JPH0236223B2 - - Google Patents
Info
- Publication number
- JPH0236223B2 JPH0236223B2 JP57149917A JP14991782A JPH0236223B2 JP H0236223 B2 JPH0236223 B2 JP H0236223B2 JP 57149917 A JP57149917 A JP 57149917A JP 14991782 A JP14991782 A JP 14991782A JP H0236223 B2 JPH0236223 B2 JP H0236223B2
- Authority
- JP
- Japan
- Prior art keywords
- antioxidant
- sage
- oil
- rosemary
- proline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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- 241001529742 Rosmarinus Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
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Description
本発明は油脂性食品の酸化による不都合な変質
変化を効果的に防止できる油脂性食品の酸化防止
方法に関し、とくに、油脂性食品に、プロリンも
しくはプロリンのアルコール溶液及びローズマリ
ー及び／又はセージの天然源抗酸化成分の両者を
添加することにより、改善された且つ相剰的効果
を発揮できる油脂性食品の酸化防止方法に関す
る。
従来油脂或いは油脂含有飲食品の酸化防止方法
としては、ブチルヒドロキシ・アニソール
（BHA）、ジブチルヒドロキシトルエン（BHT）、
ノルジヒドログアヤレチツク酸（NDGA）、没食
子酸エステルの如き合成の抗酸化剤が使用されて
きたが、近年その安全性に凝問がもたれるように
なり、これに代るより安全性の高い天然の抗酸化
剤が種々検討されている。かかる天然の抗酸化剤
の利用としては、例えば天然ビタミンＥ、γ―オ
リザノール、ケルセチン、セザモール、セザモリ
ン、没食子酸、ルチン、及びハーブ系香辛料抽出
物の利用など多数の提案がなされ、これらのうち
幾つかのものは、既に実用に供されている。
しかし乍ら上記の如き天然の抗酸化剤は、経済
性、供給安定性及び抗酸化効果のどどの面からみ
ても必ずしも満足できるものではなかつた。更に
上記例示した如き合成及び天然の抗酸化剤は全て
脂溶性であるから、予め油脂に溶解しなければ、
酸化防止効果を充分に発揮させることができな
い。従つて水を媒体とする食品中に存在する油脂
の酸化を防止することは困難であつた。かかる欠
点を改善する方法として例えば、前記の如き天然
の抗酸化性物質に食品用乳化剤を添加して、分散
性を改善する幾つかの提案がなされている（特公
昭56−16196、特開昭55−89383、特開昭56−
32982）。しかしながら、上記例示の如き提案によ
つても抗酸化剤は分散されるにとどまり、その抗
酸化性改善効果には限度がある不利益があつた。
更に、アミノ酸類を酸化防止剤のシネルギストと
して利用する提案が知られている。例えばフラボ
ノイド類のシネルギストとしてメチオニン、トリ
プトフアン及びヒスチジンの如きアミノ酸を利用
する提案（特開昭55−54883）、或いは、ビタミン
Ｅと乳化剤の混合系に、更にシネルギストとして
アラニン、グリシン、ロイシン、セリン、バリ
ン、スレオニン及びイソロイシンの如きアミノ酸
を配合する提案（特開昭55−19048）が知られて
いる。
本発明者等は、前述の如き合成もしくは天然の
従来抗酸化剤の欠点乃至不利益を克服でき、食品
に完全に溶解し、油脂に対しても相溶性のある抗
酸化性物質を種々検索した結果、プロリンとロー
ズマリー及び／又はセージの天然源抗酸化成分の
両者を、油脂性食品に添加することによつて前記
の如き欠点乃至不利益を完全に解決して、特異的
に油脂性食品に対して優れた抗酸化効果を賦与で
き且つ従来提案されている天然抗酸化剤に比較
し、著しく酸化防止効果の大きいことを発見し
た。
従つて、本発明の目的は改善された油脂性食品
の酸化防止方法を提案するにある。
本発明の上記目的及び更に多くの他の目的及び
利点は以下の説明から一層明らかとなるであろ
う。
本発明で用いるプロリンとしては、例えば、ゼ
ラチン、カゼイン、グリアジン及びツエインの如
き蛋白質の加水分解物をイオン交換樹脂で処理
し、中性アミノ酸区分をピクリン酸またはライネ
ツケ塩で処理して得られるＬ―プロリン、或いは
醗酵法などによつて得られる天然のＬ―プロリン
を例示することができる。更には、Ｌ―オルニチ
ン又はＬ―グルタミン酸を原料とする合成法等に
よつて得られるＬ―プロリンのほか、DL―プロ
リン、Ｄ―プロリン等を例示することがきるが、
殊に天然物由来のＬ―プロリンを好ましく例示す
ることができる。
本発明方法の実施に際しては、油脂性食品もし
くはその製造工程の任意の段階に於て、プロリン
もしくはプロリンのアルコール溶液及びローズマ
リー及び／又はセージの天然源抗酸化剤を添加す
ることにより、油脂性食品の酸化を防止すること
ができる。
上記プロリンのアルコール溶液におけるアルコ
ールの例としては、エタノール、プロピレングリ
コール、グリセリン、Ｄ―ソルビツト、これらの
任意の混合物、これらの含水物、これらの少なく
とも一種と中鎖脂肪酸のトリグリセリドの如きト
リグリグリセリド類との混合物及び該トリグリセ
リド類単独など広義の体内摂取可能なアルコール
類を例示することができる。溶解性及び取扱いの
点からエタノールとくに含水エタノールの利用が
好ましい。
本発明方法に於ては、プロリンとローズマリー
及び／又はセージの天然源抗酸化を併用すること
