JP3683880B2 - Degradation preventive agent for flavor components - Google Patents

Description

【００４８】
表１より明らかなように、本発明品は、比較品に比べ、乳化粒子径が１μｍ以下となり、５５℃、２週間の保存後も分離等が認められず安定であった。
また、比較品１〜４の劣化防止剤は保存中に不均一になり、フェルラ酸由来と思われる針状結晶が認められたが、本発明品１〜４の劣化防止剤は分離、結晶等が認められず安定であった。
【００４９】
比較例５
多価アルコールとして、グリセリン（日本油脂（株）製）９５ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）３ｇを添加し、６５℃に加温溶解した。これをホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品９の劣化防止剤を得た。
【００５０】
比較例６
多価アルコールとして、グリセリン（日本油脂（株）製）９５ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇを添加し、６５℃に加温溶解した。抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品１０の劣化防止剤を得た。
【００５１】
比較例７
多価アルコールとして、グリセリン（日本油脂（株）製））９５ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）３ｇを添加し、６５℃に加温溶解した。これをホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品１１の劣化防止剤を得た。
【００５２】
比較例８
多価アルコールとして、グリセリン（日本油脂（株）製）９５ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇと酵素処理ルチン（キリヤ化学（株）製、酵素処理ルチン５０％）２ｇを添加し、６５℃に加温溶解した。抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）１ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品１２の劣化防止剤を得た。
【００５３】
比較例９
多価アルコールとして、グリセリン（日本油脂（株）製）９５ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとヤマモモ抽出物（三栄原エフエフアイ（株）製、ヤマモモ抽出物２０％）２ｇを添加し、６５℃に加温溶解した。抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）１ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品１３の劣化防止剤を得た。
【００５４】
実施例６
グラニュー糖１０％、クエン酸０．１５％およびクエン酸ナトリウム０．０２％、レモンエッセンス０．１％を水９０％に溶解してＢｘ．７．５、ｐＨ＝３のレモン飲料ベースを調製した。このレモン飲料ベースに実施例１〜３で得られた本発明品１〜３をそれぞれ０．１％添加し、９３℃達温にて加熱殺菌後、無色透明のペットボトルにホットパック充填し、冷却して本発明品９〜１１のレモン飲料を得た。また本発明品１〜３を０．１％添加の代わりに比較例５〜９にて得られた比較品９〜１３をそれぞれ０．１％添加した比較品１４〜１８のレモン飲料を得た。また、同様にして本発明品１を含まない比較品１９のレモン飲料を得た。
【００５５】
試験例２
実施例６で得られたそれぞれのレモン飲料を直射日光下に８時間（平均温度２３℃）放置した後、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。その結果を表２に示す。
【００５６】
【表２】

【００５７】
なお、表２中の評価の点数は、下記の基準で採点した各パネラーの平均点である。
（評価基準）
冷蔵保存試料と同等（変化なし） ：５点
冷蔵保存試料と比べわずかに変化している：４点
冷蔵保存試料と比べ少し変化している ：３点
冷蔵保存試料と比べかなり変化している ：２点
冷蔵保存試料と比べ著しく変化している ：１点
【００５８】
また、レモン等の柑橘類特有の香味成分であるシトラール量を高速液体クロマトグラフィー（ＨＰＬＣ）にて測定し、その残存率によって風味劣化の度合いとした。シトラールの残存率は高いほど、風味劣化が少ない事を示している。その結果を表２に示す。
【００５９】
なお、シトラール量の測定条件は次の通りである。
（測定条件）
装置：ＣＬＡＳＳ−ＬＣ１０（島津製作所製）
カラム：ＣＡＰＣＥＬＬ ＰＡＫ Ｃ１８ ＵＧ１２０（ＳＨＩＳＥＩＤＯ）
【００６０】
溶離液：６０％メタノール／水
流速：１ｍｌ／分
検出波長：ＵＶ ２４０ｎｍ
【００６１】
また、シトラール残存率は（％）は以下の式にしたがって計算した。
冷蔵保存試料のシトラール量：Ａ
光照射試料のシトラール量：Ｂ
Ｂ／Ａ×１００＝シトラール残存率（％）
【００６２】
表２より明らかなように、本発明品は比較品と比べ、光による風味劣化を効果的に防止した。また、本発明品は比較品と比べ、レモンの香味成分であるシトラールの残存率が高く、レモンのフレッシュな風味を効果的に維持した。
【００６３】
実施例７
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）５ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）５ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品１２のコーヒー乳化香料を得た。
【００６４】
実施例８
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）２ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）３ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）５ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品１３のコーヒー乳化香料を得た
【００６５】
比較例１０
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）９０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇを６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２０のコーヒー乳化香料を得た。
【００６６】
比較例１１
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）１０ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２１のコーヒー乳化香料を得た。
【００６７】
比較例１２
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）１０ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２２のコーヒー乳化香料を得た。
【００６８】
比較例１３
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）１０ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２３のコーヒー乳化香料を得た。
【００６９】
比較例１４
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇと生コーヒー豆抽出物（長谷川香料（株）製、クロロゲン酸含有３０％）１０ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２４のコーヒー乳化香料を得た。
【００７０】
比較例１５
多価アルコールとして、還元澱粉水飴（東和化成工業（株）製）８０ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）５ｇとブドウ種子エキス（キッコーマン（株）製、プロアントシアニジン３８％以上）１０ｇを添加し、６５℃に加温溶解した。コーヒー油性香料（アイ・エフ・エフ日本（株）製）５ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品２５のコーヒー乳化香料を得た。
【００７１】
試験例３
実施例７、８で得られた本発明品１２、１３および、比較例１０〜１５で得られた比較品２０〜２５のコーヒー乳化香料を３７℃で２ケ月間保存した後、５℃の冷蔵庫に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表３に示す。
【００７２】
【表３】

【００７３】
表１から明らかなように、本発明品は比較品に比べ、保存中における香味劣化を効果的に防止し、異味異臭の発生を著しく抑制した。
【００７４】
実施例９
コーヒー豆（Ｌ値：１８）２５０ｇに約１０重量倍の沸騰水を加えてＢｘ．２．５のコーヒー抽出液２５００ｇを得た。この抽出液を使用し、以下の＜処方１＞に示す割合にしたがってコーヒー飲料を調製した。このコーヒー飲料に実施例７、８にて得られた本発明品１２、１３のコーヒー乳化香料を０．１％添加した後、ホモジナイザー（１５０ｋｇ／ｃｍ^２）にて均質化し、ＵＨＴ殺菌（１４２℃、３０秒）後、３５０ｍｌ透明ペットボトルに充填し、本発明品１４、１５のペットボトル入りコーヒー飲料を得た。また本発明品７、８を０．１％添加の代わりに比較例１０〜１５にて得られた比較品２０〜２５をそれぞれ０．１％添加した比較品２６〜３１のペットボトル入りコーヒー飲料を得た。
【００７５】
＜処方１＞

【００７６】
試験例４
実施例９で得られたそれぞれのペットボトル入りコーヒー飲料を、５５℃にて２週間、１ヶ月保存した後、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表４に示す。
【００７７】
また、それぞれのペットボトル入りコーヒー飲料を、蛍光灯２００００ルクス照射下にて１ヶ月間保存し、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表４に示す。
【００７８】
【表４】

【００７９】
表４より明らかなように、本発明品の劣化防止剤を添加したコーヒー香料を使用することにより、熱、及び光による劣化を効果的に防止しており、発生する異味異臭を著しく抑制していることが明らかとなった。また、本発明品１５は５５℃、２ヶ月においても風味の変化が少なく、長期保存においても劣化防止効果を十分に発揮した。
【００８０】
実施例１０
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）３ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品１６のミルク乳化香料を得た。
【００８１】
実施例１１
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）２ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）１ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品１７のミルク乳化香料を得た。
【００８２】
比較例１６
多価アルコールとして、ソルビトール（東和化成工業（株）製）９７ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３２のミルク乳化香料を得た。
【００８３】
比較例１７
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）６ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３３のミルク乳化香料を得た。
【００８４】
比較例１８
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）６ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３４のミルク乳化香料を得た。
【００８５】
比較例１９
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）６ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３５のミルク乳化香料を得た。
【００８６】
比較例２０
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノオレート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとローズマリー抽出物（三菱化学（株）製、ローズマリー抽出物含有４５％）３ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３６のミルク乳化香料を得た。
【００８７】
比較例２１
多価アルコールとして、ソルビトール（東和化成工業（株）製）９１ｇにポリグリセリン脂肪酸エステルであるペンタグリセリンモノミリステート（太陽化学（株）製、ＨＬＢ値１４、ポリグリセリン組成中ペンタグリセリン含有４５％）２ｇとアスコルビン酸（田辺製薬（株）製）３ｇを添加し、６５℃に加温溶解した。ミルク油性香料（アイ・エフ・エフ日本（株）製）１ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品３７のミルク乳化香料を得た。
【００８８】
実施例１２
牛乳９５ｇ、脱脂粉乳５ｇを混合し、殺菌（９０℃、１５分）を行い、冷却（３０〜４５℃）した後、スターターを接種した。これをｐＨ４．３まで発酵させた後、冷却し、これをヨーグルトベースとした。一方、砂糖１６ｇ、ペクチン１．２ｇ、水８２．８ｇを混合後、殺菌（９５℃、５分）を行い、これをシロップ液とした。上記ヨーグルトベースとシロップ液を１：１にて混合したところに、実施例１０、１１にて得られた本発明品１６、１７のミルク乳化香料を０．１％添加し、無菌状態にてホモミキサー及びホモジナイザー（１５０ｋｇ／ｃｍ^２）にて均質化した。これを半透明プラスチック容器（１２０ｍｌ）に充填し、本発明品１８、１９のヨーグルト飲料とした。また、同様に本発明品１６、１７を０．１％添加の代わりに比較例１６〜２１にて得られた比較品３２〜３７をそれぞれ０．１％添加した比較品３８〜４３のヨーグルト飲料を得た。
【００８９】
試験例５
実施例１２で得られたそれぞれのヨーグルト飲料を、蛍光灯２０００ルクス照射下にて２週間保存（５℃）した後、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表５に示す。
【００９０】
【表５】

