JPH0812511A - Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its use - Google Patents
Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its useInfo
- Publication number
- JPH0812511A JPH0812511A JP17040094A JP17040094A JPH0812511A JP H0812511 A JPH0812511 A JP H0812511A JP 17040094 A JP17040094 A JP 17040094A JP 17040094 A JP17040094 A JP 17040094A JP H0812511 A JPH0812511 A JP H0812511A
- Authority
- JP
- Japan
- Prior art keywords
- antibacterial material
- sustained release
- antibacterial
- sustained
- starch
- 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.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、安定的な徐放性に優れ
た徐放性抗菌材を安価に製造する方法、該方法により得
られる徐放性抗菌材、及びその用途に関し、本発明の徐
放性抗菌材は鮮度保持の目的で、食品に直接混ぜたり、
或いは食品等の包装物や容器へ混練、印刷により用いる
ことができる。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for inexpensively producing a sustained release antibacterial material having excellent stable sustained release properties, a sustained release antibacterial material obtained by the method, and its use. The sustained-release antibacterial material of is mixed directly with food for the purpose of keeping freshness,
Alternatively, it can be used by kneading it into a package such as food or a container and printing it.
【０００２】[0002]
【従来の技術】従来より抗菌作用をもつ揮発成分がいく
つか知られている。しかしながら、これらの成分は揮発
性であるため、抗菌効果を持続させるためには揮発量を
制御する必要があり、その目的で抗菌性成分を担体に担
持させ、徐放性とする方法がこれまでに幾つか開発され
ている。例えば、特開昭５２−１０２３号公報には、シ
リカゲルへの含浸、特公平３−１２８５７号公報にはゼ
オライトへの吸着、特公平５−２８５８９号公報にはサ
イクロデキストリンへの包接、特開平２−１１３８７６
号公報には繊維状結晶構造を持つ粘土鉱物へ含有させる
ことが、それぞれ開示されている。また、特開平４−７
９８６９号公報には食品保存用具として香辛料抽出物等
を担持可能な物質に担持させることが開示されており、
担持可能な物質は特に限定されないとし、その例として
紙、布、シリカ、デンプン、サイクロデキストリン、セ
ルロース、活性炭、ゼオライトが挙げられている。2. Description of the Related Art Some volatile components having an antibacterial action have been known. However, since these components are volatile, it is necessary to control the amount of volatilization in order to maintain the antibacterial effect. For that purpose, a method of supporting the antibacterial component on a carrier and providing sustained release has hitherto been known. Some have been developed in. For example, Japanese Patent Application Laid-Open No. 52-1023 discloses impregnation with silica gel, Japanese Patent Publication No. 3-12857 discloses adsorption to zeolite, and Japanese Patent Publication No. 5-28589 discloses inclusion with cyclodextrin. 2-113876
The gazettes disclose the inclusion of clay minerals having a fibrous crystal structure. In addition, JP-A-4-7
Japanese Patent No. 9869 discloses that a substance capable of carrying a spice extract or the like is supported as a food storage tool,
The substance that can be supported is not particularly limited, and examples thereof include paper, cloth, silica, starch, cyclodextrin, cellulose, activated carbon, and zeolite.
【０００３】しかしながら、食品の鮮度保持にこれらの
揮発性成分を利用する方法は、製造方法が複雑であるこ
と、抗菌成分の徐放性の制御がうまくできないこと、さ
らに他の鮮度保持方法に比較して価格が高いなどの欠点
があり、一般にはあまり使用されていない。現在、サイ
クロデキストリンにアリルイソチオシアン酸を包接させ
た鮮度保持用物質が市販されているが、サイクロデキス
トリンは比較的高価であることに加えて、包接力が強い
ためアリルイソチオシアン酸が徐放されにくく、多くの
アリルイソチオシアン酸を担持させなくてはいけない点
や、水分の多いところではアリルイソチオシアン酸の保
持力が著しく低下するなどの欠点がある。However, the method of utilizing these volatile components for maintaining the freshness of foods is complicated in the manufacturing method, cannot control the sustained release of the antibacterial component well, and is more difficult than other methods. It has drawbacks such as high price, and is not commonly used. Currently, a freshness-retaining substance in which cyclodextrin is clathrated with allyl isothiocyanic acid is commercially available.However, cyclodextrin is relatively expensive, and because of its strong clathrate, allyl isothiocyanate is difficult to be released slowly. However, there are drawbacks such as the fact that a large amount of allylisothiocyanic acid must be supported, and that the holding power of allylisothiocyanic acid is remarkably reduced in a place with a lot of water.