により、優れた相剰的抗酸化効果を達成すること
ができる。このようなローズマリー及び／又はセ
ージの天然源抗酸化成分は、種々の該抗酸化成分
含有材料から、溶媒抽出処理、吸着剤処理、蒸留
処理その他の分離単位手段を利用して採取するこ
とができる。
利用するローズマリー及び／又はセージの抗酸
化成分含有材料としては、例えば、ローズマリー
及び／又はセージの乾燥物、微粉砕物；それらに
水蒸気蒸留その他の処理を施して精油を採取した
残りの精油採取残渣；これら材料を、たとえば、
ｎ―ペンタン、イソペンタン、石油エーテル、リ
グロイン、ｎ―ヘキサン、メチレンクロライド、
エチレンジクロライド、エチルエーテル、アセト
ン、酢酸メチル、酢酸エチル、メタノール、エタ
ノール、ｎ―プロパノール、イソプロパノール、
ｎ―ブタノール、これらの複数種の混合物などの
有機溶媒で抽出し、抽出液から溶媒を除去して、
たとえば大気圧乃至減圧条件下に留去して得られ
るオレオレジンやその抽出残渣；などを挙げるこ
とができる。
ローズマリー及び／又はセージの天然源抗酸化
成分は、例えば、上記例示の如き該抗酸化成分含
有材料を有機溶媒で抽出処理した抽出物として得
ることができ、更に脱色処理、脱臭処理などを施
すことができる。
上記抽出処理に用いる有機溶媒の例としては、
例えば、メタノール、エタノール、ｎ―プロピル
アルコール、イソプロピルアルコール、アセト
ン、プロピレングリコール、グリセリン、酢酸エ
チル等の極性溶剤、あるいは例えば、ｎ―ペンタ
ン、ｎ―ヘキサン、シクロヘキサン、石油エーテ
ル、リグロイン、四塩化炭素、メチレンクロライ
ド、エチレンジクロライド、ベンゼン、トルエン
等の非極性溶剤あるいはこれらの複数種の混合物
を例示することができるが、エタノールで抽出す
ることが特に好ましい。
更に上述の極性溶剤は含水系、例えば水分含有
率約10〜約50％の含水溶剤の形で用いることもで
きる。
抽出操作及び抽出条件は種々選択できるが、例
えばローズマリー及び／又はセージの抗酸化成分
含有材料に約0.2〜約50倍重量の極性溶剤あるい
は非極性溶剤を添加し、室温乃至使用溶剤の沸点
温度で、たとえば約５分〜約24時間、静置もしく
は撹拌して行うことができる。抽出処理はバツチ
方式でも連続方式でも実施でき、たとえば、ロー
ズマリー及び又はセージの粉砕物、もしくはその
精油採取残渣の粉砕物乃至細断物の如き抗酸化成
分含有材料を、抽出カラムに詰めて、該カラムの
上部もしくは下部より有機溶媒たとえばアルコー
ル類を連続的に送入してカラム抽出するカラム抽
出方式を例示することができる。
このようにして抽出操作を行つたのち、例えば
遠心分離、過、圧搾その他の固液分離手段を利
用して不溶性固形物残渣を除去することにより、
ローズマリー及び／又はセージの天然源抗酸化成
分を含有した抽出液を得ることができる。必要な
らば、不溶性固形分抽出残渣に更に極性溶剤ある
いは非極性溶剤を添加して同様の操作をくり返
し、抽出することもできる。
本発明においては、ローズマリー及び／又はセ
ージから上記例示の如き方法で得られた抽出液を
濃縮して、溶媒を除去することにより得られるロ
ーズマリー及び／又はセージの天然源抗酸化成分
含有濃縮物を利用することができる。更には、上
記方法によつて得られた抽出液は、活性炭、活性
アルミナ、シリカゲル、ベントナイト、酸性白
土、あるいはケイソウ土の如き吸着剤を用いて脱
色処理後、濃縮することが望ましい。また更に
は、上記の如き方法によつて得られた濃縮物を水
蒸気蒸留その他の手段で脱臭処理して用いてもよ
い。
本発明で用いるローズマリー及び／又はセージ
の天然源抗酸化成分は、前述のようにして、該抗
酸化成分含有材料から抽出採取することがきる
が、同一出願人の出願に係わる優れた無色、無臭
のローズマリー及び／又はセージの抗酸化成分の
製法を利用して得られる抗酸化成分の利用が好ま
しい。
例えば、同一出願人の出願に係わる発明の名称
“天然源抗酸化成分の製法”に詳しく開示された
製法で得られる抗酸化成分を挙げることができる
出願：昭和57年５月８日（特願昭57−075988号）
（特開昭58−194973号）。
この提案の製法によれば、例えば、ローズマリ
ー及び／又はセージ、その精油採取残渣、そのオ
レオレジンからえらばれたローズマリー及び／又
はセージの抗酸化成分含有材料をアルコール類で
抽出して得られた抽出液；又は該材料をアルコー
ル類以外の有機溶媒で抽出して得られた抽出液か
ら有機溶媒を除去し、これをアルコール類に溶解
した溶液；などの前記例示の如きローズマリー及
び／又はセージの抗酸化成分含有アルコール溶液
を、固体吸着剤処理及び陽イオン交換樹脂処理す
ることによつて、優れた品質のローズマリー及
び／又はセージの天然源抗酸化成分を得ることが
できる。
他の製法による天然源抗酸化成分として、同一
出願人の出願に係わる発明の名称“天然源抗酸化
成分の製造方法”に詳しく開示された製法で得ら
れる抗酸化成分を挙げることができる出願：昭和
57年５月８日（特願昭57−075989号）（特開昭58
−194974号）。
この提案の製法によれば、前提案について例示
したと同様なローズマリー及び／又はセージの抗
酸化成分含有アルコール溶液を、アルコール濃度
約80重量％以下のアルカリ性含水アルコール溶液
となし、該溶液を多孔性樹脂吸着剤で処理し、得
られた処理液を酸性にして形成される固形分を採
取することによつて、優れた品質のローズマリー
及び／又はセージの天然源抗酸化成分を得ること
ができる。この製法に於ては、上記アルカリ性含
水アルコール溶液となす前に、該抗酸化成分含有
アルコール溶液を、固体吸着剤処理及び／又は陽
イオン交換樹脂処理することができる。
更に他の製法による抗酸化成分として、同一出
願人の出願に係わる発明の名称“天然源抗酸化成
分を製造する方法”に詳しく開示された製法で得
られる抗酸化成分を挙げることができる出願：昭
和57年５月８日（特願昭57−075990号）（特開昭
