JPH03224468A - Antioxidant - Google Patents
AntioxidantInfo
- Publication number
- JPH03224468A JPH03224468A JP1702590A JP1702590A JPH03224468A JP H03224468 A JPH03224468 A JP H03224468A JP 1702590 A JP1702590 A JP 1702590A JP 1702590 A JP1702590 A JP 1702590A JP H03224468 A JPH03224468 A JP H03224468A
- Authority
- JP
- Japan
- Prior art keywords
- antioxidant
- essential oil
- aniseed
- extracted
- extracting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 46
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 43
- 240000004760 Pimpinella anisum Species 0.000 claims abstract description 23
- 235000012550 Pimpinella anisum Nutrition 0.000 claims abstract description 23
- 239000000341 volatile oil Substances 0.000 claims abstract description 20
- 235000013599 spices Nutrition 0.000 claims abstract description 14
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 7
- 239000002798 polar solvent Substances 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001256 steam distillation Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract 2
- 235000007265 Myrrhis odorata Nutrition 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 22
- 239000000284 extract Substances 0.000 abstract description 6
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 4
- 235000013409 condiments Nutrition 0.000 abstract 3
- 235000011089 carbon dioxide Nutrition 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 15
- 239000003925 fat Substances 0.000 description 11
- 235000019197 fats Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- 235000013305 food Nutrition 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000020094 liqueur Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000001909 pimpinella anisum Substances 0.000 description 1
- -1 rhodan iron compound Chemical class 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、香辛料の一種であるアニスシードから抽出し
た抗酸化剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to an antioxidant extracted from aniseed, which is a type of spice.
（従来の技術）
従来、油脂を含む食品の抗酸化剤としてジブチルヒドロ
キシトルエン（ＢＨＴ） 、ブチルヒドロキシアニソー
ル（ＢＨＡ） 、トコフェロール等が使用されている。(Prior Art) Dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), tocopherol, and the like have been used as antioxidants for foods containing fats and oils.
これらの抗酸化剤は、ぞれぞれの特徴をいかして食品に
使い分けられている。しかし、ＢＨＴ、ＢＨＡ等の合成
抗酸化剤には、−定の使用基準があり、添加量、添加食
品が厳しく制限されている。そのため天然の抗酸化剤が
要望され、ローズマリー、セージ、クローブ等の香辛料
の植物の抽出物を天然抗酸化剤としている製品がある。These antioxidants are used in foods depending on their characteristics. However, synthetic antioxidants such as BHT and BHA have certain usage standards, and the amounts added and foods to which they can be added are strictly limited. Therefore, there is a demand for natural antioxidants, and there are products that use extracts of spice plants such as rosemary, sage, and cloves as natural antioxidants.
香辛料の一種であるアニスシードは、主に精油成分がス
ープ類、リキュール類、菓子、肉製品等に用いられてい
る。また、アニスシードの粉末または溶媒抽出物が抗酸
化効果を示すという報告（新田ゆり：調理科学 Ｖｏ
１．１．０．Ｎｏ、４、ｐ２５４−２５７，１９７７・
または・Ｓ、Ａ・Ｋａｌｏｙｅｒａａｓ：ＶＯｌ、２４
＋ ｐ３９−４１．１９４７）と効果を示さないとい
う報告（斉ｍｉ 他：栄ｌと食ｎ、Ｖｏ１．２９．Ｎ
０−７．９４０４−４０９．１９７６、または、斉胚浩
他：栄１１ト食糧、Ｖｏ１．２９．Ｎｏ、９゜ｐ５０５
−５１０．１９７６）があり、その効果については定か
でなかった。また、本発明者が知す得る限りでは、アニ
スシードの精油成分または脂肪成分を除いた香りの少な
い抽出物に高い抗酸化効果があるという報告は見いださ
れなかった。Aniseed, a type of spice, is mainly used for its essential oil components in soups, liqueurs, sweets, meat products, etc. There is also a report that anise seed powder or solvent extract exhibits antioxidant effects (Yuri Nitta: Cooking Science Vo.
1.1.0. No. 4, p254-257, 1977.
Or・S.A.Kaloyeraas: VOl, 24
+ p39-41.1947) and reports that it has no effect (Simi et al.: Ei I and Shokun, Vol. 1.29.N
0-7.9404-409.1976, or Qi Huo et al.: Sakae 11 To Shokuhin, Vol. 1.29. No, 9°p505
-510.1976), and its effect was unclear. Furthermore, to the best of the knowledge of the present inventors, no report has been found that a low-scented extract of aniseed seed from which essential oil components or fat components have been removed has a high antioxidant effect.