【０００４】また、鮮度保持のため一般によく知られて
いる方法としては、脱酸素剤の使用が挙げられる。しか
しながら、脱酸素剤は食品の酸化防止には大きな効果を
持つが、嫌気性微生物による鮮度低下が起こることや、
包装を密封にしなくてはいけない等の欠点がある。Further, as a generally well-known method for maintaining freshness, use of an oxygen absorber is mentioned. However, oxygen absorbers have a great effect on preventing food oxidation, but anaerobic microorganisms cause a decrease in freshness,
There are drawbacks such as having to make the package hermetic.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、このような
従来の欠点を解消し、密封でない条件下で使用すること
ができ、抗菌性成分を安価で効率的に、安価で安全な担
体に担持することができ、安定的な徐放性に優れた徐放
性抗菌材を製造する方法と、該方法により得られる徐放
性抗菌材、及びその用途を提供することを目的とするも
のである。DISCLOSURE OF THE INVENTION The present invention solves the above drawbacks of the prior art and can be used under non-sealed conditions to provide an antibacterial component at low cost, efficiently, at low cost and as a safe carrier. It is intended to provide a method for producing a sustained release antibacterial material which can be carried and is excellent in stable sustained release property, a sustained release antibacterial material obtained by the method, and its use. is there.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記課題
を解決するため鋭意研究を重ねた結果、抗菌性を有する
揮発性物質をデンプンに担持させた徐放性抗菌材であっ
て、真空乾燥によって揮発性抗菌物質を一部除去し、残
った揮発性抗菌物質が、特に真空乾燥させた後に、デン
プンの重量に対して０．１〜３％の割合で担持されたも
のが、優れた徐放性の抗菌作用を有することを見出し、
この知見に基づいて本発明を完成するに到った。Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that a sustained-release antibacterial material in which a volatile substance having an antibacterial property is carried on starch, It is excellent that the volatile antibacterial substance is partially removed by vacuum drying, and the remaining volatile antibacterial substance is carried at a rate of 0.1 to 3% relative to the weight of starch, especially after vacuum drying. Found to have a sustained release antibacterial effect,
The present invention has been completed based on this finding.
【０００７】すなわち、本発明は、揮発性抗菌物質を有
機溶媒に溶解した後、デンプンに混合し、その後、有機
溶媒を留去して得られる徐放性抗菌材から、真空乾燥法
により揮発性抗菌物質を一部除去することを特徴とする
徐放性抗菌材の製造方法を提供するものである。That is, according to the present invention, a volatile antibacterial substance is dissolved in an organic solvent, mixed with starch, and then the organic solvent is distilled off to obtain a volatile antibacterial substance by a vacuum drying method. Disclosed is a method for producing a sustained-release antibacterial material, which is characterized by partially removing an antibacterial substance.
【０００８】本発明の方法で用いる揮発性抗菌物質とし
ては特に制限はなく、例えば香辛料抽出物、植物抽出物
等が挙げられる。ここで香辛料抽出物を得るための香辛
料としては特に制限はなく、例えばカラシ、ワサビ、コ
ショウ、ニンニク、唐辛子、ナツメグ、ターメリック、
パプリカ、オニオン、シナモン、オールスパイス、パセ
リ、セロリ、シソ、ローズマリー等が挙げられる。ま
た、植物抽出物を得るための植物としては、香辛料が得
られる植物や、その他にヒバ、ヒノキ、ダイコン、アマ
クサ等が挙げられる。これらの中でも特にカラシを用い
ることが好ましい。The volatile antibacterial substance used in the method of the present invention is not particularly limited, and examples thereof include spice extracts and plant extracts. There is no particular limitation as a spice to obtain the spice extract here, for example, mustard, wasabi, pepper, garlic, pepper, nutmeg, turmeric,
Examples include paprika, onion, cinnamon, allspice, parsley, celery, perilla, rosemary and the like. Examples of plants for obtaining the plant extract include plants from which spices can be obtained, and other plants such as hiba, cypress, Japanese radish, and axa. Of these, it is particularly preferable to use mustard.
【０００９】本発明の方法で用いる揮発性抗菌物質とし
ては、これらの香辛料や植物より、如何なる方法で抽出
したものであってもよく、例えばヘキサン、トルエン、
アセトン、アルコール、ジエチルエーテル、酢酸エチル
等の有機溶媒などで抽出し、濃縮したものを挙げること
ができる。さらに、本発明の方法で用いる揮発性抗菌物
質としては、これらの抽出物を精製して得られる、香辛
料中の抗菌成分であるアリルイソチオシアン酸、シンナ
ミックアルデヒド、オイゲノール、アリルチオスルフィ
ナート、ヒノキチオール、トラクリン等を使用してもよ
いし、或いはこれらの物質を化学的に合成して得たもの
を用いてもよい。本発明の方法においては、これらの揮
発性抗菌物質の一種を単独で用いてもよいし、或いは二
種以上を混合して用いてもよい。The volatile antibacterial substances used in the method of the present invention may be those extracted from these spices and plants by any method, for example, hexane, toluene,
Examples include those extracted with an organic solvent such as acetone, alcohol, diethyl ether, and ethyl acetate, and concentrated. Further, as the volatile antibacterial substance used in the method of the present invention, obtained by purifying these extracts, allyl isothiocyanic acid, cinnamic aldehyde, eugenol, allylthiosulfinate, hinokitiol which are antibacterial components in spices. , Tracrine, etc., or those obtained by chemically synthesizing these substances may be used. In the method of the present invention, one kind of these volatile antibacterial substances may be used alone, or two or more kinds thereof may be mixed and used.