【００９１】
表５より明らかなように、比較品に比べ、本発明品の劣化防止剤を添加したミルク香料を使用することにより光による劣化を効果的に防止しており、発生する異味異臭を著しく抑制した。
【００９２】
実施例１３
以下の＜処方２＞に示す配合にて原料を混合し、加熱溶解（９０℃）後、ホモジナイザー（１５０ｋｇ／ｃｍ^２）にて均質化した。ここに実施例１０、１１で得られた本発明品１６、１７のミルク香料を０．１％添加した後、１００ｍｌ容のプラスチック容器に注入し、本発明品２０、２１の抹茶プリンを得た。また、本発明品１６、１７を０．１％添加の代わりに比較例１６〜２１にて得られた比較品３６〜３７をそれぞれ０．１％添加した比較品４４〜４９の抹茶プリンを得た。
【００９３】
＜処方２＞

【００９４】
試験例６
実施例１３にて得られたそれぞれの抹茶プリンを蛍光灯２０００ルクス照射下にて１０日間保存（１０℃）した後、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表６に示す。
【００９５】
【表６】

【００９６】
表６より明らかなように、比較品に比べ、本発明品の劣化防止剤を添加したミルク香料を使用することにより光による劣化を効果的に防止しており、発生する異味異臭を著しく抑制した。
【００９７】
実施例１４
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）３ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）３ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品２２のユズ乳化香料を得た。
【００９８】
実施例１５
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）２ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）２ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）２ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、本発明品２３のユズ乳化香料を得た。
【００９９】
比較例２２
多価アルコールとして、グリセリン（日本油脂（株）製）９４ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５０のユズ乳化香料を得た。
【０１００】
比較例２３
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇとフェルラ酸（フェルラ酸含量９８％以上 築野食品工業（株）製）６ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５１のユズ乳化香料を得た。
【０１０１】
比較例２４
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇを６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）６ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５２のユズ乳化香料を得た。
【０１０２】
比較例２５
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノパルミテート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇと緑茶抽出物（商品名：サンフェノンＢＧ、カテキン類含量７０％、太陽化学（株）製）６ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５３のユズ乳化香料を得た。
【０１０３】
比較例２６
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇと没食子酸４ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）２ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５４のユズ乳化香料を得た。
【０１０４】
比較例２７
多価アルコールとして、グリセリン（日本油脂（株）製）８８ｇに、ポリグリセリン脂肪酸エステルであるペンタグリセリンモノステアレート（太陽化学（株）製、ＨＬＢ値１３、ポリグリセリン組成中ペンタグリセリン含有４５％）３ｇとアスコルビン酸Ｎａ４ｇを添加し、６５℃に加温溶解した。ユズ精油（曽田香料（株）製）３ｇと抽出トコフェロール（タマ生化学（株）製、δ−トコフェロール含量８６％）２ｇを混合し、これを油相とし、これを多価アルコール中に添加し、ホモミキサー（特殊機化工業（株）製）にて回転数７０００ｒｐｍで乳化させて、比較品５５のユズ乳化香料を得た。
【０１０５】
実施例１６
市販のだしつゆ（塩濃度＝１０％）８０ｍｌと穀物酢（純米酢）１２０ｍｌを混合し、ノンオイルタイプの和風ドレッシングのベースとした。ここに実施例１４、１５にて得られた本発明品２２、２３を０．１％添加した後、１００ｍｌ容のプラスチックボトルに注入し、本発明品２４、２５の和風ドレッシングを得た。また本発明品２２、２３を０．１％添加の代わりに比較例２２〜２７にて得られた比較品５０〜５５をそれぞれ０．１％添加した比較品５６〜６１の和風ユズドレッシングを得た。
【０１０６】
試験例７
実施例１６で得られたそれぞれの和風ユズドレッシングを蛍光灯１５００ルクス照射下にて２ヶ月間保存（１０℃）した後、５℃の冷蔵庫（遮光）に保存しておいた試料を標準としてそれに対する香味劣化の程度を、よく訓練された１０名のパネラーにより官能評価を行った。評価は試験例２と同様の基準で採点した。その結果を表７に示す。
【０１０７】
また、実施例１６で得られたそれぞれの和風ユズドレッシングを３７℃、２ヶ月間保存した後、よく訓練されたパネラー１０名によって官能評価を行った。評価方法は試験例２と同様に行なった。その結果を表７に示す。
【０１０８】
【表７】