（本発明者が解決しようとする問題点）香辛料から抽出
した抗酸化剤は、香辛料の香味を有するものが多い０本
発明は、アニスシードの精油成分を抽出した残渣の有効
利用と共に天然物由来のもので、かつ合成抗酸化荊と同
等以上の効力を持つもので、かつ食品に利用しやすいよ
うに、特異的な香りの少ない抗酸化剤を得ることを目的
とする。(Problems to be Solved by the Inventor) Antioxidants extracted from spices often have the flavor of spices. The purpose of the present invention is to obtain an antioxidant that has an efficacy equal to or higher than that of a synthetic antioxidant, and that has less specific odor so that it can be easily used in foods.
（問題を解決するための手段）
本発明者らは、香辛料の一種であるアニスシードの精油
成分または脂肪成分を抽出した残渣に高い抗酸化能を有
することを見いだした０本発明は、この知見をもとに天
然香辛料のアニスシードから超臨界炭酸ガス抽出法、水
蒸気蒸留法により精油成分または脂肪成分を抽出し、そ
の残渣を極性溶媒または非極性溶媒で抽出した抽出物を
有効成分とする抗酸化剤である。または、アニスシード
から極性溶媒または非極性溶媒で抽出し、その抽出物を
分画し、精油成分または脂肪成分以外の画分を有効成分
する抗酸化剤である。(Means for Solving the Problem) The present inventors have discovered that the residue obtained by extracting the essential oil component or fat component of aniseed, which is a type of spice, has a high antioxidant ability.The present invention is based on this finding. The essential oil component or fat component is extracted from the natural spice aniseed using supercritical carbon dioxide gas extraction method and steam distillation method, and the residue is extracted with a polar or non-polar solvent. It is an oxidizing agent. Alternatively, it is an antioxidant that is extracted from aniseed with a polar or non-polar solvent, fractionated, and contains fractions other than essential oil components or fat components as active ingredients.
（作用）
天然の香辛料から抽出した抗酸化剤であり、精油成分を
除いているため香りが少な（、ＢＨＡと同等以上の抗酸
化力を持っている。(Action) It is an antioxidant extracted from natural spices, and has little fragrance because it does not contain essential oil components (and has an antioxidant power equal to or higher than BHA).
（実施例１）
超臨界炭酸ガス抽出法により精油成分または脂肪成分を
除去したアニスシードの残渣を極性溶媒または非極性溶
媒で抽出し、その抽出物を存効成分とする抗酸化剤の効
果について具体的に述べる。(Example 1) Regarding the effect of an antioxidant using a polar or non-polar solvent to extract the residue of aniseed seeds from which essential oil components or fat components have been removed by supercritical carbon dioxide extraction method and using the extract as an active ingredient. Let's be specific.
アニスシードの粉末（１３０，１３ｇ）を超臨界炭酸ガ
ス抽出装置に供した。抽出条件は、２０５ ｋ ｇ ／
ｃ ｍ富、温度４０℃、抽出時間３時間であった。抽
出条件は、必ずしもこれに限られるものではない、この
抽出によりアニスシードの精油成分、一部の油脂（合計
６．７１ｇ）が抽出された。アニスシードの抽出残渣に
エタノールを約４倍重量入れ、−晩４℃の暗所で振盪し
濾紙で濾過した。濾過残渣を熱エタノールで抽出を行い
濾過する操作を２回繰り返した。それぞれの濾液を集め
約４０℃〜５０℃で加温しながらロターリーエバボレー
ターで乾固物（２５，０２ｇ）を得た。Aniseed powder (130.13 g) was subjected to a supercritical carbon dioxide extraction device. The extraction conditions are 205 kg/
cm rich, temperature 40°C, extraction time 3 hours. The extraction conditions are not necessarily limited to these. Through this extraction, essential oil components of aniseed and some fats and oils (6.71 g in total) were extracted. Approximately 4 times the weight of ethanol was added to the anise seed extraction residue, and the mixture was shaken overnight at 4°C in the dark and filtered through a filter paper. The operation of extracting the filtration residue with hot ethanol and filtration was repeated twice. The respective filtrates were collected and heated at about 40°C to 50°C using a rotary evaporator to obtain a dry product (25.02 g).