【００１０】本発明の方法では、まず上記した如き揮発
性抗菌物質を有機溶媒に溶解する。ここで揮発性抗菌物
質を溶解させる有機溶媒は、例えばエタノール、ヘキサ
ン、アセトン、酢酸エチルであり、通常はエタノールが
用いられる。本発明の方法においては特に食品用に使用
されている有機溶媒を使用するのが良い。また、揮発性
抗菌物質が水溶液で分解する場合には、有機溶媒として
は無水の有機溶媒にすることが必要である。本発明の方
法では、有機溶媒、例えばエタノールに上記した如き揮
発性抗菌物質を１〜５０重量％、好ましくは５〜２０重
量％溶解する。In the method of the present invention, the volatile antibacterial substance as described above is first dissolved in an organic solvent. Here, the organic solvent in which the volatile antibacterial substance is dissolved is, for example, ethanol, hexane, acetone or ethyl acetate, and usually ethanol is used. In the method of the present invention, it is particularly preferable to use the organic solvent used for food. When the volatile antibacterial substance decomposes in an aqueous solution, it is necessary to use an anhydrous organic solvent as the organic solvent. In the method of the present invention, the volatile antibacterial substance as described above is dissolved in an organic solvent such as ethanol in an amount of 1 to 50% by weight, preferably 5 to 20% by weight.
【００１１】次に、本発明の方法では、上記のようにし
て揮発性抗菌物質を有機溶媒に溶解した後、デンプンに
混合する。デンプンへの混合は、好ましくは滴下混合に
より行なう。本発明の方法で用いるデンプンとしては、
種類或いはデンプンの加工物や誘導体など如何なるもの
でもよいが、好ましくはアミロースを３０重量％以上、
特に５０重量％以上含有したものが良い。デンプン中の
アミロース量は、ヨウ素呈色比色法、ヨウ素親和力測定
法のような公知の方法で求めることができる。かかるデ
ンプンとしては、ハイアミロースコーンスターチ、天然
アミロース、酵素合成アミロース等がある。また、揮発
性抗菌物質の担持量を増加させるために、様々な方法で
デンプンに前処理を施したものであってもよい。前処理
法としては、デンプンの脱脂、スプレードライし、
多孔質の形状を取らせること、一旦、デンプンを熱水
に溶解、或いはオートクレーブして溶解又はアルカリや
ＤＭＳＯ（ジメチルスルホキシド）に溶解した後、プロ
パノール、ｎ−ブタノール、α−ナフトール等を添加
し、沈澱物を精製して得られるデンプンを用いる、等の
方法がある。Next, in the method of the present invention, the volatile antibacterial substance is dissolved in an organic solvent as described above and then mixed with starch. Mixing with starch is preferably done by drop mixing. As the starch used in the method of the present invention,
Any kind, such as a processed product or a derivative of starch, may be used, but preferably 30% by weight or more of amylose,
Particularly, it is preferable that the content is 50% by weight or more. The amount of amylose in starch can be determined by a known method such as an iodine colorimetric colorimetric method or an iodine affinity measuring method. Examples of such starch include high amylose corn starch, natural amylose, and enzymatically synthesized amylose. In addition, starch may be pretreated by various methods in order to increase the amount of the volatile antibacterial substance supported. As a pretreatment method, degreasing starch, spray drying,
Having a porous shape, once dissolving starch in hot water, or autoclaving to dissolve or dissolve in alkali or DMSO (dimethylsulfoxide), add propanol, n-butanol, α-naphthol, etc., There is a method such as using starch obtained by purifying the precipitate.
【００１２】なお、混合法は特に制限はないが、次のよ
うな操作を行なうのが好ましい。すなわち、有機溶媒溶
液がデンプン中に均一に混合できるようにデンプンを攪
拌させながら、有機溶媒溶液を滴下する。ここで用いら
れる有機溶媒溶液は、使用するデンプン重量の約７０％
以下、好ましくは３０〜６０％の重量のものをデンプン
に滴下する。The mixing method is not particularly limited, but it is preferable to carry out the following operation. That is, the organic solvent solution is added dropwise while stirring the starch so that the organic solvent solution can be uniformly mixed in the starch. The organic solvent solution used here is approximately 70% of the weight of starch used.
Below, preferably a weight of 30-60% is added dropwise to the starch.
【００１３】本発明の方法では、上記のようにしてデン
プンに混合した後、有機溶媒を留去する。具体的には、
ロータリーエバポレーターなどの減圧乾燥方法により、
エタノールなどのような有機溶媒を取り除く。有機溶媒
の留去は、減圧下、通常は１０〜２００ｍｍＨｇ（１，
３３３〜２６，６６４Ｐａ）の減圧下で行なわれる。こ
の後、必要に応じて再び有機溶媒溶液の滴下と減圧下で
の有機溶媒の留去を繰り返す。通常は、この操作を何回
か繰り返し行なう。繰り返す回数は特に限定されない
が、揮発性抗菌物質の担持重量が０．１〜３％程度にな
るように３〜４回繰り返すことが好ましい。In the method of the present invention, the organic solvent is distilled off after mixing with starch as described above. In particular,
By a reduced pressure drying method such as a rotary evaporator,
Remove organic solvents such as ethanol. The organic solvent is distilled off under reduced pressure, usually 10 to 200 mmHg (1,
333 to 26,664 Pa) under reduced pressure. Then, if necessary, the dropping of the organic solvent solution and the distillation of the organic solvent under reduced pressure are repeated again. Normally, this operation is repeated several times. The number of repetitions is not particularly limited, but it is preferable to repeat 3 to 4 times so that the supported weight of the volatile antibacterial substance is about 0.1 to 3%.