【０１０９】
表７より明らかなように、比較品に比べ、本発明品の劣化防止剤を添加したユズ香料を使用することにより光、及び熱による劣化を効果的に防止しており、発生する異味異臭を著しく抑制していることが明らかとなった。また、本発明品２４、２５は１５００ルクス照射、３７℃２ヶ月のいずれにおいても風味の変化が少なく、長期保存においても劣化防止効果を十分に発揮した。
【０１１０】
本発明の実施態様ならびに目的生成物を挙げれば以下のとおりである。
（１）総トコフェロール中、４５％以上がｄ−δ−トコフェロールである抽出トコフェロールとフェルラ酸を含有し、ポリグリセリン脂肪酸エステルを用い、水および／または多価アルコール中油型の乳化物とすることを特徴とする劣化防止剤。
（２）前記（１）記載の乳化物に茶抽出物を併用することを特徴とする劣化防止剤。
（３）ポリグリセリン脂肪酸エステルのポリグリセリン組成中、グリセリンの縮合度がトリ，テトラ，ペンタ，ヘキサ，ヘプタ，オクタ，ノナ，デカから選ばれる１種のポリグリセリンの含量が３５％以上である前記（１）または（２）記載の劣化防止剤。
（４）ポリグリセリン脂肪酸エステルのポリグリセリン組成中、グリセリンの縮合度がトリ，テトラ，ペンタ，ヘキサ，ヘプタ，オクタ，ノナ，デカから選ばれる１種のポリグリセリンの含量が４５％以上である前記（１）〜（３）いずれか記載の劣化防止剤。
（５）茶抽出物が（＋）−カテキン、（−）−エピカテキン、（＋）−ガロカテキン、（−）−エピガロカテキン、（−）−カテキンガレート、（−）−エピカテキンガレート、（−）−エピガロカテキンガレートおよび（−）−ガロカテキンガレートからなる群より選ばれる１種または２種以上である前記（２）〜（４）いずれか記載の劣化防止剤。
（６）茶抽出物が緑茶抽出物である前記（２）〜（５）いずれか記載の劣化防止剤。
（７）抽出トコフェロール中のｄ−δ―トコフェロール含量が８０％以上である（１）〜（６）いずれか記載の劣化防止剤。
（８）フェルラ酸の純度が８０％以上である前記（１）〜（７）いずれか記載の劣化防止剤。
（９）フェルラ酸の純度が９５％以上である前記（１）〜（７）いずれか記載の劣化防止剤。
（１０）多価アルコールがグリセリンである（１）〜（９）いずれか記載の劣化防止剤。
（１１）多価アルコールがプロピレングリコールである（１）〜（９）いずれか記載の劣化防止剤。
（１２）多価アルコールが糖である（１）〜（９）いずれか記載の劣化防止剤。
（１３）多価アルコールが糖の水溶液である（１）〜（９）いずれか記載の劣化防止剤。
（１４）多価アルコールが糖アルコールである（１）〜（９）いずれか記載の劣化防止剤。
（１５）多価アルコールが糖アルコールの水溶液である（１）〜（９）いずれか記載の劣化防止剤。
（１６）多価アルコールがソルビトールである（１）〜（９）いずれか記載の劣化防止剤。
（１７）水および／または多価アルコール中油型の乳化物を水に分散させた時の粒子径が１．０μｍ以下である前記（１）〜（１６）いずれか記載の劣化防止剤。
（１８）水および／または多価アルコール中油型の乳化物を水に分散させた時の粒子径が０．６μｍ以下である前記（１）〜（１６）いずれか記載の劣化防止剤。
（１９）水および／または多価アルコール中油型の乳化物を水に分散させた時の粒子径が０．４μｍ以下である前記（１）〜（１６）いずれか記載の劣化防止剤。
（２０）水および／または多価アルコール中油型の乳化物を水に分散させた時の粒子径が０．２μｍ以下である前記（１）〜（１６）のいずれか記載の劣化防止剤。
（２１）水および／または多価アルコール中油型の乳化物を水に分散させた時の粒子径が０．１μｍ以下である前記（１）〜（１６）のいずれか記載の劣化防止剤。
（２２）前記（１）〜（２１）いずれか記載の劣化防止剤を含有する香料製剤。
（２３）前記（１）〜（２１）いずれか記載の劣化防止剤を含有する食品香料製剤。
（２４）前記（１）〜（２１）いずれか記載の劣化防止剤を含有する飲食品。
（２５）前記（１）〜（２１）いずれか記載の劣化防止剤を含有する香料製剤を含有する飲食品。
【０１１１】
【発明の効果】
本発明により、食品香料または飲食品に総トコフェロール中にｄ−δ−トコフェロールを４５％以上含有する抽出トコフェロールとフェルラ酸、さらにポリグリセリン脂肪酸エステルを用い微細かつ安定な、水および／または多価アルコール中油型の乳化物とすることによって、食品香料及び飲食品中の香味成分の劣化を防止することができ、また香味の劣化によって生じる異味異臭の発現を抑制し、香味の良好な飲食品を提供することができる。また、該乳化物にさらに茶抽出物を併用することによって目的とする効果が顕著に向上し、長期間の保存に対しても効果を持続することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a flavor component deterioration preventing agent (hereinafter abbreviated as a deterioration preventing agent) and a food flavor or food or drink containing the same. Specifically, in the total tocopherol, 45% by weight (hereinafter referred to as%) or more contains extracted tocopherol and ferulic acid, which is d-δ-tocopherol, and water and / or oil in polyhydric alcohol using polyglycerin fatty acid ester. The present invention relates to a deterioration preventing agent characterized in that it is a fine emulsion, and further relates to a deterioration preventing agent characterized in that the emulsion and tea extract are used in combination, and further a food flavoring agent provided with the deterioration preventing agent. Or, it relates to a food and drink having a good flavor.
[0002]
[Prior art]
In foods and drinks, flavor is a very important component and characterizes food, but it is a component that tends to deteriorate over time due to various factors during processing, distribution and storage. Degradation factors of flavor components vary, and at each stage of processing processes such as sterilization and the distribution, storage, and sales of food and drinks, they deteriorate significantly due to the influence of heat, oxygen, light, etc. Cause a decline. Furthermore, the chances of food and beverages being exposed to light have increased dramatically due to the recent spread of beverages in transparent or translucent plastic containers, foods in transparent bags, and sales in convenience store showcases, and the deterioration of flavor due to light The situation is likely to occur. In particular, it is known that citrus beverages, foods and drinks containing milk components, and the like are severely deteriorated in flavor under light irradiation. In addition, hot sales of foods and drinks in plastic containers, such as hot sales of containers with high oxygen permeability, are likely to be affected by heat and oxygen.
[0003]
It is known that fragrances for food and drink such as citrus flavors, coffee flavors, and milk flavors are affected by heat, oxygen, light, etc., and deteriorate over time, such as changes in flavor components and the generation of off-flavors. It has been. Natural fragrances and those similar to natural fragrances are particularly prone to this.
In order to solve this, various studies have been made such as sterilization in a short time, distribution at a low temperature, development of a functional container having UV absorption ability, addition of an antioxidant, and the like. Among them, synthetic antioxidants such as dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and propyl gallate have long been used as antioxidants. However, in recent years, it has been pointed out that these antioxidants have an unfavorable effect on human health, and the use of these antioxidants has been avoided. Accordingly, there are demands for natural-derived antioxidants and flavor deterioration inhibitors that replace these synthetic antioxidants, and various proposals have been made. For example, methods for preventing flavor deterioration of foods and beverages using chlorogenic acid, caffeic acid and the like extracted from green coffee beans (for example, see Patent Document 1 and Patent Document 2), combined use of ferulic acid and proanthocyanidins (for example, Patent Document) 2), and a method for preventing deterioration of a water-soluble fragrance composition using enzyme-treated rutin (see, for example, Patent Document 3). However, many of these deterioration inhibitors need to be used in a large amount in order to obtain an effect, and there is a drawback that the flavor of the deterioration inhibitor itself adversely affects the flavor of food and drink. In particular, ferulic acid has an unfavorable flavor such as fermented odor, rice bran odor and astringency derived from its origin, and its use for food is greatly limited. In addition, the crystallinity of ferulic acid is also an obstacle to use. Ferulic acid added to beverages and foods forms crystals during storage, and the commercial value of the added product is lost, so it is effective as an antioxidant but has not yet been put into practical use. is there.
[0004]
In addition, dl-α-tocopherol and extracted tocopherol are widely used for the prevention of oxidation of oily foods. There are many reports on the prevention of oxidation of tocopherols using POV and COV indicators, but there are few reports on the prevention of deterioration of flavor components in combination with water-soluble antioxidants. The fact is that the effect of preventing the deterioration of components is weak. In general, oil-based antioxidants such as tocopherol need to be water or polyhydric alcohol-in-oil emulsions when used in water-based foods, but emulsification is unstable in water or polyhydric alcohols, and fragrances Under the influence of ingredients, flavonoids, catechins, etc., there is a problem that tocopherol is separated and the appearance of food is impaired. As described above, various methods have been taken as flavor deterioration inhibitors, but there are still few that have sufficient effects and practicality, and further development is required.
[0005]
[Patent Document 1]
JP-A-4-27374 (page 3-5)
[Patent Document 2]
JP-A-6-38723 (page 2-7)
[Patent Document 3]
JP-A-4-36395 (page 2-5)
[0006]
[Problems to be solved by the invention]
The present invention has been made in view of the above-described prior art, and suppresses deterioration of flavor during storage of food and drink, and flavors for food and drink, and further impairs the appearance and flavor of the food and drink. The purpose is to develop an anti-degradation agent excellent in dispersibility and emulsion stability in foods.
[0007]
[Means for Solving the Problems]
As a result of intensive studies to solve the above-mentioned problems, the inventors of the present invention contain an extracted tocopherol and ferulic acid containing 45% or more of d-δ-tocopherol in the total tocopherol, and further using a polyglycerol fatty acid ester. Deterioration preventing agent obtained by making stable water and / or oil-in-polyhydric alcohol emulsion is excellent in flavor, and heat, oxygen, light, etc. during processing or storage of foods and drinks, food fragrances, etc. It has been found that the change in flavor components due to the effect of odor, the occurrence of off-flavor and odor, etc. can be remarkably suppressed. Moreover, it discovered that the said deterioration prevention effect could further be heightened by using a tea extract together with this emulsion.
[0008]
The present invention has been completed based on these findings. The total tocopherol contains an extracted tocopherol containing 45% or more of d-δ-tocopherol and ferulic acid, and further using a polyglycerin fatty acid ester. Furthermore, the present invention provides an anti-degradation agent in foods and drinks that is an oil-in-water emulsion of water and / or polyhydric alcohol.
[0009]
In addition, the present invention further includes the use of a tea extract in combination with a fine and stable emulsion containing an extracted tocopherol and ferulic acid, and a polyglycerin fatty acid ester. It is intended to provide an anti-degradation agent that can suppress the expression of and maintain the effect even for long-term storage.
[0010]
Furthermore, this invention relates to the food fragrance | flavor containing the said deterioration inhibitor, or food-drinks. The present invention is described in detail below.
[0011]
DETAILED DESCRIPTION OF THE INVENTION
The deterioration preventing agent of the present invention refers to a preparation that can remarkably suppress changes in flavor components due to the influence of heat, oxygen, light, etc. during the processing or storage of foods and beverages and food fragrances, the occurrence of off-flavors, etc. It is not an antioxidant.
[0012]
In general, the extracted tocopherol refers to a product extracted and purified from oils and fats derived from plant materials. Although the kind of plant raw material extracted is not specifically limited, Soybean oil, wheat germ oil, palm oil etc. are mentioned as a representative example. Among these, extracted tocopherol derived from soybean oil contains more d-δ-tocopherol than other plants, and is also suitable from the industrial supply aspect.
[0013]
In addition, d-α, β, γ, and δ are mixed in the extracted tocopherol, but the component ratio is also affected by the type, variety, and production area of the plant. Moreover, the product which raised the component ratio of the specific homologous composition industrially by processes, such as molecular distillation, is also marketed.
The extracted tocopherol in the present invention is not particularly limited, and in addition to these general ones, those obtained by derivatizing general extracted tocopherols are also included.
[0014]
In addition, the method for purifying the extracted tocopherol in the present invention is not particularly limited, but the total tocopherol must contain 45% or more of d-δ-tocopherol, preferably 70% or more of d-δ-tocopherol. More preferably, it contains 85% or more of d-δ-tocopherol. Of the homologues of extracted tocopherol, d-δ-tocopherol is particularly effective in suppressing flavor deterioration, and the higher the ratio of d-δ-tocopherol in total tocopherol, the more effective. If the d-δ-tocopherol content is less than 45% in the total tocopherols, not only the effect of suppressing flavor deterioration is low, but also the occurrence of off-flavours and odors that may be caused by the deterioration of d-α-tocopherol, etc. occurs. .
The d-δ-tocopherol in the present invention includes not only d-δ-tocopherol but also derivatives thereof. For example, an acetic ester of d-δ-tocopherol obtained by esterifying d-δ-tocopherol with acetic acid is more preferable because stability can be improved and a continuous flavor deterioration suppressing effect can be expected.
[0015]
In order to measure the content of each homologue of the extracted tocopherol, it is possible to use the measurement method (high performance liquid chromatograph method) described in the Food Additives Official Document.
[0016]
The content of the extracted tocopherol in the deterioration preventing agent of the present invention is not particularly limited, but is preferably 0.001% to 50%. More preferably, 0.01% to 10% is desirable. If it is less than 0.001%, the expected effect is hardly obtained, and if it is added at a concentration exceeding 50%, it becomes difficult to obtain a stable emulsification system when an oil-in-water type emulsion is used.
[0017]
Ferulic acid used in the present invention is not particularly limited, and is widely distributed in various organs of most plants. As raw materials, clove, corn, coffee beans, barley, wheat, rice, Rubber resin etc. are mentioned. Ferulic acid is cultivated bacteria (Pseudomonas) in a clove oil obtained by steam distillation from buds and leaves of asteraceae, or eugenol obtained by purification from clove oil, and the culture solution is separated, After the refined product or rice bran oil was distributed with water-containing ethanol and hexane under mild alkalinity at room temperature, γ-oryzanol obtained in the water-containing ethanol fraction was hydrolyzed with sulfuric acid when heated under pressure. And those obtained by purification. Ferulic acid may be a purified product or an unpurified product, but since the antioxidant capacity depends on its purity, it is desirable to use a purified product having a ferulic acid content of 80% or more, preferably 95% or more.
[0018]
The addition amount of ferulic acid in the deterioration preventing agent of the present invention is not particularly limited, but is preferably 0.005% to 10%. More preferably, 0.01% to 5% is desirable. If it is less than 0.005%, the expected effect is difficult to obtain, and if the concentration exceeds 10%, ferulic acid is crystallized and affects the stability of the deterioration preventing agent.
[0019]
The raw material of the tea extract used in the present invention is not particularly limited, and botany is green tea, which is a non-fermented tea produced from leaves of Camellia sinensis, which is a plant of the camellia family, and oolong tea, which is a semi-fermented tea. And black tea that is fermented tea. Among them, it is preferable to use green tea which is preferably unfermented tea. Examples of the extract include tea leaves or pulverized tea leaves extracted with water, hot water, alcohols such as glycerin and ethanol, or ethyl acetate-soluble fractions and acetone-soluble fractions. More preferably, (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin, (−) catechin gallate, (−)-epicatechin gallate, (−) -1 type, or 2 or more types of catechin chosen from the group which consists of -gallocatechin gallate and (-)-epigallocatechin gallate is mentioned. The content of the catechins is not particularly limited, but is preferably 60% or more, more preferably 70% or more in the tea extract to be used.
[0020]
The total content of these catechins can be measured by a colorimetric method using iron tartrate, but in order to measure the composition of each catechin in detail, it is preferable to measure by high performance liquid chromatography. .
[0021]
The content of the tea extract in the deterioration preventing agent of the present invention is not particularly limited, but is preferably 0.005% to 20%. More preferably, 0.1% to 10% is desirable. If it is less than 0.005%, it is difficult to obtain the expected effect. If the concentration exceeds 20%, the flavor of the deterioration inhibitor affects the flavor of the food.
[0022]
The polyglycerin fatty acid ester used in the present invention is not particularly limited, but the composition distribution of the polyglycerin used as the raw material has a great influence on the emulsion particle diameter described later. Preferably, in the polyglycerin composition, the content of one kind of polyglycerin selected from tri, tetra, penta, hexa, hepta, octa, nona, and deca is preferably 35% or more, and more preferably Is preferably 45% or more. This composition distribution can be analyzed by gas chromatography or liquid chromatography, and in particular, it can be easily analyzed by subjecting polyglycerin to a trimethylsilylated derivative followed by gas chromatography.
[0023]
Emulsions containing an extracted tocopherol in the oil phase and further containing flavonoids, catechins, etc. in the aqueous phase generally have poor emulsification stability and cause problems such as separation of the oil phase. Polyglycerin fatty acid esters are effective for such emulsification. The polyglycerin fatty acid ester in which the content of one kind of glycerin condensed in the polyglycerin composition is 35% or more is particularly excellent in emulsion stability and can be solubilized, so its application range is expanded. can do. More preferably, a polyglycerin fatty acid ester in which the content of one kind of glycerin condensed in penta or more in the polyglycerin composition is 35% or more is preferable.
[0024]
The constituent fatty acid of the polyglycerol fatty acid ester used in the present invention is a linear saturated or unsaturated fatty acid having 8 to 22 carbon atoms, and may be a single product or a mixture thereof. The degree of esterification is not particularly limited, but those having a high monoester content and a low esterification degree are preferred. Moreover, the emulsifier used for emulsification of this degradation inhibitor is not restricted to polyglycerin fatty acid ester, You may use together 1 type, or 2 or more types of another emulsifier. Examples of such an emulsifier include monoglycerin fatty acid ester, organic acid monoglyceride, monoglyceride derivative, propylene glycol fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, enzymatically decomposed lecithin, quilla extract, and polyoxyethylene derivative.
[0025]
The polyhydric alcohol used in the present invention is a general term for compounds having two or more hydroxyl groups in one molecule, and the type is not particularly limited. For example, glycerin, propylene glycol, sorbitol, maltitol, xylitol, erythritol, lactitol, sorbitan, xylose, arabinose, mannose, lactose, sugar, coupling sugar, glucose, enzyme starch syrup, acidified starch syrup, maltose starch syrup, maltose, isomerization Examples thereof include sugar, fructose, reduced maltose, reduced starch syrup, and honey. These may be used alone or in admixture of two or more, or may be an aqueous solution. In addition, for the purpose of reducing the viscosity of the deterioration preventing agent and making it easier to use, water, ethanol or the like may be mixed within a range that does not affect the emulsification.
[0026]
In the water and / or polyhydric alcohol-in-oil type deterioration preventive agent of the present invention, an oil phase containing an extracted tocopherol is added after dissolving an emulsifier essential for polyglycerol fatty acid ester in water and / or polyhydric alcohol. And obtained by emulsification using an emulsification apparatus. The emulsifying apparatus is not particularly limited, and specific examples include a homomixer, a colloid mill, a high-pressure homogenizer, and an ultrahigh-pressure homogenizer. The method for adding ferulic acid is not particularly limited and may be before or after emulsification, but it is preferably added before emulsification and dissolved well in water and / or polyhydric alcohol. The method of adding the tea extract is not particularly limited, and may be any before or after emulsification, but is preferably added at the same time as ferulic acid from the viewpoint of simplicity during production, and in water and / or polyhydric alcohol. It is desirable to dissolve it well. In order to prevent the deterioration of the raw material and improve the stability of the preparation, preparation under an inert gas stream such as nitrogen and helium is desirable throughout all the steps.
[0027]
In the present invention, the water- and / or polyhydric alcohol-in-oil type degradation inhibitor is a fine emulsion particle having an average particle size of 1.0 μm or less using a polyglycerin fatty acid ester, so that tocopherol which is an oil-based antioxidant is used. Since there is no separation and the crystallization of ferulic acid, which is hardly soluble in water, is suppressed and the dispersibility is improved, the deterioration of flavor can be effectively prevented without impairing the appearance of the food or drink. When the particle size exceeds 1.0 μm, separation and floating of the extracted tocopherol, which is an oil-soluble antioxidant, are recognized, and the effect of preventing deterioration is not sufficiently exhibited, and the appearance of food and drink may be impaired. Preferably, it is 0.6 μm or less, more preferably 0.4 μm or less, and still more preferably 0.2 μm or less. By making a fine emulsification of 0.4 μm or less, the emulsion stability is further improved, and at 0.2 μm or less, solubilization is possible, so that it can be used for a transparent beverage or the like. In addition, the smaller the average particle size, the larger the surface area in contact with the deterioration inhibitor and the flavor component in the food and drink, so that the effect of preventing deterioration is increased, and the effect can be sufficiently exerted with a small amount of addition. it can.
[0028]
The average particle diameter when the deterioration inhibitor in the present invention is dispersed in water can be easily measured using a particle size distribution analyzer such as Beckman Coulter (L-230).
[0029]
In the deterioration preventing agent of the present invention, it is possible to prevent the deterioration of flavor components by containing an extracted tocopherol and ferulic acid, and further using a polyglycerol fatty acid ester to form a fine and stable emulsion. By using acid as the deterioration preventing agent of the present invention, it is difficult to use ferulic acid alone because undesirable flavors such as fermentation odor, rice bran odor and astringency derived from the origin of ferulic acid are suppressed. The range of use for food and drink can be expanded.
[0030]
Moreover, the above-mentioned effect on ferulic acid can be enhanced by further using a tea extract in combination with an emulsion containing extracted tocopherol and ferulic acid and using polyglycerin fatty acid ester, and further, heat, oxygen, light It is possible to remarkably improve the effect of preventing deterioration of flavor components due to the above, and the effect of suppressing malodors and off-flavor components that develop during long-term storage.
[0031]
The deterioration preventing agent of the present invention contains an extracted tocopherol in which 45% or more of d-δ-tocopherol and ferulic acid are contained in total tocopherol and an emulsion of water and / or polyhydric alcohol in oil using a polyglycerol fatty acid ester. In addition, the desired effect can be obtained by using the tea extract together with the tea extract, but a known antioxidant may be used in combination as necessary. Examples include oil-soluble antioxidants (licorice oil extract, sesame oil unsaponifiable matter, γ-oryzanol, rapeseed oil extract), water-soluble antioxidants (L-ascorbic acid, L-ascorbic acid ester, sodium L-ascorbate) Erythorbic acid, sodium erythorbate, gallic acid, chlorogenic acid, enzyme-treated rutin, grape seed extract, rosemary extract, sunflower extract, quercetin, bayberry extract, edible canna extract, blueberry leaf extract, etc.), Antioxidants that are poorly soluble in water and oil (Dokudami extract, mallow flower extract, pimenta extract, etc.), sequestering agents (gluconic acid, kojic acid, phytic acid, polyphosphoric acid, chitin, chitosan, etc.) , Amino acids, organic acids such as citric acid or salts thereof, hesperidin, hesperetin and the like. Or it may be used in combination blending of two or more.
[0032]
In the present invention, food fragrance is not particularly limited, but for example, natural fragrance materials such as essential oil, extract, oleoresin, recovered flavor, isolated fragrance, alcohols, esters, aldehydes, ketones And a mixture of one or more selected from synthetic fragrance materials such as lactones, and forms include flavors such as oil-soluble fragrances, water-soluble fragrances, emulsified fragrances, and powder fragrances. Can do. Oil-soluble and water-soluble can be used alone or in combination.
[0033]
The mixing method of the deterioration inhibitor of the present invention and these food fragrances is not particularly limited, but in order to effectively suppress the deterioration of the fragrances, the oil-soluble flavor component is extracted with tocopherol in advance before emulsification. It is better to mix, and the water-soluble flavor component should be mixed after emulsification.
[0034]
The mixing ratio of the deterioration preventive agent of the present invention with these food flavors is not particularly limited, and since it varies depending on the composition of the flavor components of the food flavor, the type of food used, etc. Specifically, it is preferable to mix in the range of food flavors 99: 1 to 1:99.
[0035]
In the present invention, the food and drink is not particularly limited, and is effective for all foods and drinks whose flavor components deteriorate due to the influence of heat, oxygen, light, etc. Beverages such as vegetable drinks, lactic acid bacteria drinks, tea drinks, carbonated drinks, coffee drinks, soup drinks, alcoholic drinks, mineral-containing drinks, vitamin-containing drinks, drinks containing functional food materials, milk drinks, lactic acid bacteria drinks, fermented milk, Milk such as condensed milk, concentrated milk, yogurt, ice cream, etc., products made mainly from milk, dessert foods such as jelly, bavaroa, pudding, confectionery such as chocolate, caramel, candy, snack food, soup, sauce, Examples include seasonings such as dressings, cooked foods such as retort foods, and other instant foods.
[0036]
The amount of addition of the deterioration inhibitor of the present invention to these foods and drinks is not particularly limited, and varies depending on the purity of the ingredients in the deterioration inhibitor to be used, the blending ratio, the type of food and drink to be added, etc. Generally, it is preferable to add in the range of 0.005 to 0.5% of food and drink. More preferably, 0.01% to 0.3% is preferable. If it is less than 0.005%, it is difficult to obtain the expected effect. If the concentration exceeds 0.5%, the flavor of the deterioration inhibitor affects the flavor of the food or drink.
Next, the present invention will be described in more detail based on examples, but the present invention is not limited only to such examples.
[0037]
【Example】
Example 1
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) And 2 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., d-δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) The deterioration preventive agent of the product 1 of the present invention was obtained by emulsification at a rotational speed of 7000 rpm.
[0038]
Example 2
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) And 1 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) and 1 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.), 65 Dissolved by warming to ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a deterioration inhibitor of the product 2 of the present invention was obtained.
[0039]
Example 3
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation), pentaglycerin monomyristate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, 15% containing pentaglycerin in polyglycerin composition) 2 g, ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Foods Industry Co., Ltd.) and green tea extract (trade name: Sanphenon BG, catechin content 70%, Taiyo Kagaku Co., Ltd.) 1 g are added, Dissolved by heating to 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a deterioration inhibitor of the product 3 of the present invention was obtained.
[0040]
Example 4
As polyhydric alcohol, 80 g of glycerin (manufactured by NOF Corporation), 5 g of pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% containing pentaglycerin in polyglycerin composition) And 2 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) and 3 g of green tea extract (trade name: Sanphenon BG, catechin content of 70%, manufactured by Taiyo Kagaku Co., Ltd.), 65 Dissolved by warming to ° C. 10 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol and rotated at a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a deterioration inhibitor of the product 4 of the present invention was obtained.
[0041]
Comparative Example 1
As polyhydric alcohol, glycerin (manufactured by NOF Corporation) 95g, sucrose fatty acid ester sucrose stearate (manufactured by Mitsubishi Chemical Foods Co., Ltd., HLB value 15) and ferulic acid (ferulic acid content 98) % Or more 2 g of Tsukino Food Industry Co., Ltd.) was added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). The deterioration preventing agent of Comparative product 1 was obtained by emulsification at 7000 rpm.
[0042]
Comparative Example 2
As polyhydric alcohol, glycerin (manufactured by NOF Corporation) 95g, sucrose fatty acid ester sucrose stearate (manufactured by Mitsubishi Chemical Foods Co., Ltd., HLB value 15) and ferulic acid (ferulic acid content 98) % 1 or more Tsukino Food Industry Co., Ltd. 1 g and green tea extract (trade name: Sanphenon BG, catechin content 70%, Taiyo Kagaku Co., Ltd.) 1 g were added and heated to 65 ° C and dissolved. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). The deterioration preventing agent of Comparative product 2 was obtained by emulsification at 7000 rpm.
[0043]
Comparative Example 3
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation), 2 g of enzyme-treated soybean lecithin (manufactured by Taiyo Kagaku Co., Ltd., HLB value 12) and ferulic acid (ferulic acid content of 98% or more Tsukino Foods Industry Co., Ltd.) 1 g) and 1 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). The deterioration preventing agent of Comparative product 3 was obtained by emulsification at 7000 rpm.
[0044]
Comparative Example 4
As polyhydric alcohol, 95 g of glycerin (manufactured by Nippon Oil & Fats Co., Ltd.), 2 g of gum arabic (manufactured by Sankyo Food Industry Co., Ltd.) and 1 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukuno Food Industry Co., Ltd.) And 1 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a degradation inhibitor of Comparative product 4 was obtained.
[0045]
Example 5
Fructose glucose liquid sugar 10%, citric acid 0.25% and sodium citrate 0.05% were dissolved in water 90% to obtain Bx. An acid sugar solution of 7.5, pH: 2.8 was prepared. 0.1% of each of the products 1 to 4 of the present invention obtained in Examples 1 to 4 are added to the acid sugar solution, and after heat sterilization at a temperature of 93 ° C., a colorless transparent glass bottle is filled with a hot pack and cooled. Thus, acid sugar solutions of the present invention products 5 to 8 were obtained. Moreover, the acid sugar liquid of the comparative products 5-8 which added 0.1% of the comparative products 1-4 obtained in Comparative Examples 1-4 instead of adding 0.1% of the present invention products 1-4 is obtained. It was.
[0046]
Test example 1
The turbidity of each acid sugar solution containing the deterioration inhibitor obtained in Example 5 was measured as an absorption luminous intensity at a wavelength of 650 nm using a spectrophotometer, and the state was visually confirmed. Moreover, the average particle diameter was measured with the particle size distribution measuring device (Beckman Coulter company make: L-230). Further, the acid sugar solution was stored at 55 ° C. for 2 weeks, the turbidity after storage and the average particle size were measured in the same manner, and the state was visually confirmed.
[0047]
[Table 1]