58−194975号）。
この提案の製造によれば、例えばローズマリー
及び／又はセージ、その精油採取残渣、そのオレ
オレジンからえらばれたローズマリー及び／又は
セージの抗酸化成分含有材料の如きローズマリー
及び／又はセージの抗酸化成分含有材料を、固体
吸着剤の存在下に、既に例示したような有機溶媒
で抽出処理することによつて、優れた品質の天然
源抗酸化成分を得ることができる。この態様に於
ては、有機溶媒としてアルコール類を用い、該ア
ルコール類で抽出処理して得られた処理液を陽イ
オン交換樹脂処理することがきる。
又更に、同一出願人の出願に係わる発明の名称
“天然源抗酸化成分の抽出法”に詳しく開示され
た製法で得られるローズマリー及び／又はセージ
の天然源抗酸化成分も利用できる出願：昭和57年
５月８日（特願昭57−075991号）（特開昭58−
194976号）。
この提案の製法によれば、ローズマリー及び／
又はセージの抗酸化成分含有材料を、加圧条件下
に約90℃〜約180℃で既に例示したような有機溶
媒抽出処理し、処理液を採取することによつて、
優れた品質の天然源抗酸化成分を得ることができ
る。該有機溶媒はすでに例示したような極性有機
溶媒もしくはその含水物であることができ、又、
該抽出処理を不活性ガス雰囲気下で行うことがで
きる。
又更に、同一出願人の出願に係わる発明の名称
“抗酸化液剤”（特願昭57−91281号、昭和57年５
月31日出願）（特開昭58−208383号）に詳しく開
示された製法で得られるローズマリー及び／又は
セージの天然源抗酸化成分を、C6〜C12の飽和の
脂肪酸グリセリドの少なくとも一種に溶解するこ
とによつて得られた抗酸化液剤も利用できる。こ
の提案によれば、前記の如き同一出願人に係る発
明（特願昭57−075988号、同57−075989号、同57
−075990号、同57−075991号）によつて得られた
ローズマリー及び／又はセージ天然源抗酸化成分
をC6〜C12飽和脂肪酸トリグリセリド或いは該ト
リグリセリドとアルコール類の混合物に溶解する
ことにより該天然源抗酸化成分を高濃度に溶解せ
しめた液剤として得ることができる。
本発明方法によれば、以上に述べたような、プ
ロリンもしくはプロリンのアルコール溶液とロー
ズマリー及び／又はセージの天然源抗酸化成分の
両者を、油脂性食品に添加することによつて、優
れた酸化防止効果を達成することができる。これ
らの添加の時期は適宜に選択でき、油脂性食品原
料、油脂性食品製造工程及び油脂性食品製造後の
任意の時期に添加することができる。
本発明に於て油脂性食品は、最も広義に、油脂
類（精油類を包含する）及びそれらを含有する体
内摂取可能な食品類（嗜好品、調味料類、保健・
滋養強壮剤類を包含する）と定義される。このよ
うな油脂類及び食品類を包含する油脂性食品の例
としては、例えば、以下の如き油脂性食品を例示
することができる。例えば、ラード、ヘツド、チ
キンオイル、タロー、乳脂、魚油、肝油、などの
動物性油脂、サフラワー油、大豆油、コーン油、
菜種油、ごま油、やし油、綿実油、ひまわり油、
落花生油、パーム油、パーム核油、コーヒー油、
米油、などの植物性油脂；バター、チーズ、マー
ガリン、シヨートニング、マヨネーズ、ドレツシ
ング、などの油脂性食品；ハム、ソーセージ、ベ
ーコン、コンビーフ、畜肉缶詰などの畜肉加工食
品；かまぼこ、魚肉ソーセージ、干魚、などの水
産加工食品；その他揚麺類、揚菓子類、焼肉た
れ、乳飲料、清涼飲料などの如き飲食品類、更に
は錠剤、液状経口薬、粉末状経口薬などの如き油
脂含有保健医薬品；レモン油、ライム油、グレー
プフルーツ油なの天然精油を例示することができ
る。
本発明方法の実施に際して、プロリンもしくは
プロリンのアルコール溶液及びローズマリー及
び／又はセージの天然源抗酸化成分の両者を添加
するほかに、所望により、他の添加剤を添加併用
することができる。このような添加剤としては、
天然抗酸化剤、例えばビタミンＥ、オリザノー
ル、フイチン酸、、レシチン及びルチン、ケルセ
チン、ナリンゲニン、ゴシペチンなどのフラボノ
イド類、これらの混合物など；シネルギスト、例
えばクエン酸、Ｌ―アスコルビン酸、及びグリシ
ン、アラニン、セリン、バリン、ロイシン、スレ
オニン、イソロイシン、メチオニン、トリプトフ
アン、ヒスチジン、リジン、アルギニン、グルタ
ミン酸、アスパラギン酸の如きアミノ酸類及びこ
れらの混合物などを例示することができる。
本発明方法の実施に際して、プロリンもしくは
プロリンのアルコール溶液（プロリンとして）及
びローズマリー及び／又はセージの天然源抗酸化
成分、の添加量は比較的少量で充分であり、適宜
に選択することができる。例えば、油脂性食品に
対して約0.0001〜約５重量％程度の添加量を例示
でき、より好ましくは約0.001〜約２重量％の添
加量を例示することができる。又、ローズマリー
及び／又はセージの天然源抗酸化成分とプロリン
の併用割合は任意に選択することができるが、例
えば、約１：100〜約100：１を例示することがで
き、更に好ましくは約１：10〜約10：１を例示す
ることができる。
以下実施例により本発明方法実施の数態様につ
いて更に詳しく例示する。
比較例 １
Ｌ―プロリン10ｇを95％エタノール30ｇに加
え、30℃に加温溶解し、Ｌ―プロリンの25％エタ
ノール溶液を調製した。次いで、このアルコール
溶液をラードに0.08％（Ｌ―プロリンとして0.02
％）添加し試験用試料を調製した（比較品No.１）。
実施例 １
セージ粉末100ｇに95％エタノール500ｇを加え
て、約75℃で２時間攪拌した。次いで遠心分離に
よつて不溶性固形物を分離、除去して抗酸化成分
含有アルコール溶液を得た。次いでこの溶液に活
性炭５ｇを添加した室温にて約30分間攪拌後濾紙
濾過し、次いで得られた活性炭処理液を予めエタ
ノールに浸漬した強酸性陽イオン交換樹脂（商品
名ダウエツクス50W）200mlを充填したガラスカ