【００１４】以上のようにして、揮発性抗菌物質をデン
プンへ担持させ、揮発性抗菌物質をデンプンに担持させ
た徐放性抗菌材が得られる。本発明の方法では、上記の
如く有機溶媒を留去して得られる徐放性抗菌材から、真
空乾燥法により揮発性抗菌物質を一部除去し、目的とす
る徐放性抗菌材を製造する。すなわち、上記のようにし
て得られる、揮発性抗菌物質をデンプンに担持させた徐
放性抗菌材について、さらに真空乾燥によって揮発性抗
菌物質を一部除去し、残存する成分が目的とする徐放性
抗菌材である。As described above, a sustained-release antibacterial material in which a volatile antibacterial substance is supported on starch and the volatile antibacterial substance is supported on starch is obtained. In the method of the present invention, a volatile antibacterial substance is partially removed by a vacuum drying method from the sustained-release antibacterial material obtained by distilling off the organic solvent as described above to produce the desired sustained-release antibacterial material. . That is, with respect to the sustained-release antibacterial material obtained by supporting the volatile antibacterial substance on the starch obtained as described above, the volatile antibacterial substance is partially removed by vacuum drying, and the remaining components release the desired sustained release. It is an antibacterial material.
【００１５】ここで真空乾燥は、例えば「有機合成ハン
ドブック」（有機合成化学協会編、丸善株式会社、１９
９０年発行）の第１０１頁に記載されているような一般
的方法を使用することができる。The vacuum drying is performed, for example, in "Organic Synthesis Handbook" (edited by The Society of Organic Synthesis Chemistry, Maruzen Co., Ltd., 19).
General methods such as those described on page 101 of the 1990 issue can be used.
【００１６】真空乾燥の条件は特に制限はないが、真空
乾燥時の温度は揮発性抗菌物質が安定であることが必要
なため、室温〜６０℃の範囲の温度であることが望まし
い。また、弱く担持された揮発性抗菌物質を充分に除去
するため、真空容器内の圧力は、１Ｔｏｒｒ以下である
ことが望ましく、また乾燥時間は２時間以上であること
が望ましい。The conditions for vacuum drying are not particularly limited, but the temperature during vacuum drying is preferably in the range of room temperature to 60 ° C. because the volatile antibacterial substance must be stable. Further, in order to sufficiently remove the weakly supported volatile antibacterial substance, the pressure in the vacuum container is preferably 1 Torr or less, and the drying time is preferably 2 hours or more.
【００１７】このような真空乾燥によって、揮発性抗菌
物質が一部除去されたものが得られる。すなわち、この
ような真空乾燥によって、弱くデンプンに担持された揮
発性抗菌物質が除去され、強くデンプンに担持された揮
発性抗菌物質が残る。この残存成分、すなわち揮発性抗
菌物質が強くデンプンに担持された物質が、目的とする
徐放性抗菌材である。なお、真空乾燥の際には、同時に
有機溶媒も完全に除去される。ここで本発明の方法で得
られる徐放性抗菌材においては、デンプンに担持された
揮発性抗菌物質の重量が、デンプン重量に対して０．１
〜３％、特に０．１〜１％であるものが好ましい。ここ
でデンプンに担持された揮発性抗菌物質の重量が、デン
プン重量に対して０．１％未満であると抗菌作用が不充
分となる。一方、デンプンに担持された揮発性抗菌物質
の重量が、デンプン重量に対して３％をを超えると、揮
発性抗菌物質、例えばワサビの臭いが強くなり、食品に
使用するのが不適当となる。By such vacuum drying, a product obtained by partially removing the volatile antibacterial substance can be obtained. That is, by such vacuum drying, the volatile antibacterial substance weakly supported on the starch is removed, and the volatile antibacterial substance strongly supported on the starch remains. This residual component, that is, the substance in which the volatile antibacterial substance is strongly supported on the starch is the desired sustained-release antibacterial material. At the time of vacuum drying, the organic solvent is also completely removed. In the sustained-release antibacterial material obtained by the method of the present invention, the weight of the volatile antibacterial substance supported on starch is 0.1% based on the weight of starch.
It is preferably -3%, particularly 0.1-1%. If the weight of the volatile antibacterial substance carried on the starch is less than 0.1% with respect to the weight of the starch, the antibacterial action becomes insufficient. On the other hand, when the weight of the volatile antibacterial substance supported on starch exceeds 3% of the weight of starch, the odor of the volatile antibacterial substance, for example, wasabi becomes strong, making it unsuitable for use in foods. .
【００１８】上記した如き本発明の第１の方法によれ
ば、安定的な徐放性に優れた徐放性抗菌材が安価に得ら
れる。本発明は第２に、上記本発明の第１の方法により
得られた徐放性抗菌材を提供するものである。According to the first method of the present invention as described above, a sustained release antibacterial material excellent in stable sustained release can be obtained at a low cost. The present invention secondly provides a sustained-release antibacterial material obtained by the first method of the present invention.
【００１９】このような本発明の第２の徐放性抗菌材
は、揮発性抗菌物質をデンプンに担持させた徐放性抗菌
材であって、さらに真空乾燥によって揮発性抗菌物質を
一部除去し、残存する成分からなるものである。このよ
うな真空乾燥によって、弱くデンプンに担持された揮発
性抗菌物質が除去され、強くデンプンに担持された揮発
性抗菌物質が残るが、この残存成分、すなわち揮発性抗
菌物質が強くデンプンに担持された物質が、目的とする
本発明の第２の徐放性抗菌材である。The second sustained-release antibacterial material of the present invention is a sustained-release antibacterial material in which a volatile antibacterial substance is supported on starch, and the volatile antibacterial substance is partially removed by vacuum drying. However, it is composed of the remaining components. By such vacuum drying, the volatile antibacterial substance weakly supported on the starch is removed and the volatile antibacterial substance strongly supported on the starch remains, but the residual component, that is, the volatile antibacterial substance is strongly supported on the starch. The substance is the intended second sustained release antibacterial material of the present invention.
