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JPH0582196B2 - - Google Patents
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JPH0582196B2 - - Google Patents

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Publication number
JPH0582196B2
JPH0582196B2 JP61072324A JP7232486A JPH0582196B2 JP H0582196 B2 JPH0582196 B2 JP H0582196B2 JP 61072324 A JP61072324 A JP 61072324A JP 7232486 A JP7232486 A JP 7232486A JP H0582196 B2 JPH0582196 B2 JP H0582196B2
Authority
JP
Japan
Prior art keywords
lipase
hydrolysis
oils
fats
weight
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 - Fee Related
Application number
JP61072324A
Other languages
Japanese (ja)
Other versions
JPS62228289A (en
Inventor
Masayuki Abe
Takehiko Oofuji
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kanegafuchi Chemical Industry Co Ltd
Original Assignee
Kanegafuchi Chemical Industry Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd
Priority to JP61072324A priority Critical patent/JPS62228289A/en
Publication of JPS62228289A publication Critical patent/JPS62228289A/en
Publication of JPH0582196B2 publication Critical patent/JPH0582196B2/ja
Granted legal-status Critical Current

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  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

「産業上の利用分野」 本発明はリパーゼを用いる油脂の加水分解方法
に関し、更に詳しくは、特定の基質油脂に対して
20〜500重量倍の特定の緩衝液の存在する系にお
いて1,3位特異性を有するリパーゼを作用さ
せ、モノグリセリド含有量の高い油脂の加水分解
生成物を得ることを特徴とする油脂の加水分解方
法に関する。 「従来の技術と問題点」 従来のリパーゼによる油脂の加水分解方法は加
水分解率を95%以上に上げるための方法であり、
例えばすべてのグリセリド位の脂肪酸に対して作
用するキヤンデイダ・シリンドラツセ(Candida
Cylindracea)等のリパーゼを用い、基質油脂に
対して10〜300重量%の水分の存在する系におい
て約20〜60時間の加水分解反応を行い97〜98%以
上の分解率を得ている(特開昭57−57799号)。 これら公知の方法のリパーゼによる油脂の加水
分解方法は脂肪酸とグリセリンにまで加水分解を
行うものであり、モノグリセリド含有量の高い油
脂の加水分解生成物を得ることは困難である。 「問題点を解決するための手段」 本発明は、上記実情に鑑み、リパーゼを用いる
油脂の加水分解において、モノグリセリド含有量
の高い加水分解生成物を得る方法を提供すること
を目的とするものである。 本発明者らは、従来の加水分解率を上げ油脂を
脂肪酸とグリセリンに分解するのではなく、食品
用乳化剤等として有用なモノグリセリド含有量の
高い油脂の加水分解生成物を得るために鋭意研究
を重ねた結果、特定の基質油脂に対して20〜500
重量倍の特定の緩衝液の存在する系において、
1,3位特異性を有するリパーゼを作用させるこ
とにより、モノグリセリド含有量の高い加水分解
生成物を得ることに成功したものである。 即ち、本発明はグリセリドの1,3位脂肪酸残
基が飽和脂肪酸である油脂を基質油脂として用
い、該基質油脂に対して20〜500重量倍のマツク
イルブアイン(McIlvaine)緩衝液の存在する系
において、1,3位特異性を有するリパーゼを作
用させることにより、モノグリセリド含有量の高
い加水分解生成物を得ることを特徴とする油脂の
加水分解方法を内容とするものである。 本発明に用いる基質油脂としては、1,3ジパ
ルミト−2−オレインを主成分とするパーム油中
融点画分、1,3−ジステアロ−2−オレインを
主成分とするシア脂中融点画分等のグリセリドの
1,3位脂肪酸残基が飽和脂肪酸である油脂が用
いられる。即ち、基質油脂としてのオリーブ油の
如く、1,3位脂肪酸残基が不飽和脂肪酸である
油脂に比べて、高含有量のモノグリセリドが得ら
れる。 本発明に用いられる水分としては、マツクイル
ブアイン(McIlvaine)緩衝液を用いる。この緩
衝液を用いると、イオン交換水を用いた場合に比
べて高含量のモノグリセリドが得られる。基質油
脂と水分の組合わせにより、加水分解生成物のモ
ノグリセリド含有量は変化し、パーム油中融点画
分等とマツクイルブアイン(McIlvaine)緩衝液
の場合は50重量%以上に達するが、オリーブ油と
マツクイルブアイン(McIlvaine)緩衝液の場
合、パーム油中融点画分とイオン交換水の場合あ
るいはヘキサンが存在する場合等は15〜50重量%
のモノグリセリド含有量となる。 水分として500重量倍を超えても可能であるが、
工業的利用においては反応槽の巨大化等のためコ
ストアツプとなり不利である。 本発明に用いるリパーゼとしては1,3位特異
性を有するリパーゼであればどのようなリパーゼ
でもよい。具体的には、すい臓リパーゼ、米ぬか
リパーゼ、リゾプス属リパーゼ、ムコール属リパ
ーゼ等の動・植物起源あるいは微生物起源のリパ
ーゼ等である。 リパーゼを直接反応系に加えて加水分解反応を
実施することもできるが、支持体上への吸着等公
知の方法による固定化リパーゼとして分散性を向
上させて加水分解反応を実施することができる。
支持体としてはケイソウ土、多糖類誘導体、イオ
ン交換樹脂等、公知の支持体を用いることができ
る。リパーゼ溶液あるいは固定化リパーゼ分散液
は再使用が可能である。 本発明の加水分解反応はリパーゼの種類により
異なるが、通常30〜50℃の範囲で実施することが
望ましい。耐熱性リパーゼを用いる場合は60℃以
上でも可能である。 加水分解反応は5時間以内で実施されるのが望
ましい。3時間以内の加水分解反応は特に望まし
い。5時間を越える反応はグリセリドの2位の脂
肪酸の1あるいは3位への転位のため、更に加水
分解が進み、脂肪酸とグリセリンを生成しモノグ
リセリド含有量の低下をもたらすために望ましく
ない。 本発明の方法は1種または2種以上の基質油脂
100部、水分2000〜50000部および1,3位特異性
を有する市販のリパーゼ(4000〜40000単位程度
の活性を有する市販標準品リパーゼ)0.05〜20部
を直接あるいは固定化リパーゼとして添加し、30
〜50℃で攪拌することによつて加水分解反応を実
施する。 従来の加水分解反応で使用される500部程度以
下の水分量ではモノグリセリドの蓄積量は10重量
%未満であるが、本発明による加水分解反応では
モノグリセリドの含有量を60重量%以上にするこ
とも可能である。 「実施例」 以下、本発明を実施例を挙げて説明するが、本
発明はこれらにより何ら制限されるものではな
い。 実施例 1 パーム油中融点画分100部、マツクイルブアイ
ン(McIlvaine)緩衝液(PH8.0)30000部、1モ
ル塩化カルシウム水溶液60部、ムコール・ジヤバ
