JPS6148520B2 - - Google Patents
Info
- Publication number
- JPS6148520B2 JPS6148520B2 JP53032489A JP3248978A JPS6148520B2 JP S6148520 B2 JPS6148520 B2 JP S6148520B2 JP 53032489 A JP53032489 A JP 53032489A JP 3248978 A JP3248978 A JP 3248978A JP S6148520 B2 JPS6148520 B2 JP S6148520B2
- Authority
- JP
- Japan
- Prior art keywords
- phospholipids
- oil
- oils
- fats
- heating
- 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
Links
- 150000003904 phospholipids Chemical class 0.000 claims description 43
- 239000003921 oil Substances 0.000 claims description 27
- 239000003925 fat Substances 0.000 claims description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 13
- 239000001384 succinic acid Substances 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 description 26
- 235000019197 fats Nutrition 0.000 description 14
- KZQSXALQTHVPDQ-UHFFFAOYSA-M sodium;butanedioate;hydron Chemical compound [Na+].OC(=O)CCC([O-])=O KZQSXALQTHVPDQ-UHFFFAOYSA-M 0.000 description 5
- 239000008347 soybean phospholipid Substances 0.000 description 5
- 235000019482 Palm oil Nutrition 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- -1 skimming Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】
本発明は油脂中に0.2重量%以上の濃度で溶解
または分散しているリン脂質を150℃以上の温度
に加熱した際に必然的に生ずるリン脂質の褐変現
象を抑制する方法に関するものである。Detailed Description of the Invention The present invention suppresses the browning phenomenon of phospholipids that inevitably occurs when phospholipids dissolved or dispersed in fats and oils at a concentration of 0.2% by weight or higher are heated to a temperature of 150°C or higher. It's about how to do it.
リン脂質は、乳化作用等の界面活性作用に優れ
ているほか、抗酸化作用や血中コレステロール低
下作用等の薬理効果もあることが知られているた
め、食品工業、一般工業、医薬、飼料用等として
大量に利用されている。 Phospholipids have excellent surfactant effects such as emulsifying effects, and are also known to have pharmacological effects such as antioxidant effects and blood cholesterol lowering effects, so they are used in the food industry, general industry, medicine, and feed. It is widely used as such.
また、最近、鉄板焼き料理の普及にともないリ
ン脂質のスパツタリング現象(油滴がパチパチと
激しく飛びはねる現象)抑制効果が注目され、該
リン脂質を植物性液状油に溶解することにより油
滴のはねを防止した鉄板焼き用油が脚光を浴びて
いる。 In addition, recently, with the spread of teppanyaki cooking, the effect of phospholipids on suppressing the sputtering phenomenon (a phenomenon in which oil droplets crackle and fly violently) has attracted attention. Teppanyaki oil that prevents splashing is in the spotlight.
しかしながら、リン脂質は極めて不安定な物質
で、油脂に保護された状態にあつても150℃以上
の温度に加熱すると褐変現象を生じて黒褐色に着
色してしまうという欠点を有するため用途、利用
法、使用量等がかなり限定されてしまう。 However, phospholipids are extremely unstable substances, and even when they are protected by fats and oils, they have the disadvantage of browning and becoming blackish brown when heated to temperatures above 150°C. , the amount of use, etc. is quite limited.
本発明者は、かかるリン脂質の加熱褐変現象に
基づく欠点を解消するため種々研究の結果、油脂
中に0.2重量%以上の濃度で溶解または分散して
いるリン脂質を150℃以上の温度に加熱するに当
り、加熱前または加熱中の段階において、コハク
酸またはクハク酸のナトリウム塩を混合すること
によりリン脂質の加熱褐変現象を抑制し得ること
を見出し、本発明を完成した。 In order to solve the drawbacks of phospholipids caused by heat browning, the present inventor conducted various studies and found that phospholipids dissolved or dispersed in fats and oils at a concentration of 0.2% by weight or more were heated to a temperature of 150°C or higher. In doing so, the present invention was completed based on the discovery that the heating browning phenomenon of phospholipids can be suppressed by mixing succinic acid or a sodium salt of succinic acid before or during heating.
本発明の目的に使用し得るリン脂質の例として
は、大豆リン脂質、コーンリン脂質、綿実油リン
脂質、ナタネリン脂質等があり、また、これらの
リン脂質には、ケフアリン含分を持つにもかかわ
らずレシチンと言われる市販のリン脂質、あるい
はケフアリン含量の少ないもしくはケフアリン含
量の無い精製レシチン等が含まれる。 Examples of phospholipids that can be used for the purposes of the present invention include soybean phospholipids, corn phospholipids, cottonseed oil phospholipids, rapeseed phospholipids, etc.; These include commercially available phospholipids called lecithin, purified lecithins with low or no kephalin content, and the like.
