JP5719113B2 - Deodorant and deodorant composition using the same - Google Patents
Deodorant and deodorant composition using the same Download PDFInfo
- Publication number
- JP5719113B2 JP5719113B2 JP2010035458A JP2010035458A JP5719113B2 JP 5719113 B2 JP5719113 B2 JP 5719113B2 JP 2010035458 A JP2010035458 A JP 2010035458A JP 2010035458 A JP2010035458 A JP 2010035458A JP 5719113 B2 JP5719113 B2 JP 5719113B2
- Authority
- JP
- Japan
- Prior art keywords
- deodorant
- composition
- thymoquinone
- extract
- fragrance
- 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.)
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Images
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- Confectionery (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
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Description
本発明は、メルカプタン等の悪臭成分に対して良好な消臭効果を有する消臭剤及びそれを用いた消臭剤組成物又は消臭性香料組成物に関し、特に、その安全性が高く、口腔用、家庭用、工業用などで好適に使用できる消臭剤組成物及びそれを用いた消臭性香料組成物に関する。 The present invention relates to a deodorant having a good deodorizing effect on malodorous components such as mercaptans, and a deodorant composition or a deodorant fragrance composition using the same, in particular, its safety is high and the oral cavity The present invention relates to a deodorant composition that can be suitably used for industrial use, household use, industrial use, and the like, and a deodorant fragrance composition using the same.
従来、生ゴミや、冷蔵庫内などの臭い、ペットや家畜に由来する臭い等の悪臭を抑制或いは消臭することが望まれており、特に、口臭を、効率よく、抑制或いは消臭する方法が望まれている。これらの悪臭のなかでも、特に、硫化水素やメルカプタンのような硫黄化合物が問題であり、その消臭方法としては、活性炭、シリカゲル、シクロデキストリンなどの吸着剤への吸着、触媒や酸化剤による酸化、香気成分によるマスキング、消臭剤による方法等が知られているが、特に、口腔内に適用する場合には、その安全性が高いことが必要とされている。 Conventionally, it has been desired to suppress or deodorize odors such as garbage, odors in refrigerators, odors derived from pets and livestock, and in particular, there is a method for efficiently suppressing or deodorizing bad breath. It is desired. Among these bad odors, sulfur compounds such as hydrogen sulfide and mercaptans are particularly problematic. Deodorizing methods include adsorption to adsorbents such as activated carbon, silica gel and cyclodextrin, and oxidation by catalysts and oxidizing agents. In addition, masking with an aroma component, a method using a deodorant, and the like are known, but particularly when applied to the oral cavity, the safety is required to be high.
そこで、従来、口臭の除去、一般家庭や工場などで発生する悪臭に対する消臭剤としては、消臭力を有する、セージ、タイム、ミント、ローズマリー、オレガノなどのシソ科植物、クローブ、茶類等の植物の抽出物、或いは、キノコ類又は褐藻類を消臭有効成分として用いた消臭剤が用いられている（特許文献１〜４、非特許文献１〜３等）。
しかしながら、これらの植物性の消臭有効成分は、単独ではその消臭効果が低く、得られる効果が不十分であり、また、消臭有効成分を多量に配合すると、着色や味覚の低下、沈殿等の問題が生じる場合がある。
一方、消臭有効成分として化学薬品を使用した消臭剤は、比較的消臭効果が強いが、人体への安全面で問題があるものがある、という問題がある。
Therefore, as a deodorant for the removal of bad breath and bad odor generated in general households and factories, sage, thyme, mint, rosemary, oregano and other Lamiaceae plants, cloves, teas. And the like, or deodorants using mushrooms or brown algae as a deodorizing active ingredient are used (
However, these plant-based deodorizing active ingredients alone have low deodorizing effects, resulting in insufficient effects. When a large amount of the deodorizing active ingredient is blended, coloring, taste deterioration, precipitation Such a problem may occur.
On the other hand, a deodorant using a chemical as a deodorant active ingredient has a relatively strong deodorizing effect, but has a problem that there is a problem in terms of safety to the human body.
上記の問題点を解決するものとして、これらの植物性の消臭有効成分を用いた消臭剤に、パーオキシダーゼ、ラッカーゼ、チロシナーゼ等の酸化酵素を併用することにより、両者が相乗的に作用して非常に消臭効果の高い消臭剤が得られることが発見されており（特許文献５〜８、非特許文献４，５等）、特に、植物抽出物と酸化酵素を併用した消臭剤は、口臭予防を目的としたチューインガムや、義歯洗浄剤等に配合されるようになっている。 As a solution to the above problems, the use of these plant-based deodorant active ingredients in combination with oxidases such as peroxidase, laccase, and tyrosinase allows both to act synergistically. It has been discovered that a deodorant having a very high deodorizing effect can be obtained (Patent Documents 5 to 8, Non-Patent Documents 4 and 5, etc.), and in particular, a deodorant using a plant extract and an oxidase in combination. It is Chu in Gamuya for the purpose of Breath, and is formulated into a denture cleaning agent.
しかしながら、植物抽出物に、パーオキシダーゼ、ラッカーゼ、チロシナーゼ等の酸化酵素を併用した消臭剤は、中性域では非常に高い消臭効果を示すが、酸性条件下では消臭効果が低下するという問題点を有している。その理由は、酸化酵素の至適ｐＨが弱酸性〜中性であり、酸性条件下では、酵素による消臭成分の活性化反応が充分に進行しないため、消臭効果が低下するものと推察される。 However, deodorants that combine plant extracts with oxidases such as peroxidase, laccase, and tyrosinase exhibit a very high deodorizing effect in the neutral range, but the deodorizing effect decreases under acidic conditions. Has a problem. The reason is that the optimum pH of the oxidase is weakly acidic to neutral, and under the acidic conditions, the activation reaction of the deodorizing component by the enzyme does not proceed sufficiently, so the deodorizing effect is presumed to decrease. The
本発明は、以上のような事情に鑑みてなされたものであって、酸性〜中性〜弱塩基性の、幅広いｐＨ領域で、高い消臭効果を示す消臭剤組成物及び消臭性香料組成物を提供することを目的とするものである。 The present invention has been made in view of the circumstances as described above, and is a deodorant composition and a deodorant fragrance exhibiting a high deodorizing effect in a wide pH range from acidic to neutral to weakly basic. The object is to provide a composition.
本発明者等は、上記目的を達成すべく、鋭意検討を重ねた結果、ブラッククミン種子に含有されるチモキノンが、従来の植物抽出物に酸化酵素を併用した消臭剤に匹敵する、非常に高い消臭効果を示し、しかも、酸性条件下においても消臭効果が低下せず、さらには、溶液中での褐変反応などの経時変化が少ないという知見を得た。 As a result of intensive studies to achieve the above object, the present inventors have found that thymoquinone contained in black cumin seeds is comparable to a deodorant in which a conventional plant extract is used in combination with an oxidase. The present inventors have found that a high deodorizing effect is exhibited, the deodorizing effect is not lowered even under acidic conditions, and further, there is little change with time such as browning reaction in the solution.
本発明は、これらの知見に基づいて完成に至ったものであり、以下のとおりのものである。
［１］ チモキノンを消臭有効成分とすることを特徴とする消臭剤。
［２］ 上記［１］の消臭剤を含有することを特徴とする消臭剤組成物。
［３］ ブラッククミン種子の粉砕物、溶媒抽出物、又は精油を配合したことを特徴とする上記［２］の消臭剤組成物。
［４］ その他の植物性消臭剤をさらに添加したことを特徴とする上記［２］又は［３］の消臭剤組成物。
［５］ 抗酸化成分を添加したことを特徴とする上記［２］〜［４］のいずれか１項に記載の消臭剤組成物。
［６］ 上記［２］〜［５］のいずれかの消臭組成物に香料成分を配合したことを特徴とする消臭性香料組成物。
［７］ 上記［２］〜［５］のいずれかの消臭剤組成物又は上記［６］の消臭性香料組成物を配合したことを特徴とする口臭予防食品。
［８］ 前記消臭剤組成物又は前記消臭性香料組成物が配合される食品のｐＨが５以下であることを特徴とする、上記［７］の口臭予防食品。
［９］ 上記［２］〜［５］のいずれかの消臭剤組成物又は上記［６］の消臭性香料組成物を配合したことを特徴とする口腔消臭用組成物。
［１０］ 前記消臭剤組成物又は前記消臭性香料組成物が配合される組成物のｐＨが５以下であることを特徴とする、上記［９］の口腔消臭用組成物。
The present invention has been completed based on these findings, and is as follows.
[1] A deodorant comprising thymoquinone as a deodorant active ingredient.
[2] A deodorant composition comprising the deodorant of [1] above.
[3] The deodorant composition according to the above [2], wherein black cumin seed pulverized product, solvent extract, or essential oil is blended.
