JP3919916B2 - Allyl isothiocyanate for food - Google Patents
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- JP3919916B2 JP3919916B2 JP01050298A JP1050298A JP3919916B2 JP 3919916 B2 JP3919916 B2 JP 3919916B2 JP 01050298 A JP01050298 A JP 01050298A JP 1050298 A JP1050298 A JP 1050298A JP 3919916 B2 JP3919916 B2 JP 3919916B2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
Description
【０００１】
【発明の属する技術分野】
この発明は、食品用清浄剤や鮮度保持剤などに用いられる食品用イソチオシアン酸アリル製剤に関する。
【０００２】
【従来の技術】
イソチオシアン酸アリル（ＣＨ2 ＝ＣＨＣＨ2 Ｎ＝Ｃ＝Ｓ）は、黒カラシやワサビの種子から得られるカラシ油中に主成分として含まれ、食品の辛味成分として良く知られている。
【０００３】
また、イソチオシアン酸アリルは、水に溶け難く、油に溶けやすい物性であり、油溶の状態では揮散し難く、分解に対しても比較的よく安定している。因みに、イソチオシアン酸アリルの溶解度は、常温の水や７０％エタノールに対して０．２ｇ／１００ｍｌ、９０％エタノールやエーテル、ベンゼンに対しては７〜１０ｇ／１００ｍｌである。
【０００４】
ところで、食品素材は親水性のものが多いので、低濃度のイソチオシアン酸アリルの水溶液を調製し、食品素材への浸透分散性を高めるようにして用いることが好ましい。
【０００５】
また、イソチオシアン酸アリルは、カラシやワサビなどの食用植物に含まれている物質であって、香辛性の他に抗菌性も認められるため、これを食品に添加したり、微生物増殖抑制剤や生鮮食品の鮮度保持剤として利用する試みが、特開平６−３０３９５２号公報に開示されている。
【０００６】
上記公報によると、イソチオシアン酸アリル０．００１〜８０重量％と、ショ糖脂肪酸エステル（ＨＬＢ値３〜９）などの乳化剤と、プロピレングリコールなどの乳化助剤とを混合した乳化物を調製し、このものを水と任意の割合で混合できる水溶性製剤が開示されている。
【０００７】
【発明が解決しようとする課題】
しかし、上記した従来のイソチオシアン酸アリル製剤に関する技術では、イソチオシアン酸アリルと水とを任意の割合で混合した際に乳化させており、この乳化混合物は完全な水溶液ではないので、放置すると固液分離現象が起こるという問題点がある。
【０００８】
また、前記イソチオシアン酸アリルを含有する乳化混合物は、乳化状態で水中に均一に分散してもイソチオシアン酸アリルの刺激臭が若干残っており、この臭気は種々の食品に添加するときの制限要因となって好ましくないという問題点もあった。
【０００９】
また、従来のイソチオシアン酸アリル含有の水溶性製剤は、低濃度で用いるとイソチオシアン酸アリルが分解しやすいので、生鮮食品の鮮度を保持する効果が長時間維持できないという問題点もあった。
【００１０】
そこで、この発明の課題は、上記した問題点を解決して、食品用イソチオシアン酸アリル製剤を、完全に水溶化した製剤形態にして、その水溶液が固液分離せず充分に安定したものとすることである。
【００１１】
また、この発明の他の課題は、食品用イソチオシアン酸アリル製剤のイソチオシアン酸アリルの刺激臭を抑制し、しかも鮮度保持効果が長期間維持できるようにした食品用イソチオシアン酸アリル製剤を提供することである。
【００１２】
【課題を解決するための手段】
上記した課題を解決するため、本願の発明においては、ＨＬＢ値１１以上のショ糖脂肪酸エステルと、イソチオシアン酸アリルと、クエン酸ナトリウムとを水に溶解した水溶液からなる食品用イソチオシアン酸アリル製剤としたのである。
【００１３】
または、ＨＬＢ値１１以上のショ糖脂肪酸エステルと、イソチオシアン酸アリルと、クエン酸ナトリウムと、香料とを水に溶解した水溶液からなる食品用イソチオシアン酸アリル製剤としたのである。前記香料は、レモン精油またはスカッシュ精油を採用することが好ましい。
【００１４】