【００２０】本発明は、このようにして得られる徐放性
抗菌材からなる鮮度保持剤をも提供するものである。こ
の鮮度保持剤は、食品用、医薬品用或いは飼料用として
利用される。すなわち、以上の如き本発明の徐放性抗菌
材は、真空乾燥した後の形状である粉状或いは粒状のま
ま鮮度保持剤として利用することができるし、必要に応
じて適宜形状に成形して鮮度保持剤として用いてもよ
い。The present invention also provides a freshness-retaining agent comprising the sustained-release antibacterial material thus obtained. This freshness-retaining agent is used for food, medicine or feed. That is, the sustained-release antibacterial material of the present invention as described above can be used as a freshness-retaining agent in a powdery or granular form which is the shape after vacuum drying, and can be formed into an appropriate shape if necessary. You may use as a freshness maintenance agent.
【００２１】また、本発明の徐放性抗菌材は、合成樹脂
等への混練や印刷が可能であるため、鮮度保持の目的で
食品等の包装物や容器へ混練したり、或いは印刷したり
することができる。また、天然の香辛料抽出物から製造
したものは、安全性に何ら問題がないため、食品に直接
混ぜることにより、鮮度保持能の高い食品とすることも
可能である。Further, since the sustained-release antibacterial material of the present invention can be kneaded or printed on a synthetic resin or the like, it can be kneaded or printed on a package or container of food or the like for the purpose of keeping freshness. can do. In addition, since a product produced from a natural spice extract has no problem in safety, it can be made into a food having a high freshness-keeping ability by directly mixing it with food.
【００２２】以下、本発明の実施例を示すが、本発明は
これにより何ら制限されるものではない。Examples of the present invention will be shown below, but the present invention is not limited thereto.
実施例１ ハイアミロースコーンスターチ（アミロース含量＝５０
重量％）３ｇを、なす型フラスコに採り、攪拌させなが
ら、カラシ油をエタノールに２０重量％溶解したもの
を、１ｇ／分の割合で一滴ずつ滴下し、充分に混合し
た。次に、ロータリーエバポレーターにてエタノールを
留去した。さらに、カラシ油を同様に添加し、エタノー
ルを留去する操作を更に２回繰り返した。なお、カラシ
油の添加量は０．６ｇであった。その後、４０℃で２時
間真空乾燥（約０．１Ｔｏｒｒ）を行ない、揮発性抗菌
物質が一部除去された徐放性抗菌材を得た。得られた徐
放性抗菌材について、担持された成分をジクロロメタン
にて抽出し、ガスクロマト分析にて担持されていたアリ
ルイソチオシアン酸（カラシ油の主成分）の量を求め
た。結果を第１表に示す。Example 1 High amylose corn starch (amylose content = 50)
3% by weight) was placed in an eggplant-shaped flask, and 20% by weight of mustard oil dissolved in ethanol was added drop by drop at a rate of 1 g / min with thorough stirring to thoroughly mix. Next, ethanol was distilled off with a rotary evaporator. Furthermore, the operation of adding mustard oil in the same manner and distilling off ethanol was repeated twice more. The added amount of mustard oil was 0.6 g. Then, vacuum drying (about 0.1 Torr) was performed at 40 ° C. for 2 hours to obtain a sustained release antibacterial material from which volatile antibacterial substances were partially removed. With respect to the obtained sustained-release antibacterial material, the loaded components were extracted with dichloromethane, and the amount of allylisothiocyanic acid (the main component of mustard oil) loaded was determined by gas chromatography analysis. The results are shown in Table 1.
【００２３】なお、アリルイソチオシアン酸は以下の方
法に従って測定した。 〔アリルイソチオシアン酸の測定方法〕デンプンに辛子
油を担持させた徐放性抗菌材５０ｍｇをキャップ付き試
験管に採り、ジメチルスルフォキシド（ＤＭＳＯ）１ｍ
ｌによく分散し、水４ｍｌを添加した後、素早くジクロ
ロメタン５ｍｌを添加し、５分間タッチミキサー及び超
音波でよく攪拌した。その後、遠心分離にて水相とジク
ロロメタン相に分離し、ジクロロメタン相をガスクロマ
トグラフィー分析に供し、担持されたアリルイソチオシ
アン酸量を測定した。 ＊ガスクロマトグラフィー分析の条件 ・カラム：０．５２ｍｍ×１５ｍ、ＦＦＡＰ（ＧＬサイ
エンス社製） ・温度：注入口１６０℃、カラム１００℃ ・キャリア：Ｎ2 ２０ｍｌ／ｍｉｎ． ・検出：ＦＩＤ ・サンプル注入量：２μｌAllylisothiocyanic acid was measured according to the following method. [Measurement method of allyl isothiocyanic acid] 50 mg of a sustained-release antibacterial material in which pepper oil is carried on starch was placed in a test tube with a cap, and dimethyl sulfoxide (DMSO) 1 m was added.