ニカス(Mucor javanicus)起源市販粉末リパー
ゼ(天野製薬製)5部を40℃で攪拌し、加水分解
反応を実施した。 反応終了後ヘキサンを添加し、攪拌、遠心分離
後ヘキサン溶液を回収し、加水分解生成物を抽出
した。 分析方法: 検出器として示差屈折計を用い、ゲル浸透クロ
マトグラフイー(GPC)カラムを利用した高速
液体クロマトグラフイー(HPLC)にて加水分解
生成物の各グリセリドおよび脂肪酸組成を分析し
た。また、モノグリセリドの分析は検出器として
示差屈折計を用いたHPLCにて実施した。分析結
果(重量%、以下同様)を表1に示す。
"Field of Industrial Application" The present invention relates to a method for hydrolyzing fats and oils using lipase, and more specifically, to a method for hydrolyzing fats and oils using lipase.
Hydrolysis of fats and oils, characterized by obtaining a hydrolysis product of fats and oils with a high monoglyceride content by allowing a lipase having 1,3-position specificity to act in a system containing 20 to 500 times the weight of a specific buffer solution. Regarding the method. "Conventional technology and problems" The conventional method of hydrolyzing fats and oils using lipase is a method that increases the hydrolysis rate to over 95%.
For example, Candida cylindracea, which acts on fatty acids at all glyceride positions.
Using a lipase such as Cylindracea, the hydrolysis reaction is carried out for about 20 to 60 hours in a system containing 10 to 300% water by weight based on the substrate fat and oil, and a decomposition rate of 97 to 98% or more is obtained (specially (No. 57-57799). These known methods of hydrolyzing fats and oils using lipase hydrolyze fatty acids and glycerin, and it is difficult to obtain hydrolysis products of fats and oils with a high monoglyceride content. "Means for Solving the Problems" In view of the above circumstances, an object of the present invention is to provide a method for obtaining a hydrolysis product with a high monoglyceride content in the hydrolysis of fats and oils using lipase. be. The present inventors have conducted intensive research to obtain a hydrolysis product of fats and oils with a high monoglyceride content that is useful as a food emulsifier, etc., instead of increasing the hydrolysis rate and decomposing fats and oils into fatty acids and glycerin. As a result of stacking, 20 to 500 for specific substrate fats and oils.
In a system where twice the weight of a specific buffer is present,
By using a lipase with specificity for the 1 and 3 positions, we succeeded in obtaining a hydrolysis product with a high monoglyceride content. That is, in the present invention, an oil or fat in which the 1 and 3 fatty acid residues of glyceride are saturated fatty acids is used as a substrate oil, and a McIlvaine buffer solution is present in an amount of 20 to 500 times the weight of the substrate oil. The present invention is a method for hydrolyzing fats and oils, which is characterized in that a hydrolysis product with a high monoglyceride content is obtained by applying a lipase having 1,3-position specificity to the system. Substrate fats and oils used in the present invention include palm oil medium melting point fraction containing 1,3 dipalmito-2-olein as a main component, shea butter medium melting point fraction containing 1,3-distearo-2-olein as a main component, etc. An oil or fat in which the fatty acid residues at positions 1 and 3 of the glyceride are saturated fatty acids is used. That is, a higher content of monoglycerides can be obtained compared to a substrate oil such as olive oil in which the fatty acid residues at the 1 and 3 positions are unsaturated fatty acids. As the water used in the present invention, McIlvaine buffer is used. Using this buffer, a higher content of monoglycerides can be obtained than when using ion-exchanged water. The monoglyceride content of the hydrolyzed product changes depending on the combination of the substrate fat and water, reaching more than 50% by weight in the case of palm oil medium melting point fraction and McIlvaine buffer, but in the case of olive oil and McIlvaine buffer, 15 to 50% by weight in the case of palm oil medium melting point fraction and ion-exchanged water or in the presence of hexane, etc.
