JPH06116585A - Method for purifying fat and oil - Google Patents
Method for purifying fat and oilInfo
- Publication number
- JPH06116585A JPH06116585A JP4271781A JP27178192A JPH06116585A JP H06116585 A JPH06116585 A JP H06116585A JP 4271781 A JP4271781 A JP 4271781A JP 27178192 A JP27178192 A JP 27178192A JP H06116585 A JPH06116585 A JP H06116585A
- Authority
- JP
- Japan
- Prior art keywords
- dha
- docosahexaenoic acid
- fats
- oils
- lipase
- 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
- 238000000034 method Methods 0.000 title claims abstract description 21
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims abstract description 79
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims abstract description 43
- 229940090949 docosahexaenoic acid Drugs 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000019197 fats Nutrition 0.000 claims abstract description 21
- 108090001060 Lipase Proteins 0.000 claims abstract description 12
- 102000004882 Lipase Human genes 0.000 claims abstract description 12
- 239000004367 Lipase Substances 0.000 claims abstract description 11
- 235000019421 lipase Nutrition 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 239000003921 oil Substances 0.000 abstract description 24
- 235000019198 oils Nutrition 0.000 abstract description 24
- 239000003925 fat Substances 0.000 abstract description 20
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 17
- 229930195729 fatty acid Natural products 0.000 abstract description 17
- 239000000194 fatty acid Substances 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 125000005456 glyceride group Chemical group 0.000 abstract description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 9
- 150000004665 fatty acids Chemical class 0.000 abstract description 8
- 235000021323 fish oil Nutrition 0.000 abstract description 5
- 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 abstract description 4
- 238000003756 stirring Methods 0.000 abstract description 3
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 abstract description 2
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 abstract description 2
- 235000012000 cholesterol Nutrition 0.000 abstract description 2
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010898 silica gel chromatography Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- -1 DHA Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229940040461 lipase Drugs 0.000 description 8
- 239000000758 substrate Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241001149724 Cololabis adocetus Species 0.000 description 1
- 108010048733 Lipozyme Proteins 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000269851 Sarda sarda Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ドコサヘキサエン酸
（ＤＨＡ）を含有する油脂をリパーゼを触媒として低級
アルコールと反応させることにより、ドコサヘキサエン
酸またはそのエステルを濃縮分離する方法に関するもの
である。TECHNICAL FIELD The present invention relates to a method for concentrating and separating docosahexaenoic acid or its ester by reacting an oil or fat containing docosahexaenoic acid (DHA) with a lower alcohol using a lipase as a catalyst.
【０００２】[0002]
【従来の技術および発明が解決しようとする課題】ドコ
サヘキサエン酸は通常、海産魚の魚油中に含有されてお
り、近年の研究の進展により、学習機能向上作用、制ガ
ン作用やコレステロール低下作用など種々の生理活性機
能があることが判明してきており、とくに注目されてい
る。Docosahexaenoic acid is usually contained in fish oil of marine fish. Due to the progress of research in recent years, various effects such as learning function improving effect, anticancer effect and cholesterol lowering effect have been obtained. It has been revealed that it has a physiologically active function, and thus it is particularly attracting attention.
【０００３】このようなＤＨＡのような高度不飽和脂肪
酸を濃縮分離する方法に関しては、尿素付加法や銀複合
体法（いずれも英国特許第1240513 号）などが知られて
おり、その他に分子蒸留法、低温溶剤分別結晶化法、液
液分配法、超臨界ガス抽出法、逆相クロマトグラフィー
法などがある。しかし、これらの方法をＤＨＡを含む油
脂からＤＨＡを高純度に濃縮分離することに適用したば
あい、いずれのばあいもコスト面、純度、品質の安定性
などの問題点があり、工業的規模で実施するのは困難で
ある。As a method for concentrating and separating highly unsaturated fatty acids such as DHA, a urea addition method and a silver complex method (both British Patent No. 1240513) are known, and molecular distillation is also used. Method, low temperature solvent fractional crystallization method, liquid-liquid distribution method, supercritical gas extraction method, reverse phase chromatography method and the like. However, when these methods are applied to concentrate and separate DHA from DHA-containing fats and oils with high purity, there are problems such as cost, purity, and stability of quality in all cases. Difficult to implement in.
【０００４】一方、リパーゼのＤＨＡに対する基質特異
性を利用してＤＨＡを濃縮分離する方法は一般的によく
知られている。すなわち、ＤＨＡを含有する油脂を水と
加水分解反応させる（特開昭58-165796 号）か、あるい
は脂肪酸（エステル）とエステル交換反応させることに
よりＤＨＡ以外の脂肪酸をより多くグリセリドから遊離
させ、その後、ＤＨＡ高含有グリセリドを分離して得る
ことによりＤＨＡを濃縮分離する方法である。On the other hand, a method for concentrating and separating DHA by utilizing the substrate specificity of lipase for DHA is generally well known. That is, the fats and oils containing DHA are hydrolyzed with water (Japanese Patent Laid-Open No. 58-165796) or transesterified with fatty acids (esters) to liberate more fatty acids other than DHA from glycerides. , A DHA-rich glyceride is separated and obtained to concentrate and separate DHA.