[4] The deodorant composition according to the above [2] or [3], wherein another plant deodorant is further added.
[5] The deodorant composition according to any one of [2] to [4], wherein an antioxidant component is added.
[6] A deodorant fragrance composition, wherein a fragrance component is blended with the deodorant composition according to any one of [2] to [5].
[7] A bad breath preventive food comprising the deodorant composition according to any one of [2] to [5] or the deodorant fragrance composition according to [6].
[8] The bad breath preventive food according to [7] above, wherein the food containing the deodorant composition or the deodorant fragrance composition has a pH of 5 or less.
[9] An oral deodorant composition comprising the deodorant composition according to any one of [2] to [5] or the deodorant fragrance composition according to [6].
[10] The composition for oral deodorization according to [9] above, wherein the composition of the deodorant composition or the deodorant fragrance composition is 5 or less in pH.
本発明は、酸性〜中性〜弱塩基性の、幅広いｐＨ域において非常に高い消臭効果を示す消臭剤組成物及び消臭性香料組成物を提供することが可能となる。また、本発明の消臭剤組成物は、従来調味料として用いられているブラッククミンに由来するものであるため、本発明の消臭剤組成物及び消臭性香料組成物を、チューインガムやキャンディー、錠菓などの菓子類に配合できるほか、歯磨、マウスウォッシュ、義歯洗浄剤などの口腔用組成物にも使用できるものである。さらに、本発明の消臭剤組成物は、褐変反応などの経時変化が少なく、安定した消臭効果を有するものである。 The present invention can provide a deodorant composition and a deodorant fragrance composition that exhibit an extremely high deodorizing effect in a wide pH range from acidic to neutral to weakly basic. Further, since the deodorant composition of the present invention is derived from black cumin conventionally used as a seasoning, the deodorant composition and the deodorant fragrance composition of the present invention are used as chewing gum or candy. In addition to being able to be blended into confectionery such as tablet confectionery, it can also be used in oral compositions such as toothpaste, mouthwash, and denture cleaning agents. Furthermore, the deodorant composition of the present invention has a stable deodorizing effect with little change over time such as browning reaction.
本発明は、ブラッククミン種子に含有されるチモキノンが、従来の植物抽出物に酸化酵素を併用した消臭剤に匹敵する、非常に高い消臭効果を示し、しかも、酸性条件下においても消臭効果が低下しないという知見に基づくものである。 The present invention shows that thymoquinone contained in black cumin seeds has a very high deodorizing effect comparable to that of a conventional plant extract in which an oxidase is used in combination, and is also deodorant even under acidic conditions. This is based on the knowledge that the effect does not decrease.
ブラッククミンは、学名が、Nigella sativa L.、和名が、クロタネソウ、英名が、ブラッククミン（Black Cumin）であり、ブラックキャラウェイ、ニゲラ、カロンジなどの別名でも呼ばれる植物であり、地中海沿岸原産で、食用に中東やインドで広く栽培されている。キンポウゲ科に属し、高さ２０〜３０ｃｍになる一年草で、花期は６〜７月、羽状葉と灰青色の花をつけ、花後に黒い種子入りの朔果をつける（上記非特許文献６参照）。 Black cumin has the scientific name Nigella sativa L., the Japanese name is black ginseng, the English name is black cumin, and is also known as the black caraway, nigella, caronji, etc. It is widely cultivated in the Middle East and India for food. An annual plant that belongs to the family Ranunculaceae and has a height of 20 to 30 cm. The flowering period is from June to July, with feathered leaves and grayish blue flowers, and after the flowers with black seeded fruit. 6).
ブラッククミンの種子は、長さ３ｍｍ、径１．５ｍｍ、厚さ１ｍｍで、芳香が強く、辛味があり、調味料として用い、インド、エジプト、ギリシャ、トルコ料理でよく使用される。パンやケーキに風味をつけ、インドでは、ガラムマサラの原料として用いられ、カレーや野菜料理の香味づけに利用される。 Black cumin seeds are 3mm in length, 1.5mm in diameter, 1mm in thickness, strong aroma, pungent, used as a seasoning and often used in Indian, Egyptian, Greek and Turkish cuisine. Flavored bread and cakes, used in India as a raw material for garam masala, and used for flavoring curry and vegetable dishes.
ブラッククミン種子の精油成分として、α-Pinene、p-Cymene、γ-Terpinene、Thymoquinone、Carvacrol等が報告されている。
ブラッククミン種子は、伝承薬として、喘息、咳、気管支炎、頭痛、リューマチ、熱、湿疹の治療に用いられるほか、利尿薬、催乳剤、駆虫剤として使用される。最近では、抗菌作用、抗酸化作用、抗炎症作用、平滑筋弛緩効果、抗腫瘍、鎮痛作用などを有することが知られている（非特許文献７〜９等）。
Α-Pinene, p-Cymene, γ-Terpinene, Thymoquinone, Carvacrol and the like have been reported as essential oil components of black cumin seeds.
Black cumin seed is used as a traditional medicine for the treatment of asthma, cough, bronchitis, headache, rheumatism, fever and eczema, as well as diuretics, emetics and anthelmintics. Recently, it is known to have an antibacterial action, an antioxidant action, an anti-inflammatory action, a smooth muscle relaxation effect, an antitumor, an analgesic action and the like (Non-Patent Documents 7 to 9 etc.).
本発明においてその消臭効果を見いだしたチモキノンは、前述のブラッククミン種子に含有される精油成分の１つであり、図１において、矢印で示すピークがチモキノンである。
チモキノンは、下記の式で表される、２−イソプロピル−５−メチル−１，４−ベンゾキノンであって、分子量１６４．２０、沸点２３０〜２３２℃、融点４５〜４７℃（ＳＩＧＭＡ−ＡＬＤＲＩＣＨ社 ２００９−２０１０版カタログ 第２３７７頁参照）の化合物である。
Thymoquinone, which has found its deodorizing effect in the present invention, is one of the essential oil components contained in the aforementioned black cumin seeds. In FIG. 1, the peak indicated by the arrow is thymoquinone.
Thymoquinone is 2-isopropyl-5-methyl-1,4-benzoquinone represented by the following formula, having a molecular weight of 164.20, a boiling point of 230 to 232 ° C., a melting point of 45 to 47 ° C. (SIGMA-ALDRICH Co., Ltd. 2009) -2010 edition catalog (see page 2377)).
本発明における消臭剤を含有する消臭剤組成物には、ブラッククミン種子の粉砕物、溶媒抽出物、蒸留物、チモキノン高純度品を適宜使用することができる。
粉砕物としては、ブラッククミンの種子を粉砕ミルにかけて粉砕した後、適当なサイズのメッシュを通して作製した粉末を使用することが出来る。
ブラッククミン種子から、チモキノン含有品を得るための方法は特に限定されないが、各種溶媒による抽出、超臨界炭酸ガス抽出、水蒸留、水蒸気蒸留、マイクロウエーブ抽出法、圧搾法（コールドプレス法）などにより得ることができ、これらの方法は適宜組み合わせて利用される。抽出に用いる溶媒は、極性溶媒、非極性溶媒のいずれでもよく、水、メタノール、エタノール、アセトン、酢酸エチル、ジエチルエーテル、ｎ−ヘキサン等およびそれらの混合液を用いることが出来るが、より好ましくはメタノール、含水メタノール、エタノール、含水エタノール、アセトン、酢酸エチルが使用される。
また上記抽出溶媒に有機および無機の酸を添加した酸性溶媒や有機および無機の塩基を添加した塩基性溶媒も使用することが出来る。
In the deodorant composition containing the deodorant in the present invention, a pulverized product of black cumin seed, a solvent extract, a distillate, and a high-purity product of thymoquinone can be appropriately used.
As the pulverized product, a powder prepared by pulverizing black cumin seeds on a pulverizing mill and then passing through a mesh of an appropriate size can be used.
The method for obtaining thymoquinone-containing products from black cumin seeds is not particularly limited, but by various solvent extraction, supercritical carbon dioxide extraction, water distillation, steam distillation, microwave extraction method, pressing method (cold press method), etc. These methods can be obtained and used in combination as appropriate. The solvent used for the extraction may be either a polar solvent or a nonpolar solvent, and water, methanol, ethanol, acetone, ethyl acetate, diethyl ether, n-hexane, and the like, and mixtures thereof can be used, but more preferably Methanol, hydrous methanol, ethanol, hydrous ethanol, acetone, and ethyl acetate are used.
In addition, an acidic solvent in which organic and inorganic acids are added to the extraction solvent and a basic solvent in which organic and inorganic bases are added can also be used.