monoglyceride content. Although it is possible to exceed 500 times the weight of water,
In industrial use, it is disadvantageous as the cost increases due to the large size of the reaction tank. The lipase used in the present invention may be any lipase as long as it has 1,3 position specificity. Specifically, lipases of animal/plant origin or microbial origin, such as pancreatic lipase, rice bran lipase, Rhizopus lipase, and Mucor lipase, are used. Although the hydrolysis reaction can be carried out by directly adding lipase to the reaction system, the hydrolysis reaction can also be carried out by immobilizing lipase by a known method such as adsorption onto a support to improve dispersibility.
As the support, known supports such as diatomaceous earth, polysaccharide derivatives, and ion exchange resins can be used. The lipase solution or immobilized lipase dispersion can be reused. Although the hydrolysis reaction of the present invention varies depending on the type of lipase, it is generally desirable to carry out the reaction at a temperature in the range of 30 to 50°C. When using a thermostable lipase, it is possible to perform the reaction at temperatures of 60°C or higher. Preferably, the hydrolysis reaction is carried out within 5 hours. A hydrolysis reaction within 3 hours is particularly desirable. A reaction exceeding 5 hours is undesirable because the fatty acid at the 2nd position of the glyceride is rearranged to the 1st or 3rd position, resulting in further hydrolysis, producing fatty acids and glycerin, and resulting in a decrease in the monoglyceride content. The method of the present invention uses one or more types of substrate fats and oils.
Add 100 parts of water, 2000 to 50,000 parts of water, and 0.05 to 20 parts of commercially available lipase with 1,3 position specificity (commercial standard lipase with activity of about 4000 to 40,000 units) directly or as immobilized lipase,
The hydrolysis reaction is carried out by stirring at ~50°C. When the amount of water used in conventional hydrolysis reactions is about 500 parts or less, the amount of monoglyceride accumulated is less than 10% by weight, but in the hydrolysis reaction of the present invention, the content of monoglycerides can be increased to 60% by weight or more. It is possible. "Examples" The present invention will be described below with reference to Examples, but the present invention is not limited to these in any way. Example 1 100 parts of palm oil medium melting point fraction, 30,000 parts of McIlvaine buffer (PH8.0), 60 parts of 1 molar calcium chloride aqueous solution, commercially available powdered lipase originating from Mucor javanicus (Amano (manufactured by Pharmaceutical Co., Ltd.) were stirred at 40°C to carry out a hydrolysis reaction. After the reaction was completed, hexane was added, and after stirring and centrifugation, the hexane solution was collected and the hydrolysis product was extracted. Analysis method: Using a differential refractometer as a detector, each glyceride and fatty acid composition of the hydrolysis product was analyzed by high performance liquid chromatography (HPLC) using a gel permeation chromatography (GPC) column. Furthermore, analysis of monoglycerides was performed by HPLC using a differential refractometer as a detector. The analysis results (weight %, same below) are shown in Table 1.