この抽出条件は、−例であって必ず・しもこれに限られ
るわけではない、乾固物の一部は、８０％エタノールに
溶かし、抗酸化剤（Ａ）として使用した。また、乾固物
の一部を９９．５％エタノールに懸濁し、その上清液を
抗酸化剤（Ｂ）として使用した。These extraction conditions are examples and are not necessarily limited to these. A portion of the dried solids was dissolved in 80% ethanol and used as an antioxidant (A). Further, a part of the dried product was suspended in 99.5% ethanol, and the supernatant liquid was used as an antioxidant (B).
以下、抗酸化剤（Ａ）と（Ｂ）の抗酸化効果の試験結果
について述べる。The test results of the antioxidant effects of antioxidants (A) and (B) will be described below.
抗酸化剤（Ａ）の効果は、リノール酸の酸化の抑制の程
度を測定するロダン鉄性によって調べた。The effect of the antioxidant (A) was examined by rhodan iron resistance, which measures the degree of inhibition of linoleic acid oxidation.
ロダン鉄性は、食品工学実験書（上）、京都大学農学部
食品工学教室編、Ｐ２Ｓ５−６３５、養賢堂（１９７９
）を参考に抗酸イヒ剤（Ａ）を乾固物重量７０．０２％
添加し、保存温度を６０℃で行った。ＢＨＡ （０，０
２％添加）、ｂｌａｎｋ （無添加）を対照とした。結
果を表１に示した。抗酸化剤（Ａ）は、ＢＨＡより抗酸
化力が強いことがわかる。Rodan iron properties are described in Food Engineering Experiment Book (Part 1), edited by Department of Food Engineering, Faculty of Agriculture, Kyoto University, P2S5-635, Yokendo (1979).
), the dry weight of anti-acid agent (A) was 70.02%.
and storage temperature was 60°C. BHA (0,0
2% addition) and blank (no addition) were used as controls. The results are shown in Table 1. It can be seen that the antioxidant (A) has stronger antioxidant power than BHA.
表１ 吸光度（５００ｎｍ）
日数 （Ａ） ＢＨＡ ｂｌａｎｋ
ｏ ０．００６ ０．０Ｇ４ ０．００５
１ ０．０２５ ０．０９７ Ｇ、３５１
２ ０．０３２ ０．４０８ １．４２
５４ ０．０５６ Ｇ、５１７抗酸化剤（Ｂ
）の効果は、ラードの酸化に対する試験を行った。市販
されている抗酸化剤無添加のラードに対して抗酸化剤Ｃ
Ｂ）を乾固物重量で０．０２％になるように添加し、６
０℃保存し、過酸化物価を経日的に測定した。対照とし
て無添加のラードとＢＨＡを０．０２％添加したラード
を同時に６０℃で保存し、過酸化物価を測定した。Table 1 Absorbance (500nm) Days (A) BHA blank
o 0.006 0.0G4 0.005
1 0.025 0.097 G, 351
2 0.032 0.408 1.42
54 0.056 G, 517 Antioxidant (B
) was tested against the oxidation of lard. Antioxidant C compared to commercially available lard without antioxidants.
B) was added to 0.02% by dry weight, and 6
It was stored at 0°C and the peroxide value was measured over time. As a control, lard without any additives and lard with 0.02% BHA added were simultaneously stored at 60°C and their peroxide values were measured.
表２にその結果を示した。抗酸化剤（Ｂ）の方はＢＨＡ
と同等に抗酸化効果が強いことがわかる。Table 2 shows the results. Antioxidant (B) is BHA
It can be seen that the antioxidant effect is equally strong.
日数
０
５
０
表２ ＰＯＶ （ｍｅ ｑ／ｋ ｇ）ＣＢ）
ＢＨＡ ｂｌａｎｋｌ、６１
１．６１ １．６１３．７？
４．２３ ４．５１？、９５ ９．
２３ １０．４０１４．６６ １５．８３
２２．２６２９’、２４ ２２．１０ ５
８．０．６（実施例２）
アニスシードを水蒸気蒸留し、精油成分を除いた残渣を
有効成分とする抗酸化剤の効果について具体的に述べる
。Number of days 0 5 0 Table 2 POV (me q/kg g) CB)
BHA blankl, 61
1.61 1.613.7?
4.23 4.51? , 95 9.
23 10.4014.66 15.83
22.2629', 24 22.10 5
8.0.6 (Example 2) The effect of an antioxidant whose active ingredient is the residue obtained by steam distilling aniseed and removing essential oil components will be specifically described.