ラム（直径４cm、高さ20cm）上部から滴下してイ
オン交換樹脂処理液490ｇを得た。
次いで上記処理液を常圧下約80℃で約50ｇに濃
縮し、これに約85゜−90℃の熱水300ｇを加えて10
分間混合攪拌した後濾紙濾過して水不溶性固形物
を採取し、50〜60℃／0.4〜0.02mmHgにて真空乾
燥して無色、無味、無臭の抗酸化性成分濃縮物
7.8ｇを得た。次いで該濃縮物１ｇを95％エタノ
ール100ｇに溶解し、セージ抗酸化成分の１％エ
タノール溶液を調製した。ラードに対し、該アル
コール溶液を１％（セージの抗酸化成分として
0.01％）と比較例１で用いたプロリンの25％エタ
ノール溶液を0.04％（プロリンとして0.01％）と
を添加した試料を調製した（本発明品No.１）
比較例 ２及び３
同様に、比較のために前記セージ抗酸化成分の
１％エタノール溶液をラードに２％（抗酸化成分
として0.02％）添加品（比較品No.２）及び、トコ
フエロールミツクス（エーザイ(株)天然ビタミン
Ｅ）の50％エタノール溶液0.04％（トコフエロー
ルミツクスとして0.02％）添加品（比較品No.３）
を調製し、これらの試料を抗酸化剤無添加のラー
ドをコントロールとして、AOM法による抗酸化
力の比較を行つた。即ち、上記試料20mlを試験管
に入れ、97.8℃にて毎分2.33mlの空気を吹き込
み、POV（過酸化物価）が30meq／Kgに達するま
での時間を測定した。
結果を第１表に示す。
The present invention relates to a method for preventing the oxidation of oil-based foods, which can effectively prevent unfavorable deterioration due to oxidation of oil-based foods. The present invention relates to a method for preventing oxidation of oil-based foods, which can exhibit improved and complementary effects by adding both source antioxidant components. Conventional methods for preventing oxidation of fats or oil-containing foods and drinks include butylated hydroxy anisole (BHA), dibutylated hydroxytoluene (BHT),
Synthetic antioxidants such as nordihydroguaiaretic acid (NDGA) and gallic acid esters have been used, but in recent years their safety has been questioned, and safer natural alternatives have been used. Various antioxidants have been studied. Many proposals have been made for the use of such natural antioxidants, such as the use of natural vitamin E, γ-oryzanol, quercetin, sezamol, sezamorin, gallic acid, rutin, and herbal spice extracts. Some of them are already in practical use. However, the above-mentioned natural antioxidants are not necessarily satisfactory in terms of economy, supply stability, and antioxidant effect. Furthermore, all of the synthetic and natural antioxidants exemplified above are fat-soluble, so if they are not dissolved in fats and oils in advance,
The antioxidant effect cannot be fully exhibited. Therefore, it has been difficult to prevent the oxidation of fats and oils present in foods that use water as a medium. As a method to improve such drawbacks, several proposals have been made, for example, adding food-grade emulsifiers to the above-mentioned natural antioxidant substances to improve their dispersibility (Japanese Patent Publication No. 56-16196, 55-89383, Japanese Patent Publication No. 56-
32982). However, even with the proposals as exemplified above, the antioxidant is only dispersed, and there is a disadvantage in that the antioxidative improvement effect thereof is limited.