It was well dispersed in 1 ml, and after adding 4 ml of water, 5 ml of dichloromethane was quickly added and well stirred for 5 minutes with a touch mixer and ultrasonic waves. Then, it was separated into an aqueous phase and a dichloromethane phase by centrifugation, and the dichloromethane phase was subjected to gas chromatography analysis to measure the amount of allylisothiocyanic acid supported. * Conditions for gas chromatography analysis-Column: 0.52 mm x 15 m, FFAP (GL Science Co.)-Temperature: inlet 160 ° C, column 100 ° C-Carrier: N 2 20 ml / min.・ Detection: FID ・ Sample injection volume: 2 μl
【００２４】比較例１ ハイアミロースコーンスターチ（アミロース含量＝５０
重量％）３ｇを、ジメチルスルフォキシド（ＤＭＳＯ）
１５ｍｌに溶解し、これにカラシ油０．６ｇを添加し、
１時間攪拌した。その後、水を１００ｍｌ添加し、生成
した沈澱を遠心分離にて回収した。得られたものは、水
で洗浄した後、４０℃で２時間真空乾燥した（約０．１
Ｔｏｒｒ）。得られた抗菌材について、担持された成分
を実施例１と同様にして担持されていたアリルイソチオ
シアン酸（カラシ油の主成分）の量を求めた。結果を第
１表に示す。Comparative Example 1 High amylose corn starch (amylose content = 50)
3% by weight of dimethyl sulfoxide (DMSO)
Dissolve in 15 ml, add 0.6 g of mustard oil to this,
Stir for 1 hour. Then, 100 ml of water was added, and the formed precipitate was collected by centrifugation. The obtained product was washed with water and then vacuum dried at 40 ° C. for 2 hours (about 0.1
Torr). With respect to the obtained antibacterial material, the amount of allylisothiocyanic acid (the main component of mustard oil) on which the loaded component was loaded was determined in the same manner as in Example 1. The results are shown in Table 1.
【００２５】[0025]
【表１】 [Table 1]
【００２６】第１表の結果からは、実施例１のものは、
比較例１のものに比べて、カラシ油がよく粉末状のハイ
アミロースコーンスターチに担持されることが分かる。
すなわち、粉末状のデンプンを溶解させて用いるより
も、そのままの粉末状状態で用いた方が担持量が多いこ
とが分かった。From the results shown in Table 1, the results of Example 1 are as follows.
It can be seen that mustard oil is better supported on powdered high-amylose cornstarch than that of Comparative Example 1.
That is, it was found that the amount of supported powder was larger when the powdery starch was used as it was, rather than when the powdery starch was dissolved and used.
【００２７】実施例２（鮮度保持能力試験） 実施例１で得られた徐放性抗菌材について、その鮮度保
持能力を調べた。比較のために、サイクロデキストリン
にカラシ油を担持させたものを、以下に示す方法で製造
し、両者の鮮度保持能力を比較した。すなわち、β−サ
イクロデキストリン１０ｇに、水１００ｍｌを加え加熱
し、沸騰させた後、５０℃まで冷却し、カラシ油１ｇを
添加し、よく攪拌しながら、常温まで冷却し、得られた
白色沈澱を、４０℃で２時間真空乾燥し、サイクロデキ
ストリンにカラシ油を担持させた抗菌材を得た。実施例
１で得られた徐放性抗菌材、すなわちハイアミロースコ
ーンスターチにカラシ油を担持させたもの０．０２ｇ、
０．１ｇ、０．５ｇ（第２表においてはそれぞれ順に試
験区１，２，３と表記した。）と、β−サイクロデキス
トリンにカラシ油を担持させたもの０．０２ｇ、０．１
ｇ、０．５ｇ（第２表においてはそれぞれ順に試験区
４，５，６と表記した。）とを、それぞれ蓋なしのシャ
ーレに入れ、餅５０ｇと共に容積約１リットルの容器中
に密閉し、３０℃で保存する試験（鮮度保持能力試験）
を行なった。結果を第２表に示す。なお、試験区７は抗
菌材を使用しなかった区である。Example 2 (Freshness Retaining Capacity Test) The sustained release antibacterial material obtained in Example 1 was examined for its freshness retaining capacity. For comparison, cyclodextrin carrying mustard oil was produced by the method described below, and the freshness-retaining ability of both was compared. That is, 100 ml of water was added to 10 g of β-cyclodextrin, heated and boiled, then cooled to 50 ° C., 1 g of mustard oil was added, and the mixture was cooled to room temperature with thorough stirring to obtain a white precipitate. After vacuum drying at 40 ° C. for 2 hours, an antibacterial material in which mustard oil was supported on cyclodextrin was obtained. 0.02 g of the sustained-release antibacterial material obtained in Example 1, that is, high amylose corn starch supporting mustard oil,
0.1 g, 0.5 g (indicated in Table 2 as test sections 1, 2, 3 respectively) and β-cyclodextrin with mustard oil 0.02 g, 0.1
g and 0.5 g (indicated in the Table 2 as test sections 4, 5 and 6 respectively) in a petri dish without a lid and sealed together with 50 g of rice cake in a container having a volume of about 1 liter, Test stored at 30 ℃ (freshness retention test)
Was performed. The results are shown in Table 2. The test section 7 is a section in which no antibacterial material was used.