[0048]
As is clear from Table 1, the product of the present invention had an emulsified particle size of 1 μm or less as compared with the comparative product, and was stable without separation or the like after being stored at 55 ° C. for 2 weeks.
In addition, the deterioration inhibitors of comparative products 1 to 4 became non-uniform during storage, and acicular crystals believed to be derived from ferulic acid were observed. However, the deterioration inhibitors of the present invention products 1 to 4 were separated, crystals, etc. Was not recognized.
[0049]
Comparative Example 5
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) And 3 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. This was emulsified at a rotational speed of 7000 rpm with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain a deterioration preventing agent for Comparative Product 9.
[0050]
Comparative Example 6
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) Was added and dissolved by heating to 65 ° C. 3 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to polyhydric alcohol, and rotated at a homomixer (made by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a degradation inhibitor of Comparative Product 10 was obtained.
[0051]
Comparative Example 7
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation), pentaglycerin monomyristate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% containing pentaglycerin in polyglycerin composition) 2 g and 3 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. This was emulsified at a rotational speed of 7000 rpm with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain an anti-degradation agent for Comparative Product 11.
[0052]
Comparative Example 8
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) And 2 g of enzyme-treated rutin (Kyria Chemical Co., Ltd., enzyme-treated rutin 50%) were added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a deterioration preventing agent of Comparative Product 12 was obtained.
[0053]
Comparative Example 9
As polyhydric alcohol, 95 g of glycerin (manufactured by NOF Corporation) and 2 g of pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) And 2 g of bayberry extract (manufactured by Saneihara FFI, Inc., bayberry extract 20%) were added and dissolved by heating at 65 ° C. 1 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) is used as an oil phase, which is added to a polyhydric alcohol, and the number of revolutions is determined with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.). By emulsifying at 7000 rpm, a deterioration preventing agent of Comparative Product 13 was obtained.
[0054]
Example 6
Dissolve 10% granulated sugar, 0.15% citric acid and 0.02% sodium citrate, 0.1% lemon essence in 90% water to dissolve Bx. A lemon beverage base of 7.5, pH = 3 was prepared. Add 0.1% each of the products 1 to 3 of the present invention obtained in Examples 1 to 3 to this lemon beverage base, and after heat sterilization at a temperature of 93 ° C., fill a colorless transparent plastic bottle with a hot pack, The lemon drink of this invention products 9-11 was obtained by cooling. Moreover, the lemon drink of the comparative products 14-18 which added 0.1% of the comparative products 9-13 obtained in Comparative Examples 5-9 instead of 0.1% addition of the present invention products 1-3 was obtained. . Moreover, the lemon drink of the comparative product 19 which does not contain this invention product 1 similarly was obtained.
[0055]
Test example 2
Each of the lemon drinks obtained in Example 6 was left in direct sunlight for 8 hours (average temperature 23 ° C.) and then stored in a 5 ° C. refrigerator (light-shielded) as a standard. The degree was subjected to sensory evaluation by 10 well-trained panelists. The results are shown in Table 2.
[0056]
[Table 2]