Furthermore, proposals are known to utilize amino acids as antioxidant synergists. For example, there has been a proposal to use amino acids such as methionine, tryptophan, and histidine as synergists of flavonoids (Japanese Patent Application Laid-open No. 55-54883), or a mixture of vitamin E and emulsifiers, and alanine, glycine, leucine, serine, and valine as synergists. , a proposal to incorporate amino acids such as threonine and isoleucine (Japanese Patent Application Laid-open No. 19048/1983) is known. The present inventors have searched for various antioxidant substances that can overcome the drawbacks and disadvantages of conventional synthetic or natural antioxidants as described above, are completely soluble in foods, and are compatible with fats and oils. As a result, by adding both proline and natural antioxidant components of rosemary and/or sage to oily foods, the above-mentioned drawbacks and disadvantages can be completely solved, and the above-mentioned drawbacks and disadvantages can be completely solved, and it can be specifically formulated into oily foods. It has been discovered that the antioxidant effect is significantly greater than that of conventionally proposed natural antioxidants. Therefore, it is an object of the present invention to propose an improved method for preventing oxidation of fatty foods. The above objects and many other objects and advantages of the present invention will become more apparent from the following description. Proline used in the present invention can be obtained, for example, by treating a hydrolyzate of proteins such as gelatin, casein, gliadin, and tzein with an ion exchange resin, and then treating the neutral amino acid fraction with picric acid or Reinetske's salt. Examples include proline and natural L-proline obtained by fermentation. Furthermore, in addition to L-proline obtained by a synthetic method using L-ornithine or L-glutamic acid as a raw material, examples include DL-proline, D-proline, etc.
A particularly preferred example is L-proline derived from natural products. When carrying out the method of the present invention, at any stage of the oleaginous food or the manufacturing process thereof, proline or an alcoholic solution of proline and a naturally occurring antioxidant of rosemary and/or sage can be added to the oleaginous food. Can prevent food oxidation. Examples of the alcohol in the alcohol solution of proline include ethanol, propylene glycol, glycerin, D-sorbit, any mixture thereof, hydrated products thereof, at least one of these and triglycerides such as triglycerides of medium chain fatty acids. Examples of alcohols that can be ingested in the body in a broad sense include mixtures of these triglycerides and triglycerides alone. From the viewpoint of solubility and handling, it is preferable to use ethanol, especially hydrous ethanol. In the method of the present invention, an excellent complementary antioxidant effect can be achieved by combining proline with natural antioxidant sources of rosemary and/or sage. Such natural source antioxidant components of rosemary and/or sage can be collected from various materials containing the antioxidant components using solvent extraction treatment, adsorbent treatment, distillation treatment, or other separation unit means. can. Examples of materials containing antioxidant components of rosemary and/or sage include dried and pulverized products of rosemary and/or sage; remaining essential oil obtained by subjecting them to steam distillation or other processing to obtain essential oil. Collection residue; these materials can be collected, e.g.
