHg）で５
％の改質精油を得る手法である。なお、かかる分子蒸留
法それ自体は、一般に油脂等の精製に用いられる他、オ
レンジ等の精油の脱テルペン分画に用いられているが、
採油対象物から得られた精油をさらに改質するために適
用されることは知られていない。In addition, using a centrifugal thin film type molecular distillation apparatus,
By subjecting the same raw material to molecular distillation three times,
The modified essential oil can be obtained with a high yield of 80 to 90%. That is, a 5% modified essential oil is obtained by the first molecular distillation (temperature of 60 ° C., pressure 2-3 mmHg), and a 70% modified essential oil is obtained by the second molecular distillation (80 ° C., 2-3 mmHg). And a third molecular distillation (100 ° C., 0.1-1 mmHg).
% Modified essential oil. In addition, such a molecular distillation method itself is generally used for purification of fats and oils, and is used for deterpene fractionation of essential oils such as orange.
It is not known to be applied for further reforming essential oils obtained from oil extraction objects.
【００１２】本発明で適用される分子蒸留の条件は、供
する原材料や目的とする製品の品質に応じて適宜設定す
るものであるが、圧力条件は０.００１〜１０.０mmHgが
好ましく、特に好ましくは０.０１〜７.０mmHg、殊更好
ましくは０.１〜５.０mmHg、最も好ましくは０.１〜１.
０mmHgである。０.００１mmHg未満の圧力条件では、好
ましい香味を放つ低沸点成分の多くが失われる傾向にあ
り、１０.０mmHgを超える圧力においては好ましい香味
を放つ高沸点成分の多くが失われる傾向にあるからであ
る。The molecular distillation conditions applied in the present invention are appropriately set according to the raw materials to be supplied and the quality of the target product, and the pressure conditions are preferably 0.001 to 10.0 mmHg, particularly preferably. Is from 0.01 to 7.0 mmHg, particularly preferably from 0.1 to 5.0 mmHg, most preferably from 0.1 to 1.0 mmHg.
0 mmHg. At a pressure condition of less than 0.001 mmHg, many of the low-boiling components that emit a favorable flavor tend to be lost, and at a pressure of more than 10.0 mmHg, many of the high-boiling components that emit a favorable flavor tend to be lost. is there.
【００１３】蒸留温度は、４０〜１００℃、特に５０〜
８０℃が好ましい。４０℃未満においては蒸留時間が長
くなる傾向があり、１００℃を超える場合は加熱による
劣化が大きくなる傾向がある。[0013] The distillation temperature is 40 to 100 ° C, especially 50 to 100 ° C.
80 ° C. is preferred. If the temperature is lower than 40 ° C., the distillation time tends to be long, and if it is higher than 100 ° C., deterioration due to heating tends to increase.
【００１４】また、処理液は０.０５〜５.０mm厚の薄膜
状態とし、加熱時間０.１〜５.０秒間で蒸発させること
が適当であり、好ましくは０.０７〜１.０mmの薄膜状態
で加熱時間０.５〜３.０秒で蒸発させ、最も好ましくは
０.０８〜０.１５mmの薄膜状態で加熱時間が０.８〜２.
０秒で蒸発させる。こうした蒸留条件であれば、好まし
い香気成分は蒸発留分として捕集され、一方、不揮発性
樹脂状着色成分は残存除去される。処理液の薄膜状態が
０.０５mm未満であれば単位時間あたりの処理量に限界
があり、５.０mmを超える厚みであれば蒸発が抑えられ
る傾向がある。また、処理液の加熱時間が０.１秒間未
満であれば蒸発が抑えられる傾向があり、５.０秒間を
超える場合は加熱による劣化が進む傾向がある。The treatment liquid is suitably formed into a thin film having a thickness of 0.05 to 5.0 mm, and is preferably evaporated for a heating time of 0.1 to 5.0 seconds, preferably 0.07 to 1.0 mm. The thin film is evaporated in a heating time of 0.5 to 3.0 seconds, most preferably in a thin film of 0.08 to 0.15 mm in a heating time of 0.8 to 2.5 seconds.
Evaporate in 0 seconds. Under such distillation conditions, a preferable fragrance component is collected as an evaporating fraction, while a non-volatile resinous coloring component remains and is removed. When the thin film state of the processing liquid is less than 0.05 mm, the amount of processing per unit time is limited, and when the thickness exceeds 5.0 mm, evaporation tends to be suppressed. If the heating time of the treatment liquid is less than 0.1 second, evaporation tends to be suppressed, and if it exceeds 5.0 seconds, deterioration due to heating tends to progress.