また、これらのリン脂質を溶解または分散せし
める油脂としては、例えば大豆油、とうもろこし
油、綿実油、ナタネ油、ゴマ油、ひまわり油、落
花生油等の常温で液状を呈する植物油、パーム
油、パーム核油、ヤシ油、各種硬化油、バター、
マーガリン、シヨートニング、ヘツト、ラード等
の常温で固状または半固状を呈する動植物油脂等
があり、これらの油脂には未だ精製されていない
粗製の油脂あるいは脱ガム、脱酸、脱色、脱臭
等、公知の油脂精製工程の1種または2種以上を
施した精製油脂等が含まれる。 Examples of oils and fats that dissolve or disperse these phospholipids include vegetable oils that are liquid at room temperature such as soybean oil, corn oil, cottonseed oil, rapeseed oil, sesame oil, sunflower oil, and peanut oil; palm oil; palm kernel oil; Coconut oil, various hydrogenated oils, butter,
There are animal and vegetable oils and fats that are solid or semi-solid at room temperature, such as margarine, skimming, fat, and lard. Refined oils and fats that have been subjected to one or more known oil and fat refining processes are included.
本発明において油脂中に溶解または分散してい
るリン脂質の濃度を0.2重量%以上と限定したの
は、これ以下の濃度、例えば精製油脂中に痕跡程
度存在しているリン脂質の濃度では、150℃以上
の温度に加熱してもリン脂質の褐変現象に基づく
油脂の着色がほとんど無いため、実用上、問題を
生じないからである。 In the present invention, the concentration of phospholipids dissolved or dispersed in fats and oils is limited to 0.2% by weight or more, because if the concentration is lower than this, for example, the concentration of phospholipids present in trace amounts in refined fats and oils, 150% This is because even if heated to a temperature of .degree. C. or higher, there is almost no coloration of the oil or fat due to the browning phenomenon of phospholipids, so no problem arises in practice.
また、リン脂質の加熱温度を150℃以上と限定
したのは、油脂中に0.2重量%以上の濃度で溶解
または分散しているリン脂質は150℃程度の温度
から急激に褐変現象を生じて黒褐色化するためで
あり、それ以下の温度ではほとんど褐変しないか
らである。 In addition, the heating temperature of phospholipids was limited to 150℃ or higher because phospholipids dissolved or dispersed in fats and oils at a concentration of 0.2% by weight or higher rapidly turn brown from a temperature of about 150℃, turning black. This is because browning occurs at lower temperatures.
本発明においては、コハク酸またはコハク酸の
ナトリウム塩を油脂中に溶解または分散している
リン脂質に対し3重量%以上、好ましくは20重量
%以上、該リン脂質の加熱前または加熱中の段階
において添加、混合することにより、リン脂質の
加熱褐変現象を著るしく抑制し得るものである。 In the present invention, succinic acid or a sodium salt of succinic acid is added in an amount of 3% by weight or more, preferably 20% by weight or more, based on the phospholipid dissolved or dispersed in fat or oil, before or during heating of the phospholipid. By adding and mixing the phospholipids in the phospholipids, the heating browning phenomenon of phospholipids can be significantly suppressed.
油脂中に溶解または分散しているリン脂質を
150℃以上の温度に加熱するに当り、加熱前また
は加熱中の段階において、コハク酸またはコハク
酸のナトリウム塩を混合するとリン脂質の加熱褐
変現象を抑制し得る事実は本発明者らが現象とし
て捕えたものであり、その詳細な理由については
未だ明らかでない。 Phospholipids dissolved or dispersed in fats and oils
The present inventors have discovered that the heating browning phenomenon of phospholipids can be suppressed by mixing succinic acid or a sodium salt of succinic acid before or during heating when heating to a temperature of 150°C or higher. The detailed reason for this is still unclear.
本発明方法によれば、油脂中に溶解または分散
しているリン脂質の加熱褐変現象を抑制し得るの
でリン脂質の加熱時の欠点を有してその利用面を
さらに拡大することができる。 According to the method of the present invention, the heating browning phenomenon of phospholipids dissolved or dispersed in fats and oils can be suppressed, so that the use of phospholipids can be further expanded despite the disadvantages of heating phospholipids.
次に本発明の実施例を示す。 Next, examples of the present invention will be shown.
実施例 1
精製とうもろこし油100gに大豆リン脂質(豊
年製油K.K.製、AYレシチン)3gを溶解して得
たリン脂質の油脂溶液を容量300mlのフラスコに
採り、これに無水コハク酸2gを加え、よく撹拌
した後、180℃に加熱した油浴中で10分間加熱し
たところ、リン脂質の油脂溶液は該リン脂質の褐
変現象に基づく着色がかなり抑制され、該油脂溶
液は透明な淡褐色を呈していた。Example 1 A phospholipid oil/fat solution obtained by dissolving 3 g of soybean phospholipids (AY lecithin manufactured by Hounen Oil KK) in 100 g of purified corn oil was placed in a 300 ml flask, and 2 g of succinic anhydride was added thereto. After stirring, the phospholipid oil solution was heated for 10 minutes in an oil bath heated to 180°C, and the coloring caused by the browning phenomenon of the phospholipids was significantly suppressed, and the oil solution had a transparent light brown color. Ta.
一方、対照として、同じ濃度の大豆リン脂質の
油脂溶液を無水コハク酸を加えることなく同様に
加熱したところ、該溶液はリン脂質が褐変し、黒
褐色に着色した。 On the other hand, as a control, when an oil and fat solution of soybean phospholipids at the same concentration was heated in the same manner without adding succinic anhydride, the phospholipids in the solution turned brown and turned blackish brown.