n-pentane, isopentane, petroleum ether, ligroin, n-hexane, methylene chloride,
Ethylene dichloride, ethyl ether, acetone, methyl acetate, ethyl acetate, methanol, ethanol, n-propanol, isopropanol,
Extract with an organic solvent such as n-butanol or a mixture of multiple types of these, remove the solvent from the extract,
For example, oleoresin obtained by distillation under atmospheric pressure to reduced pressure conditions and its extraction residue can be mentioned. Naturally sourced antioxidant components of rosemary and/or sage can be obtained, for example, as an extract obtained by extracting the antioxidant component-containing material as exemplified above with an organic solvent, and further subjected to decolorization treatment, deodorization treatment, etc. be able to. Examples of organic solvents used in the above extraction process include:
For example, polar solvents such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, acetone, propylene glycol, glycerin, ethyl acetate, or, for example, n-pentane, n-hexane, cyclohexane, petroleum ether, ligroin, carbon tetrachloride, Examples include non-polar solvents such as methylene chloride, ethylene dichloride, benzene, toluene, etc., or mixtures of a plurality of these solvents, but extraction with ethanol is particularly preferred. Furthermore, the above-mentioned polar solvents can also be used in the form of a hydrous system, for example a hydrous solvent with a water content of about 10 to about 50%. Various extraction operations and extraction conditions can be selected, but for example, about 0.2 to about 50 times the weight of a polar solvent or a non-polar solvent is added to a material containing antioxidant components such as rosemary and/or sage, and the temperature ranges from room temperature to the boiling point temperature of the solvent used. For example, it can be left standing or stirred for about 5 minutes to about 24 hours. The extraction process can be carried out either batchwise or continuously. For example, an extraction column is packed with a material containing antioxidant components, such as crushed rosemary and/or sage, or crushed or shredded essential oil extraction residue. An example is a column extraction method in which an organic solvent such as an alcohol is continuously introduced from the upper or lower part of the column for column extraction. After performing the extraction operation in this manner, insoluble solid residues are removed using, for example, centrifugation, filtration, compression, or other solid-liquid separation means.
An extract containing naturally occurring antioxidant components of rosemary and/or sage can be obtained. If necessary, a polar solvent or a non-polar solvent may be further added to the insoluble solid content extraction residue and the same operation may be repeated for extraction. In the present invention, a concentrated extract containing natural antioxidant components of rosemary and/or sage obtained by concentrating the extract obtained from rosemary and/or sage by the method as exemplified above and removing the solvent is used. can use things. Further, the extract obtained by the above method is desirably decolorized using an adsorbent such as activated carbon, activated alumina, silica gel, bentonite, acid clay, or diatomaceous earth, and then concentrated. Furthermore, the concentrate obtained by the above method may be deodorized by steam distillation or other means before use. The natural antioxidant components of rosemary and/or sage used in the present invention can be extracted and collected from the antioxidant component-containing material as described above. It is preferable to use an antioxidant component obtained using a method for producing an odorless rosemary and/or sage antioxidant component. For example, an application filed on May 8, 1982 (Patent Application (Sho 57-075988)
(Japanese Patent Publication No. 58-194973). According to the proposed production method, for example, a material containing antioxidant components of rosemary and/or sage selected from rosemary and/or sage, its essential oil extraction residue, and its oleoresin is extracted with alcohol. or a solution obtained by removing the organic solvent from the extract obtained by extracting the material with an organic solvent other than alcohol, and dissolving this in alcohol; rosemary and/or as exemplified above. By treating an alcoholic solution containing antioxidant components of sage with a solid adsorbent and a cation exchange resin, it is possible to obtain naturally sourced antioxidant components of rosemary and/or sage of excellent quality. Examples of natural source antioxidant ingredients produced by other manufacturing methods include those obtained by the manufacturing method disclosed in detail in the title of the invention related to the application filed by the same applicant: "Method for producing natural source antioxidant ingredients": Showa
May 8, 1957 (Patent Application No. 57-075989)
−194974). According to the manufacturing method of this proposal, an alcoholic solution containing antioxidant components of rosemary and/or sage similar to those exemplified in the previous proposal is made into an alkaline hydroalcoholic solution with an alcohol concentration of about 80% by weight or less, and the solution is made into a porous Excellent quality naturally sourced antioxidant components of rosemary and/or sage can be obtained by treating the rosemary and/or sage with a natural resin adsorbent, acidifying the resulting treatment solution, and collecting the solid content. can. In this production method, the antioxidant component-containing alcoholic solution can be treated with a solid adsorbent and/or with a cation exchange resin before being made into the alkaline hydrous alcoholic solution. Furthermore, examples of antioxidant components obtained by other manufacturing methods include the antioxidant components obtained by the manufacturing method disclosed in detail in the title of the invention related to the application filed by the same applicant: "Method for producing natural source antioxidant components": May 8, 1981 (Patent Application No. 57-075990)
58-194975). According to the proposed production, antioxidants of rosemary and/or sage, such as materials containing antioxidant components of rosemary and/or sage, selected from rosemary and/or sage, essential oil extraction residues thereof, and oleoresins thereof, can be obtained. Naturally sourced antioxidant components of excellent quality can be obtained by extracting the oxidized component-containing material with an organic solvent such as those already exemplified in the presence of a solid adsorbent. In this embodiment, an alcohol is used as the organic solvent, and the treatment liquid obtained by extraction with the alcohol can be treated with a cation exchange resin. Furthermore, an application in which the natural source antioxidant components of rosemary and/or sage obtained by the manufacturing method disclosed in detail in the title of the invention filed by the same applicant, ``Method for Extracting Natural Source Antioxidant Components,'' can also be used: Showa May 8, 1957 (Patent Application No. 57-075991)
No. 194976). According to this proposed manufacturing method, rosemary and/or
Or, by subjecting the sage antioxidant component-containing material to an organic solvent extraction treatment as already exemplified at about 90°C to about 180°C under pressurized conditions and collecting the treated liquid,
High quality natural source antioxidant ingredients can be obtained. The organic solvent can be a polar organic solvent or a water-containing product thereof as already exemplified, and
The extraction process can be performed under an inert gas atmosphere. Furthermore, the title of the invention related to the application filed by the same applicant is "Antioxidant liquid agent" (Patent Application No. 1981-91281, May 1982).