本発明の消臭剤の有効成分であるチモキノンは、天然品、合成品のいずれでもよいが、より好ましくは、（１）種子の粉砕品に水蒸気を通じて蒸留液を得、その浮油を採取する方法、（２）（１）の蒸留液にｎ−ヘキサンや酢酸エチル等の有機溶媒を加えて分液操作を行った後に得られた有機相を濃縮する方法、（３）種子の極性または非極性溶媒抽出物に水蒸気を通じて蒸留した後にｎ−ヘキサンや酢酸エチル等の有機溶媒を加えて分液操作、さらにこの有機相を濃縮する方法等により得たチモキノン含有量を高めた精油を使用することができる。 The thymoquinone, which is an active ingredient of the deodorant of the present invention, may be either a natural product or a synthetic product. More preferably, (1) a distillate is obtained through pulverized seeds through steam and the floating oil is collected. Method, (2) a method of concentrating the organic phase obtained after performing a liquid separation operation by adding an organic solvent such as n-hexane or ethyl acetate to the distillate of (1), (3) polarity of seeds or non- Use an essential oil with increased thymoquinone content obtained by distilling the polar solvent extract through water vapor and then adding an organic solvent such as n-hexane or ethyl acetate to separate the liquid and concentrating the organic phase. Can do.
また、本発明の消臭剤の有効成分であるチモキノンに天然品を用いる場合、前記のブラッククミン以外にチモキノン（ＴＱ）を含有する植物として、オレガノ（学名：Origanum vulgare）、タイム（学名：Thymus vulgaris L.）ウィンターセーボリー（学名：Satureja montana L.）などが用いられる。
また、本発明の消臭有効成分はそれ単独で用いてもよく、他の消臭有効成分と組み合せて用いてもよく、例えば、本発明の消臭剤組成物に、消臭力を有する、セージ、タイム、ミント、ローズマリー、オレガノなどのシソ科植物、クローブ、茶類等の、その他の植物性消臭剤をさらに添加することができる。
また、褐変化抑制のため、本発明の消臭剤組成物にアスコルビン酸等の抗酸化成分を添加することができる。
Moreover, when using a natural product for thymoquinone, which is an active ingredient of the deodorant of the present invention, as a plant containing thymoquinone (TQ) in addition to the above black cumin, oregano (scientific name: Origanum vulgare), thyme (scientific name: Thymus vulgaris L.) Winter savory (scientific name: Satureja montana L.) is used.
In addition, the deodorant active ingredient of the present invention may be used alone or in combination with other deodorant active ingredients.For example, the deodorant composition of the present invention has a deodorizing power. Other botanical deodorants such as sage, thyme, mint, rosemary, oreganoceae, clove, tea, etc. can be further added.
Moreover, antioxidant components, such as ascorbic acid, can be added to the deodorant composition of this invention for brown change suppression.
本発明の消臭剤は、種々の剤型に調製し得る。例えば、本発明の消臭有効成分であるチモキノンを適宜な溶媒に溶解した溶液状のもの、或いはペースト状、粉粒状、ブロック状、更にはマイクロカプセル状など、所望の形態に調製したものを使用し得る。 The deodorant of the present invention can be prepared in various dosage forms. For example, a solution in which thymoquinone, which is the deodorizing active ingredient of the present invention, is dissolved in an appropriate solvent, or a paste, powder, block, or even a microcapsule is used. Can do.
本発明の、チモキノンを消臭有効成分とする消臭剤は、幅広いｐＨ域において非常に高い消臭効果を示すので、種々の消臭剤組成物及び消臭性香料組成物を提供することができる。
特に、本発明の消臭性香料組成物は、口臭予防を目的とするチューインガムや、キャンデー、錠菓等の菓子類に配合できる他、歯磨、マウスウォッシュ、義歯洗浄剤などの口腔用組成物に使用でき、通常は、後述の消臭性香料処方例をはじめとする各種の香料を配合して口臭予防食品、口腔用消臭剤等として用いられる。
例えば、本発明の消臭剤又は消臭剤組成物を、所定の割合で、チューインガム、キャンデー等の菓子素材に添加し、常法に従って加工することにより製造することができる。
また、口臭予防、口臭除去のための口腔用消臭剤として使用する場合、研磨剤（通常２０〜６０重量％）、粘結剤（通常０．３〜５重量％）、粘稠剤（通常１０〜７０重量％）、発泡剤（通常０．１〜５重量％）と、それに香料、甘味剤、防腐剤などの成分が配合され、これら成分を水と混和し、常法に従って製造する。また、マウスウォッシュ等の口腔洗浄剤その他においても、製品の性状に応じた成分が適宜配合される。
Since the deodorant containing thymoquinone as the deodorant active ingredient of the present invention exhibits a very high deodorant effect in a wide pH range, various deodorant compositions and deodorant perfume compositions can be provided. it can.
In particular, deodorant perfume composition of the present invention, and chewing Nga arm for the purpose of Breath, Candy, other that can be incorporated into confectionery tablets菓等, toothpaste, mouthwash, the composition for oral cavity, such as denture cleaners Various kinds of fragrances including a deodorant fragrance formulation example to be described later are blended and used as a bad breath prevention food, a deodorant for oral cavity, and the like.
For example, it can be produced by adding the deodorant or deodorant composition of the present invention to a confectionery material such as chewing gum or candy at a predetermined ratio and processing it according to a conventional method.
In addition, when used as a deodorant for oral cavity for the prevention of bad breath and removal of bad breath, abrasives (usually 20 to 60% by weight), binders (usually 0.3 to 5% by weight), viscous agents (usually 10 to 70% by weight), a foaming agent (usually 0.1 to 5% by weight), and ingredients such as fragrances, sweeteners, preservatives and the like are blended, and these ingredients are mixed with water and produced according to a conventional method. In addition, in oral cleaning agents such as mouthwash and the like, components according to the properties of the product are appropriately blended.
以下、実施例及び比較例を用いて本発明について説明するが、本発明はこれらによって何ら限定されるものではない。
消臭試験法および成分分析法
１．メチルメルカプタン消臭試験の方法
以下、本発明に係わる消臭成分の試験法について説明する。
＜試薬の調製＞
（１）メチルメルカプタン１０ｎｇ／μｌ希釈液
メチルメルカプタン標準液１μｇ／μｌベンゼン溶液（和光純薬）２ｍｌを９９％エタ
ノールで２００ｍｌにメスアップして供試した。
（２）１／１５Ｍ燐酸緩衝液ｐＨ７．０・・・中性域での消臭試験時に使用する。
燐酸緩衝液３（２０倍濃縮液）（三菱化学メディエンス(株)製）１瓶を精製水で希釈して1リットルにメスアップした。
（３）１／１０Ｍクエン酸緩衝液ｐＨ３．０・・・ｐＨ変化による消臭試験時に使用する。
０．１Ｍクエン酸二ナトリウム１．５水和物水溶液、０．１Ｎ ＨＣｌ水溶液を混合し、クエン酸にてｐＨ３．０に調整した。
（４）１／１０Ｍクエン酸緩衝液ｐＨ５．０・・・ｐＨ変化による消臭試験時に使用する。
０．１Ｍクエン酸二ナトリウム１．５水和物水溶液に０．１Ｎ ＨＣｌ水溶液を混合し、クエン酸にてｐＨ５．０に調整した。
EXAMPLES Hereinafter, although this invention is demonstrated using an Example and a comparative example, this invention is not limited at all by these.
Deodorization test method and component analysis method Methyl Mercaptan Deodorization Test Method Hereinafter, the test method for the deodorant component according to the present invention will be described.
<Preparation of reagents>
(1) Diluted solution of
(2) 1 / 15M phosphate buffer pH 7.0: Used during a deodorization test in a neutral range.
One bottle of phosphate buffer 3 (20-fold concentrated solution) (manufactured by Mitsubishi Chemical Medience Corporation) was diluted with purified water to make up to 1 liter.
(3) 1 / 10M citrate buffer pH 3.0: Used during a deodorization test by pH change.
0.1M disodium citrate hemihydrate aqueous solution and 0.1N HCl aqueous solution were mixed and adjusted to pH 3.0 with citric acid.
(4) 1/10 M citrate buffer pH 5.0: Used during a deodorization test by pH change.
0.1N HCl aqueous solution was mixed with 0.1M disodium citrate hemihydrate aqueous solution and adjusted to pH 5.0 with citric acid.
＜試料の調製＞
各溶媒抽出物、精油およびテルペン類を９５％（ｗ／ｗ）エタノールにてそれぞれ１％（ｗ／ｗ）に希釈したものを消臭試験に供した。
<Preparation of sample>
Each solvent extract, essential oil, and terpenes diluted with 95% (w / w) ethanol to 1% (w / w) were subjected to a deodorization test.