【００２８】[0028]
【表２】 [Table 2]
【００２９】〔第２表の脚注〕 −：カビの発生なし ＋：カビの発生コロニー数１〜３個 ＋＋：カビの発生コロニー数４〜９個 ＋＋＋：カビの発生コロニー数１０個以上[Footnotes in Table 2]-: No mold development +: 1-3 mold colonies ++: Mold colonization 4-9 +++: Mold colonization 10 or more
【００３０】第２表の結果、ハイアミロースコーンスタ
ーチにカラシ油を担持させた本発明の徐放性抗菌材は、
少ない量であっても食品の鮮度保持能力が非常に高いこ
とが分かる。As shown in Table 2, the sustained release antibacterial material of the present invention in which mustard oil was carried on high amylose corn starch was
It can be seen that the food retainability of the food is very high even with a small amount.
【００３１】実施例３（保存試験） 酵素合成アミロース（中埜酢店社製、分子量７０００
０）にカラシ油を様々な濃度にて実施例１と同様の方法
で添加し、アリルイソチオシアン酸担持量の異なる徐放
性抗菌材（試験区１〜７）を得た。なお、アリルイソチ
オシアン酸担持量は、実施例１記載の測定方法により測
定した。製造した各徐放性抗菌材を０．２ｇずつ、蓋の
ないシャーレに入れ、容積約１リットルの容器に３色団
子１個と共に密封し、３０℃で保存試験を行なった。結
果を第３表に示す。Example 3 (preservation test) Enzymatically synthesized amylose (produced by Nakanosu Co., Ltd., molecular weight 7,000)
Mustard oil was added to 0) at various concentrations in the same manner as in Example 1 to obtain sustained-release antibacterial materials (test groups 1 to 7) having different amounts of allylisothiocyanic acid carried. The amount of allyl isothiocyanic acid supported was measured by the measuring method described in Example 1. 0.2 g of each of the manufactured sustained-release antibacterial materials was placed in a petri dish without a lid, and the container was sealed with one 3-color dumpling in a container having a volume of about 1 liter and a storage test was conducted at 30 ° C. The results are shown in Table 3.
【００３２】[0032]
【表３】 [Table 3]
【００３３】〔第３表の脚注〕 −：カビの発生なし ＋：カビの発生コロニー数１〜３個 ＋＋：カビの発生コロニー数４〜９個 ＋＋＋：カビの発生コロニー数１０個以上[Footnotes in Table 3]-: No mold development +: Number of mold colonies 1-3 ++: Number of mold colonies 4-9 +++: Number of mold colonies 10 or more
【００３４】第３表の結果、アリルイソチオシアン酸担
持量は０．１重量％以上あれば抗菌作用に優れているこ
とが分かる。From the results shown in Table 3, it can be seen that the antibacterial action is excellent when the supported amount of allyl isothiocyanic acid is 0.1% by weight or more.
【００３５】実施例４ 実施例３で製造した各徐放性抗菌材（試験区２〜７のも
の）を０．２ｇずつ、蓋のないシャーレに入れ、容積約
１リットルの容器に３色団子１個と共に密封し、２０℃
で２４時間保存した。その後、３色団子を１５人に食べ
てもらい、団子にわさび臭がするかどうかを調べた。結
果を第４表に示す。Example 4 0.2 g of each of the sustained-release antibacterial materials (test groups 2 to 7) produced in Example 3 was placed in a petri dish without a lid, and a three-color dumpling was placed in a container having a volume of about 1 liter. Seal with 1 piece, 20 ℃
And stored for 24 hours. After that, we asked 15 people to eat the three-colored dumplings, and examined whether the dumplings had a wasabi smell. The results are shown in Table 4.
【００３６】[0036]
【表４】 [Table 4]
【００３７】第４表の結果、アリルイソチオシアン酸を
３重量％以下の割合で担持した場合に食品に臭いがつか
ず、実用に優れていることが分かる。The results shown in Table 4 show that when allylisothiocyanic acid was carried in a proportion of 3% by weight or less, the food did not smell and was excellent in practical use.
【００３８】[0038]
【発明の効果】本発明の方法によれば、抗菌性成分を安
価で効率的に、安価で安全な担体に担持することがで
き、安定的な徐放性に優れた徐放性抗菌材が得られる。
このようにして得られる徐放性抗菌材からなる鮮度保持
剤は、食品用、医薬品用或いは飼料用として利用され
る。また、本発明の方法により得られる徐放性抗菌材
は、合成樹脂等への混練や印刷が可能であるため、鮮度
保持の目的で食品等の包装物や容器へ混練したり、或い
は印刷したりすることができる。また、天然の香辛料抽
出物から製造したものは、安全性に何ら問題がないた
め、食品に直接混ぜることにより、鮮度保持能の高い食
品とすることも可能である。INDUSTRIAL APPLICABILITY According to the method of the present invention, an antibacterial component capable of supporting an antibacterial component inexpensively and efficiently on an inexpensive and safe carrier, and having a stable and sustained release property is provided. can get.
The freshness-retaining agent composed of the sustained-release antibacterial material thus obtained is used for foods, pharmaceuticals, or feeds. Further, since the sustained-release antibacterial material obtained by the method of the present invention can be kneaded or printed on a synthetic resin or the like, it can be kneaded or printed on a package or container such as food for the purpose of keeping freshness. You can In addition, since a product produced from a natural spice extract has no problem in safety, it can be made into a food having a high freshness-keeping ability by directly mixing it with food.
Claims (5)
後、デンプンに混合し、その後、有機溶媒を留去して得
られる徐放性抗菌材から、真空乾燥法により揮発性抗菌
物質を一部除去することを特徴とする徐放性抗菌材の製
造方法。1. A sustained-release antibacterial material obtained by dissolving a volatile antibacterial substance in an organic solvent, mixing it with starch, and then distilling off the organic solvent to remove the volatile antibacterial substance by vacuum drying. A method for producing a sustained-release antibacterial material, which comprises removing part of the material.