Naturally sourced antioxidant components of rosemary and/or sage obtained by the manufacturing method disclosed in detail in Japanese Patent Application Laid-open No. 58-208383) (filed on March 31, 1983) are combined with at least one type of C 6 to C 12 saturated fatty acid glyceride. Antioxidant solutions obtained by dissolving in can also be used. According to this proposal, inventions related to the same applicant as mentioned above (Japanese Patent Application Nos. 57-075988, 57-075989, 57
-075990, No. 57-075991) by dissolving the natural source antioxidant ingredients of rosemary and/or sage in C6 - C12 saturated fatty acid triglyceride or a mixture of said triglyceride and alcohol. It can be obtained as a liquid preparation containing naturally sourced antioxidant components dissolved in high concentration. According to the method of the present invention, as described above, by adding both proline or an alcoholic solution of proline and naturally sourced antioxidant components of rosemary and/or sage to an oil-based food, excellent Antioxidant effect can be achieved. The timing of these additions can be selected as appropriate, and they can be added at any time of the oleaginous food raw material, the oleaginous food production process, or after the oleaginous food production. In the present invention, oil and fat foods in the broadest sense include oils and fats (including essential oils) and foods containing them that can be ingested (luxury items, seasonings, health care products, etc.).
(including nutrient tonics). Examples of oil-based foods including such oils and fats and foods include the following oil-based foods. For example, animal fats and oils such as lard, head, chicken oil, tallow, milk fat, fish oil, liver oil, safflower oil, soybean oil, corn oil,
rapeseed oil, sesame oil, coconut oil, cottonseed oil, sunflower oil,
peanut oil, palm oil, palm kernel oil, coffee oil,
Vegetable oils and fats such as rice oil; Oil-based foods such as butter, cheese, margarine, toning, mayonnaise, and dressings; Processed meat foods such as ham, sausage, bacon, corned beef, and canned meat; Kamaboko, fish sausage, and dried fish Processed marine foods such as , and other foods and drinks such as fried noodles, fried confectionery, yakiniku sauce, milk drinks, soft drinks, etc., as well as oil- and fat-containing health drugs such as tablets, liquid oral medicines, powdered oral medicines, etc.; Lemon Examples include natural essential oils such as oil, lime oil, and grapefruit oil. In carrying out the method of the present invention, in addition to adding both proline or an alcoholic solution of proline and naturally occurring antioxidant components of rosemary and/or sage, other additives may be added and used in combination, if desired. Such additives include
Natural antioxidants such as vitamin E, oryzanol, phytic acid, lecithin and rutin, flavonoids such as quercetin, naringenin, gossypetin, mixtures thereof; synergists such as citric acid, L-ascorbic acid, and glycine, alanine, Examples include amino acids such as serine, valine, leucine, threonine, isoleucine, methionine, tryptophan, histidine, lysine, arginine, glutamic acid, and aspartic acid, and mixtures thereof. When carrying out the method of the present invention, a relatively small amount of proline or an alcoholic solution of proline (as proline) and naturally sourced antioxidant components of rosemary and/or sage is sufficient and can be selected as appropriate. . For example, the amount added may be about 0.0001 to about 5% by weight, more preferably about 0.001 to about 2% by weight, relative to the oil-based food. Further, the ratio of the combination of naturally sourced antioxidant components of rosemary and/or sage and proline can be selected arbitrarily, but for example, about 1:100 to about 100:1 can be exemplified, and more preferably An example is about 1:10 to about 10:1. Hereinafter, several embodiments of the method of the present invention will be illustrated in more detail with reference to Examples. Comparative Example 1 10 g of L-proline was added to 30 g of 95% ethanol and dissolved by heating at 30°C to prepare a 25% ethanol solution of L-proline. Next, add this alcohol solution to lard at 0.08% (0.02% as L-proline).
%) was added to prepare a test sample (comparative product No. 1). Example 1 500 g of 95% ethanol was added to 100 g of sage powder and stirred at about 75° C. for 2 hours. Next, insoluble solids were separated and removed by centrifugation to obtain an alcoholic solution containing antioxidant components. Next, 5 g of activated carbon was added to this solution, and after stirring at room temperature for about 30 minutes, it was filtered with a filter paper. Then, the obtained activated carbon-treated solution was filled with 200 ml of a strongly acidic cation exchange resin (trade name: Dowex 50W) that had been soaked in ethanol in advance. It was dropped from the top of a glass column (diameter 4 cm, height 20 cm) to obtain 490 g of an ion exchange resin treated solution. Next, the above treated solution was concentrated to about 50 g at about 80°C under normal pressure, and 300 g of hot water at about 85°-90°C was added to it for 10 minutes.
After mixing and stirring for a minute, water-insoluble solids were collected by filter paper filtration, and vacuum dried at 50-60℃/0.4-0.02mmHg to obtain a colorless, tasteless, and odorless antioxidant component concentrate.