アニスシードの粉末（３０ｇ）を精油成分がほとんど出
なくなるまで水蒸気蒸留を行った。その残渣を濾紙で濾
過した。濾液を凍結乾燥し乾固物（７，５９ｇ）を得た
。これをイオン交換水に溶解し、抗酸化剤（Ｃ）とした
、濾過した残渣をヘキサンで一晩抽出し、４０℃で加温
しながらロータリーエバポレーターで濃縮乾固（４，７
８ｇ）し、７０％エタノールに溶解し、これを抗酸化剤
（Ｄ）とした、それぞれの抗酸化剤のリノール酸に対す
る抗酸化試験を前述のロダン鉄性で行った。Aniseed powder (30 g) was subjected to steam distillation until almost no essential oil components were extracted. The residue was filtered through filter paper. The filtrate was freeze-dried to obtain a dry product (7.59 g). This was dissolved in ion-exchanged water and used as an antioxidant (C). The filtered residue was extracted with hexane overnight, and concentrated to dryness (4,7
8g) was dissolved in 70% ethanol and used as an antioxidant (D).Antioxidant tests were conducted on each antioxidant against linoleic acid using the above-mentioned rhodan iron compound.
抗酸化剤の添加量は、いずれも乾固物重量で０゜０２％
であった。また、ＢＨＡ （０，０２％添加）、ｂｌａ
ｎｋ（［添加）を対照とした。結果を表３に示した。抗
酸化剤（Ｃ）、（Ｄ）は、Ｂ）ＩＡより効果があること
がわかる。The amount of antioxidant added was 0.02% by dry weight in all cases.
Met. In addition, BHA (0.02% addition), bla
nk ([added)] was used as a control. The results are shown in Table 3. It can be seen that antioxidants (C) and (D) are more effective than B) IA.
表３ 吸光度
（Ｃ）
０．０６７
０．０６５
０．０５Ｂ
０．８５１
０．０４５
（５００ｎｍ）
（Ｄ＞
０．０７４
０．１１１
０．１３８
０．１４７
０．１８９
日数
０ ０゜
ｌ ０゜
２ ０゜
３ ０゜
４ ０゜
ＢＨＡ ｂｌａｎｋ
０６９ ０、 ０？２
０７４ １．１６７
１５
４７
７２
（実施例３）
アニスシードを極性溶媒、または非橿性溶媒で抽出し、
その抽出物を分画し、精油成分または脂肪成分以外の画
分を抗酸化剤とする方法について具体的に述べる。Table 3 Absorbance (C) 0.067 0.065 0.05B 0.851 0.045 (500nm) (D> 0.074 0.111 0.138 0.147 0.189 Days 0 0゜l 0゜2 0゜3 0゜4 0゜BHA blank 069 0, 0?2 074 1.167 15 47 72 (Example 3) Extracting aniseed with a polar solvent or a non-polar solvent,
A method of fractionating the extract and using fractions other than essential oil components or fat components as an antioxidant will be specifically described.
アニスシードの粉末（３０ｇ）にエタノールを約４侶重
量入れ、１晩４℃の冷暗所て放置した。Approximately four times the weight of ethanol was added to aniseed powder (30 g), and the mixture was left in a cool, dark place at 4° C. overnight.
それを濾紙で濾過し、その減液残渣を熱エタノールで２
回抽出し、濾過した。それぞれの濾液を集め、約４０℃
で加温しながらロータリーエバポレーターで濃縮乾固し
た。この乾固物をクロロホルムと水を使用して分画した
。精油成分または脂肪成分は、クロロホルム層に抽出さ
れた。水層を凍結乾燥して乾固物（３，３３ｇ）を得た
。この乾固物を８０％エタノールに懸濁し抗酸化剤（Ｅ
）として、前述のロダン鉄性でリノール酸に対する抗酸
化試験を行った。抗酸化剤（Ｅ）は、乾固物重量で０．
０２％を添加した。対照としてＢ ＨＡ（０，０２％添
加）、ｂｌａｎｋ （無添加）も試験した０表４に結果
を示した。Ｂ１１Ａより抗酸化剤（Ｅ）の方が効果があ
ることがわかる。Filter it with filter paper, and dilute the reduced liquid residue with hot ethanol.
Extracted twice and filtered. Collect each filtrate and heat at approximately 40°C.
The mixture was concentrated to dryness using a rotary evaporator while heating. This dried product was fractionated using chloroform and water. Essential oil components or fat components were extracted into the chloroform layer. The aqueous layer was freeze-dried to obtain a dry product (3.33 g). This dry matter was suspended in 80% ethanol and an antioxidant (E
), an antioxidant test against linoleic acid was conducted using the aforementioned rhodan iron. The antioxidant (E) has a dry weight of 0.