＜方法＞
所定量の試料を３０ｍｌバイアル瓶に入れ、予め３７℃に保温した緩衝液５．０ｍｌを加え、容器を密栓した。次に上記バイアル瓶中にメチルメルカプタン１０ｎｇ／μｌ希釈
液５０μｌ（５００ｎｇ量のメチルメルカプタンに相当）を加え、３７℃で１０分間インキュベートさせた。１０分経過後にガスタイトシリンジにてバイアル瓶中のヘッドスペースガス５ｍｌを抜き取り、液体窒素によるコールドトラップ装置を装着したＧＣ−ＭＳに導入してメチルメルカプタン量を測定した。
＊なお中性域（ｐＨ７．０）での消臭試験にはリン酸緩衝液を用い、酸性域での消臭試験の場合には、クエン酸−クエン酸ニナトリウム緩衝液（ｐＨ３．０および５．０）をそれぞれ使用した。
メチルメルカプタンのピーク検出は、本成分に由来する特有のＭＳフラグメントイオン４７および４８を選択して検出するＳＩＭ法により行った。各検体のメチルメルカプタン消臭率は、緩衝液のみをバイアル瓶に入れたものを対照液として下式（１）にしたがって算出した。
メチルメルカプタン消臭率（%）＝（Ｃ−Ｓ）／Ｃ×１００・・・・ （１）
（式中、Ｃは、対照液のヘッドスペース中のメルカプタン量、Ｓは、検体のヘッドスペース中のメチルメルカプタン量を示す。
<Method>
A predetermined amount of the sample was put in a 30 ml vial, 5.0 ml of a buffer kept at 37 ° C. in advance was added, and the container was sealed. Next, 50 μl of a 10 ng / μl diluted solution of methyl mercaptan (corresponding to a 500 ng amount of methyl mercaptan) was added to the vial and incubated at 37 ° C. for 10 minutes. After 10 minutes, 5 ml of the headspace gas in the vial was extracted with a gas tight syringe and introduced into a GC-MS equipped with a cold trap device using liquid nitrogen to measure the amount of methyl mercaptan.
* Phosphate buffer is used for the deodorization test in the neutral range (pH 7.0). In the case of the deodorization test in the acidic range, citric acid-disodium citrate buffer (pH 3.0 and 5.0) were used respectively.
The methyl mercaptan peak was detected by the SIM method in which specific MS fragment ions 47 and 48 derived from this component were selected and detected. The methyl mercaptan deodorization rate of each specimen was calculated according to the following formula (1) using a buffer solution alone as a control solution.
Methyl mercaptan deodorization rate (%) = (C−S) / C × 100 (1)
(In the formula, C represents the amount of mercaptan in the head space of the control solution, and S represents the amount of methyl mercaptan in the head space of the specimen.
＜ＧＣ−ＭＳ分析条件＞
［装置］ ＧＣ：Agilent 6890A ＭＳ：Agilent 5973N
コールドトラップ装置： Gerstel CIS
［コールドトラップの条件］ −１２０℃ 、３０秒間、スプリットレス
［カラム］ ガス分析用HP-PLOTQ： ３０ｍ×０．３２mm×２０μm
［温度条件］ 初期温度５０℃（１．５分間保持）→２０℃昇温／min.→１２０℃（５分間保持）
［流量］ １．８ｍｌ／ｍｉｎ
〔イオン化電圧〕 ７０ｅＶ
<GC-MS analysis conditions>
[Apparatus] GC: Agilent 6890A MS: Agilent 5973N
Cold trap device: Gerstel CIS
[Cold trap conditions] -120 ° C, 30 sec, splitless [Column] HP-PLOTQ for gas analysis: 30m x 0.32mm x 20μm
[Temperature conditions] Initial temperature 50 ° C. (hold for 1.5 minutes) → 20 ° C. temperature rise / min. → 120 ° C. (hold for 5 minutes)
[Flow rate] 1.8ml / min
[Ionization voltage] 70 eV
２．揮発成分の分析方法（チモキノンの検出）
ブラッククミン種子の各溶媒抽出物および精油に含有される揮発成分の分析に用いたＧＣおよびＧＣ−ＭＳ分析の基本条件は下記の通り。
＜ＧＣ分析条件＞
〔装置〕 ＧＣ： HP 5890 Series 2
〔カラム〕 ＧＬ Sciences TC-1：３０ｍ×０．２５ｍｍ×０．２５μm
〔温度条件〕 初期温度５０℃→３℃昇温／ｍｉｎ→３００℃（２０分間保持）
〔キャリアガス〕 Ｈｅ
〔流量〕 ０．７ｍｌ／ｍｉｎ
〔注入口温度〕 ３００℃
〔注入量〕 ・各溶媒抽出物：１０％（ｗ／ｗ）エタノール溶液を１．０μｌずつ注
入した。
・各蒸留精油：０．１μｌずつ注入した。
2. Analysis method of volatile components (detection of thymoquinone)
The basic conditions of GC and GC-MS analysis used for analysis of volatile components contained in each solvent extract and essential oil of black cumin seed are as follows.
<GC analysis conditions>
[Equipment] GC: HP 5890 Series 2
[Column] GL Sciences TC-1: 30 m × 0.25 mm × 0.25 μm
[Temperature conditions] Initial temperature 50 ° C. → 3 ° C. temperature increase / min → 300 ° C. (hold for 20 minutes)
[Carrier gas] He
[Flow rate] 0.7ml / min
[Inlet temperature] 300 ° C
[Injection volume]-Each solvent extract: 1.0 μl of 10% (w / w) ethanol solution was poured.
I entered.
Each distilled essential oil: 0.1 μl was injected.
＜ＧＣ−ＭＳ分析条件＞
〔装置〕 ＧＣ：Agilent 6890A ＭＳ：Agilent 5973N
〔カラム〕 ＧＬ Sciences TC-1：３０ｍ×０．２５ｍｍ×０．２５μm
〔温度条件〕 初期温度５０℃→３℃昇温／ｍｉｎ→３００℃（２０分間保持）
〔キャリアガス〕 Ｈｅ
〔流量〕 ０．８ｍｌ／ｍｉｎ
〔イオン化電圧〕 ７０ｅＶ
〔注入口温度〕 ３００℃
〔注入量〕 ・各溶媒抽出物：１０％（ｗ／ｗ）エタノール溶液を１．０μｌずつ注
入した。
・各蒸留精油：０．１μｌずつ注入した。
<GC-MS analysis conditions>
[Equipment] GC: Agilent 6890A MS: Agilent 5973N
[Column] GL Sciences TC-1: 30 m × 0.25 mm × 0.25 μm
[Temperature conditions] Initial temperature 50 ° C. → 3 ° C. temperature increase / min → 300 ° C. (hold for 20 minutes)
[Carrier gas] He
[Flow rate] 0.8ml / min
[Ionization voltage] 70 eV
[Inlet temperature] 300 ° C
[Injection volume]-Each solvent extract: 1.0 μl of 10% (w / w) ethanol solution was poured.
I entered.
Each distilled essential oil: 0.1 μl was injected.
（実施例１：ブラッククミン粉砕種子の作製）
ブラッククミン種子１５０ｇを電池式ごますり器（CB-AA10-WB（象印社製））により粉砕後、３０メッシュをパスさせた。この粉砕種子１０ｍｇ、３０ｍｇ、５０ｍｇを用いた時のメチルメルカプタンに対する消臭試験を実施した（ｐＨ７．０）。
ブラッククミン粉砕種子のメチルメルカプタン消臭試験結果を表１に示す。
(Example 1: Production of ground seed of black cumin)
After pulverizing 150 g of black cumin seeds with a battery-type grinder (CB-AA10-WB (manufactured by Zojirushi)), 30 mesh was passed. A deodorization test was performed on methyl mercaptan when 10 mg, 30 mg, and 50 mg of the pulverized seeds were used (pH 7.0).
The methyl mercaptan deodorization test results of black cumin ground seeds are shown in Table 1.
表１の結果より、ブラッククミンの粉砕種子に消臭効果があり、用量依存的にその消臭率（％）が高まることが判った。 From the results in Table 1, it was found that the ground seeds of black cumin have a deodorizing effect and the deodorization rate (%) increases in a dose-dependent manner.
（実施例２：ブラッククミン未粉砕種子あるいは粉砕種子の水蒸気蒸留）
ブラッククミン種子を上記と同様に粉砕して、以下の実験に供した。
（１）Linkens-Nickerson連続蒸留装置の試料用フラスコに未粉砕種子１．０ｋｇ、溶媒フラスコにペンタン：ジエチルエーテル混合液（１：１、ｖ／ｖ）を入れ、蒸留−溶媒抽出を同時に行った。３．５時間蒸留した後に得られた有機相をロータリーエバポレーターにて減圧下で濃縮して精油分を得た。
（２）未粉砕種子５００ｇに水蒸気を通じて３．０時間蒸留し、得られた蒸留液から浮油を採取した。
（３）粉砕種子５００ｇに水蒸気を通じて３．０時間蒸留し、得られた蒸留液から浮油を採取した。
（４）粉砕種子５００ｇに水蒸気を通じて３．０時間蒸留し、得られた蒸留液を酢酸エチル６００ｍｌで分配した。酢酸エチル相を減圧下で濃縮し、精油分を得た。
(Example 2: Steam cumulation of black cumin unground seed or ground seed)
Black cumin seeds were crushed in the same manner as described above and subjected to the following experiment.