上記したように構成される食品用イソチオシアン酸アリル製剤は、イソチオシアン酸アリルとＨＬＢ値１１以上のショ糖脂肪酸エステルとクエン酸ナトリウムを必須成分として水に溶解したことにより、完全に水溶化した製剤形態となり、その水溶液は長時間放置されても固液分離せずに安定したものになる。
【００１５】
また、前記水溶液からなる食品用イソチオシアン酸アリル製剤は、従来の乳化混合物のようなイソチオシアン酸アリルの刺激臭がなく、しかも鮮度保持効果は長期間充分に保たれる食品用イソチオシアン酸アリル製剤になる。
【００１６】
特に、レモン精油またはスカッシュ精油その他の香料を添加した食品用イソチオシアン酸アリル製剤は、上述した作用を示すと共にイソチオシアン酸アリルの刺激臭が全くなく、好ましいものである。
【００１７】
【発明の実施の形態】
この発明に用いるイソチオシアン酸アリル（ＣＨ2 ＝ＣＨＣＨ2 Ｎ＝Ｃ＝Ｓ）は、黒カラシやワサビの種子などを原料とする天然のカラシ油中に主成分として含まれている物質であり、抽出によっても得られるが合成品であってもよい。これを合成する場合は、アリルベンジルスルフィドにシアン化臭素を作用させるか、ｐ−トルエンスルホン酸アリルエステルにチオシアン酸カリウムを作用させて製造できる。イソチオシアン酸アリルの市販品としては、純度９９％以上の化学合成品である試薬特級（和光純薬工業社製）が挙げられる。
【００１８】
この発明では、上記したイソチオシアン酸アリルの安定化を図るため、クエン酸ナトリウムを添加する。クエン酸ナトリウムは、エタノールに不溶であるが、常温（２５℃）水に７２ｇ／１００ｇの溶解性を示し、水溶液はややアルカリ性となる。
【００１９】
この発明に用いるＨＬＢ値１１以上のショ糖脂肪酸エステルは、多価アルコール型の非イオン界面活性剤であって、ショ糖の水酸基（ショ糖１分子中に８個存在する）に食用油脂由来の脂肪酸をエステル結合させたものである。このようなショ糖脂肪酸エステルのＨＬＢ（親水性−疎水性バランス）値の調整は、脂肪酸１〜８分子までのエステル結合度が異なるショ糖脂肪酸エステルの混合比率と、脂肪酸の種類を変えることによってなされる。具体例として、脂肪酸の種類と、ＨＬＢ値と、エステル組成（モノ・ジ・トリ・ポリエステル）の関係を下記の表１に示した。
【００２０】
【表１】
上述のように、この発明ではＨＬＢ値１１以上に調整したショ糖脂肪酸エステルを採用する。なぜなら、ＨＬＢ値１１未満のショ糖脂肪酸エステルでは、イソチオシアン酸アリルが完全に水溶化せず、その水溶液が長時間放置されると固液分離するからである。一方、ＨＬＢ値１１以上に調整したショ糖脂肪酸エステルおよびクエン酸ナトリウムを必須成分としてイソチオシアン酸アリルを水に溶解すると、完全に水溶化した製剤形態となり、食品用イソチオシアン酸アリル製剤は、従来の乳化混合物のようなイソチオシアン酸アリル刺激臭がなくなり、かつ固液分離の現象を起こさないものとなる。実用上好ましいショ糖脂肪酸エステルのＨＬＢ値は、表１中の１１〜１６である。
【００２２】
また、この発明の食品用イソチオシアン酸アリル製剤は、上記した必須成分以外にも、通常使用される乳化助剤、安定化剤や希釈成分を添加してもよく、特にイソチオシアン酸アリルのマスキング性を考慮して精油等の香料を添加することは好ましい。
【００２３】
なお、この発明でいう香料は、精油を含む食品用香料であり、調合香料や天然香料のいずれであってもよい。天然香料である精油は、テルペン系化合物を含む混合物である。このような精油は、揮発性で酸化されやすい物質であり、水蒸気蒸留、分留、揮発性有機溶媒などによる抽出、圧搾などにより採油される。精油の代表例としては、オレンジ油、レモン油、スカッシュ（squash: カボチャ）油、ハッカ油、ローズ油、ジャスミン油、ラベンダー油、シトロネラ油、針葉（マツ属植物の枝葉）油などが挙げられる。
【００２４】
この発明では、上記した精油のうち、レモン油またはスカッシュ油を使用して特に好ましいマスキング効果を得ている。
【００２５】
【実施例】
〔実施例１〜５〕
水６５０ｇに、ショ糖脂肪酸エステルを主成分とする食品用界面活性剤〔三菱化学株式会社製：リョートーシュガーエステル ＬＷＡ−１５７０、ショ糖ラウリン酸エステルを９５重量％含むショ糖脂肪酸エステル（ＨＬＢ値１５）４０％と、エタノール約４％と、水約５６％の混合物〕を５０ｇ、クエン酸ナトリウム１５０ｇ、プロピレングリコール１２０ｇ配合すると共に、イソチオシアン酸アリル（以下、ＡＩＴと略記する。）を５０ｇ（実施例１）、１００ｇ（実施例２）、２５０ｇ（実施例３）、５００ｇ（実施例４）、２００ｇ（実施例５）を配合し、常温（２３℃）でガラス棒で静かに攪拌混合して均一水溶液を得た。上記各水溶液の成分（重量％）は、表２に示した。
【００２６】
【表２】
〔実施例６〜１０〕
水６５０ｇに、ショ糖脂肪酸エステルを主成分とする食品用界面活性剤（三菱化学株式会社製：リョートーシュガーエステル Ｓ−１１７０Ｓ、結合脂肪酸の７０％がステアリン酸であり、ＨＬＢ値１１、強熱残留物含量を調整したもの）５０ｇ、クエン酸ナトリウム１５０ｇ、プロピレングリコール１２０ｇを配合すると共に、イソチオシアン酸アリル（以下、ＡＩＴと略記する。）を５０ｇ（実施例６）、１００ｇ（実施例７）、２５０ｇ（実施例８）、５００ｇ（実施例９）、２００ｇ（実施例１０）を配合し、常温（２３℃）でガラス棒で静かに攪拌混合して均一水溶液を得た。
【００２８】
〔比較例１〕
表２中に示した配合割合で、５０℃のＡＩＴに対して、ショ糖脂肪酸エステル（三菱化学株式会社製：リョートーシュガーエステル Ｓ−３７０：結合脂肪酸の７０％がステアリン酸であり、ＨＬＢ値３のショ糖脂肪酸エステル）と、同様に加温したプロピレングリコールとエタノールをガラス棒で静かに攪拌し、さらに水を添加混合して混合物からなる製剤を得た。
【００２９】
〔比較例２〕
比較例１と全く同じ配合割合で、５０℃のＡＩＴに対して、ショ糖脂肪酸エステル（三菱化学株式会社製：リョートーシュガーエステル Ｓ−９７０：結合脂肪酸の７０％がステアリン酸であり、ＨＬＢ値９のショ糖脂肪酸エステル）と、同様に加温したプロピレングリコールとエタノールをガラス棒で静かに攪拌し、さらに水を添加混合して混合物からなる製剤を得た。
【００３０】
▲１▼固液分離試験：
前記実施例１〜１０、比較例１および比較例２をビーカーに収容し、製造後３日間静置したものを観察した。
【００３１】
その結果、比較例１および比較例２のＡＩＴ製剤は、白濁し析出物が肉眼で確認されたが、実施例１〜１０のＡＩＴ製剤は、水溶性を保っており、白濁や析出現象は全く認められなかった。
【００３２】
▲２▼鮮度保持性試験：
実施例１〜５をそれぞれ２リットルの水に希釈溶解し、ＡＩＴ濃度が２５０ｐｐｍ、５００ｐｐｍ、１２５０ｐｐｍ、２５００ｐｐｍ、１０００ｐｐｍのテスト用ＡＩＴ水溶液ａ、ｂ、ｃ、ｄ、ｅを製造した。また、ブランクとしては、水道水を用いた。
【００３３】
３〜５ｍｍ幅に細切りしたゴボウ、キャベツまたはサラダ菜を２分間水道水で水洗した後、テスト用水溶液ａまたはｃに２分間または５分間浸漬し、その後、２分間水道水で水洗した。そして、これらの試験対象品を冷蔵庫（庫内温度５〜６℃、湿度２０％）中に５日間保存した後、色の変化を４段階に評価し、結果を○印（色の変化なし）、○〜△（僅かな変色がある）、△（部分的に変色がある）、×（全体に色の変化有り）として表３に示した。
【００３４】
【表３】
表３の結果からも明らかなように、テスト用ＡＩＴ水溶液ａ、ｃに２分または５分浸漬した試験対象品のゴボウ、キャベツまたはサラダ菜は、５日保存後に色の変化が殆どなく（○〜△）または全くなく（○）、鮮度保持性に優れていた。
【００３６】
しかし、水道水で水洗する処理のブランクは、ゴボウおよびキャベツに変色がみられ、鮮度低下が顕著であった。なお、表３の他に、水道水で水洗したゴボウの細切りを室内（室温）で１日保存したところ、変色（×印評価）したが、テスト用水溶液ｃに２分浸漬したゴボウの細切りは、同条件で殆ど変色がなかった（○〜△評価）。
【００３７】
以上の鮮度保持性試験に加えて、実施例６または実施例８をそれぞれ２リットルの水に希釈溶解し、ＡＩＴ濃度が２５０ｐｐｍまたは１２５０ｐｐｍのテスト用ＡＩＴ水溶液を製造し、これらについても前記した鮮度保持性試験を全く同様の条件で行なったが、その結果はテスト用水溶液ａまたはｃについて行なった試験結果と全く同様であり、鮮度保持性に優れていた。
【００３８】
次に、３〜５ｍｍ幅に細切りしたキャベツまたはゴボウを２分間水道水で水洗した後、テスト用ＡＩＴ水溶液ｄに２分間浸漬し、その後、２分間水道水で水洗した。そして、これらの試験対象品を冷蔵庫（庫内温度５〜６℃、湿度２０％）中に４日間保存した後、色の変化を４段階に評価し、結果を○印（色の変化なし）、○〜△、△、×（色の変化有り）として表４に示した。
【００３９】
【表４】