【００１５】蒸発した成分を捕集する際、蒸留装置の一
次冷却器の温度は−５℃〜３０℃が適当であり、二次冷
却器の温度は−４０℃以下が好ましい。一次冷却器の温
度が−５℃未満であれば不快臭を伴った水分が多く捕集
される傾向があり、一方、３０℃を超えると好ましい香
気を持つ比較的低沸点成分が多く失われる傾向がある。
また、二次冷却器の温度が−４０℃を超えた場合は真空
ポンプの効率が悪くなる可能性がある。このような条件
によって連続的に蒸留する事により、単一の操作で水分
及び不快臭成分は揮散除去され、さらに樹脂状の不揮発
着色成分は残存除去された留分を得ることができる。When collecting the evaporated components, the temperature of the primary cooler of the distillation apparatus is suitably -5 ° C to 30 ° C, and the temperature of the secondary cooler is preferably -40 ° C or less. If the temperature of the primary cooler is lower than −5 ° C., a large amount of water with an unpleasant odor tends to be collected, while if it exceeds 30 ° C., a relatively large amount of relatively low-boiling components having a favorable aroma tends to be lost. There is.
If the temperature of the secondary cooler exceeds -40C, the efficiency of the vacuum pump may be reduced. By performing continuous distillation under such conditions, water and unpleasant odor components are volatilized and removed by a single operation, and a fraction in which the resinous non-volatile coloring component remains and is removed can be obtained.
【００１６】このようにして得られた改質ミント精油
は、水分含量が０.０１〜０.５％の範囲であるため濁り
等の品質不良を起こす事が無く、製剤化等の取り扱いが
容易であり、香料原料として優れている。また、同時に
着色物質等が取り除かれており、極めて無色性の高い
（４００nmにおける吸光度が０.０８以下である）、優
れた品質のものである。The modified mint essential oil thus obtained has a water content in the range of 0.01 to 0.5%, so that it does not cause quality defects such as turbidity and is easy to handle in preparation and the like. And is excellent as a fragrance raw material. At the same time, coloring substances and the like have been removed, and the colorlessness is extremely high (the absorbance at 400 nm is 0.08 or less), which is excellent in quality.
【００１７】[0017]
【実施例】以下に実施例を挙げ、本発明をより詳細に説
明する。 ［実施例１］通常の水蒸気蒸留法にて採油されたペパー
ミント精油（小川香料社製；以下「未改質ペパーミント
精油」という）１０００ｇを分子蒸留法で改質した。す
なわち、未改質ペパーミント精油を大科工業社製「遠心
薄膜式分子蒸留装置２７０５ＭＳ−Ｃ型」に仕込み、
０.１〜１mmHgの減圧条件下、５ｇ／分間の速度でフィ
ードノズルより加熱伝熱面に流入させ、コンデンサーに
は、−１〜１℃のブラインを通水し、コールドトラップ
を液体窒素で冷却し薄膜蒸留を行った。このときの処理
液の加熱条件は、平均して０.１mmの薄膜状で約１.０秒
間の加熱であった。蒸留後、コールドトラップには水及
び不快臭成分が合計５１.０ｇ分画除去され、釜残には
不揮発性樹脂状着色物質が４３.０ｇ残存除去され、製
品部として改質ペパーミント精油９０１.０ｇが得られ
た。かかる改質精油の水分は０.１％であり、４００nm
の吸光度が０.０７の極めて無色性の高いものであっ
た。なお、吸光度測定に使用した機器及び測定条件は次
のとおりである。 機 器 島津製作所製「分光光度計ＵＶ−２１００
ＰＣ」 測定条件 セル：石英、光路長：１cm、サンプル：希
釈せずに測定（対象は蒸留水）、スリット幅：２nm、測
定温度：室温。 この改質ペパーミント精油を用い、下記表１の処方に従
い、チューインガム組成物を調製した。The present invention will be described in more detail with reference to the following examples. [Example 1] 1000 g of peppermint essential oil (manufactured by Ogawa Koran Co., Ltd .; hereinafter, referred to as "unmodified peppermint essential oil") collected by a normal steam distillation method was modified by a molecular distillation method. That is, the unmodified peppermint essential oil was charged into a "centrifugal thin film molecular distillation apparatus 2705MS-C type" manufactured by Daika Kogyo Co., Ltd.