実施例 2
大豆から溶剤(n−ヘキサン)で抽出して得ら
れた未精製の大豆粗油を活性白土で脱色して得ら
れる、リン脂質を約2重量%含有する脱色油100
gを、容量300mlのフラスコに採り、これにコハ
ク酸一ナトリウム1gを加え、撹拌しながら200
℃に加熱した油浴中で10分間加熱したところ、リ
ン脂質を含有する大豆脱色油は、該リン脂質の褐
変現象に基づく着色がかなり抑制され、該油は透
明なオレンジ色を呈していた。Example 2 Decolorized oil 100 containing about 2% by weight of phospholipids obtained by decolorizing unrefined soybean crude oil obtained by extracting soybeans with a solvent (n-hexane) with activated clay.
200 g into a 300 ml flask, add 1 g of monosodium succinate, and add 200 g of monosodium succinate while stirring.
When heated for 10 minutes in an oil bath heated to 0.degree. C., the decolorized soybean oil containing phospholipids was significantly inhibited from coloring due to the browning phenomenon of the phospholipids, and the oil took on a transparent orange color.
一方、対照のコハク酸一ナトリウムを加えない
大豆脱色油はリン脂質が褐変し、黒褐色に着色し
た。 On the other hand, in the control decolorized soybean oil to which monosodium succinate was not added, the phospholipids were browned and colored blackish brown.
実施例 3
大豆リン脂質1重量部とコハク酸二ナトリウム
0.2重量部をよく混練したもの3gを精製パーム
油100gに加え、60℃程度に加熱、溶解して得た
リン脂質の油脂溶液を容量300mlのフラスコに採
り、撹拌しながら約180℃の油浴中で10分間加熱
したところ、リン脂質の油脂溶液は該リン脂質の
褐変現象に基づく着色がかなり抑制され、該油脂
溶液は透明な淡褐色を呈していた。Example 3 1 part by weight of soybean phospholipid and disodium succinate
Add 3 g of 0.2 parts by weight of well-kneaded mixture to 100 g of refined palm oil, heat to about 60°C and dissolve. Take the resulting phospholipid oil solution into a 300 ml flask, and place in an oil bath at about 180°C while stirring. When heated for 10 minutes in a phospholipid solution, the coloring caused by the browning phenomenon of the phospholipids was considerably suppressed, and the oil solution had a transparent light brown color.
一方、対照のコハク酸二ナトリウムを加えない
大豆リン脂質含有パーム油はリン脂質が褐変し、
黒褐色に着色した。 On the other hand, in the control palm oil containing soybean phospholipids without the addition of disodium succinate, the phospholipids turned brown;
Colored blackish brown.
Claims (1)
分散しているリン脂質を150℃以上の温度に加熱
するに当り、加熱前または加熱中の段階におい
て、コハク酸またはコハク酸のナトリウム塩を混
合することを特徴とするリン脂質の加熱褐変抑制
法。1. When heating phospholipids dissolved or dispersed in fats and oils at a concentration of 0.2% by weight or higher to a temperature of 150°C or higher, succinic acid or a sodium salt of succinic acid is mixed before or during heating. A method for suppressing heating browning of phospholipids.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3248978A JPS54124009A (en) | 1978-03-22 | 1978-03-22 | Suppression of heat browning of phospholipids |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3248978A JPS54124009A (en) | 1978-03-22 | 1978-03-22 | Suppression of heat browning of phospholipids |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS54124009A JPS54124009A (en) | 1979-09-26 |
JPS6148520B2 true JPS6148520B2 (en) | 1986-10-24 |
Family
ID=12360394
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3248978A Granted JPS54124009A (en) | 1978-03-22 | 1978-03-22 | Suppression of heat browning of phospholipids |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS54124009A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105475609A (en) * | 2014-10-07 | 2016-04-13 | 辻制油株式会社 | Method for suppressing heat discoloration of lecithin |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4528201A (en) * | 1983-06-20 | 1985-07-09 | The Procter & Gamble Co. | Alkali-treated lecithin in fats |
US4524085A (en) * | 1983-11-14 | 1985-06-18 | The Procter & Gamble Company | Lecithin containing cooking fats with reduced thermal discoloration |
US4654221A (en) * | 1984-03-30 | 1987-03-31 | The Procter & Gamble Company | Anti-sticking compositions |
US4943389A (en) * | 1988-04-04 | 1990-07-24 | Emulsion Technology, Inc. | Emulsifier for water-in-oil emulsions |
IN2014MU04013A (en) | 2013-12-27 | 2015-08-28 | Tsuji Oil Mills Co Ltd |
-
1978
- 1978-03-22 JP JP3248978A patent/JPS54124009A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105475609A (en) * | 2014-10-07 | 2016-04-13 | 辻制油株式会社 | Method for suppressing heat discoloration of lecithin |
Also Published As
Publication number | Publication date |
---|---|
JPS54124009A (en) | 1979-09-26 |
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