(1) 1.0 kg of unground seeds were put in a sample flask of a Linkens-Nickerson continuous distillation apparatus, and a pentane: diethyl ether mixed solution (1: 1, v / v) was put in a solvent flask, and distillation-solvent extraction was simultaneously performed. . The organic phase obtained after distillation for 3.5 hours was concentrated under reduced pressure on a rotary evaporator to obtain an essential oil.
(2) Distilled on 500 g of unground seeds through steam for 3.0 hours, and collected floating oil from the obtained distillate.
(3) 500 g of pulverized seeds were distilled through steam for 3.0 hours, and floating oil was collected from the obtained distillate.
(4) 500 g of ground seeds were distilled through steam for 3.0 hours, and the resulting distillate was distributed with 600 ml of ethyl acetate. The ethyl acetate phase was concentrated under reduced pressure to obtain an essential oil.
上記（１）〜（４）の精油につき、それぞれＧＣおよびＧＣ−ＭＳに供して、抽出物中のチモキノン量について比較分析した。また各抽出物（１）〜（４）の１．０ｍｇを用いた時のメチルメルカプタンに対する消臭試験も実施した（ｐＨ７．０）。
ブラッククミン未粉砕あるいは粉砕種子から得た抽出物の収量（ｇ）、チモキノン量（ＧＣ−ＭＳPeak Area）および消臭試験の結果を表２に示す。
About the essential oil of said (1)-(4), it used for GC and GC-MS, respectively, and compared and analyzed about the amount of thymoquinone in an extract. Moreover, the deodorizing test with respect to methyl mercaptan when 1.0 mg of each extract (1)-(4) was used was also implemented (pH 7.0).
Table 2 shows the yield (g) of the extract obtained from unground or crushed seeds of black cumin, the amount of thymoquinone (GC-MS Peak Area) and the results of the deodorization test.
表２の結果より、ブラッククミン種子を粉砕処理することにより、チモキノンの含有量が増加すること、粉砕種子の蒸留液から酢酸エチル等の有機溶媒を用いて分液操作を行うことにより、精油収量（ｇ）が増加し、さらに消臭率（％）も高まることが判った。 From the results of Table 2, the essential oil yield is obtained by increasing the content of thymoquinone by pulverizing black cumin seeds, and performing a liquid separation operation using an organic solvent such as ethyl acetate from a distilled liquid of pulverized seeds. It was found that (g) increased and the deodorization rate (%) also increased.
（実施例３：ブラッククミン未粉砕種子の溶媒抽出）
ブラッククミンは、インド産種子（商品名：カロンジ）を東京上野の大津屋より購入して実験に供した。濾液の濃縮には、ロータリーエバポレーターを使用した。
（１）未粉砕種子１００ｇをイオン交換水２００ｇに浸漬し、９０℃で１時間加温抽出した。つぎに抽出液を吸引濾過（ADVANTEC TOYO No.2濾紙を使用）し、濾液を減圧下、４５℃以下で濃縮した。
（２）未粉砕種子１００ｇをメタノール２００ｇに浸漬し、常温下で３日間静置抽出した。
つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。
（３）未粉砕種子１００ｇを９５％（ｗ／ｗ）エタノール２００ｇに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。
（４）未粉砕種子１００ｇを７０％（ｗ／ｗ）エタノール２００ｇに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。
（５）未粉砕種子１００ｇを５０％（ｗ／ｗ）エタノール２００gに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。
（６）未粉砕種子１００ｇをアセトン２００ｇに浸漬し、５℃で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、２５℃以下で溶媒臭がなくなるまで濃縮した。
（７）未粉砕種子１００ｇを酢酸エチル２００ｇに浸漬し、５℃で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。
（８）未粉砕種子１００ｇをジエチルエーテル２００ｇに浸漬し、５℃で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、１０℃以下で溶媒臭がなくなるまで濃縮した。
（９）未粉砕種子１００ｇをｎ−ヘキサン２００ｇに浸漬し、５℃で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、２５℃以下で溶媒臭がなくなるまで濃縮した。
(Example 3: Solvent extraction of unground seed of black cumin)
Black cumin purchased Indian seeds (trade name: Karonji) from Otsuya in Ueno, Tokyo for experiment. A rotary evaporator was used for concentration of the filtrate.
(1) 100 g of unground seeds were immersed in 200 g of ion-exchanged water and extracted by heating at 90 ° C. for 1 hour. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated at 45 ° C. or lower under reduced pressure.
(2) 100 g of unground seeds were immersed in 200 g of methanol, and extracted by standing at room temperature for 3 days.
Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared.
(3) 100 g of unground seeds were immersed in 200 g of 95% (w / w) ethanol and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared.
(4) 100 g of unground seeds were immersed in 200 g of 70% (w / w) ethanol and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared.
(5) 100 g of unground seeds were immersed in 200 g of 50% (w / w) ethanol, and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared.
(6) 100 g of unground seeds were immersed in 200 g of acetone and extracted by standing at 5 ° C. for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 25 ° C. or less until the solvent odor disappeared.
(7) 100 g of unground seeds were immersed in 200 g of ethyl acetate, and extracted by standing at 5 ° C. for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared.
(8) 100 g of unground seeds were immersed in 200 g of diethyl ether, and extracted by standing at 5 ° C. for 3 days. The extract was then suction filtered (using ADVANTEC TOYO No. 2 filter paper) and the filtrate was concentrated under reduced pressure at 10 ° C. or less until the solvent odor disappeared.
(9) 100 g of unground seeds were soaked in 200 g of n-hexane and extracted by standing at 5 ° C. for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 25 ° C. or less until the solvent odor disappeared.
上記（１）〜（９）抽出物につき、それぞれＧＣおよびＧＣ−ＭＳに供して、抽出物中のチモキノン量について比較分析した。また各抽出物（１）〜（９）の１．０ｍｇを用いた時のメチルメルカプタンに対する消臭試験も実施した（ｐＨ７．０）。
ブラッククミン種子の抽出溶媒の違いによる抽出物の収量（ｇ）、チモキノン量（ＧＣ Peak Area）および消臭試験の結果を表３に示す。
About the said (1)-(9) extract, it used for GC and GC-MS, respectively, and compared and analyzed about the amount of thymoquinone in an extract. Moreover, the deodorizing test with respect to methyl mercaptan when 1.0 mg of each extract (1)-(9) was used was also implemented (pH 7.0).
Table 3 shows the extract yield (g), the amount of thymoquinone (GC Peak Area), and the results of the deodorization test according to the difference in the extraction solvent of black cumin seeds.
表３の結果より、ブラッククミン種子から各種溶媒によりチモキノンが抽出されること、および（２）メタノール、（３）95%エタノール、（６）アセトン、（７）酢酸エチル、（９）ｎ−ヘキサン抽出物では１．０ｍｇという微量で高い消臭率（％）を示すことが判った。 From the results in Table 3, thymoquinone is extracted from black cumin seeds with various solvents, and (2) methanol, (3) 95% ethanol, (6) acetone, (7) ethyl acetate, (9) n-hexane. It was found that the extract showed a high deodorization rate (%) with a trace amount of 1.0 mg.
（実施例４：ブラッククミン未粉砕種子の溶媒抽出物からの水蒸気蒸留）
下記方法により、ブラッククミン種子の各抽出物から水蒸気蒸留法により精油を得た。ｎ−ヘキサン相の濃縮には、ロータリーエバポレーターを使用した。
（１）未粉砕種子１００ｇをメタノール２００ｇに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。つぎにこの濃縮物に水蒸気を通じ、３．０時間蒸留した。得られた蒸留液をｎ−ヘキサン６００ｍｌで分配し、ｎ−ヘキサン相を減圧下で濃縮し、精油分を得た。
（２）未粉砕種子１００ｇを９５％エタノール２００ｇに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。つぎにこの濃縮物に水蒸気を通じ、３．０時間蒸留した。得られた蒸留液をｎ−ヘキサン６００ｍｌで分配し、ｎ−ヘキサン相を減圧下で濃縮し、精油分を得た。
（３）未粉砕種子１００ｇを酢酸エチル２００ｇに浸漬し、５℃で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。つぎにこの濃縮物に水蒸気を通じ、３．０時間蒸留した。得られた蒸留液をｎ−ヘキサン６００ｍｌで分配した。ｎ−ヘキサン相を減圧下で濃縮し、精油分を得た。
（４）未粉砕種子１００ｇをメタノール２００ｇに浸漬し、常温下で３日間静置抽出した。つぎに抽出液を吸引濾過し、（ADVANTEC TOYO No.2濾紙を使用）濾液を減圧下、４５℃以下で溶媒臭がなくなるまで濃縮した。つぎにこの濃縮物に水蒸気を通じ、３．０時間蒸留した。得られた蒸留液を酢酸エチル６００ｍｌで分配し、酢酸エチル相を減圧下で濃縮し、精油分を得た。
(Example 4: Steam distillation from solvent extract of unground seed of black cumin)
Essential oil was obtained from each extract of black cumin seeds by the steam distillation method by the following method. A rotary evaporator was used for concentration of the n-hexane phase.