At a reduced pressure of 0.1 to 1 mmHg, the feed nozzle is allowed to flow into the heat transfer surface at a rate of 5 g / min at a rate of 5 g / min, brine is passed through the condenser at -1 to 1 ° C, and the cold trap is cooled with liquid nitrogen. Then, thin-film distillation was performed. The heating conditions of the treatment liquid at this time were heating for about 1.0 second in a thin film of 0.1 mm on average. After the distillation, a total of 51.0 g of water and unpleasant odor components were fractionated and removed in the cold trap, and 43.0 g of the non-volatile resinous coloring material was removed and removed from the bottom, and 901.0 g of modified peppermint essential oil was used as a product part. was gotten. The moisture content of the modified essential oil is 0.1%,
Was very colorless with an absorbance of 0.07. The equipment and measurement conditions used for the absorbance measurement are as follows. Equipment Spectrophotometer UV-2100 manufactured by Shimadzu Corporation
PC "Measurement conditions Cell: quartz, optical path length: 1 cm, sample: measured without dilution (target is distilled water), slit width: 2 nm, measurement temperature: room temperature. Using this modified peppermint essential oil, a chewing gum composition was prepared according to the formulation in Table 1 below.
【００１８】［比較例１］実施例１と同じ未改質ペパー
ミント精油１０００ｇを常法に従って常圧水蒸気蒸留
し、当初留出部分（オイル部分の重量は対原料比５％）
を除去し、これに続く留出部分よりオイル部を分離する
事により８９８ｇの改質ペパーミント精油を得た。かか
る改質精油の水分は０.９％であり、４００nmの吸光度
が０.０９であった。この改質ペパーミント精油を用
い、下記表１の処方に従い、チューインガム組成物を調
製した。Comparative Example 1 The same unmodified peppermint essential oil (1000 g) as in Example 1 was subjected to normal-pressure steam distillation according to a conventional method, and an initially distilled portion (the weight of the oil portion was 5% of the raw material ratio)
Was removed, and the oil portion was separated from the distilling portion to obtain 898 g of a modified peppermint essential oil. The water content of the modified essential oil was 0.9%, and the absorbance at 400 nm was 0.09. Using this modified peppermint essential oil, a chewing gum composition was prepared according to the formulation in Table 1 below.
【００１９】［比較例２］比較例１で得られた改質ペパ
ーミント精油１００ｇに対し、無水硫酸マグネシウム５
ｇを加えて攪拌後、１時間静置し、続いて濾紙で濾過す
る事により９３ｇの改質ペパーミント精油を得た。この
精油中の水分は０.６％であり、４００nmの吸光度が０.
０９であった。この改質ペパーミント精油を用い、下記
表１の処方に従い、チューインガム組成物を調製した。Comparative Example 2 Anhydrous magnesium sulfate 5 was added to 100 g of the modified peppermint essential oil obtained in Comparative Example 1.
After adding g and stirring, the mixture was allowed to stand for 1 hour, and then filtered through filter paper to obtain 93 g of a modified peppermint essential oil. The water content in this essential oil is 0.6% and the absorbance at 400 nm is 0.6.
09. Using this modified peppermint essential oil, a chewing gum composition was prepared according to the formulation in Table 1 below.
【００２０】［比較例３］実施例１と同じ未改質ペパー
ミント精油を常法に従って減圧精密蒸留（減圧度６〜１
０mmHg）し、初期留出部分（対原料比５％）を除去し、
これに続く留出部分として８９５ｇの改質ペパーミント
精油を得た。かかる精油の水分は０.１％であり、４０
０nmの吸光度が０.０７であった。この改質ペパーミン
ト精油を用い、下記表１の処方に従い、チューインガム
組成物を調製した。Comparative Example 3 The same unmodified peppermint essential oil as in Example 1 was subjected to precise distillation under reduced pressure according to a conventional method (degree of reduced pressure 6-1).
0 mmHg) to remove the initial distillate (5% of raw material)
As a subsequent distillate portion, 895 g of a modified peppermint essential oil was obtained. The water content of such essential oils is 0.1%,
The absorbance at 0 nm was 0.07. Using this modified peppermint essential oil, a chewing gum composition was prepared according to the formulation in Table 1 below.