7.8g was obtained. Next, 1 g of the concentrate was dissolved in 100 g of 95% ethanol to prepare a 1% ethanol solution of the sage antioxidant component. Add 1% of the alcohol solution to lard (as an antioxidant component of sage)
A sample was prepared by adding 0.01%) and 0.04% (0.01% as proline) of the 25% ethanol solution of proline used in Comparative Example 1 (invention product No. 1) Comparative Examples 2 and 3 Similarly, comparison For this purpose, a 1% ethanol solution of the sage antioxidant component was added to lard at 2% (0.02% as an antioxidant component) (comparative product No. 2), and tocopherolmics (Eisai Co., Ltd. Natural Vitamin E) 50% ethanol solution 0.04% (0.02% as tocopherolmics) additive product (comparative product No. 3)
The antioxidant power of these samples was compared using the AOM method using lard with no antioxidant added as a control. That is, 20 ml of the above sample was placed in a test tube, 2.33 ml of air was blown in per minute at 97.8°C, and the time until the POV (peroxide value) reached 30 meq/Kg was measured. The results are shown in Table 1.
【表】
比較例 ４
Ｌ―プロリン１ｇを95％エタノール49ｇに溶解
し、プロリンの２％エタノール溶液を調製し、次
いでこの溶液を、パーム油に１重量％（Ｌ―プロ
リンとして0.02％）添加し、試験用試料を調製し
た（比較品No.４）。
実施例 ２
同様にパーム油に対し、上記プロリンの２％エ
タノール溶液を0.5重量％（プロリンとして0.01
％）と、実施例１で用いたセージ抗酸化成分の１
％エタノール溶液を１重量％（セージ抗酸化成分
として、0.01％）とを添加した試料を調製した
（本発明品No.２）。
比較例 ５及び６
更に比較のため、上記セージ抗酸化成分１％エ
タノール溶液を単独でパーム油に２重量％（セー
ジ抗酸化成分として0.02％）添加試料（比較品No.
５）及びトコフエロールミツクスの２％エタノー
ル溶液をパーム油に１重量％（トコフエロールと
して0.02％）添加試料（比較品No.６）を調製し、
これらの試料を抗酸化剤無添加のパーム油をコン
トロールとして、実施例１と同様にAOM法によ
る試験を実施した。結果を第２表に示した。[Table] Comparative Example 4 1 g of L-proline was dissolved in 49 g of 95% ethanol to prepare a 2% ethanol solution of proline, and this solution was then added to palm oil at 1% by weight (0.02% as L-proline). A test sample was prepared (comparative product No. 4). Example 2 Similarly, 0.5% by weight of the above 2% ethanol solution of proline (0.01% as proline) was added to palm oil.
%) and 1 of the sage antioxidant component used in Example 1.
% ethanol solution (0.01% as sage antioxidant component) was prepared (invention product No. 2). Comparative Examples 5 and 6 For further comparison, a sample (Comparative Product No.
5) and a 2% ethanol solution of tocopherolmics added to palm oil at 1% by weight (0.02% as tocopherol) to prepare a sample (comparative product No. 6).
These samples were tested by the AOM method in the same manner as in Example 1, using palm oil to which no antioxidant was added as a control. The results are shown in Table 2.
【表】【table】
【表】
第１表及び第２表に示した如く、本発明品はラ
ード及びパーム油に対する酸化防止効果が顕著で
あり、トコフエロールに比較しても著しく優れて
いた。[Table] As shown in Tables 1 and 2, the product of the present invention had a remarkable antioxidant effect on lard and palm oil, and was significantly superior to tocopherol.
Claims (1)
アルコール溶液及びローズマリー及び／又はセー
ジの天然源抗酸化成分の両者を添加することを特
徴とする油脂性食品の酸化防止方法。1. A method for preventing oxidation of oil-based foods, which comprises adding both proline or an alcoholic solution of proline and naturally-sourced antioxidant components of rosemary and/or sage to oil-based foods.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57149917A JPS5939279A (en) | 1982-08-31 | 1982-08-31 | Method for preventing oxidation of oleaginous food |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57149917A JPS5939279A (en) | 1982-08-31 | 1982-08-31 | Method for preventing oxidation of oleaginous food |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5939279A JPS5939279A (en) | 1984-03-03 |
| JPH0236223B2 true JPH0236223B2 (en) | 1990-08-16 |
Family
ID=15485407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57149917A Granted JPS5939279A (en) | 1982-08-31 | 1982-08-31 | Method for preventing oxidation of oleaginous food |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5939279A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0490611A (en) * | 1990-08-03 | 1992-03-24 | Murata Mfg Co Ltd | Electronic parts |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6192935B2 (en) * | 2010-10-25 | 2017-09-06 | Ｍｃフードスペシャリティーズ株式会社 | Flavor improver |
| CN104363772B (en) * | 2012-05-01 | 2019-02-12 | Mc食品科技株式会社 | Flavor improving agent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58183796A (en) * | 1982-04-21 | 1983-10-27 | 協和醗酵工業株式会社 | Oil and fat antioxidant and method |
-
1982
- 1982-08-31 JP JP57149917A patent/JPS5939279A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58183796A (en) * | 1982-04-21 | 1983-10-27 | 協和醗酵工業株式会社 | Oil and fat antioxidant and method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0490611A (en) * | 1990-08-03 | 1992-03-24 | Murata Mfg Co Ltd | Electronic parts |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5939279A (en) | 1984-03-03 |
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