(1) 100 g of unground seeds were immersed in 200 g of methanol, and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared. Next, steam was passed through this concentrate for 3.0 hours. The obtained distillate was distributed with 600 ml of n-hexane, and the n-hexane phase was concentrated under reduced pressure to obtain an essential oil.
(2) 100 g of unground seeds were immersed in 200 g of 95% ethanol and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared. Next, steam was passed through this concentrate for 3.0 hours. The obtained distillate was distributed with 600 ml of n-hexane, and the n-hexane phase was concentrated under reduced pressure to obtain an essential oil.
(3) 100 g of unground seeds were immersed in 200 g of ethyl acetate, and extracted by standing at 5 ° C. for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared. Next, steam was passed through this concentrate for 3.0 hours. The obtained distillate was partitioned with 600 ml of n-hexane. The n-hexane phase was concentrated under reduced pressure to obtain an essential oil.
(4) 100 g of unground seeds were dipped in 200 g of methanol, and extracted by standing at room temperature for 3 days. Next, the extract was subjected to suction filtration (using ADVANTEC TOYO No. 2 filter paper), and the filtrate was concentrated under reduced pressure at 45 ° C. or less until the solvent odor disappeared. Next, steam was passed through this concentrate for 3.0 hours. The obtained distillate was partitioned with 600 ml of ethyl acetate, and the ethyl acetate phase was concentrated under reduced pressure to obtain an essential oil.
上記（１）〜（４）の精油につき、それぞれＧＣおよびＧＣ−ＭＳに供して、精油中のチモキノン量について比較分析した。
図１は、（１）の精油のガスクロマトグラムを示すものである。
各精油（１）〜（４）の１．０ｍｇを用いた時のメチルメルカプタンに対する消臭試験も実施した（ｐＨ７．０）。
ブラッククミン未粉砕種子の溶媒抽出物からの精油収量（ｇ）、チモキノン量（ＧＣ Peak Area）および消臭試験の結果を表４に示す。
About the essential oil of said (1)-(4), it used for GC and GC-MS, respectively, and compared and analyzed about the amount of thymoquinone in essential oil.
FIG. 1 shows a gas chromatogram of the essential oil (1).
A deodorization test for methyl mercaptan when 1.0 mg of each essential oil (1) to (4) was used was also carried out (pH 7.0).
Table 4 shows the essential oil yield (g), the thymoquinone amount (GC Peak Area), and the results of the deodorization test from the solvent extract of the black cumin unground seed.
表４の結果から、ブラッククミン種子溶媒抽出物の水蒸気蒸留によりチモキノンを含有する精油を得ることが出来、特にメタノール抽出物由来の精油では１．０ｍｇという微量で９２％（ヘキサン抽出）、94％（酢酸エチル抽出）という非常に高い消臭率（％）を示すことが判った。 From the results of Table 4, essential oil containing thymoquinone can be obtained by steam distillation of the black cumin seed solvent extract. In particular, the essential oil derived from methanol extract is 92% (hexane extraction) and 94% in a trace amount of 1.0 mg. It was found that the deodorization rate (%) (extracted with ethyl acetate) was very high.
（実施例５：チモキノンとテルペン化合物のメチルメルカプタンに対する消臭試験）
チモキノンと各種香料に使用されるテルペン類の試料１．０ｍｇを用いた時のメチルメルカプタンに対する消臭効果について比較検討した（ｐＨ７．０）。消臭試験の結果を表５に示す。
＜供試試料＞
チモキノンは、SIGMA-ALDRICH社製の試薬（９９％品）を使用した。その他のテルペン類は、香料原料として使用されているグレードのものをそれぞれ、α−Pinene（日本テルペン化学(株)製）、β−Pinene（ヤスハラケミカル(株)）、ｐ−Cymene（日本テルペン化学(株)製）、Limonene（(株)佐々木香料店製）、１，８−Cineole（高陽ケミカル(株)製）、γ−Terpinene（高砂香料工業(株)製）、４−Terpineol（シムライズ(株)製）、Carvone（塩野香料(株)製）、Thymol（シグマアルドリッチジャパン(株)製）、Carvacrol（シグマアルドリッチジャパン(株)製）、β−Caryophyllene（(株)井上香料製造所製）を使用した。
チモキノンとテルペン類のメチルメルカプタンに対する消臭効果の比較を表５に示す。
(Example 5: Deodorization test for methyl mercaptan of thymoquinone and terpene compound)
The deodorizing effect on methyl mercaptan when using 1.0 mg of terpene samples used for thymoquinone and various fragrances was compared (pH 7.0). Table 5 shows the results of the deodorization test.
<Test sample>
As thymoquinone, a reagent (99% product) manufactured by SIGMA-ALDRICH was used. Other terpenes are grades used as perfume raw materials, α-Pinene (manufactured by Nippon Terpene Chemical Co., Ltd.), β-Pinene (Yasuhara Chemical Co., Ltd.), p-Cymene (Nihon Terpene Chemical ( Co., Ltd.), Limonene (manufactured by Sasaki Inc.), 1,8-Cineole (manufactured by Koyo Chemical Co., Ltd.), γ-Terpinene (manufactured by Takasago Inc.), 4-Terpineol (Simrise Co., Ltd.) )), Carvone (manufactured by Shiono Perfume Co., Ltd.), Thymol (manufactured by Sigma Aldrich Japan Co., Ltd.), Carvacrol (manufactured by Sigma Aldrich Japan Co., Ltd.), β-Caryophyllene (manufactured by Inoue Fragrance Co., Ltd.) used.
Table 5 shows a comparison of the deodorizing effect of thymoquinone and terpenes on methyl mercaptan.
表５の結果から、チモキノンが香料に使用されるテルペン類（（２）〜（１２））と比較して特に高い消臭率（％）を示すことが判った。 From the results shown in Table 5, it was found that thymoquinone exhibits a particularly high deodorization rate (%) as compared with the terpenes ((2) to (12)) used in the fragrance.
（実施例６：チモキノンの用量−消臭率（％）について）
チモキノンの消臭効果における用量依存性について確認することを目的に、ｐＨ７．０におけるチモキノン量（ｍｇ）−
消臭率（％）の関係について調べた。消臭試験の結果を図２に示す。
図２の結果より、チモキノンは０．０５ｍｇという極微量で６０％近い消臭率を示し、その効果は用量依存的であることがわかった。
(Example 6: Thymoquinone dose-deodorization rate (%))
The amount of thymoquinone at pH 7.0 (mg) − for the purpose of confirming the dose dependency in the deodorant effect of thymoquinone
The relationship between the deodorization rate (%) was examined. The result of the deodorization test is shown in FIG.
From the results shown in FIG. 2, it was found that thymoquinone showed a deodorization rate close to 60% at a very small amount of 0.05 mg, and the effect was dose-dependent.
（実施例７：ブラッククミン抽出物、チモキノンと酵素酸化型消臭剤のｐＨの違いによるメチルメルカプタンに対する消臭試験）
次に本発明品と酵素酸化型消臭剤の酸度条件の違い（ｐＨ＝３、５、７）による消臭効果を比較検討した。消臭試験の結果を表６に示す。
＊酵素酸化型消臭剤＝「ポリフェノール化合物と酸化酵素（ラッカーゼやパーオキシダーゼ等）の組み合わせによる消臭剤」
＜緩衝液＞
中性域： １／１５Ｍリン酸緩衝液ｐＨ７．０を使用
酸性域： １／１０Ｍクエン酸−クエン酸ナトリウム緩衝液（ｐＨ３．０あるいは５．０）
を使用。
(Example 7: Black cumin extract, deodorization test for methyl mercaptan by pH difference between thymoquinone and enzyme-oxidized deodorant)
Next, the deodorizing effect due to the difference in the acidity condition (pH = 3, 5, 7) between the product of the present invention and the enzyme-oxidized deodorant was compared. Table 6 shows the results of the deodorization test.
* Enzyme-oxidizing deodorant = “deodorant with a combination of polyphenol compound and oxidase (laccase, peroxidase, etc.)”
<Buffer solution>
Neutral range:
use.