【００２１】［試験例１］下記表１の処方にて、未改質
ペパーミント精油、実施例１及び参考例１〜３の改質ペ
パーミント精油を配合した板状のチューインガムの香味
評価を下記方法により行った。まず、ガムベース、砂
糖、ブドウ糖、コーンシロップ（糖度８５％）を混合
し、これに未改質ペパーミント精油または上記で製造し
た各種改質ペパーミント精油を添加し、常法に従って高
剪断型ミキサーを用いて約５０℃で混和した。次いで、
冷却後ローラーにより圧展成形し、１枚３ｇとなるよう
に、未改質ペパーミント精油、実施例１及び参考例１〜
３の改質精油を配合した板状のチューインガムを各々調
製した。Test Example 1 The flavor of plate-shaped chewing gum containing the unmodified peppermint essential oil and the modified peppermint essential oils of Example 1 and Reference Examples 1 to 3 in the formulation shown in Table 1 below was evaluated by the following method. went. First, a gum base, sugar, glucose and corn syrup (sugar content 85%) are mixed, and unmodified peppermint essential oil or various modified peppermint essential oils produced above are added thereto, and a high shear mixer is used in accordance with a conventional method. Mix at about 50 ° C. Then
Uncooled peppermint essential oil, Example 1 and Reference Examples 1 to 3 g each after cooling.
Each of the plate-shaped chewing gums containing the modified essential oils No. 3 was prepared.
【００２２】このチューインガムを専門パネラー１０名
にて試食し、香気香味の官能評価を行った。評価基準
は、未改質ペパーミント精油を含有するガムを基準(評
価点４)とし、強さ、美味しさの面で各パネラーが下記
基準にて総合点１〜７の７段階評価とした。評価点（パ
ネラー１０人の平均値）とその香味特性を表２に示す。 １点：非常に劣悪な香気香味である。 ２点：劣悪な香気香味である。 ３点：やや劣悪な香気香味である。 ４点：未改質ペパーミント精油と同等の香気香味であ
る。 ５点：やや良好な香気香味である。 ６点：良好な香気香味である。 ７点：非常に良好な香気香味である。The chewing gum was tasted by 10 expert panelists, and the sensory evaluation of aroma and flavor was performed. The evaluation criteria were a gum containing unmodified peppermint essential oil as a reference (evaluation point 4), and each panel was evaluated on a seven-point scale of 1-7 based on the following criteria in terms of strength and taste. Table 2 shows the evaluation points (average value of 10 panelists) and their flavor characteristics. 1 point: Very poor flavor. 2 points: Poor aroma flavor. 3 points: Slightly poor flavor. 4 points: Flavor and flavor equivalent to unmodified peppermint essential oil. 5 points: Slightly good flavor. 6 points: good aroma and flavor. 7 points: Very good flavor.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【表２】 [Table 2]
【００２５】上記表１及び２の結果から明らかなよう
に、本発明となる実施例１のガムは、従来の技術である
比較例１〜３のガムに比べて、香味特性、香味の強さ及
び美味しさにおいて極めて優れていることが判明した。As is clear from the results shown in Tables 1 and 2, the gum of Example 1 according to the present invention has a flavor characteristic and an intensity of flavor which are higher than those of Comparative Examples 1 to 3 which are the prior art. And it turned out to be extremely excellent in taste.
【００２６】［実施例２］通常の水蒸気蒸留法で採油さ
れたスペアミント精油（小川香料社製；以下「未改質ス
ペアミント精油」という）１０００ｇを分子蒸留法で改
質した。すなわち、未改質スペアミント精油を大科工業
社製「遠心薄膜式分子蒸留装置２７０５ＭＳ−Ｃ型」に
仕込み、０.１〜１mmHgの減圧条件下、５ｇ／分間の速
度でフィードノズルより加熱伝熱面に流入させ、コンデ
ンサーには、−１〜１℃のブラインを通水し、コールド
トラップを液体窒素で冷却下に薄膜蒸留を行った。Example 2 1000 g of spearmint essential oil (made by Ogawa Koran; hereinafter, referred to as "unmodified spearmint essential oil") collected by a normal steam distillation method was modified by a molecular distillation method. That is, unmodified spearmint essential oil was charged into a “centrifugal thin film molecular distillation apparatus 2705MS-C” manufactured by Daika Kogyo Co., Ltd., and heat was transferred from a feed nozzle at a rate of 5 g / min under a reduced pressure of 0.1 to 1 mmHg. Then, brine was passed through the condenser at -1 to 1 ° C, and thin film distillation was performed while cooling the cold trap with liquid nitrogen.