02% was added. As a control, BHA (added at 0.02%) and blank (no addition) were also tested, and the results are shown in Table 4. It can be seen that antioxidant (E) is more effective than B11A.
表４ 吸光度（５００ｎｍ）
日数 （Ｅ） ＢＨＡ ｂｌａｎｋ
Ｏ，０，０１？ ０．００９ ０．０２２１
０．０６４ ０．１０８ １．５０
０２ ０．１００ ０．２４８ ２
．６Ｂ１３ ０．１３２ ０．７７３
３．０８５（実施例４）
次に、更に分画し、酸性区分の抗酸化効果について述べ
る。アニスシードの粉末（３０ｇ）を前述したようにエ
タノールで抽出した。抽出乾固物を水で洗い取り、６Ｎ
の塩酸を用いてｐ Ｈ３に下げ、酢酸エチルで数回抽出
した。その酢酸エチルを取り、イオン交換水で水洗いし
、濃縮乾固した。Table 4 Absorbance (500nm) Days (E) BHA blank
O, 0, 01? 0.009 0.0221
0.064 0.108 1.50
02 0.100 0.248 2
．． 6B13 0.132 0.773
3.085 (Example 4) Next, the antioxidant effect of the acidic fraction will be described by further fractionation. Aniseed powder (30 g) was extracted with ethanol as described above. Wash the extracted dry matter with water and add 6N
The pH was lowered to 3 using hydrochloric acid and extracted several times with ethyl acetate. The ethyl acetate was removed, washed with ion-exchanged water, and concentrated to dryness.
この乾固物を０．１Ｍリン酸緩衝液（ｐＨ８）に懸濁し
、再び酢酸エチルで数回抽出した。この酢酸エチルを中
性百分として除去した。この中性画分に精油成分、脂肪
成分が移行した。水層部を６Ｎの塩酸でｐＨ３に調整し
、酢酸エチルで数回抽出した。この酢酸エチルを取り約
４０℃で加温しながら減圧下にて酢酸エチルを完全に留
去して乾固物を得た。これをエタノールに溶解したもの
を抗酸化剤（Ｆ）とした。This dried product was suspended in 0.1M phosphate buffer (pH 8) and extracted several times with ethyl acetate again. The ethyl acetate was removed as a neutral percentage. Essential oil components and fat components were transferred to this neutral fraction. The aqueous layer was adjusted to pH 3 with 6N hydrochloric acid and extracted several times with ethyl acetate. This ethyl acetate was taken and heated at about 40°C, and ethyl acetate was completely distilled off under reduced pressure to obtain a dry product. This was dissolved in ethanol and used as an antioxidant (F).
この抗酸化剤（Ｆ）のラードに対する抗酸化試験を行っ
た。試験条件は、無添加のラードに対して乾固物で０．
０２％添加して１７０℃で６０分間加熱した後、６０℃
で保存し経日的に過酸化物価を測定した。ＢＨＡ （０
，０２％）、無添加（ｂｌａｎｋ）も同様に試験した。This antioxidant (F) was tested for antioxidation against lard. The test conditions were 0.0% on dry matter for unadded lard.
After adding 02% and heating at 170℃ for 60 minutes, 60℃
The peroxide value was measured over time. BHA (0
, 02%) and no additives (blank) were similarly tested.
実験結果を表５に示した。アニスシードの酸性画分は、
Ｂｆ（Ａより効果があり、熱にも強いことがわかる。The experimental results are shown in Table 5. The acidic fraction of aniseed is
Bf (It can be seen that it is more effective than A and is resistant to heat.
表５ ＰＯＶ （ｍｅｑ／ｋｇ）
日数 （Ｆ） ＢＨＡ ｂｌａｎ
ｋｏ ２．５６ ２．７３ ２
．７９１ ２．７７ ３．３３
３．５１７ ４．１？ ８．３３
８．０６１３ ６．８Ｂ １５．４７
１５．４０１６ １２．９７ ２６．２２
３０．２２（発明の効果）
本発明により得られた抗酸化剤は・ＢＨＡ、！−同等以
上の抗酸化力を有し・かつ香辛料特有の臭いが少ないた
め多種の食品に利用できる。また、アニスシードの精油
成分または脂肪成分を抽出した残渣の有効利用ができる
・Table 5 POV (meq/kg) Days (F) BHA blanc
ko 2.56 2.73 2
．． 791 2.77 3.33
3.517 4.1? 8.33
8.0613 6.8B 15.47
15.4016 12.97 26.22
30.22 (Effect of the invention) The antioxidant obtained by the present invention is -BHA! -It can be used in a wide variety of foods because it has an antioxidative power equal to or higher than that of spices and has less odor characteristic of spices. In addition, the residue after extracting the essential oil component or fat component of anise seed can be effectively used.