＜供試試料＞
（１）チモキノン（１．０ｍｇ）・・・SIGMA-ALDRICH社製試薬（９９％品）
（２）メタノール抽出物（１．０ｍｇ）・・・実施例３．−（２）と同一
（３）メタノール抽出物由来の精油（１．０ｍｇ）・・・実施例４．−（１）と同一
（４）ミントリーフ（１．０ｍｇ）＋ラッカーゼ（０．５ｍｇ）
「ミントリーフ」・・・インド、Arjuna社製「ミントリーフ」脱臭品を使用。
「ラッカーゼ」・・・大和化成(株)製「ラッカーゼダイワM120」を使用。
（５）ミントリーフ（１．０ｍｇ）＋パーオキシダーゼ（０．５ｍｇ）
「ミントリーフ」・・・同上
「パーオキシダーゼ」・・・和光純薬工業(株)製「パーオキシダーゼ」を使用。
（６）オウゴン抽出物（１．０ｍｇ）＋ラッカーゼ（０．５ｍｇ）
「オウゴン抽出物」・・・局方オウゴン（栃本天海堂薬局社製、刻み）１００ｇにイオ
ン交換水７００ｇを加え、液温８８〜９０℃で１時間加熱抽出
を行い、No.2濾紙（ADVANTEC TOYO社製）を用いて吸引濾過
した（濾液１：４７４．５３ｇ）。さらに上記抽出残渣にイオ
ン交換水７００ｇを加え、液温８８〜９０℃上記同様に１時間
加熱抽出後、吸引濾過を行った（濾液２：６９１．０２ｇ）。濾
液１および濾液２を合わせ、減圧下で濃縮乾固（収量：５１．
９４ｇ）したものを試験に供した。
「ラッカーゼ」・・・同上。
（７）オウゴン抽出物（１．０ｍｇ）＋パーオキシダーゼ（０．５ｍｇ）
「オウゴン抽出物」・・・同上
「パーオキシダーゼ」・・・同上
（８）、（９）ローズマリー抽出物・・・油溶性ローズマリーエキス（インドSynthite社製）を使用。
＊なお対照液は各ｐＨの緩衝液をそれぞれ使用した。
ブラッククミン抽出物、チモキノンと酵素酸化型消臭剤のｐＨの違いによるメチルメルカプタン消臭効果の比較を表６に示す。
<Test sample>
(1) Thymoquinone (1.0 mg): Reagents manufactured by SIGMA-ALDRICH (99% product)
(2) Methanol extract (1.0 mg) ... Example 3. -Same as (2) (3) Essential oil derived from methanol extract (1.0 mg) ... Example 4 -Same as (1) (4) Mint leaf (1.0 mg) + Laccase (0.5 mg)
“Mint leaf”: Deodorized product of “Mint leaf” manufactured by Arjuna, India.
“Laccase”: Uses “Laccase Daiwa M120” manufactured by Daiwa Kasei Co., Ltd.
(5) Mint leaf (1.0 mg) + peroxidase (0.5 mg)
“Mint leaf”: Same as above “Peroxidase”: “Peroxidase” manufactured by Wako Pure Chemical Industries, Ltd. is used.
(6) Ogon extract (1.0 mg) + laccase (0.5 mg)
"Ogon extract" ... pharmacopoeia Ogon (made by Tochimoto Tenkaido Pharmacy Co., Inc.) 100g
700g water is added and heated at 88-90 ° C for 1 hour.
And suction filtration using No.2 filter paper (ADVANTEC TOYO)
(Filtrate 1: 474.53 g). Further, the extraction residue
700 g of water exchanged with water, and a liquid temperature of 88 to 90 ° C. for 1 hour as above.
After heat extraction, suction filtration was performed (filtrate 2: 691.02 g). Filter
94 g) was subjected to the test.
"Laccase" ... Same as above.
(7) Ogon extract (1.0 mg) + peroxidase (0.5 mg)
"Ougon extract" ... Same as above "Peroxidase" ... Same as (8), (9) Rosemary extract ... Oil-soluble rosemary extract (India Synthite) is used.
* As a control solution, a buffer solution of each pH was used.
Table 6 shows a comparison of the deodorizing effect of methyl mercaptan by the difference in pH between black cumin extract, thymoquinone and enzyme-oxidized deodorant.
表６の結果から、酵素酸化型消臭剤（４）〜（９）はｐＨ３において、著しい消臭効果の低下を示すが、チモキノン（１）およびブラッククミン種子のメタノール抽出物由来の精油（３）は、中性域〜酸性域の幅広いｐＨ域で高い消臭率（％）を示すことが判った。 From the results of Table 6, the enzyme-oxidized deodorants (4) to (9) show a significant decrease in the deodorizing effect at pH 3, but the essential oil derived from the methanol extract of thymoquinone (1) and black cumin seed (3 ) Showed a high deodorization rate (%) in a wide pH range from neutral to acidic.
（実施例８：チモキノンとベンゾキノンの経時的褐変化の比較、及びアスコルビン酸添
加による褐変化抑制実験）
本実施例においては、チモキノンとベンゾキノンの経時的褐変化の比較ならびにアスコルビン酸（ビタミンＣ）添加による褐変化への影響を比較検討した。
＜試料＞
（１）チモキノン
（２）ベンゾキノン（東京化成製）
（３）アスコルビン酸（イワキ社製）
(Example 8: Comparison of time-dependent browning of thymoquinone and benzoquinone, and browning suppression experiment by ascorbic acid addition)
In this example, the comparison of the time-dependent browning of thymoquinone and benzoquinone and the effect of ascorbic acid (vitamin C) addition on the browning were compared.
<Sample>
(1) Thymoquinone (2) Benzoquinone (manufactured by Tokyo Chemical Industry)
(3) Ascorbic acid (Iwaki)
＜試料溶液の調製＞
（１） チモキノン溶液
チモキノン０．０１ｇを精秤して試験管（ガラス製、径１２ｍｍ×１２０ｍｍ長）に入れ、９５％エタノール０．９９ｇを加え溶解させた後、さらに１／１５Ｍリン酸緩衝液（ｐＨ７．０）４．０ｇを加えた。
（２）チモキノン＋アスコルビン酸溶液
上記（１）で得られた溶液にさらにアスコルビン酸５．０ｍｇ（終濃度：０．１％）を加えた。
（３）ベンゾキノン溶液
ベンゾキノン０．０１ｇを精秤して試験管（ガラス製、径１２ｍｍ×１２０ｍｍ長）に入れ、１／１５Ｍリン酸緩衝液（ｐＨ７．０）４．０ｇを加え溶解させた後、９５％エタノール０．９９ｇを加えた。
（４）ベンゾキノン＋アスコルビン酸溶液
上記（３）で得られた溶液にさらにアスコルビン酸５．０ｍｇ（終濃度：０．１％）を加えた。
<Preparation of sample solution>
(1) Thymoquinone solution 0.01 g of thymoquinone is precisely weighed and placed in a test tube (glass, diameter 12 mm × 120 mm length), 0.99 g of 95% ethanol is added and dissolved, and then 1/15 M phosphate buffer solution is added. 4.0 g (pH 7.0) was added.
(2) Thymoquinone + ascorbic acid solution Ascorbic acid 5.0 mg (final concentration: 0.1%) was further added to the solution obtained in the above (1).
(3) Benzoquinone solution After 0.01 g of benzoquinone was precisely weighed and placed in a test tube (made of glass, diameter 12 mm × 120 mm length), 4.0 g of 1/15 M phosphate buffer (pH 7.0) was added and dissolved. 0.99 g of 95% ethanol was added.
(4) Benzoquinone + ascorbic acid solution Ascorbic acid 5.0 mg (final concentration: 0.1%) was further added to the solution obtained in the above (3).
＜測定方法＞
経時的褐変化の様子を調べるため、光電比色計（東京光電社製、製品名：ANA-18A+）を用いて、室温条件下で、上記（１）〜（４）の各試料溶液の一定時間経過後の４２０ｎｍにおける吸光度（Ａｂｓ．）を測定し、各試料溶液の０分時に対する吸光度の差（変化値）を求めた。
ベンゾキノンは０、５、１５、３０、及び６０分後まで測定した。一方、チモキノンもベンゾキノン同様に測定を行い、６０分経過後も表７の通りに１２日目まで測定を継続した。
測定結果を表７に示す。
表８は、チモキノン及びベンゾキノンの消臭率（ｐＨ７．０）を示すものである。
<Measurement method>
In order to investigate the state of browning over time, a constant of each of the sample solutions (1) to (4) above was obtained at room temperature using a photoelectric colorimeter (manufactured by Tokyo Kogyo Co., Ltd., product name: ANA-18A +). Absorbance (Abs.) At 420 nm after the passage of time was measured, and the difference (change value) in absorbance of each sample solution with respect to 0 minutes was obtained.
Benzoquinone was measured after 0, 5, 15, 30, and 60 minutes. On the other hand, thymoquinone was measured in the same manner as benzoquinone, and the measurement was continued until day 12 as shown in Table 7 even after 60 minutes had passed.