また、比較例１を２リットルの水に希釈溶解し、テスト用ＡＩＴ混合液ｆを製造し、実施例５（テスト用ＡＩＴ水溶液ｅ）および比較例１（テスト用ＡＩＴ混合液ｆ）の鮮度保持性を比較した。すなわち、前記同様に細切りしたゴボウを２分間水道水で水洗した後、テスト用ＡＩＴ水溶液ｅまたはテスト用ＡＩＴ混合液ｆに２分間浸漬し、その後、２分間水道水で水洗した。そして、ゴボウおよびキャベツを室温で１２〜４８時間保存した後、試験当初からの色の変化を４段階に評価し、結果を○印（色の変化なし）、○〜△、△、×（全体に色の変化有り）として表５に示した。
【００４１】
【表５】
表５の結果からも明らかなように、ＡＩＴの乳化混合液である比較例１（水溶液ｆ）は４８時間後に変色したが、ＡＩＴの水溶液である実施例５（水溶液ｅ）は、４８時間後に試験当初からの色の変化がなく、長期鮮度保持効果に優れていた。
【００４３】
また、実施例１０を２リットルの水に希釈溶解したＡＩＴ１０００ppm テスト用水溶液についても実施例５（水溶液ｅ）に対する上記試験と同じ長期鮮度保持試験を行なったが、この結果は実施例５の結果と同様であり、ＨＬＢ値１１のＡＩＴを使用した場合も長期鮮度保持効果は優れていた。
【００４４】
〔実施例１１、１２〕
実施例５のＡＩＴの水溶液を２リットルの水に希釈溶解してＡＩＴ濃度を１０００ｐｐｍにし、これにレモン精油（長谷川香料社製：レモン精油＃４９０）を３００ppm 、５００ppm または１０００ppm 添加して実施例１１のテスト用ＡＩＴ水溶液ｅ1 、ｅ2 、ｅ3 を調製し、スカッシュ精油（長谷川香料社製：スカッシュ精油＃４８９）を５００ppm または１０００ ppm添加して実施例１２のテスト用ＡＩＴ水溶液ｅ4 、ｅ5 を調製した。
【００４５】
▲３▼ＡＩＴ臭および香料臭の官能試験
前記のようにして得られたテスト用ＡＩＴ水溶液ｅ1 、ｅ2 、ｅ3 、ｅ4 およびｅ5 のＡＩＴ臭と、香料臭について、８人のパネラーによる官能試験を行なった。評価は、ＡＩＴ臭または香料臭の強さ（１．なし、２．やっと感知できる、３．楽に感知できる、４．やや強い臭い、５．強い臭い）の５段階とし、結果を表６に示した。
【００４６】
【表６】
表６の結果からも明らかなように、レモン精油またはスカッシュ精油を添加した実施例１１または実施例１２のテスト用ＡＩＴ水溶液は、ＡＩＴ臭がなく、香料臭のみが知覚された。なお、香料の臭気は１０００ｐｐｍでは刺激的で好ましくなく、３００〜５００ｐｐｍの中程度（２〜３）に調整することで充分であった。また、鮮度保持効果について前記同様にして、香料を添加したものと、添加しないものについても調べたが、両者に鮮度保持効果の差はなく全く同等であった。
【００４８】
また、実施例１０のＡＩＴ水溶液を２リットルの水に希釈溶解してＡＩＴ濃度１０００ppm とし、これにレモン精油（長谷川香料社製：レモン精油＃４９０）またはスカッシュ精油（長谷川香料社製：スカッシュ精油＃４８９）を５００ppm または１０００ppm となるように配合してテスト用ＡＩＴ水溶液を調製した。これらに対して前記のＡＩＴ臭および香料臭の官能試験を全く同じ条件で行なったところ、実施例１１または実施例１２の試験結果と全く同様に良好な結果が得られた。
【００４９】
これらのことから、レモン精油またはスカッシュ精油を混合した系において、水溶液中のショ糖脂肪酸エステルが、より選択的にＡＩＴを取り込んでその臭気を抑制していると考えられ、所期したＡＩＴ臭の抑制効果が認められた。
【００５０】
【発明の効果】
本願の発明は、以上説明したように、ＨＬＢ値１１以上のショ糖脂肪酸エステルおよびクエン酸ナトリウムを採用した食品用イソチオシアン酸アリル製剤としたので、必須成分が完全に水溶化され水溶液からなる製剤形態となり、固液分離せず安定した鮮度保持効果のある食品用イソチオシアン酸アリル製剤となる利点がある。
【００５１】
また、レモン精油またはスカッシュ精油を添加してなる食品用イソチオシアン酸アリル製剤は、上述したように安定した水溶液であるという利点と共に、イソチオシアン酸アリルの刺激臭が全くなく、鮮度保持効果も長時間維持できるという利点がある。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an allyl isothiocyanate preparation for foods that is used as a food detergent or a freshness-keeping agent.
[0002]
[Prior art]
Allyl isothiocyanate (CH 2 ═CHCH 2 N═C = S) is contained as a main component in mustard oil obtained from black mustard and wasabi seeds, and is well known as a pungent component of food.
[0003]
In addition, allyl isothiocyanate is a physical property that is hardly soluble in water and easily soluble in oil, hardly volatilizes in an oil-soluble state, and is relatively well stable against decomposition. Incidentally, the solubility of allyl isothiocyanate is 0.2 g / 100 ml for normal temperature water and 70% ethanol, and 7-10 g / 100 ml for 90% ethanol, ether and benzene.
[0004]
By the way, since many food materials are hydrophilic, it is preferable to prepare an aqueous solution of low-concentration allyl isothiocyanate so as to increase the osmotic dispersibility in the food material.
[0005]
In addition, allyl isothiocyanate is a substance contained in edible plants such as mustard and wasabi, and it has antibacterial properties in addition to spiciness, so it can be added to foods, microbial growth inhibitors and fresh foods. An attempt to use it as a freshness-preserving agent for foods is disclosed in JP-A-6-303952.
[0006]
According to the above publication, an emulsion obtained by mixing 0.001 to 80% by weight of allyl isothiocyanate, an emulsifier such as sucrose fatty acid ester (HLB value 3 to 9), and an emulsification aid such as propylene glycol, A water-soluble preparation that can be mixed with water at an arbitrary ratio is disclosed.
[0007]
[Problems to be solved by the invention]
However, in the above-described conventional allyl isothiocyanate preparation, allyl isothiocyanate and water are emulsified when mixed in an arbitrary ratio, and this emulsified mixture is not a complete aqueous solution. There is a problem that the phenomenon occurs.
[0008]
In addition, the emulsified mixture containing allyl isothiocyanate has a slight irritating odor of allyl isothiocyanate even when uniformly dispersed in water in an emulsified state, and this odor is a limiting factor when added to various foods. There was also a problem that it was not preferable.
[0009]
In addition, conventional allyl isothiocyanate-containing water-soluble preparations have a problem in that the effect of maintaining the freshness of fresh food cannot be maintained for a long time because allyl isothiocyanate is easily decomposed when used at a low concentration.
[0010]
Thus, the object of the present invention is to solve the above-mentioned problems, and to make the food allyl isothiocyanate preparation into a completely water-soluble preparation form, and the aqueous solution is sufficiently stable without solid-liquid separation. That is.
[0011]
Another object of the present invention is to provide an allyl isothiocyanate preparation for foods that suppresses the irritating odor of allyl isothiocyanate of the allyl isothiocyanate preparation for foods and that can maintain the freshness maintaining effect for a long period of time. is there.
[0012]
[Means for Solving the Problems]
In order to solve the above problems, in the invention of the present application, an allyl isothiocyanate preparation for foods comprising an aqueous solution in which a sucrose fatty acid ester having an HLB value of 11 or more, allyl isothiocyanate, and sodium citrate is dissolved in water. It is.
[0013]
Alternatively, an allyl isothiocyanate preparation for foods comprising an aqueous solution in which a sucrose fatty acid ester having an HLB value of 11 or more, allyl isothiocyanate, sodium citrate, and a fragrance are dissolved in water is prepared. Lemon essential oil or squash essential oil is preferably used as the fragrance.
[0014]
The allyl isothiocyanate preparation for food constituted as described above is a preparation form that is completely water-soluble by dissolving allyl isothiocyanate, a sucrose fatty acid ester having an HLB value of 11 or more, and sodium citrate as essential components. Thus, even if the aqueous solution is left for a long time, it is stable without being separated into solid and liquid.
[0015]
Further, the allyl isothiocyanate preparation for food comprising the above aqueous solution is an allyl isothiocyanate preparation for food that does not have the irritating odor of allyl isothiocyanate as in the conventional emulsified mixture, and that the effect of maintaining freshness is sufficiently maintained for a long period of time. .
[0016]
In particular, the allyl isothiocyanate preparation for foods to which lemon essential oil or squash essential oil and other fragrances are added is preferable because it exhibits the above-described action and has no irritating odor of allyl isothiocyanate.
[0017]
DETAILED DESCRIPTION OF THE INVENTION
Allyl isothiocyanate (CH 2 ═CHCH 2 N═C = S) used in the present invention is a substance contained as a main component in natural mustard oil made from black mustard, wasabi seeds, etc. However, it may be a synthetic product. When this is synthesized, it can be produced by reacting allyl benzyl sulfide with bromide bromide or by reacting p-toluenesulfonic acid allyl ester with potassium thiocyanate. As a commercial product of allyl isothiocyanate, a reagent special grade (manufactured by Wako Pure Chemical Industries, Ltd.) which is a chemically synthesized product having a purity of 99% or more can be mentioned.
[0018]
In the present invention, sodium citrate is added to stabilize the above-mentioned allyl isothiocyanate. Sodium citrate is insoluble in ethanol, but exhibits a solubility of 72 g / 100 g in normal temperature (25 ° C.) water, and the aqueous solution becomes slightly alkaline.
[0019]
The sucrose fatty acid ester having an HLB value of 11 or more used in the present invention is a polyhydric alcohol type nonionic surfactant, and is derived from edible fats and oils on the sucrose hydroxyl groups (eight exist in one sucrose molecule). Fatty acid ester-bonded. Adjustment of the HLB (hydrophilic-hydrophobic balance) value of such a sucrose fatty acid ester is achieved by changing the mixing ratio of sucrose fatty acid esters having different ester bond degrees of fatty acid 1 to 8 molecules and the type of fatty acid. Made. As a specific example, the relationship between the type of fatty acid, the HLB value, and the ester composition (mono-di-tri-polyester) is shown in Table 1 below.
[0020]
[Table 1]
As described above, sucrose fatty acid esters adjusted to an HLB value of 11 or higher are employed in the present invention. This is because, in sucrose fatty acid esters having an HLB value of less than 11, allyl isothiocyanate does not completely dissolve in water, and the aqueous solution is solid-liquid separated when left for a long time. On the other hand, when allyl isothiocyanate is dissolved in water using sucrose fatty acid ester adjusted to an HLB value of 11 or more and sodium citrate as essential components, it becomes a completely water-soluble preparation form. The allyl isothiocyanate irritating odor like the mixture is eliminated, and the phenomenon of solid-liquid separation does not occur. HLB values of practically preferred sucrose fatty acid esters are 11 to 16 in Table 1.
[0022]
In addition, the allyl isothiocyanate preparation for food of the present invention may be added with commonly used emulsification aids, stabilizers and dilution components in addition to the above-mentioned essential components. It is preferable to add a fragrance such as essential oil in consideration.
[0023]
In addition, the fragrance | flavor said by this invention is a fragrance | flavor for foodstuffs containing essential oil, and any of a mixing | blending fragrance | flavor and a natural fragrance | flavor may be sufficient. Essential oil, which is a natural fragrance, is a mixture containing a terpene compound. Such an essential oil is a volatile and easily oxidized substance, and is collected by steam distillation, fractional distillation, extraction with a volatile organic solvent, or compression. Representative examples of essential oils include orange oil, lemon oil, squash oil, mint oil, rose oil, jasmine oil, lavender oil, citronella oil, and coniferous (pine branch) oil. .
[0024]
In the present invention, among the above essential oils, lemon oil or squash oil is used to obtain a particularly preferable masking effect.
[0025]
【Example】
[Examples 1 to 5]
Surfactant for food mainly composed of sucrose fatty acid ester in 650 g of water [manufactured by Mitsubishi Chemical Co., Ltd .: Ryoto sugar ester LWA-1570, sucrose fatty acid ester containing 95% by weight of sucrose laurate (HLB value) 15) 50 g of a mixture of 40%, about 4% ethanol and about 56% water], 150 g of sodium citrate and 120 g of propylene glycol, and 50 g of allyl isothiocyanate (hereinafter abbreviated as AIT). Example 1), 100 g (Example 2), 250 g (Example 3), 500 g (Example 4), and 200 g (Example 5) were blended and gently stirred and mixed at room temperature (23 ° C.) with a glass rod. A homogeneous aqueous solution was obtained. The components (% by weight) of each aqueous solution are shown in Table 2.
[0026]
[Table 2]
[Examples 6 to 10]
Surfactant for food mainly composed of sucrose fatty acid ester in 650 g of water (Mitsubishi Chemical Co., Ltd .: Ryoto Sugar Ester S-1170S, 70% of bound fatty acid is stearic acid, HLB value of 11, high heat Residue content adjusted 50 g, sodium citrate 150 g, propylene glycol 120 g, and allyl isothiocyanate (hereinafter abbreviated as AIT) 50 g (Example 6), 100 g (Example 7), 250 g (Example 8), 500 g (Example 9), and 200 g (Example 10) were blended and gently stirred and mixed with a glass rod at room temperature (23 ° C.) to obtain a uniform aqueous solution.
[0028]
[Comparative Example 1]
In the blending ratio shown in Table 2, sucrose fatty acid ester (Mitsubishi Chemical Co., Ltd .: Ryoto Sugar Ester S-370: 70% of bound fatty acid is stearic acid, and HLB value with respect to AIT at 50 ° C. No. 3 sucrose fatty acid ester), similarly heated propylene glycol and ethanol were gently stirred with a glass rod, and water was further added and mixed to obtain a preparation comprising the mixture.
[0029]
[Comparative Example 2]
In the same blending ratio as in Comparative Example 1, sucrose fatty acid ester (Mitsubishi Chemical Co., Ltd .: Ryoto Sugar Ester S-970: 70% of bound fatty acid is stearic acid, and HLB value with respect to AIT at 50 ° C. No. 9 sucrose fatty acid ester), similarly heated propylene glycol and ethanol were gently stirred with a glass rod, and water was added and mixed to obtain a preparation comprising the mixture.
[0030]
(1) Solid-liquid separation test:
The said Examples 1-10, the comparative example 1 and the comparative example 2 were accommodated in the beaker, and what was left still for 3 days after manufacture was observed.
[0031]
As a result, the AIT preparations of Comparative Examples 1 and 2 were cloudy and precipitates were confirmed with the naked eye. However, the AIT preparations of Examples 1 to 10 maintained water solubility, and the cloudiness and precipitation phenomenon were completely absent. I was not able to admit.
[0032]
(2) Freshness retention test:
Each of Examples 1 to 5 was diluted and dissolved in 2 liters of water to prepare test AIT aqueous solutions a, b, c, d, and e having AIT concentrations of 250 ppm, 500 ppm, 1250 ppm, 2500 ppm, and 1000 ppm. Moreover, tap water was used as a blank.
[0033]
The burdock, cabbage, or salad vegetable cut into 3-5 mm widths was washed with tap water for 2 minutes, then immersed in the test aqueous solution a or c for 2 minutes or 5 minutes, and then washed with tap water for 2 minutes. And after these test object goods are preserve | saved for five days in a refrigerator (inside temperature 5-6 degreeC, humidity 20%), a color change is evaluated in four steps and a result is (circle) (no color change). The results are shown in Table 3 as ◯, Δ to Δ (there is slight discoloration), Δ (there is partial discoloration), and × (there is a color change throughout).
[0034]
[Table 3]
As is clear from the results in Table 3, the burdock, cabbage, or salad vegetable of the test object immersed in the test AIT aqueous solution a, c for 2 minutes or 5 minutes has almost no color change after storage for 5 days (○ to (Triangle | delta)) or nothing at all ((circle)), It was excellent in the freshness-keeping property.
[0036]
However, in the blank treated with tap water, discoloration was observed in burdock and cabbage, and the freshness was significantly reduced. In addition to Table 3, when the burdock slices washed with tap water were stored indoors (room temperature) for one day, they changed color (evaluated by x), but the burdock slices immersed in the test aqueous solution c for 2 minutes were Under the same conditions, there was almost no discoloration (◯ to Δ evaluation).
[0037]
In addition to the above-described freshness retention test, Example 6 or Example 8 was diluted and dissolved in 2 liters of water, respectively, to produce test AIT aqueous solutions having an AIT concentration of 250 ppm or 1250 ppm. The test was performed under exactly the same conditions, but the results were exactly the same as the test results for the aqueous test solution a or c, and the freshness retention was excellent.
[0038]
Next, cabbage or burdock chopped to a width of 3 to 5 mm was washed with tap water for 2 minutes, then immersed in the test AIT aqueous solution d for 2 minutes, and then washed with tap water for 2 minutes. And after these test object goods are preserve | saved for four days in a refrigerator (inside temperature 5-6 degreeC, humidity 20%), a color change is evaluated in four steps and a result is (circle) (no color change). , O to Δ, Δ, × (color change) are shown in Table 4.
[0039]
[Table 4]
Further, Comparative Example 1 was diluted and dissolved in 2 liters of water to produce a test AIT mixed solution f, and the freshness of Example 5 (test AIT aqueous solution e) and Comparative Example 1 (test AIT mixed solution f) was maintained. Sex was compared. That is, the burdock chopped in the same manner as described above was washed with tap water for 2 minutes, then immersed in the test AIT aqueous solution e or the test AIT mixed solution f for 2 minutes, and then washed with tap water for 2 minutes. Then, after storing burdock and cabbage at room temperature for 12 to 48 hours, the color change from the beginning of the test was evaluated in four stages, and the results were marked with ○ (no color change), ○ to Δ, Δ, × (whole Are shown in Table 5.
[0041]
[Table 5]
As is clear from the results of Table 5, Comparative Example 1 (aqueous solution f), which is an emulsified mixture of AIT, changed color after 48 hours, but Example 5 (aqueous solution e), which is an aqueous solution of AIT, changed after 48 hours. There was no color change from the beginning of the test, and the long-term freshness retention effect was excellent.
[0043]
Moreover, the same long-term freshness-keeping test as in the above test for Example 5 (aqueous solution e) was also conducted on the AIT 1000 ppm test aqueous solution obtained by diluting and dissolving Example 10 in 2 liters of water. The same was true, and the long-term freshness retaining effect was also excellent when AIT having an HLB value of 11 was used.
[0044]
[Examples 11 and 12]
The aqueous solution of AIT of Example 5 was diluted and dissolved in 2 liters of water to make the AIT concentration 1000 ppm, and 300 ppm, 500 ppm or 1000 ppm of lemon essential oil (manufactured by Hasegawa Fragrance Co., Ltd .: Lemon Essential Oil # 490) was added to this Example 11 of preparing a test AIT solution e 1, e 2, e 3 , squash essential oils: test AIT aqueous (T. Hasegawa Co. squash essential oil # 489) was added 500ppm or 1000 ppm in example 12 e 4, e 5 was prepared.
[0045]
(3) Sensory test of AIT odor and fragrance odor Eight panelists on the AIT odor and fragrance odor of the test AIT aqueous solutions e 1 , e 2 , e 3 , e 4 and e 5 obtained as described above. A sensory test was conducted. The evaluation was made in five levels: strength of AIT odor or fragrance odor (1. None, 2. Finally, 3. Easy to detect, 4. Slightly strong odor, 5. Strong odor). It was.
[0046]
[Table 6]
As is clear from the results in Table 6, the test AIT aqueous solution of Example 11 or Example 12 to which lemon essential oil or squash essential oil was added had no AIT odor and only perfume odor was perceived. It should be noted that the odor of the fragrance was not preferable because it was irritating at 1000 ppm, and it was sufficient to adjust it to a medium level (2 to 3) of 300 to 500 ppm. In addition, the freshness-keeping effect was examined in the same manner as described above for the case where a fragrance was added and for the case where no fragrance was added.
[0048]
In addition, the AIT aqueous solution of Example 10 was diluted and dissolved in 2 liters of water to give an AIT concentration of 1000 ppm, and this was added to lemon essential oil (manufactured by Hasegawa Fragrance Co., Ltd .: lemon essential oil # 490) or squash essential oil (manufactured by Hasegawa Fragrance Co., Ltd .: squash essential oil # 489) was blended to 500 ppm or 1000 ppm to prepare a test AIT aqueous solution. When the sensory test for the AIT odor and the fragrance odor was conducted under the same conditions, good results were obtained in exactly the same manner as the test results of Example 11 or Example 12.
[0049]
From these facts, it is considered that the sucrose fatty acid ester in the aqueous solution more selectively incorporates AIT and suppresses its odor in a system in which lemon essential oil or squash essential oil is mixed. An inhibitory effect was observed.
[0050]
【The invention's effect】
As described above, the invention of the present application is an allyl isothiocyanate preparation for food that employs a sucrose fatty acid ester having an HLB value of 11 or more and sodium citrate. Therefore, there is an advantage that the allyl isothiocyanate preparation for foods has a stable freshness maintaining effect without solid-liquid separation.
[0051]
In addition, the allyl isothiocyanate preparation for foods, to which lemon essential oil or squash essential oil is added, has the advantage that it is a stable aqueous solution as described above, has no irritating odor of allyl isothiocyanate, and maintains the freshness maintaining effect for a long time. There is an advantage that you can.
Claims (3)
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| JP01050298A JP3919916B2 (en) | 1998-01-22 | 1998-01-22 | Allyl isothiocyanate for food |
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|---|---|---|---|
| JP01050298A JP3919916B2 (en) | 1998-01-22 | 1998-01-22 | Allyl isothiocyanate for food |
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