[0057]
In addition, the score of evaluation in Table 2 is an average score of each paneler scored according to the following criteria.
(Evaluation criteria)
Same as refrigerated sample (no change): 5 points
Slightly changed compared to refrigerated samples: 4 points
A little change compared to refrigerated samples: 3 points
Compared to refrigerated samples: 2 points
Significant changes compared to refrigerated samples: 1 point
[0058]
Moreover, the amount of citral which is a flavor component peculiar to citrus fruits, such as lemon, was measured by the high performance liquid chromatography (HPLC), and it was set as the degree of flavor deterioration by the residual rate. The higher the residual ratio of citral, the less the flavor deterioration. The results are shown in Table 2.
[0059]
The measurement conditions for the amount of citral are as follows.
(Measurement condition)
Device: CLASS-LC10 (manufactured by Shimadzu Corporation)
Column: CAPCELL PAK C18 UG120 (SHISEIDO)
[0060]
Eluent: 60% methanol / water
Flow rate: 1 ml / min
Detection wavelength: UV 240nm
[0061]
The citral residual rate (%) was calculated according to the following formula.
Citral content of refrigerated samples: A
Citral content of light irradiated sample: B
B / A × 100 = citral residual ratio (%)
[0062]
As is clear from Table 2, the product of the present invention effectively prevented flavor deterioration due to light as compared with the comparative product. Moreover, compared with the comparative product, the product of the present invention had a high residual ratio of citral, which is a flavor component of lemon, and effectively maintained the fresh flavor of lemon.
[0063]
Example 7
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) And 5 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 5 g of coffee oily perfume (manufactured by IF Japan Co., Ltd.) and 5 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to form an oil phase. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the coffee emulsification fragrance | flavor of this invention product 12.
[0064]
Example 8
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) 5 g, ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Foods Industry Co., Ltd.) and green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.) And dissolved by heating to 65 ° C. 5 g of coffee oily perfume (manufactured by IF Japan Co., Ltd.) and 5 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to form an oil phase. It was added into alcohol and emulsified at a rotation speed of 7000 rpm with a homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain a coffee emulsified fragrance of Invention Product 13.
[0065]
Comparative Example 10
As polyhydric alcohol, 90 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin containing 45 in polyglycerin composition) %) 5 g was dissolved by heating at 65 ° C. 5 g of coffee oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to the polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries, Ltd.) at a rotation speed of 7000 rpm. Thus, a coffee emulsified fragrance of Comparative product 20 was obtained.
[0066]
Comparative Example 11
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) And 10 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 5 g of coffee oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to the polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries, Ltd.) at a rotation speed of 7000 rpm. Thus, a coffee emulsified flavor of Comparative product 21 was obtained.
[0067]
Comparative Example 12
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) 5 g was added and dissolved by heating to 65 ° C. 5 g of coffee oily fragrance (manufactured by IF Japan Co., Ltd.) and 10 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to make an oil phase, which is polyvalent. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the coffee emulsification fragrance | flavor of the comparative product 22.
[0068]
Comparative Example 13
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) 5 g and 10 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. Mix 5g of coffee oily fragrance (IFF Japan Co., Ltd.), make it an oil phase, add it to polyhydric alcohol, and use a homomixer (Special Machine Industries Co., Ltd.). The coffee emulsified flavor of Comparative product 23 was obtained by emulsification at a rotational speed of 7000 rpm.
[0069]
Comparative Example 14
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) 5 g and 10 g of fresh coffee bean extract (Hasegawa Fragrance Co., Ltd., 30% chlorogenic acid) were added and dissolved by heating at 65 ° C. 5 g of coffee oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to the polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries, Ltd.) at a rotation speed of 7000 rpm. Thus, a coffee emulsified fragrance of Comparative product 24 was obtained.
[0070]
Comparative Example 15
As a polyhydric alcohol, 80 g of reduced starch syrup (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monostearate, a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, pentaglycerin-containing 45 in polyglycerin composition) %) And 5 g of grape seed extract (Kikkoman Co., Ltd., proanthocyanidins 38% or more) were added and dissolved by heating at 65 ° C. 5 g of coffee oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to the polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries, Ltd.) at a rotation speed of 7000 rpm. Thus, a coffee emulsified fragrance of Comparative product 25 was obtained.
[0071]
Test example 3
The coffee emulsified fragrances of the inventive products 12 and 13 obtained in Examples 7 and 8 and the comparative products 20 to 25 obtained in Comparative Examples 10 to 15 were stored at 37 ° C. for 2 months, and then a refrigerator at 5 ° C. As a standard, the degree of flavor deterioration was evaluated by 10 panelists who were well trained. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 3.
[0072]
[Table 3]