【００２７】このときの処理液の加熱条件は、平均して
０.１mmの薄膜で約１.０秒間の加熱であった。蒸留後、
コールドトラップには水及び不快臭成分が合計４８.０
ｇ分画除去され、釜残には不揮発性樹脂状着色物質が５
１.０ｇ残存除去され、製品部として改質スペアミント
精油が８９７.０ｇ得られた。かかる改質精油の水分は
０.１％であり、４００nmの吸光度が０.０７の極めて無
色性の高いものであった。この改質精油を用い、下記表
３の処方に従い、ミント飲料を調製した。At this time, the heating conditions of the processing solution were such that the thin film having an average thickness of 0.1 mm was heated for about 1.0 second. After distillation,
The cold trap contains a total of 48.0 water and unpleasant odor components.
g fractionation is removed, and 5% of non-volatile resinous coloring material is
1.0 g of residual oil was removed, and 897.0 g of a modified spearmint essential oil was obtained as a product part. The water content of the modified essential oil was 0.1%, and the absorbance at 400 nm was 0.07, which was extremely colorless. Using this modified essential oil, a mint beverage was prepared according to the formulation in Table 3 below.
【００２８】［比較例４］実施例２で使用した未改質ス
ペアミント精油１０００ｇを常法に従って常圧水蒸気蒸
留し、当初留出部分（オイル部分の重量は対原料比５
％）を除去し、続く留出部分よりオイル部を分離する事
により９０３ｇの改質スペアミント精油を得た。この改
質精油の水分は０.８％であり、４００nmの吸光度が０.
０９であった。この改質精油を用い、下記表３の処方に
従い、ミント飲料を調製した。Comparative Example 4 1000 g of the unmodified spearmint essential oil used in Example 2 was subjected to normal pressure steam distillation according to a conventional method.
%) And the oil portion was separated from the subsequent distillate to obtain 903 g of a modified spearmint essential oil. This modified essential oil has a water content of 0.8% and an absorbance at 400 nm of 0.8%.
09. Using this modified essential oil, a mint beverage was prepared according to the formulation in Table 3 below.
【００２９】［比較例５］比較例４で得られた改質スペ
アミント精油１００ｇに対し、無水硫酸マグネシウム５
ｇを加え攪拌後１時間静置し、続いて濾紙で濾過する事
により９５ｇの改質スペアミント精油を得た。このもの
の水分は０.６％であり、４００nmの吸光度が０.０９あ
った。この改質精油を用い、下記表３の処方に従い、ミ
ント飲料を調製した。Comparative Example 5 Anhydrous magnesium sulfate 5 was added to 100 g of the modified spearmint essential oil obtained in Comparative Example 4.
g, and the mixture was stirred and allowed to stand for 1 hour, and then filtered through filter paper to obtain 95 g of a modified spearmint essential oil. The water content was 0.6%, and the absorbance at 400 nm was 0.09. Using this modified essential oil, a mint beverage was prepared according to the formulation in Table 3 below.
【００３０】［比較例６］実施例２で用いた未改質スペ
アミント精油を常法に従って減圧精密蒸留（減圧度６〜
１０mmHg）し、初期留出部分（対原料比５％）を除去
し、続く留出部分として９０３ｇの改質スペアミント精
油を得た。このものの水分は０.１％であり、４００nm
の吸光度が０.０７であった。この改質精油を用い、下
記表３の処方に従い、ミント飲料を調製した。[Comparative Example 6] The unmodified spearmint essential oil used in Example 2 was subjected to precision distillation under reduced pressure (degree of vacuum:
10 mmHg) to remove the initial distillate portion (5% of the raw material ratio) to obtain 903 g of a modified spearmint essential oil as a subsequent distillate portion. The water content of this is 0.1%, 400 nm
Had an absorbance of 0.07. Using this modified essential oil, a mint beverage was prepared according to the formulation in Table 3 below.