【表】 比較例 1 マツクイルブアイン緩衝液の代わりにイオン交
換水を用いた以外は実施例1の方法に従つて、2
時間加水分解反応を実施した。結果を表2に示
す。
[Table] Comparative Example 1 Following the method of Example 1 except that ion-exchanged water was used instead of the Matsukuilbuain buffer, 2
A time hydrolysis reaction was carried out. The results are shown in Table 2.

【表】 比較例 2 パーム油中融点画分の代わりにオリーブ油を用
いた以外は実施例1の方法に従つて、2時間加水
分解反応を実施した。結果を表3に示す。
[Table] Comparative Example 2 A hydrolysis reaction was carried out for 2 hours according to the method of Example 1, except that olive oil was used instead of the palm oil medium melting point fraction. The results are shown in Table 3.

【表】 比較例 3 パーム中融点画分100部の代わりにパーム油中
融点画分50部、シア脂中融点画分50部をヘキサン
200部に溶解して用いた以外は実施例1の方法に
従つて、3時間加水分解反応を実施した。結果を
表4に示す。 本例では基質油脂をヘキサンに溶解しているた
め、モノグリセリド含有量が低い。
[Table] Comparative Example 3 Instead of 100 parts of palm medium melting point fraction, 50 parts of palm oil medium melting point fraction and 50 parts of shea butter medium melting point fraction were added to hexane.
A hydrolysis reaction was carried out for 3 hours in accordance with the method of Example 1, except that the solution was dissolved in 200 parts. The results are shown in Table 4. In this example, since the substrate oil is dissolved in hexane, the monoglyceride content is low.

【表】 比較例 4 マツクイルブアイン(McIlvaine)緩衝液(PH
8.0)500部、1モル塩化カルシウム水溶液1部と
した以外は実施例1の方法に従つて、加水分解反
応を実施した。結果を表5に示す。
[Table] Comparative example 4 McIlvaine buffer solution (PH
8.0) A hydrolysis reaction was carried out according to the method of Example 1, except that 500 parts and 1 part of a 1 molar calcium chloride aqueous solution were used. The results are shown in Table 5.

【表】 比較例 5 マツクイルブアイン(McIlvaine)緩衝液1500
部、1モル塩化カルシウム水溶液3部以外は実施
例1の方法に従つて、加水分解反応を実施した。
結果を表6に示す。
[Table] Comparative example 5 McIlvaine buffer solution 1500
The hydrolysis reaction was carried out in accordance with the method of Example 1 except for using 3 parts of a 1 molar calcium chloride aqueous solution.
The results are shown in Table 6.

【表】 「作用・効果」 本発明の油脂の加水分解方法によれば、食品乳
化剤等として有用な高含有量のモノグリセリドを
得ることが可能であり、その産業上の意義は極め
て大である。
[Table] "Action/Effect" According to the method of hydrolyzing fats and oils of the present invention, it is possible to obtain a high content of monoglyceride useful as a food emulsifier, etc., and its industrial significance is extremely large.

Claims (1)

【特許請求の範囲】 1 グリセリドの1,3位脂肪酸残基が飽和脂肪
酸である油脂を基質油脂として用い、該基質油脂
に対して20〜500重量倍のマツクイルブアイン
(McIlvaine)緩衝液の存在する系において、1,
3位特異性を有するリパーゼを作用させることに
より、モノグリセリド含有量の高い加水分解生成
物を得ることを特徴とする油脂の加水分解方法。 2 加水分解生成物が全グリセリド中50重量%以
上のモノグリセリドを含有する特許請求の範囲第
1項記載の方法。
[Scope of Claims] 1. An oil or fat in which the 1 and 3 fatty acid residues of glycerides are saturated fatty acids is used as a substrate oil, and a McIlvaine buffer solution of 20 to 500 times the weight of the substrate oil is used. In the existing system, 1,
A method for hydrolyzing fats and oils, characterized in that a hydrolysis product with a high monoglyceride content is obtained by applying a lipase having 3-position specificity. 2. The method according to claim 1, wherein the hydrolysis product contains 50% or more by weight of monoglycerides based on the total glycerides.
JP61072324A 1986-03-28 1986-03-28 Hydrolysis of fat of oil Granted JPS62228289A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61072324A JPS62228289A (en) 1986-03-28 1986-03-28 Hydrolysis of fat of oil

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61072324A JPS62228289A (en) 1986-03-28 1986-03-28 Hydrolysis of fat of oil

Publications (2)

Publication Number Publication Date
JPS62228289A JPS62228289A (en) 1987-10-07
JPH0582196B2 true JPH0582196B2 (en) 1993-11-17

Family

ID=13485984

Family Applications (1)

Application Number Title Priority Date Filing Date
JP61072324A Granted JPS62228289A (en) 1986-03-28 1986-03-28 Hydrolysis of fat of oil

Country Status (1)

Country Link
JP (1) JPS62228289A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2648147B1 (en) * 1989-06-13 1991-08-16 Gattefosse Ets Sa PROCESS FOR THE PREPARATION OF BETA-MONOGLYCERIDES AND PRODUCTS OBTAINED
US5677160A (en) * 1989-10-30 1997-10-14 Henkel Corporation Fat splitting process
JPH11506006A (en) * 1995-05-31 1999-06-02 ヘンケル コーポレーション Improved decomposition method of fats and oils

Also Published As

Publication number Publication date
JPS62228289A (en) 1987-10-07

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