[0073]
As is clear from Table 1, the product of the present invention effectively prevented flavor deterioration during storage and significantly reduced the occurrence of off-flavors and odors as compared to the comparative product.
[0074]
Example 9
About 10 times weight of boiling water is added to 250 g of coffee beans (L value: 18), and Bx. 2500 g coffee extract of 2.5 was obtained. Using this extract, a coffee beverage was prepared according to the ratio shown in <Prescription 1> below. After adding 0.1% of the coffee emulsified fragrance of the products 12 and 13 of the present invention obtained in Examples 7 and 8 to this coffee beverage, a homogenizer (150 kg / cm ² ), And after UHT sterilization (142 ° C., 30 seconds), it was filled into 350 ml transparent plastic bottles to obtain coffee beverages containing plastic bottles 14 and 15 of the present invention. In addition, the present invention products 7 and 8 were added with 0.1% of the comparative products 20 to 25 obtained in Comparative Examples 10 to 15 instead of the addition of 0.1%, respectively. Got.
[0075]
<Prescription 1>

[0076]
Test example 4
Each bottled coffee drink obtained in Example 9 was stored at 55 ° C. for 2 weeks for 1 month and then stored in a 5 ° C. refrigerator (shaded) as a standard. The sensory evaluation was carried out by 10 well-trained panelists. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 4.
[0077]
In addition, each plastic bottled coffee beverage is stored for 1 month under fluorescent light 20000 lux irradiation, and a sample stored in a refrigerator at 5 ° C. (light-shielded) is used as a standard to determine the degree of flavor deterioration. Sensory evaluation was performed by 10 well-trained panelists. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 4.
[0078]
[Table 4]