【００３１】［試験例２］下記表３の処方にて、未改質
スペアミント精油、実施例２及び参考例４〜６改質スペ
アミント精油を配合したミント飲料の香味評価を下記方
法により行った。まず、グラニュー糖を蒸留水に溶解
し、これに原料スペアミント精油または上記で製造した
スペアミント精油を添加することにより未改質スペアミ
ント精油、実施例２及び比較例４〜６の改質スペアミン
ト精油入りのミント飲料を各々調製した。前記スペアミ
ント風味チューインガムと同様の手法にて、このミント
飲料を専門パネラー１０名にて香気香味の官能評価を行
った。評価基準は、下記のとおり前記チューインガムと
同様に未改質スペアミント精油を基準とし、強さ、美味
しさの面で総合点１〜７の７段階評価とした。評価結果
とその香味特性を表４に示す。 １点：非常に劣悪な香気香味である。 ２点：劣悪な香気香味である。 ３点：やや劣悪な香気香味である。 ４点：未改質スペアミント精油と同等の香気香味であ
る。 ５点：やや良好な香気香味である。 ６点：良好な香気香味である。 ７点：非常に良好な香気香味である。Test Example 2 The flavor of a mint beverage containing the unmodified spearmint essential oil, Example 2 and Reference Examples 4 to 6 modified spearmint essential oil was formulated according to the formulation shown in Table 3 below by the following method. First, the granulated sugar is dissolved in distilled water, and the raw spearmint essential oil or the spearmint essential oil produced above is added thereto to obtain unmodified spearmint essential oil, containing the modified spearmint essential oil of Example 2 and Comparative Examples 4 to 6. Each mint drink was prepared. In the same manner as in the above spearmint flavored chewing gum, the mint beverage was subjected to sensory evaluation of aroma and flavor by 10 expert panelists. The evaluation criteria were based on unmodified spearmint essential oil as in the case of the chewing gum as described below, and were evaluated on a seven-point scale from 1 to 7 in terms of strength and taste. Table 4 shows the evaluation results and the flavor characteristics. 1 point: Very poor flavor. 2 points: Poor aroma flavor. 3 points: Slightly poor flavor. 4 points: Aroma and flavor equivalent to unmodified spearmint essential oil. 5 points: Slightly good flavor. 6 points: good aroma and flavor. 7 points: Very good flavor.
【００３２】[0032]
【表３】 [Table 3]
【００３３】[0033]
【表４】 [Table 4]
【００３４】上記表３及び４の結果から明らかなよう
に、本発明となる実施例２のミント飲料は、従来の技術
である比較例４〜６のミント飲料に比べて、香味特性、
香味の強さ及び美味しさにおいて極めて優れていること
が判明した。As is evident from the results of Tables 3 and 4, the mint beverage of Example 2 according to the present invention has a better flavor characteristic and a better flavor than the conventional mint beverages of Comparative Examples 4 to 6.
It turned out to be extremely excellent in flavor intensity and taste.
【００３５】[0035]
【発明の効果】本発明の改質方法によれば、シソ科メン
タ属植物精油類を分子蒸留することにより、加熱による
劣化を受けることなく、不快臭、不快味、苦味物質、雑
草様臭、水分及び不揮発性樹脂状の着色物質を同時に除
去することができ、よりクールな、清潔で自然な風味と
香気を有する改質ミント精油を得ることができる。ま
た、本発明の改質方法により得られる改質ミント精油
は、フレーバリング対象に適した香味成分が分画された
ものなので、風味をつける際のより優れた香味料原料と
して、チューインガム、キャンディー、ゼリー、飲料等
の食品、口中清涼剤、練り歯磨、芳香剤、化粧品等の香
粧品、医薬品、及びタバコ等に配合することができる。According to the modification method of the present invention, the essential oils of the genus Menta of the Labiatae family are subjected to molecular distillation, so that they do not suffer from deterioration due to heating, and have unpleasant odors, unpleasant tastes, bitter substances, weed-like odors, and the like. It is possible to simultaneously remove the moisture and the non-volatile resinous colored substance, and to obtain a modified mint essential oil having a cooler, cleaner, natural flavor and aroma. In addition, the modified mint essential oil obtained by the modification method of the present invention is one in which a flavor component suitable for a flavoring target is fractionated, so that chewing gum, candy, It can be incorporated into foods such as jellies and beverages, mouth fresheners, toothpastes, fragrances, cosmetics such as cosmetics, pharmaceuticals, and tobacco.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ａ６１Ｋ 7/00 Ａ６１Ｋ 47/44 ４Ｈ０５９ 47/44 Ａ２３Ｌ 2/00 Ｂ Ｆターム(参考） 4B014 GB13 GK05 GL07 4B017 LC02 LK10 LL01 4B047 LB02 LG37 LP20 4C076 EE53 FF52 GG42 4C083 AA121 CC01 4H059 AA04 BC23 BC44 CA18 CA20 DA09 EA21 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) A61K 7/00 A61K 47/44 4H059 47/44 A23L 2/00 BF Term (Reference) 4B014 GB13 GK05 GL07 4B017 LC02 LK10 LL01 4B047 LB02 LG37 LP20 4C076 EE53 FF52 GG42 4C083 AA121 CC01 4H059 AA04 BC23 BC44 CA18 CA20 DA09 EA21
Claims (7)
属植物精油を分子蒸留することを特徴とするシソ科メン
タ属植物精油の改質方法。1. A method for improving the essential oil of a Labiatae menta plant, comprising subjecting the essential oil of a Labiatae menta plant extracted by a steam distillation method to molecular distillation.
０.０mmHgの圧力、４０〜１００℃の温度、処理液を０.
０５〜５.０mm厚の薄膜状、且つ０.１〜５.０秒間の加
熱時間で蒸発させるものであることを特徴とする請求項
１記載のシソ科メンタ属植物精油の改質方法。2. The evaporation conditions for molecular distillation are 0.001-1.
A pressure of 0.0 mmHg, a temperature of 40 to 100 ° C.,
2. The method of claim 1, wherein the essential oil is a thin film having a thickness of 0.5 to 5.0 mm and is evaporated by a heating time of 0.1 to 5.0 seconds.
ことを特徴とする請求項１又は２記載のシソ科メンタ属
植物精油の改質方法。3. The method according to claim 1, wherein the molecular distillation is centrifugal thin film molecular distillation.
ソ科メンタ属植物精油。4. An essential oil of a Labiatae genus plant modified by the method according to claim 1.
を特徴とする請求項４記載の改質されたシソ科メンタ属
植物精油。5. The modified Lentaceae menta plant essential oil according to claim 4, wherein the water content is from 0.01 to 0.5%.
下であることを特徴とする請求項４又は５記載の改質さ
れたシソ科メンタ属植物精油。6. The modified Lentaceae menta plant essential oil according to claim 4 or 5, wherein the absorbance at 400 nm is 0.08 or less.
ンタ属植物精油を含有する食品、香粧品、医薬品又はタ
バコ。7. A food, a cosmetic, a medicament or a tobacco containing the modified Menta genus plant essential oil according to claim 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000228857A JP2002038187A (en) | 2000-07-28 | 2000-07-28 | Method for modifying essential oil of plant belonging to genus mentha of family labiatae |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000228857A JP2002038187A (en) | 2000-07-28 | 2000-07-28 | Method for modifying essential oil of plant belonging to genus mentha of family labiatae |
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| JP2002038187A true JP2002038187A (en) | 2002-02-06 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006325539A (en) * | 2005-05-30 | 2006-12-07 | Takasago Internatl Corp | Method for producing dairy product flavor |
| JP2009215318A (en) * | 2009-06-30 | 2009-09-24 | Ogawa & Co Ltd | Method for separating polymethoxyflavones |
| US20100197801A1 (en) * | 2008-10-28 | 2010-08-05 | A. M. Todd Company | Volatile Distillate By-Product of Mint Oil That Promotes Absorption and/or Bioavailability of Compounds of Bio-Medical and Nutritional Interest |
| CN102604744A (en) * | 2012-04-17 | 2012-07-25 | 合肥工业大学 | Extraction method of dendrobium essential oil |
| CN105066590A (en) * | 2015-07-22 | 2015-11-18 | 大闽食品（漳州）有限公司 | Methods for adsorbing fragrance volatiles of grapefruit fresh flowers and drying grapefruit fresh flowers at low temperature |
| CN106811301A (en) * | 2015-12-01 | 2017-06-09 | 盐城润野生物科技有限公司 | A kind of preparation method of kostelezkya virginica seed essential oil |
| WO2019035487A1 (en) * | 2017-08-18 | 2019-02-21 | ライオン株式会社 | Lamiaceae family mentha genus plant-derived extract and method for producing same |
| CN110801051A (en) * | 2019-12-07 | 2020-02-18 | 深圳波顿香料有限公司 | Electronic cigarette oil added with mixed light components of condensed fragrance of cigarettes and preparation method of electronic cigarette oil |
| JP2020089323A (en) * | 2018-12-07 | 2020-06-11 | 小川香料株式会社 | Richness promotor of mint flavor oral product, perfume composition for richness enhancement, and richness enhancement method using them |
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| JPS58176300A (en) * | 1982-04-09 | 1983-10-15 | 株式会社資生堂 | Low contact sensitive jasmine oil, manufacture and blend |