Table 7 shows the measurement results.
Table 8 shows the deodorization rate (pH 7.0) of thymoquinone and benzoquinone.
＜結果＞
図３は、表７の結果をグラフにしたものである。
図３から明らかなように、ベンゾキノン溶液は測定開始直後から褐変化が始まり、６０分後にはＡｂｓ．１．２４８に達し、アスコルビン酸の添加によってもほとんど褐変化を抑制することは出来なかった。一方、チモキノンはベンゾキノンと比較して褐変化の進行が遅く、測定開始から緩やかに褐変化する様子が観察された。最終的に測定開始１０日後にはＡｂｓ．１．２２８に達するが、０．１％濃度のアスコルビン酸の添加によりその褐変化は著しく抑制されることが判明した。
<Result>
FIG. 3 is a graph of the results in Table 7.
As is clear from FIG. 3, the brown change of the benzoquinone solution started immediately after the start of measurement, and Abs. It reached 1.248, and even the addition of ascorbic acid could hardly suppress browning. On the other hand, thymoquinone had a slower browning progression than benzoquinone, and a modest browning was observed from the start of measurement. Finally, Abs. Although it reached 1.228, it was found that the browning was remarkably suppressed by the addition of 0.1% ascorbic acid.
（実施例９：香料の処方例）
以下にチモキノン又はブラッククミン種子溶媒抽出物（＊）を配合した消臭性香料処方例を示す。
＜ミント香料＞
Deodorant fragrance formulation examples containing thymoquinone or black cumin seed solvent extract (*) are shown below.
<Mint flavor>
＜バナナ香料＞
＜グレープ香料＞
＜ストロベリー香料＞
＜パイナップル香料＞
＜ローズ香料＞
＜ジャスミン香料＞
＜ラベンダー香料＞
＜グリーンアップル香料＞
以下に、本発明の消臭剤を配合した、水系芳香剤、消臭性チューインガム、消臭性キャンデー、練歯磨、マウスウォッシュの処方例を示す。 Hereinafter, formulation examples of an aqueous fragrance, a deodorant chewing gum, a deodorant candy, a toothpaste and a mouthwash containing the deodorant of the present invention are shown.
［水系芳香剤の処方例］
消臭剤又は消臭性香料（＊） １．５（質量％）
ソルフィット(3-Methyl-3-methoxy butanol) １．５
界面活性剤（＊＊） ２．２
水 残部
合 計 １００．０
＊：チモキノン又はブラッククミン由来の消臭剤、或いは消臭性香料
＊＊：溶解力向上の為に、以下のようなＨＬＢの異なるものをブレンド
約７０ｗｔ％の硬化ヒマシ油型非イオン性界面活性剤
約２０ｗｔ％の脂肪酸エステル型非イオン性界面活性剤
約１０ｗｔ％の硫酸塩型陰イオン性界面活性剤
[Prescription example of water-based fragrance]
Deodorant or deodorant fragrance (*) 1.5 (mass%)
Solfit (3-Methyl-3-methoxy butanol) 1.5
Surfactant (**) 2.2
Water balance
Total 100.0
*: Deodorant derived from thymoquinone or black cumin, or deodorant fragrance. **: Blended with the following different HLB to improve dissolving power. About 70 wt% hardened castor oil type nonionic surfactant. About 20 wt% fatty acid ester type nonionic surfactant About 10 wt% sulfate type anionic surfactant
［シュガーレスガムの処方例］
ガムベース ２５（質量％）
粉末マルチトール ４０
粉末キシリトール １９
粉末エリスリトール ８
マルチトール シロップ ６
スクラロース ０．０２
アセスルファムカリウム ０．０５
ＭＣＴ ０．２
消臭剤 １．０
香料 ０．７３
合 計 １００．０
[Prescription example of sugarless gum]
Gum base 25 (mass%)
Powdered xylitol 19
Maltitol syrup 6
Sucralose 0.02
Acesulfame potassium 0.05
MCT 0.2
Deodorant 1.0
Fragrance 0.73
Total 100.0
［シュガーレスキャンディーの処方例］
還元パラチノース ９７．９（質量％）
クエン酸 ０．７
アスパルテーム ０．３
色素 ０．１
消臭性香料（前記消臭性香料の処方参照） １．０
合 計 １００．０
[Prescription example of sugarless candy]
Reduced palatinose 97.9 (mass%)
Citric acid 0.7
Aspartame 0.3
Dye 0.1
Deodorant fragrance (see prescription of the above-mentioned deodorant fragrance) 1.0
Total 100.0
［練歯磨］
水酸化アルミニウム ４３（質量％）
グリセリン ２０
カルボキシメチルセルロースナトリウム ２
ソジウムラウリルサルフェート ２
香料 １
サッカリンナトリウム ０．１
消臭剤 ０．１５
ポリフェノールオキシダーゼ ０．０５
Ｎ−ラウロイルサルコシンナトリウム ０．２
水 残
合 計 １００．０
[Toothpaste]
Aluminum hydroxide 43 (mass%)
Sodium carboxymethylcellulose 2
Sodium lauryl sulfate 2
Saccharin sodium 0.1
Deodorant 0.15
Polyphenol oxidase 0.05
N-lauroyl sarcosine sodium 0.2
Water remaining
Total 100.0
［マウスウォッシュ］
エタノール ２０（質量％）
香料 １
サッカリンナトリウム ０．０５
消臭剤 ０．２
ｏ−アミノフェノールオキシダーゼ ０．１
モノフルオロリン酸ナトリウム ０．１
クロルヘキシジン塩酸塩 ０．０１
ラウリルジエタノールアマイド ０．３
水 残
合 計 １００．０
[Mouthwash]
Ethanol 20 (mass%)
Saccharin sodium 0.05
Deodorant 0.2
o-Aminophenol oxidase 0.1
Sodium monofluorophosphate 0.1
Chlorhexidine hydrochloride 0.01
Lauryl diethanolamide 0.3
Water remaining
Total 100.0
チモキノンおよびそれを含有するブラッククミン種子の粉砕物、精油または抽出物を配合することにより、幅広いpH（酸性〜中性〜弱塩基性）域において非常に高い消臭効果を示す消臭剤組成物や消臭性香料組成物を提供することが出来る。それら消臭剤組成物や消臭性香料組成物は、チューインガムやキャンディー、錠菓などの菓子類に配合できるほか、消臭芳香剤や義歯洗浄剤などの消臭にも使用できる。 Deodorant composition having a very high deodorizing effect in a wide pH range (acidic to neutral to weakly basic) by blending thymoquinone and pulverized, essential oil or extract of black cumin seeds containing the same And a deodorant fragrance composition can be provided. These deodorant compositions and deodorant fragrance compositions can be incorporated into confectionery such as chewing gum, candy, and tablet confectionery, and can also be used for deodorization such as deodorant fragrances and denture cleaning agents.
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| US9125841B2 (en) * | 2013-02-26 | 2015-09-08 | Johnson & Johnson Consumer Inc. | Oral care compositions |
| JP6405396B2 (en) * | 2016-02-01 | 2018-10-17 | アース製薬株式会社 | Oral composition |
| JP2017193489A (en) * | 2016-04-18 | 2017-10-26 | 稲畑香料株式会社 | Antibacterial agent for oral cavity and antimicrobial composition for oral cavity |
| JP2018029538A (en) * | 2016-08-25 | 2018-03-01 | 株式会社ロッテ | Deodorant |
| US11013673B2 (en) | 2016-11-03 | 2021-05-25 | Repairogen Corp. | Cosmetic compositions containing quinones and their topical use on skin and hair |
| CN110198701A (en) | 2016-11-03 | 2019-09-03 | 瑞派若基恩集团 | Cosmetic composition containing quinone and its topical use on skin and hair |
| JP7260246B2 (en) * | 2017-07-07 | 2023-04-18 | Ｄｍ三井製糖株式会社 | Deodorants |
| WO2019213494A1 (en) * | 2018-05-03 | 2019-11-07 | Repairogen Corp | Cosmetic compositions containing quinones and their topical use on skin and hair |
| JP6547050B1 (en) * | 2018-07-09 | 2019-07-17 | オリザ油化株式会社 | Body odor component reducing agent and body odor suppressing agent using the same |
| JP7297454B2 (en) * | 2019-01-31 | 2023-06-26 | オリザ油化株式会社 | Stress odor component reducer |
| EA201900596A1 (en) * | 2019-09-26 | 2021-03-31 | Зайнулла Фаритович ИБРАГИМОВ | THERAPEUTIC AND PREVENTIVE COMPOSITION FOR DENTISTRY |
| KR102696285B1 (en) * | 2023-07-06 | 2024-08-20 | 주식회사 휴트리 | Composition comprising black cumin seed oil as active ingredient for preventing or improving halitosis and sensitive teeth |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |