JPH03224437A - Method for preserving food with cyclodextrin clathrate compound - Google Patents
Method for preserving food with cyclodextrin clathrate compoundInfo
- Publication number
- JPH03224437A JPH03224437A JP2021026A JP2102690A JPH03224437A JP H03224437 A JPH03224437 A JP H03224437A JP 2021026 A JP2021026 A JP 2021026A JP 2102690 A JP2102690 A JP 2102690A JP H03224437 A JPH03224437 A JP H03224437A
- Authority
- JP
- Japan
- Prior art keywords
- food
- cyclodextrin
- clathrate compound
- cyclodextrin clathrate
- comparative example
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 37
- 235000013305 food Nutrition 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 16
- -1 isothiocyanic acid ester Chemical class 0.000 claims abstract description 30
- 229930003658 monoterpene Natural products 0.000 claims abstract description 11
- 235000002577 monoterpenes Nutrition 0.000 claims abstract description 11
- 239000005003 food packaging material Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 8
- 238000009920 food preservation Methods 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 abstract description 12
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract description 7
- 239000001116 FEMA 4028 Substances 0.000 abstract description 3
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 abstract description 3
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 abstract description 3
- 235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 3
- 229960004853 betadex Drugs 0.000 abstract description 3
- 241000233866 Fungi Species 0.000 abstract description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 22
- 230000035784 germination Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000004806 packaging method and process Methods 0.000 description 7
- 238000004321 preservation Methods 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 6
- 235000007586 terpenes Nutrition 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001353 Dextrin Polymers 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000009088 Fragaria x ananassa Species 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- XMGQYMWWDOXHJM-SNVBAGLBSA-N (-)-α-limonene Chemical compound CC(=C)[C@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-SNVBAGLBSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000004794 expanded polystyrene Substances 0.000 description 2
- 235000012055 fruits and vegetables Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 235000021012 strawberries Nutrition 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 244000163122 Curcuma domestica Species 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 240000001462 Pleurotus ostreatus Species 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 229940011037 anethole Drugs 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Storage Of Fruits Or Vegetables (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分ＩＦ）
本発明は、流通、保存時の主群食品、加工食品の防黴、
制菌を目的としたサイクロデキストリン包接化合物を用
いた食品の保存方法に関するものである。Detailed Description of the Invention (Industrial Use IF)
This invention relates to a food preservation method using a cyclodextrin clathrate compound for bacteriostatic purposes.
（従来の技術）
従来、食品の保存方法として、例えば特開昭５８−６３
３４８号公報に記載される如く、イソチオｙアネー）類
を含む植物抽出精油類を吸着させたゼオライトを青果物
と共に包装容器内に同封するか、上記ゼオライトを含む
フィルム等により青果物を包装する保存方法がある。又
、特開昭５８−１０１６７０号公報に記載される如く、
植物抽出精油類等の揮散性物質を透過性の制御された゛
フィルムからなる袋、容器に包装した包装体を食品と共
に包装する保存方法がある。さらに、特開昭６１−１０
８３５９号公報に記載される如く、ヒノキチオ−μの包
接化合物を含有する包装材料により食品を包装する保存
方法がある。(Prior art) Conventionally, as a food preservation method, for example, Japanese Patent Application Laid-Open No. 58-63
As described in Japanese Patent Application No. 348, there is a preservation method in which zeolite adsorbed with plant-extracted essential oils containing isothioyanenes is enclosed together with fruits and vegetables in a packaging container, or fruits and vegetables are wrapped in a film containing the above-mentioned zeolite. be. Also, as described in Japanese Patent Application Laid-open No. 58-101670,
There is a preservation method in which volatile substances such as plant-extracted essential oils are packaged together with food in a bag or container made of a film with controlled permeability. Furthermore, JP-A-61-10
As described in Japanese Patent No. 8359, there is a preservation method of packaging foods with packaging materials containing a hinokichio-μ clathrate compound.
（発明が解決しようとする課題）
しかしながら、特開昭５８−６３３４８号公報に記載さ
れる保存方法の場合は、ゼオライトを担体とするために
濃度の影響を受け、抗菌作用する揮発ガスを食品に適し
た一定の揮発濃度にすることが困難な欠点がある。例え
ば、この場合、包装内の湿度が９０％以上になると水と
の置換反応で吸着していた植物性精油類を放出するが、
黴、細菌等の微生物の至適繁殖湿度は６５％颯上と低湿
度からであるために、湿度の低い包装系内での効果が期
待できない欠点がある。又、特開昭５８−１０１６７０
号公報に記載される保存方法の場合は、透過性の制御さ
れたフィルムによって揮散性物質を包装しなければなら
ず簡便性に欠けると共に、揮発ガスの揮発濃度等の制御
が必ずしも十分とはいえない欠点がある。さらに、特開
昭６１−１０８３５９号公報に記載される保存方法の場
合は、抗菌効果がある反面、食品に薬害等の悪影響を及
ぼすこともあり必ずしも実用に適さない欠点がある。(Problems to be Solved by the Invention) However, in the case of the preservation method described in JP-A No. 58-63348, since zeolite is used as a carrier, it is affected by the concentration, and volatile gases with antibacterial effects are released into the food. It has the disadvantage that it is difficult to maintain a suitable constant volatile concentration. For example, in this case, when the humidity inside the package reaches 90% or more, the adsorbed vegetable essential oils are released through a displacement reaction with water.
Since the optimal breeding humidity for microorganisms such as mold and bacteria is as low as 65%, there is a drawback that no effect can be expected in a packaging system with low humidity. Also, JP-A-58-101670
In the case of the preservation method described in the publication, volatile substances must be packaged with a film whose permeability is controlled, which is not convenient, and the control of the concentration of volatile gas, etc. is not necessarily sufficient. There are no drawbacks. Furthermore, while the preservation method described in JP-A No. 61-108359 has an antibacterial effect, it also has the disadvantage that it is not necessarily suitable for practical use because it may have an adverse effect on foods, such as phytotoxicity.
本発明は、かかる現状に鑑み、食品全搬に亘って悪影響
を及ぼさず、優れた食品安全性を有し、揮発ガスの揮発
濃度を長期間一定にして防黴、制菌を目的とした食品の
保存方法を提供するものである。In view of the current situation, the present invention has been developed to provide a food product that does not have any adverse effects throughout the transportation of the food product, has excellent food safety, and has the purpose of preventing mold and bacteria by keeping the volatile concentration of volatile gas constant for a long period of time. This provides a method for preserving.
（課題を解決するための手段）
本発明は天然植物からの抽出物であるイソチオシアン酸
エステル類、モノテルペン化合物類、これら両者の配合
物が食品の防黴、制菌に特に効果があることを発見し、
しかもこれらが天然植物からのものであることにより食
品安全性を有することに着目してなされたものである。(Means for Solving the Problems) The present invention shows that isothiocyanate esters, monoterpene compounds, which are extracts from natural plants, and a combination of both are particularly effective in preventing mold and bacteria in foods. discovered,
Furthermore, this product was developed with the focus on the fact that these products are food safe because they are made from natural plants.
又、一方では上記イソチオシアン酸エステル類、モノテ
ルペン化合物類、これら両者の配合物の効果を安定して
より有効に発揮させるために、食品安全性を有するサイ
クロデキストリンに着目してなされたものである。On the other hand, in order to stably and more effectively exhibit the effects of the above-mentioned isothiocyanate esters, monoterpene compounds, and a combination of the two, this work was made with a focus on food-safe cyclodextrin. .
すなわち、本発明は、食品の保存時に、イソチオシアン
酸エステル類又はモノテルペン化合物類又はこれらの配
合物の、サイクロデキストリン包接化合物を存在させる
ことにより食品に発生する黴、細菌の増殖を抑制するサ
イクロデキストリン包接化合物を用いた食品の保存方法
である。又、上記サイクロデキストリン包接化合物に芳
香を有する物質が含有される場合も含む食品の保存方法
である。又、上記サイクロデキストリン包接化合物が食
品包装材料に塗布又は混入されることにより食品の保存
を行う方法である。That is, the present invention provides a cyclodextrin clathrate compound of isothiocyanate esters, monoterpene compounds, or combinations thereof, which suppresses the growth of mold and bacteria that occur in foods during food storage. This is a food preservation method using dextrin clathrate compounds. The present invention also includes a method for preserving foods in which the cyclodextrin clathrate compound contains a substance having an aroma. Another method is to preserve food by coating or mixing the cyclodextrin clathrate compound into food packaging materials.
イソチオシアン酸エステル類、モノテルペン化合物類、
これらの配合物は食品安全性に加え、揮散せしめて食品
の包装内雰囲気にてその効果が十分発揮されることから
食品保存剤として使用するものである。イソチオシアン
酸エステル類としては、イソチオシアン酸メチｙ１イソ
チオＶアン酸エチ〜、イソチオＶアン酸ｎ−プ四ビμ、
インチオンアン酸イソプロピμ、イソチオシアン酸亀−
ブチ〜、イソチオＶアン酸イソブチμ、イソチオシアン
酸イソアミ〜、イソチオＶアン酸アリμ、イソチオシア
ン酸フェ二〜、イソチオシアン酸ベンジｙが好適に使用
される。又、モノテルペン化合物類としては、テルペン
炭化水素、テルペンアルコ−〜、テ〜ペンアμデヒド、
テルペンケトン、テμペンオキＶド、テルペン酸が好適
に使用される。Isothiocyanate esters, monoterpene compounds,
In addition to being food safe, these compounds are used as food preservatives because they volatilize and fully exhibit their effects in the atmosphere inside food packaging. Examples of isothiocyanate esters include methyl isothiocyanate y1 isothioV ethyl anoate ~, isothioV anoate n-p4biμ,
Isopropyl inthioanate μ, Turmeric isothiocyanate
Preferably used are buty-, isothiocyanic acid isobuty-, isothiocyanic acid isoamy-, isothiocyanic acid ali-, isothiocyanic acid phenyl-, and isothiocyanic acid benzyl-y. In addition, monoterpene compounds include terpene hydrocarbons, terpene alcohols, terpene μdehydes,
Terpene ketones, terpene oxides, and terpene acids are preferably used.
本発明では、上記イソチオシアン酸エステル類又はモノ
テルペン化合物類又はこれら両者の配合物をサイクロデ
キストリンに包接させてサイクロデキストリン包接化合
物として使用するものである。担体としてサイクロデキ
ストリンが好適な理由は、上記被包接物を化学的に安定
させ、揮発の徐放化、無臭化、酸化防止、光分解の防止
を計ることにより被包接物の延命効果を引出すことがで
きるためである。又、他の理由は、サイクロデキス）９
ンの種類によって被包接物の揮発速度、揮発期間を制御
でき、一定の揮発濃度を長期ｉ（：［り得ることができ
、揮発濃度の制御ができるためである。さらに他の理由
は、食品の包装内雰囲気温度に影響されることなく安定
した揮発濃度を得ることができるためである。その他の
理由としては、消臭効果により食品より発生する異奥を
除去でき、食品安全性を有し、工業的に均質であり、廃
棄時く焼却処理が可能であり、比重が小さＩＮと＆１つ
た理由がある。又、サイクロデキストリンとして、α−
サイクロデキストリン、β−サイクロデキストリン、Ｔ
−サイクロデキストリンのいずれが使用されてもよいが
、とくにβ−サイクロデキストリンが好適に使用される
。In the present invention, the above-mentioned isothiocyanate esters, monoterpene compounds, or a combination of both are included in cyclodextrin and used as a cyclodextrin inclusion compound. The reason why cyclodextrin is suitable as a carrier is that it chemically stabilizes the clathrate, slows down the release of volatilization, makes it odorless, prevents oxidation, and prevents photodecomposition, thereby prolonging the life of the clathrate. This is because it can be withdrawn. Also, another reason is cyclodextrin)9
This is because the volatilization rate and volatilization period of the clathrate can be controlled depending on the type of clathrate, and a constant volatilization concentration can be maintained over a long period of time, making it possible to control the volatilization concentration. This is because it is possible to obtain a stable volatile concentration without being affected by the ambient temperature inside the food packaging.Another reason is that the deodorizing effect removes foreign substances generated from food, which improves food safety. It is industrially homogeneous, can be incinerated at the time of disposal, and has a low specific gravity.In addition, as a cyclodextrin, α-
Cyclodextrin, β-cyclodextrin, T
- Although any cyclodextrin may be used, β-cyclodextrin is particularly preferably used.
上記サイクワデキストリン包接化合物には芳香を有する
物質が含有されていてもよい。イソチオシアン酸エステ
〜類、モノテルペン化合物類には総じて匂いがあり、食
品とこれらの匂いの相性が合わない場合に芳香を有する
物質により上記匂いを変えたり、消したりするものであ
る。又、上記芳香を有する物質としては、一般に食品に
添加される着香料が使用されればよく、例えばケイ皮酸
、バニリン、酢酸ゲラ二ｙ、ペッパーオイル、酢酸エチ
ル等が使用されればよい。The cyclodextrin clathrate compound may contain a substance having an aroma. Isothiocyanate esters and monoterpene compounds generally have odors, and when these odors are incompatible with food, the above-mentioned odors can be changed or eliminated using aromatic substances. Further, as the above-mentioned aromatic substance, a flavoring agent that is generally added to foods may be used, and for example, cinnamic acid, vanillin, geranium acetate, pepper oil, ethyl acetate, etc. may be used.
又、サイクワデキストリン包接化合物を用いて食品を保
存する方法としては、一般に食品包装材料にサイクロデ
キストリン包接化合物を塗布又は混入し、食品包装内に
被包接物を徐々に揮散させる方法が採用される。上記食
品包装材料としては、合成樹脂フィμム、トレイ、シー
ト、容器、テープ、装飾材等が使用されればよい。なあ
、必ずしも上記方法に限定させるものではなく、包装内
に食品と共にサイクロデキストリン包接化合物を存在さ
せる方法であればよい。In addition, as a method for preserving foods using cyclodextrin clathrate compounds, the general method is to apply or mix the cyclodextrin clathrate compounds into food packaging materials and gradually volatilize the cyclodextrin clathrates into the food packaging. Adopted. As the food packaging material, synthetic resin films, trays, sheets, containers, tapes, decorative materials, etc. may be used. Note that the method is not necessarily limited to the above method, and any method may be used as long as the cyclodextrin clathrate compound is present together with the food in the package.
（実施例） 以下、実施例により本発明の効果を示す。(Example) Hereinafter, the effects of the present invention will be shown by Examples.
実施例１
イソチオノアン酸アリ、ｖ２０部を包接したサイクロデ
キストリン３ｔをウレタン系樹脂バインダーを用いて天
然パルプＳ／−）表面に塗布して下敷Ｖ −） （６ａ
ｍ Ｘ １６ ｃｍ ）を作成した。この下敷シートを
マグ四の切り身の下に敷きトレイに入れ市販のラップに
より四封包装し、冷蔵庫に４８時間保存した。このとき
、保存開始時と保存４８時間後のマグｖ−！！ ＷＪの
低温菌数の測定と商品価値の評価を行い、その結果を第
１表に示した。Example 1 3 t of cyclodextrin containing 20 parts of isothionoanoic acid is applied to the surface of natural pulp S/-) using a urethane resin binder to form an underlay V-) (6a
m x 16 cm) was created. This underlay sheet was placed under the fillets of Mugshi, placed in a tray, wrapped in commercially available plastic wrap, and stored in a refrigerator for 48 hours. At this time, mug v-! at the start of storage and after 48 hours of storage! ! The number of psychrotrophic bacteria in WJ was measured and the commercial value was evaluated, and the results are shown in Table 1.
比較例として、ヒノキチオ−〃のサイクロデキストリン
包接化合物を天然パルプ５ｙ−）表面に塗布した下敷き
シートを使用した場合（比較例１）、未処理の天然バル
ブシートを下敷きシートとじて使用した場合（比較例２
）について上記と同様方法により試験し、その結果を第
１表に合わせて示した。As comparative examples, an underlay sheet in which Hinokichio's cyclodextrin clathrate compound was applied to the surface of natural pulp 5y- was used (Comparative Example 1), and an untreated natural valve sheet was used as an undersheet ( Comparative example 2
) were tested in the same manner as above, and the results are shown in Table 1.
第１表
実施例１では菌の繁殖が抑制されて詔り、マグロ表面に
張りが見られ食味も良好で商品価値が十分認められた。In Example 1 of Table 1, the growth of bacteria was suppressed and the tuna surface was firm, the taste was good, and the product value was sufficiently recognized.
比較例１では菌の繁殖が抑制されているものの、マグロ
表面が白濁しドリップが大量に流出し商品価値が認めら
れなかった。比較例２では菌が繁殖し、マグマ表面に粘
りが観察され異夷が発生し商品価値が認められなかった
。In Comparative Example 1, although the growth of bacteria was suppressed, the surface of the tuna became cloudy and a large amount of drips flowed out, and the commercial value was not recognized. In Comparative Example 2, bacteria were propagated, stickiness was observed on the surface of the magma, and abnormalities occurred, so that the commercial value was not recognized.
実施例２
イソチオＶアン酸アリ〜２０部を包接したサイクロデキ
ストリン５部を含有する５０２解厚のポリエチレンフィ
ルムで袋（３０ａ＋Ｘ６０部ｍ）ヲ作成した。これに生
切餅１００ ｙ、カステラ１００ｒをそれぞれ封入し、
ヒートｖ−，１％／により書封して、室温（１８℃）で
３０日間保存した。このとき保存開始して２０日後、３
０日後にそれぞれ黴の発生状況を観察し、その結果を第
２表に示した。Example 2 A bag (30a + 60 parts m) was made from a polyethylene film with a thickness of 502 mm and containing 5 parts of cyclodextrin containing ~20 parts of isothio V anoate. Enclose 100 y of fresh rice cake and 100 r of castella into this,
It was sealed with heat v-, 1%/ and stored at room temperature (18°C) for 30 days. At this time, 20 days after starting storage, 3
After 0 days, the appearance of mold was observed, and the results are shown in Table 2.
比較例として、ヒノキチオールのサイクロデキストリン
包接化合物を含有した５０％ｆｉ厚のポリエチレンフィ
μムによる袋を使用した場合（比較例３）、未処理の５
０μｍ厚のポリエチレンフィルムによる袋を使用した場
合（比較例４）について上記と同様方法により黴の発生
状況を観察し、その結果を第２表に合わせて示した。As a comparative example, when a bag made of 50% fi thick polyethylene film containing a cyclodextrin clathrate compound of hinokitiol was used (comparative example 3), untreated 5
When a bag made of a polyethylene film with a thickness of 0 μm was used (Comparative Example 4), the state of mold growth was observed in the same manner as above, and the results are shown in Table 2.
第２表
（黴の発生状況
＋・・・発生
±・・・やや発生
−・・・発生なし）
実施例３
イソチオシアン酸アリルＡ／２０ｉｌを包接したサイク
ロデキストリンを天然パルプＦ−）（２０ｃｗ＊ｘ３０
ｍ＋）中に５Ｆ散在させたｖ−トを作成した。Table 2 (Mold generation status +... Occurrence ±... Slight occurrence -... No occurrence) Example 3 Natural pulp F-) (20 cw* x30
A v-t was prepared in which 5F was interspersed in m+).
このシートを、箱詰めしたＧｅｏｔｒｌｃｋｕｍ ｃａ
ｎｄｌｄｕｍ接覆レモン果実ｉｏしｇの上部に載置し、
１０℃で２０日間保存した。保存開始２０日後の菌の発
芽率、発芽径、果実の表皮障害について調べ、その結果
を第３表に示した。This sheet was packaged in Geotrlkum ca.
Place the lemon fruit on top of the ndldum,
It was stored at 10°C for 20 days. The germination rate, germination diameter, and fruit skin damage were examined 20 days after the start of storage, and the results are shown in Table 3.
比較例として、上記シートとして従来使用されているジ
フェニル含浸紙を使用した場合（比較例５）、ヒノキチ
オ−〜のサイクロデキストリン包接化合物を天然パルプ
Ｖ−）Ｋ散在させたＶ−）を使用した場合（比較例６）
、未処理の天然パルプＶ−）を使用した場合（比較例？
）Ｋついて上記と同様にして試験し、その結果を第３表
に合わせて示した。As a comparative example, when the diphenyl-impregnated paper conventionally used as the sheet was used (Comparative Example 5), a natural pulp V-) in which a cyclodextrin clathrate compound of Hinokichio--V-) K was scattered was used. Case (Comparative Example 6)
, when untreated natural pulp V-) is used (comparative example?
) K was tested in the same manner as above, and the results are shown in Table 3.
（以下余白）
第
表
実施例３では菌（レモン水宵れ病）の発芽率、発芽径を
抑制でき、箱内下部の果実が潰れることなく良好な保存
状態が認められた。比較例５では藺の発芽率、発芽径も
実施例３より大きく、箱内下部の果実が潰れていた。比
較例６では菌の発！率、発芽径を抑制できる反面、果実
の表皮傷部分に襦変が発生する表皮障害が認められた。(Margins below) In Example 3 of Table 1, the germination rate and germination diameter of the fungus (Lemon Mizuyoi blight) could be suppressed, and the fruit in the lower part of the box was observed to be in a good state of preservation without being crushed. In Comparative Example 5, the germination rate and germination diameter of strawberries were also higher than in Example 3, and the fruit at the bottom of the box was crushed. In Comparative Example 6, bacteria were generated! Although it was possible to suppress the rate and diameter of germination, epidermal damage was observed in which puckering occurred at the damaged area of the fruit's epidermis.
比較例７では菌が発芽し発芽径が大会くなったため、箱
内下部の果実が潰れていた。In Comparative Example 7, the bacteria germinated and the germination diameter became large, so the fruit at the bottom of the box was crushed.
実施例４
アネトールとオイゲノー〜の混合物を２０部包接したサ
イクロデキストダン０．１ｒを、不織布と微孔性ポリエ
チレンフィルムの積層品からなる袋に充填したパックを
作＾゛した。このパックを市販のシメジ１００り詰めト
レイパック包装内のＩ！！部に設け、８℃で４８時間保
存した。保存開始４８時間後にＶメジの気中菌糸の発生
状況、商品価値を調べ、その結果を第４表に示した。Example 4 A pack was prepared by filling a bag made of a laminate of nonwoven fabric and microporous polyethylene film with 0.1 liter of cyclodextrin containing 20 parts of a mixture of anethole and eugenol. This pack is packed in a tray pack packed with 100 shimeji mushrooms. ! and stored at 8°C for 48 hours. 48 hours after the start of storage, the occurrence of aerial mycelium and commercial value of V-Meji were investigated, and the results are shown in Table 4.
比較例として、ヒノキチオ−μのサイクロデキス）Ｔｌ
ン包接化合物０． Ｉ Ｐを上記袋に充填したパックを
使用した場合（比較例８）、乾燥剤（生石灰）を上記袋
に充填したパックを使用した場合（比較例９）、市販の
トレイパック包装のままの場合（比較例１０）について
上記と同様にして気中菌糸の発生状況、商品価値を調べ
、その結果を簡４表く合わせて示した。As a comparative example, Hinokichio-μ cyclodextrin) Tl
Inclusion compound 0. When using a pack filled with IP in the above bag (Comparative Example 8), when using a pack containing desiccant (quicklime) in the above bag (Comparative Example 9), when using a commercially available tray pack packaging. Regarding (Comparative Example 10), the occurrence of aerial mycelium and commercial value were investigated in the same manner as above, and the results are shown in 4 simple tables.
第４表
（気中菌糸発生状況
＋・・・激しく発生
±・・・やや発生
−・・・発生なし）
実施例５
Ｌ−リモネンとイソチオシアン酸アリルを１０：１の割
合で配合したオイμを２０部包接したサイクロデキスト
リンα２ｆをウレタン系樹脂バインダーを用いて発泡ポ
リスチレンＶ−）（２０５１１１Ｘ １５ ｔｓ ）表
面に塗布し、塗布面に不織布を貼合わせたシート状物を
作成した。このシート状物を市販のイチゴのトレイパッ
ク包装内の底部に設け、１１１８℃）で４８時間保存し
た。保存開始４８時間後にイチゴに発生する黴の発生状
況、商品価値を調べ、その結果を第５表に示した。Table 4 (Status of aerial mycelium occurrence +... Severe occurrence ±... Slight occurrence -... No occurrence) Example 5 Oi μ containing L-limonene and allyl isothiocyanate in a ratio of 10:1. A sheet-like product was prepared by applying 20 parts of cyclodextrin α2f to the surface of expanded polystyrene V-) (205111X 15 ts) using a urethane resin binder, and pasting a nonwoven fabric on the applied surface. This sheet-like material was placed at the bottom of a commercially available strawberry tray pack package and stored at 1118° C. for 48 hours. 48 hours after the start of storage, the status of mold growth on the strawberries and the commercial value were investigated, and the results are shown in Table 5.
比較例として、ヒノキチオ−〃のサイクロデキストリン
包接化合物０．２ｒを発泡ポサスチレンＶ−）に塗布し
た場合（比較例１１）、発泡ポリスチレンＦ−）に何も
処理しない場合（比較例１２）について、上記と同様に
して−べた結果を第５表に合わせて示した。As comparative examples, when 0.2r of the cyclodextrin clathrate compound of Hinokichio-〃 was applied to expanded posastyrene V-) (Comparative Example 11), and when no treatment was applied to expanded polystyrene F-) (Comparative Example 12), The results were also shown in Table 5 in the same manner as above.
（以下余白）
第
５
表
（発明の効果）
繊上鮮述した如く、本発明サイクルデキストリン包接化
合物を用いた食品の保存方法は、食品の保存時に、イソ
チオシアン酸エステ〜類又はモノテルペン化合物類又は
これらの配合物の、サイクロデキス）リン包接化合物を
存在させるので、流通、保存時の食品の黴や細菌の発生
を抑制し、食品の腐敗を抑制でき、悪奥や変色の発生防
止ができ、食品の商品価値を低下させることがない。し
かも、サイクルデキストリンの被包接物の揮発ガスの濃
度を制御して長期に夏り安定して抗菌効果を発揮させる
ことができ、
食品安全性の面でも問
題が生じない。(The following is a blank space) Table 5 (Effects of the Invention) As mentioned above, the food preservation method using the cycle dextrin clathrate compound of the present invention is such that when preserving the food, isothiocyanate esters or monoterpene compounds are used. Or, because of the presence of cyclodextrin (cyclodextrin) clathrate compounds in these formulations, it is possible to suppress the generation of mold and bacteria in foods during distribution and storage, suppress food spoilage, and prevent the occurrence of spoilage and discoloration. , does not reduce the commercial value of food. Furthermore, by controlling the concentration of volatile gases of cycle dextrin clathrates, the antibacterial effect can be exhibited stably over a long period of time, and no problems arise in terms of food safety.
Claims (1)
モノテルペン化合物類又はこれらの配合物の、サイクロ
デキストリン包接化合物を存在させることを特徴とする
サイクロデキストリン包接化合物を用いた食品の保存方
法。 ２）サイクロデキストリン包接化合物に芳香を有する物
質が含有されている請求項１記載のサイクロデキストリ
ン包接化合物を用いた食品の保存方法。 ３）サイクロデキストリン包接化合物が食品包装材料に
塗布又は混入されている請求項１又は２記載のサイクロ
デキストリン包接化合物を用いた食品の保存方法。[Claims] 1) Use of a cyclodextrin clathrate compound characterized by the presence of a cyclodextrin clathrate compound of isothiocyanate esters, monoterpene compounds, or combinations thereof during food preservation. How to preserve food. 2) The method for preserving food using a cyclodextrin clathrate compound according to claim 1, wherein the cyclodextrin clathrate compound contains a substance having an aroma. 3) The method for preserving food using a cyclodextrin clathrate compound according to claim 1 or 2, wherein the cyclodextrin clathrate compound is coated or mixed into a food packaging material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2102690A JP2851104B2 (en) | 1990-01-30 | 1990-01-30 | Food preservation method using cyclodextrin inclusion compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2102690A JP2851104B2 (en) | 1990-01-30 | 1990-01-30 | Food preservation method using cyclodextrin inclusion compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03224437A true JPH03224437A (en) | 1991-10-03 |
| JP2851104B2 JP2851104B2 (en) | 1999-01-27 |
Family
ID=12043502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2102690A Expired - Fee Related JP2851104B2 (en) | 1990-01-30 | 1990-01-30 | Food preservation method using cyclodextrin inclusion compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2851104B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03112295U (en) * | 1990-02-27 | 1991-11-18 | ||
| JPH03112296U (en) * | 1990-02-27 | 1991-11-18 | ||
| JP5993526B1 (en) * | 2016-01-14 | 2016-09-14 | 株式会社Ｍｉｚｋａｎ Ｈｏｌｄｉｎｇｓ | Ponzu soy sauce seasoning |
-
1990
- 1990-01-30 JP JP2102690A patent/JP2851104B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03112295U (en) * | 1990-02-27 | 1991-11-18 | ||
| JPH03112296U (en) * | 1990-02-27 | 1991-11-18 | ||
| JP5993526B1 (en) * | 2016-01-14 | 2016-09-14 | 株式会社Ｍｉｚｋａｎ Ｈｏｌｄｉｎｇｓ | Ponzu soy sauce seasoning |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2851104B2 (en) | 1999-01-27 |
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