Claims (1)
は脂肪成分を抽出除去し、得られた残渣から非極性溶媒
または極性溶媒で抽出した物質を有効成分とする抗酸化
剤 ２）アニスシードの精油成分または脂肪成分の抽出方法
が超臨界炭酸ガス抽出法である特許請求の範囲第１項記
載の抗酸化剤 ３）アニスシードの精油成分の抽出方法が水蒸気蒸留法
である特許請求の範囲第１項記載の抗酸化剤４）アニス
シードから極性溶媒または非極性溶媒で抽出し、その抽
出物を分画し、精油成分または脂肪成分以外の画分を有
効成分とする抗酸化剤[Scope of Claims] 1) Antioxidant 2 whose active ingredient is a substance extracted from aniseed, a type of spice, by extracting essential oil components or fat components and extracting the resulting residue with a non-polar solvent or a polar solvent. ) The antioxidant according to claim 1, wherein the method for extracting the essential oil component or fat component of anise seed is a supercritical carbon dioxide gas extraction method; 3) The patent, wherein the method for extracting the essential oil component of anise seed is a steam distillation method. Antioxidant according to claim 1 4) Antioxidant extracted from aniseed with a polar or non-polar solvent, fractionated, and containing fractions other than essential oil components or fat components as active ingredients. agent
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1702590A JPH03224468A (en) | 1990-01-26 | 1990-01-26 | Antioxidant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1702590A JPH03224468A (en) | 1990-01-26 | 1990-01-26 | Antioxidant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03224468A true JPH03224468A (en) | 1991-10-03 |
Family
ID=11932454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1702590A Pending JPH03224468A (en) | 1990-01-26 | 1990-01-26 | Antioxidant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03224468A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106281702A (en) * | 2016-08-25 | 2017-01-04 | 苏州森佰生物科技有限公司 | Artemisia argyi Levl. et Van. var. argyi cv. Qiai quintessence oil and its preparation method and application |
-
1990
- 1990-01-26 JP JP1702590A patent/JPH03224468A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106281702A (en) * | 2016-08-25 | 2017-01-04 | 苏州森佰生物科技有限公司 | Artemisia argyi Levl. et Van. var. argyi cv. Qiai quintessence oil and its preparation method and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0038959B1 (en) | Preservatives from herbs | |
| CA1297718C (en) | Herb flavoring and/or antioxidant composition and process | |
| US5017397A (en) | Process for extracting antioxidants from Labiatae herbs | |
| JPS6152656B2 (en) | ||
| US4877635A (en) | Herb flavoring and/or antioxidant composition and process | |
| KR0133651B1 (en) | Method for Preparing Liquid Antioxidant Fragrance Extract | |
| JP2008167685A (en) | Process for producing flavored oils and fats | |
| CA2157664C (en) | Process for obtaining ultra pure egg oil and its use | |
| JPH0617050A (en) | Process for producing natural plant antioxidants | |
| JPH01218549A (en) | Flavor oil and its production | |
| JPH03224468A (en) | Antioxidant | |
| DE69937826T2 (en) | METHOD FOR THE EXTRACTION OF ANTIOXIDANTS FROM LABIATES AND ITS EXTRACTED PRODUCTS | |
| JPS6136724B2 (en) | ||
| JP2006160825A (en) | Antioxidant composition | |
| JP2857786B2 (en) | Production method of flavor oil | |
| JPH03293001A (en) | Method for deodorizing antioxidant component extracted from natural resouce | |
| JP7009289B2 (en) | How to suppress the green leaf-like flavor of Japanese pepper oil | |
| JPS59176385A (en) | Preparation of antioxidant | |
| JPS6374463A (en) | soybean processed food | |
| JPS59157173A (en) | Antioxidant | |
| JP2519149B2 (en) | Antioxidant | |
| JPS5852215A (en) | Soft capsule pharmaceutical containing unsaturated fat or oil | |
| JPS5831962A (en) | emulsified food | |
| JPH0453895A (en) | Production of natural anti-oxidant | |
| JPH0256392B2 (en) |