[0079]
As is clear from Table 4, by using the coffee fragrance added with the deterioration preventive agent of the present invention, deterioration due to heat and light is effectively prevented, and the off-flavor odor generated is remarkably suppressed. It became clear that In addition, the product 15 of the present invention showed little change in flavor even at 55 ° C. for 2 months, and sufficiently exhibited the effect of preventing deterioration even during long-term storage.
[0080]
Example 10
As polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.), pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 2 g and 3 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of milk oily fragrance (IFF Japan Co., Ltd.) and 3 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to make an oil phase. It added in alcohol and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and the milk emulsification fragrance | flavor of this invention product 16 was obtained.
[0081]
Example 11
As polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.), pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 2 g and 2 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) and 1 g of green tea extract (trade name: Sanphenon BG, content of catechins 70%, manufactured by Taiyo Kagaku Co., Ltd.) Dissolved by heating to 65 ° C. 1 g of milk oily fragrance (IFF Japan Co., Ltd.) and 3 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to make an oil phase. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the milk emulsification fragrance | flavor of this invention product 17.
[0082]
Comparative Example 16
As polyhydric alcohol, sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) 97 g, polyglycerin fatty acid ester pentaglycerin monooleate (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, pentaglycerin content in polyglycerin composition 45%) 2 g was added and dissolved by heating to 65 ° C. 1 g of milk oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries Co., Ltd.) at a rotational speed of 7000 rpm. Thus, a milk emulsified flavor of Comparative product 32 was obtained.
[0083]
Comparative Example 17
As a polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) and 2 g of pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% containing pentaglycerin in polyglycerin composition) And 6 g of ferulic acid (ferulic acid content 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of milk oil-based fragrance (IF F Japan Co., Ltd.) is used as the oil phase, added to polyhydric alcohol, and emulsified with a homomixer (Special Machine Industries Co., Ltd.) at a rotational speed of 7000 rpm. Thus, a milk emulsified fragrance of comparative product 33 was obtained.
[0084]
Comparative Example 18
As a polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) and 2 g of pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% containing pentaglycerin in polyglycerin composition) Was added and dissolved by heating to 65 ° C. 1 g of milk oily fragrance (manufactured by IF Japan) and 6 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to form an oil phase, which is polyvalent. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the milk emulsification fragrance | flavor of the comparative product 34.
[0085]
Comparative Example 19
As a polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) and 2 g of pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in the polyglycerin composition) And 6 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. Mix 1g of milk oil flavor (IF F Japan Co., Ltd.), make it an oil phase, add it to polyhydric alcohol, and use Homomixer (Special Machine Industries Co., Ltd.) The milk emulsified flavor of comparative product 35 was obtained by emulsification at a rotational speed of 7000 rpm.
[0086]
Comparative Example 20
As a polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) and 2 g of pentaglycerin monooleate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, 45% containing pentaglycerin in polyglycerin composition) And 3 g of rosemary extract (Mitsubishi Chemical Co., Ltd., rosemary extract containing 45%) was added and dissolved by heating at 65 ° C. 1 g of milk oily fragrance (IFF Japan Co., Ltd.) and 3 g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to make an oil phase. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the milk emulsification fragrance | flavor of the comparative product 36.
[0087]
Comparative Example 21
As polyhydric alcohol, 91 g of sorbitol (manufactured by Towa Kasei Kogyo Co., Ltd.) and pentaglycerin monomyristate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 14, containing 45% of pentaglycerin in polyglycerin composition) 2 g and 3 g of ascorbic acid (manufactured by Tanabe Seiyaku Co., Ltd.) were added and dissolved by heating at 65 ° C. 1 g of milk oily fragrance (IFF Japan Co., Ltd.) and 3 g of extracted tocopherol (Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) are mixed to make an oil phase. It added in alcohol, and it emulsified at the rotation speed of 7000 rpm with the homomixer (made by Tokushu Kika Kogyo Co., Ltd.), and obtained the milk emulsification fragrance | flavor of the comparative product 37.
[0088]
Example 12
95 g of milk and 5 g of skim milk powder were mixed, sterilized (90 ° C., 15 minutes), cooled (30 to 45 ° C.), and then inoculated with a starter. This was fermented to pH 4.3 and then cooled to make a yogurt base. On the other hand, 16 g of sugar, 1.2 g of pectin, and 82.8 g of water were mixed and then sterilized (95 ° C., 5 minutes) to obtain a syrup solution. When the yogurt base and the syrup solution were mixed at a ratio of 1: 1, 0.1% of the milk emulsified flavors of the products 16 and 17 of the present invention obtained in Examples 10 and 11 were added and homogenized under aseptic conditions. Mixer and homogenizer (150 kg / cm ² ). This was filled in a translucent plastic container (120 ml) to obtain yogurt drinks of the products 18 and 19 of the present invention. Similarly, yogurt drinks of comparative products 38 to 43 in which 0.1% of the comparative products 32 to 37 obtained in Comparative Examples 16 to 21 were added instead of 0.1% of the inventive products 16 and 17 respectively. Got.
[0089]
Test Example 5
Each yoghurt beverage obtained in Example 12 was stored for 2 weeks (5 ° C.) under irradiation of 2000 lux fluorescent light, and then stored in a 5 ° C. refrigerator (shaded) as a standard. The degree of flavor deterioration was sensory evaluated by 10 well-trained panelists. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 5.
[0090]
[Table 5]

[0091]
As is clear from Table 5, the use of the milk fragrance to which the deterioration preventive agent of the present invention was added compared with the comparative product effectively prevented deterioration due to light, and remarkably suppressed the off-flavor and odor generated. .
[0092]
Example 13
The raw materials were mixed in the formulation shown in <Prescription 2> below, heated and dissolved (90 ° C.), and then homogenizer (150 kg / cm ² ). After adding 0.1% of the milk flavor of the products 16 and 17 of the present invention obtained in Examples 10 and 11, the mixture was poured into a 100 ml plastic container to obtain matcha pudding of the products 20 and 21 of the present invention. . Moreover, the green tea pudding of the comparison products 44-49 which added 0.1% of the comparison products 36-37 obtained in Comparative Examples 16-21 instead of 0.1% addition of the present invention products 16, 17 was obtained. It was.
[0093]
<Prescription 2>

[0094]
Test Example 6
Each matcha pudding obtained in Example 13 was stored (10 ° C.) for 10 days under irradiation of 2000 lux fluorescent light, and then stored in a refrigerator (shaded) at 5 ° C. as a standard. The degree of flavor deterioration was sensory evaluated by 10 well-trained panelists. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 6.
[0095]
[Table 6]