| JPH03217500A (en) * | 1990-01-24 | 1991-09-25 | Takasago Internatl Corp | Production of coffee odor ingredient |
| JPH05176689A (en) * | 1992-05-15 | 1993-07-20 | Taiyo Kagaku Co Ltd | Feed for culturing fish |
| JPH06145690A (en) * | 1991-04-22 | 1994-05-27 | Nagaoka Jitsugyo Kk | Method for modifying flavor of peppermint oil |
| JP2000072617A (en) * | 1998-08-31 | 2000-03-07 | Lion Corp | Cosmetic and modified mint oil for cosmetic |
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| JPS58176300A (en) * | 1982-04-09 | 1983-10-15 | 株式会社資生堂 | Low contact sensitive jasmine oil, manufacture and blend |
| JPH03217500A (en) * | 1990-01-24 | 1991-09-25 | Takasago Internatl Corp | Production of coffee odor ingredient |
| JPH06145690A (en) * | 1991-04-22 | 1994-05-27 | Nagaoka Jitsugyo Kk | Method for modifying flavor of peppermint oil |
| JPH05176689A (en) * | 1992-05-15 | 1993-07-20 | Taiyo Kagaku Co Ltd | Feed for culturing fish |
| JP2000072617A (en) * | 1998-08-31 | 2000-03-07 | Lion Corp | Cosmetic and modified mint oil for cosmetic |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006325539A (en) * | 2005-05-30 | 2006-12-07 | Takasago Internatl Corp | Method for producing dairy product flavor |
| US20100197801A1 (en) * | 2008-10-28 | 2010-08-05 | A. M. Todd Company | Volatile Distillate By-Product of Mint Oil That Promotes Absorption and/or Bioavailability of Compounds of Bio-Medical and Nutritional Interest |
| US8445037B2 (en) * | 2008-10-28 | 2013-05-21 | A. M. Todd Company | Volatile distillate by-product of mint oil that promotes absorption and/or bioavailability of compounds of bio-medical and nutritional interest |
| US20140186322A1 (en) * | 2008-10-28 | 2014-07-03 | Flavor Liquidating (G) Corporation (new name of A. M. Todd Group, Inc.) | Volatile Distillate By-Product of Mint Oil That Promotes Absorption and/or Bioavailability of Compounds of Bio-Medical and Nutritional Interest |
| US9119882B2 (en) * | 2008-10-28 | 2015-09-01 | Flavor Liquidating (G) Corporation (new name for A. M. Todd Group, Inc.) | Volatile distillate by-product of mint oil that promotes absorption and/or bioavailability of compounds of bio-medical and nutritional interest |
| JP2009215318A (en) * | 2009-06-30 | 2009-09-24 | Ogawa & Co Ltd | Method for separating polymethoxyflavones |
| CN102604744A (en) * | 2012-04-17 | 2012-07-25 | 合肥工业大学 | Extraction method of dendrobium essential oil |
| CN105066590A (en) * | 2015-07-22 | 2015-11-18 | 大闽食品（漳州）有限公司 | Methods for adsorbing fragrance volatiles of grapefruit fresh flowers and drying grapefruit fresh flowers at low temperature |
| CN106811301A (en) * | 2015-12-01 | 2017-06-09 | 盐城润野生物科技有限公司 | A kind of preparation method of kostelezkya virginica seed essential oil |
| WO2019035487A1 (en) * | 2017-08-18 | 2019-02-21 | ライオン株式会社 | Lamiaceae family mentha genus plant-derived extract and method for producing same |
| JP2020089323A (en) * | 2018-12-07 | 2020-06-11 | 小川香料株式会社 | Richness promotor of mint flavor oral product, perfume composition for richness enhancement, and richness enhancement method using them |
| CN110801051A (en) * | 2019-12-07 | 2020-02-18 | 深圳波顿香料有限公司 | Electronic cigarette oil added with mixed light components of condensed fragrance of cigarettes and preparation method of electronic cigarette oil |
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