ン酸である請求項１記載の徐放性抗菌材の製造方法。2. The method for producing a sustained release antibacterial material according to claim 1, wherein the volatile antibacterial substance is allyl isothiocyanic acid.
キサン及び酢酸エチルの中から選ばれた１種である請求
項１記載の徐放性抗菌材の製造方法。3. The method for producing a sustained-release antibacterial material according to claim 1, wherein the organic solvent is one selected from ethanol, acetone, hexane and ethyl acetate.
性抗菌材。4. A sustained-release antibacterial material obtained by the method according to claim 1.
度保持剤。5. A freshness-retaining agent comprising the sustained-release antibacterial material according to claim 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17040094A JPH0812511A (en) | 1994-06-30 | 1994-06-30 | Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17040094A JPH0812511A (en) | 1994-06-30 | 1994-06-30 | Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0812511A true JPH0812511A (en) | 1996-01-16 |
Family
ID=15904230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17040094A Pending JPH0812511A (en) | 1994-06-30 | 1994-06-30 | Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0812511A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033391A1 (en) * | 1997-01-30 | 1998-08-06 | Koch Enterprises, Inc. | Antimicrobial composition and method for food products |
| US6361812B1 (en) | 1999-11-18 | 2002-03-26 | The Procter & Gamble Co. | Products comprising an isothiocyanate preservative system and methods of their use |
| JP2007267639A (en) * | 2006-03-30 | 2007-10-18 | House Foods Corp | Antibacterial agent having volatile component of onion and/or lf (lacrimatory ingredient) as active ingredient, and method for utilizing the same |
-
1994
- 1994-06-30 JP JP17040094A patent/JPH0812511A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033391A1 (en) * | 1997-01-30 | 1998-08-06 | Koch Enterprises, Inc. | Antimicrobial composition and method for food products |
| US6361812B1 (en) | 1999-11-18 | 2002-03-26 | The Procter & Gamble Co. | Products comprising an isothiocyanate preservative system and methods of their use |
| US6558723B2 (en) | 1999-11-18 | 2003-05-06 | The Procter & Gamble Co. | Products comprising an isothiocyanate preservative system and methods of their use |
| US7105190B2 (en) | 1999-11-18 | 2006-09-12 | The Procter & Gamble Company | Products comprising an isothiocyanate preservative system and methods of their use |
| JP2007267639A (en) * | 2006-03-30 | 2007-10-18 | House Foods Corp | Antibacterial agent having volatile component of onion and/or lf (lacrimatory ingredient) as active ingredient, and method for utilizing the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6287603B1 (en) | Cyclodextrin flavor delivery systems | |
| Ho et al. | Release kinetics of ethylene gas from ethylene–α-cyclodextrin inclusion complexes | |
| Ahmad et al. | Preparation and characterization of antibacterial thiosemicarbazide chitosan as efficient Cu (II) adsorbent | |
| JPH0249747A (en) | Novel antioxidizing substance tetrahydrocurcumin, production and use thereof | |
| MX2007015871A (en) | Cyclodextrin inclusion complexes and methods of preparing same. | |
| Banchero et al. | Characterization of ketoprofen/methyl-β-cyclodextrin complexes prepared using supercritical carbon dioxide | |
| Li et al. | CO2 inclusion complexes of Granular V-type crystalline starch: Structure and release kinetics | |
| JPH0812511A (en) | Production of sustained release antibacterial material, sustained release antibacterial material produced thereby and its use | |
| Liang et al. | Synthesis of sulfhydryl modified bacterial cellulose gel membrane and its application in adsorption of patulin from apple juice | |
| Pauly et al. | Metathesis in water conducted by tailor-made encapsulated Grubbs’ catalyst | |
| Lindner et al. | Food flavouring with fJ-cyclodextrin-complexed flavour substances | |
| AU736431B2 (en) | Process for the stabilisation of acylglycerols comprising high amounts of (w) polyunsaturated fatty acids by means of gamma-clyclodextrin | |
| JP5590546B2 (en) | Organogel and method for producing organogel | |
| JP2004305116A (en) | Food or beverage and method for producing the same | |
| JP4902989B2 (en) | Process for producing alpha lipoic acid / cyclodextrin complex and product produced | |
| KR20140063373A (en) | Composition for odor removal comprising curcurbituril | |
| DE19808063A1 (en) | New cyclodextrin derivatives containing canal-shaped cavities | |
| JPH03249941A (en) | Deodorant composition | |
| JP3988890B1 (en) | Inclusion body and food bacteriostatic agent containing the same | |
| JPS6357669A (en) | Deodorizing film | |
| JP5182661B2 (en) | Solid oil and method for producing solid oil | |
| JP5572323B2 (en) | Low molecular weight polysaccharides that enhance the selectivity of host compounds in inclusion reactions, and methods of incorporating bitter and odorous components using the same | |
| JP2837531B2 (en) | Separation of steroid compounds | |
| Bennia et al. | Fullerene C60 for Tyrosol Retaining | |
| Nnamani et al. | EVALUATING THE FUNCTIONAL PROPERTIES OF MODIFIED MANIHOT ESCULENTA AND MANIHOT TRISTIS STARCHES FOR PHARMACEUTICAL APPLICATION |