[0096]
As is clear from Table 6, compared to the comparative product, deterioration by light is effectively prevented by using the milk fragrance to which the deterioration preventive agent of the present invention is added, and the off-flavor odor generated is remarkably suppressed. .
[0097]
Example 14
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 3 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. Mix 3g of Yuzu essential oil (manufactured by Hamada Fragrance Co., Ltd.) and 3g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) to make this an oil phase, which is added to the polyhydric alcohol. The product was emulsified with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of 7000 rpm to obtain a yuzu emulsified fragrance of the product 22 of the present invention.
[0098]
Example 15
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 2 g of ferulic acid (ferulic acid content 98% or more manufactured by Tsukino Food Industry Co., Ltd.) and 2 g of green tea extract (trade name: Sanphenon BG, content of catechins 70%, manufactured by Taiyo Kagaku Co., Ltd.) Dissolved by heating to 65 ° C. Mix 3g of Yuzu essential oil (manufactured by Iwata Fragrance Co., Ltd.) and 2g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) to make an oil phase, which is added to polyhydric alcohol. The product was emulsified with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of 7000 rpm to obtain a yuzu emulsified fragrance of the product 23 of the present invention.
[0099]
Comparative Example 22
As polyhydric alcohol, 94 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in the polyglycerin composition) 3 g was added and dissolved by heating to 65 ° C. 3 g of Yuzu essential oil (Madako Fragrance Co., Ltd.) is used as an oil phase, which is added to a polyhydric alcohol and emulsified with a homomixer (made by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of 7000 rpm. 50 yuzu emulsifying fragrances were obtained.
[0100]
Comparative Example 23
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 6 g of ferulic acid (ferulic acid content of 98% or more, manufactured by Tsukino Food Industry Co., Ltd.) were added and dissolved by heating at 65 ° C. 3 g of Yuzu essential oil (Madako Fragrance Co., Ltd.) is used as an oil phase, which is added to a polyhydric alcohol and emulsified with a homomixer (made by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of 7000 rpm. 51 yuzu emulsifying fragrances were obtained.
[0101]
Comparative Example 24
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g was dissolved by heating at 65 ° C. Mix 3g of Yuzu essential oil (manufactured by Iwata Fragrance Co., Ltd.) and 6g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) to form an oil phase, which is added to polyhydric alcohol. Then, emulsification was carried out at a rotational speed of 7000 rpm with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain a comparative product 52 yuzu emulsified fragrance.
[0102]
Comparative Example 25
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monopalmitate which is polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 6 g of green tea extract (trade name: Sanphenon BG, catechin content 70%, manufactured by Taiyo Kagaku Co., Ltd.) were added and dissolved by heating at 65 ° C. 3 g of Yuzu essential oil (Madako Fragrance Co., Ltd.) is used as an oil phase, which is added to a polyhydric alcohol and emulsified with a homomixer (made by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of 7000 rpm. 53 yuzu emulsifying fragrances were obtained.
[0103]
Comparative Example 26
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monostearate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 4 g of gallic acid were added and dissolved by heating at 65 ° C. Mix 3g of Yuzu essential oil (manufactured by Iwata Fragrance Co., Ltd.) and 2g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) to make an oil phase, which is added to polyhydric alcohol. Then, emulsification was carried out at a rotational speed of 7000 rpm with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain a yuzu emulsified fragrance of comparative product 54.
[0104]
Comparative Example 27
As polyhydric alcohol, 88 g of glycerin (manufactured by NOF Corporation), pentaglycerin monostearate which is a polyglycerin fatty acid ester (manufactured by Taiyo Kagaku Co., Ltd., HLB value 13, containing 45% of pentaglycerin in polyglycerin composition) 3 g and 4 g Na ascorbate were added and heated to 65 ° C. to dissolve. Mix 3g of Yuzu essential oil (manufactured by Iwata Fragrance Co., Ltd.) and 2g of extracted tocopherol (manufactured by Tama Seikagaku Co., Ltd., δ-tocopherol content 86%) to make an oil phase, which is added to polyhydric alcohol. Then, emulsification was carried out at a rotational speed of 7000 rpm with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain a yuzu emulsified flavor of comparative product 55.
[0105]
Example 16
80 ml of commercially available dashi soup (salt concentration = 10%) and 120 ml of cereal vinegar (pure rice vinegar) were mixed to make a base for a non-oil type Japanese dressing. 0.1% of the present invention products 22 and 23 obtained in Examples 14 and 15 were added thereto, and then poured into a 100 ml plastic bottle to obtain Japanese style dressings 24 and 25 of the present invention products. In addition, Japanese-style zu dressing of comparative products 56-61 obtained by adding 0.1% of comparative products 50-55 obtained in Comparative Examples 22-27 instead of adding 0.1% of inventive products 22, 23, respectively. It was.
[0106]
Test Example 7
Each Japanese yuzu dressing obtained in Example 16 was stored for 2 months under fluorescent lamp 1500 lux irradiation (10 ° C.) and then stored in a 5 ° C. refrigerator (shaded) as a standard. The sensory evaluation of the degree of flavor deterioration was performed by 10 well-trained panelists. Evaluation was scored according to the same criteria as in Test Example 2. The results are shown in Table 7.
[0107]
In addition, after each Japanese-style yuzu dressing obtained in Example 16 was stored at 37 ° C. for 2 months, sensory evaluation was performed by 10 well-trained panelists. The evaluation method was the same as in Test Example 2. The results are shown in Table 7.
[0108]
[Table 7]

[0109]
As is clear from Table 7, the use of the yuzu fragrance to which the deterioration preventive agent of the product of the present invention is added compared to the comparative product effectively prevents deterioration due to light and heat, and the generated off-flavor and odor is reduced. It became clear that it suppressed remarkably. In addition, the products 24 and 25 of the present invention showed little change in flavor both at 1500 lux irradiation and at 37 ° C. for 2 months, and sufficiently exhibited the effect of preventing deterioration even during long-term storage.
[0110]
Examples of the present invention and the target product are as follows.
(1) In total tocopherol, 45% or more of d-δ-tocopherol contains extracted tocopherol and ferulic acid, and uses polyglycerol fatty acid ester to form an oil-in-water emulsion in water and / or polyhydric alcohol. Deterioration preventing agent characterized.
(2) A deterioration preventing agent characterized by using a tea extract together with the emulsion according to (1).
(3) In the polyglycerol composition of the polyglycerol fatty acid ester, the content of one kind of polyglycerol selected from tri, tetra, penta, hexa, hepta, octa, nona, and deca is 35% or more (1) The deterioration inhibitor according to (2).
(4) In the polyglycerin composition of the polyglycerin fatty acid ester, the content of one kind of polyglycerin selected from tri, tetra, penta, hexa, hepta, octa, nona and deca in the polyglycerin composition is 45% or more. (1)-(3) any one deterioration prevention agent.
(5) The tea extract is (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin, (−)-catechin gallate, (−)-epicatechin gallate, ( The deterioration inhibitor according to any one of (2) to (4), which is one or more selected from the group consisting of-)-epigallocatechin gallate and (-)-gallocatechin gallate.
(6) The deterioration preventing agent according to any one of (2) to (5), wherein the tea extract is a green tea extract.
(7) The deterioration preventing agent according to any one of (1) to (6), wherein the d-δ-tocopherol content in the extracted tocopherol is 80% or more.
(8) The deterioration preventing agent according to any one of (1) to (7), wherein the purity of ferulic acid is 80% or more.
(9) The deterioration preventing agent according to any one of (1) to (7), wherein the purity of ferulic acid is 95% or more.
(10) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is glycerin.
(11) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is propylene glycol.
(12) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is a sugar.
(13) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is an aqueous solution of sugar.
(14) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is a sugar alcohol.
(15) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is an aqueous solution of a sugar alcohol.
(16) The deterioration preventing agent according to any one of (1) to (9), wherein the polyhydric alcohol is sorbitol.
(17) The deterioration preventing agent according to any one of (1) to (16), wherein a particle diameter when water and / or an oil-in-polyhydric emulsion is dispersed in water is 1.0 μm or less.
(18) The deterioration preventive agent according to any one of (1) to (16), wherein a particle diameter when water and / or an oil-in-polyhydric emulsion is dispersed in water is 0.6 μm or less.
(19) The deterioration preventive agent according to any one of (1) to (16), wherein a particle diameter when water and / or an oil-in-polyhydric emulsion is dispersed in water is 0.4 μm or less.
(20) The deterioration preventing agent according to any one of (1) to (16), wherein a particle diameter when water and / or an oil-in-polyhydric emulsion is dispersed in water is 0.2 μm or less.
(21) The deterioration preventing agent according to any one of (1) to (16), wherein a particle diameter when water and / or an oil-in-polyhydric emulsion is dispersed in water is 0.1 μm or less.
(22) A fragrance preparation containing the deterioration preventing agent according to any one of (1) to (21).
(23) A food fragrance preparation containing the deterioration inhibitor according to any one of (1) to (21).
(24) Food / beverage products containing the deterioration preventing agent in any one of said (1)-(21).
(25) Food / beverage products containing the fragrance | flavor formulation containing the deterioration inhibiting agent in any one of said (1)-(21).
[0111]
【The invention's effect】
According to the present invention, fine and stable water and / or polyhydric alcohol using an extracted tocopherol and ferulic acid containing 45% or more of d-δ-tocopherol in the total tocopherol in food fragrances or foods and beverages, and polyglycerin fatty acid ester By using a middle oil type emulsion, it is possible to prevent the deterioration of flavor components in food flavors and foods and drinks, and to suppress the expression of off-flavor and odor caused by the deterioration of flavors and provide foods and drinks with good flavors. can do. Further, by further using a tea extract in combination with the emulsion, the intended effect is remarkably improved, and the effect can be maintained even for long-term storage.

Claims (6)

  In total tocopherol, 45% by weight or more contains extracted tocopherol and ferulic acid which is d-δ-tocopherol, and in the polyglycerol composition of polyglycerol fatty acid ester, the condensation degree of glycerol is tri, tetra, penta, hexa, hepta, A flavor characterized by containing an emulsion in the form of an oil-in-water and / or polyhydric alcohol using a polyglycerin fatty acid ester in which the content of one kind of polyglycerin selected from octa, nona and deca is 35% by weight or more. An ingredient deterioration inhibitor.   The deterioration inhibitor of a flavor component characterized by using a tea extract together with the emulsion of claim 1.   The tea extract is (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin, (−)-catechin gallate, (−)-epicatechin gallate, (−) − The deterioration inhibitor for flavor components according to claim 1 or 2, which is one or more selected from the group consisting of epigallocatechin gallate and (-)-gallocatechin gallate.   5. The flavor component deterioration preventive agent according to any one of claims 1 to 4, wherein the particle diameter when water and / or an oil-in-polyhydric alcohol emulsion is dispersed in water is 1.0 μm or less.   Food fragrance | flavor containing the deterioration inhibitor of the flavor component in any one of Claims 1-4.   The food / beverage products containing the deterioration inhibitor of the flavor component in any one of Claims 1-4, or the food flavor of Claim 5.