【０００５】しかし、これらの方法は反応速度が非常に
遅いという欠点があり、また反応の効率もさほど良くな
いので得られたグリセリド中に含まれるＤＨＡ含量はさ
ほど高くない。However, these methods have the drawback that the reaction rate is very slow, and the efficiency of the reaction is not so good, so that the DHA content in the obtained glyceride is not so high.
【０００６】[0006]
【課題を解決するための手段】本発明者らはかかる実情
に鑑み、ＤＨＡを含む油脂から純度の高いＤＨＡを簡単
に得るべく鋭意研究を重ねた結果、酵素リパーゼを触媒
として用いてＤＨＡを含む油脂を低級アルコールと反応
（アルコーリシス）させれば、反応速度が大きくなり効
率良くＤＨＡが濃縮できることを見出し、本発明を完成
させた。In view of such circumstances, the inventors of the present invention have conducted diligent studies to easily obtain highly pure DHA from fats and oils containing DHA, and as a result, use enzyme lipase as a catalyst to contain DHA. The present invention has been completed by finding that the reaction rate can be increased and the DHA can be efficiently concentrated by reacting the fats and oils with a lower alcohol (alcoholization).
【０００７】すなわち、本発明はドコサヘキサエン酸を
含有する油脂をリパーゼを触媒として低級アルコールと
反応させることを特徴とするドコサヘキサエン酸または
そのエステルの濃縮分離方法に関する。That is, the present invention relates to a method for concentrating and separating docosahexaenoic acid or its ester, which comprises reacting an oil or fat containing docosahexaenoic acid with a lower alcohol using a lipase as a catalyst.
【０００８】[0008]
【実施例】より具体的には、本発明は油脂中のＤＨＡ以
外の脂肪酸をリパーゼを用いて低級アルコールと選択的
に反応させ、ＤＨＡ以外の脂肪酸エステルをより多くグ
リセリドから遊離させる。ついで得られた生成物からＤ
ＨＡ高含有グリセリドを分取することを特徴とする。EXAMPLES More specifically, in the present invention, fatty acids other than DHA in fats and oils are selectively reacted with lower alcohols using lipase to liberate more fatty acid esters other than DHA from glycerides. Then the product obtained from D
A feature is that a glyceride having a high content of HA is collected.
【０００９】本発明に用いられるＤＨＡを含有する油脂
としてはイワシ油、サバ油、サンマ油、マグロ油、カツ
オ油などの魚油や海藻や植物プランクトンなどに含まれ
る油脂があげられる。Examples of fats and oils containing DHA used in the present invention include fish oils such as sardine oil, mackerel oil, saury oil, tuna oil and bonito oil, and oils and fats contained in seaweed, phytoplankton and the like.
【００１０】本発明において用いられるリパーゼは、Ｄ
ＨＡに対する基質特異性を有する、動植物または微生物
起源のリパーゼであり、たとえばキャンディダ(Candid
a) 属、リゾプス(Rhizopus)属、アスペルギルス(Asperg
illus) 属、ムコール(Mucor)属起源のもの、あるいはブ
タ膵臓リパーゼなどがある。これらの酵素の使用量は、
通常、油脂１ｇ当たり10〜3000ユニット、好ましくは20
〜 500ユニットである。The lipase used in the present invention is D
A lipase of plant or microbial origin with substrate specificity for HA, such as Candid
a) Genus, Rhizopus, Aspergillus
illus), Mucor, or porcine pancreatic lipase. The amount of these enzymes used is
Normally, 10 to 3000 units, preferably 20 per 1 g of fats and oils
~ 500 units.
【００１１】低級アルコールとは炭素数１〜10の脂肪族
アルコールで、たとえば、メタノール、エタノール、プ
ロパノール、ブタノール、ヘキサノール、オクタノー
ル、デカノールなどであり、とりわけ好ましいのはエタ
ノール、ブタノールなどである。アルコールの添加量
は、通常、油脂に対して５〜 500％（重量％、以下同
様）である。このばあい、アルコールの添加量が 500％
をこえるとアルコールは酵素反応にとって阻害物質とな
るので反応速度が遅くなり不利である。また、添加量が
５％より少ないばあいは反応速度は速くなるが、原料油
脂の一部しか反応しなくなるので生成したグリセリド中
のＤＨＡ含量は高くならない。好ましい添加量の範囲は
10〜 100％である。The lower alcohol is an aliphatic alcohol having 1 to 10 carbon atoms, for example, methanol, ethanol, propanol, butanol, hexanol, octanol, decanol and the like, with ethanol and butanol being particularly preferable. The amount of alcohol added is usually 5 to 500% (% by weight, the same applies hereinafter) with respect to fats and oils. In this case, the amount of alcohol added is 500%
Above this, alcohol becomes an inhibitory substance for the enzymatic reaction, which is disadvantageous because the reaction rate becomes slow. If the amount added is less than 5%, the reaction rate will be faster, but the DHA content in the glyceride produced will not be high because only part of the raw material fat will react. The preferred range of addition is
10 to 100%.
【００１２】油脂とアルコールとの反応は通常の酵素反
応の条件とほぼ同じ温度（20℃〜60℃）で行なうことが
できる。20℃未満では反応速度が遅く、60℃を超えると
酵素が失活する。とくに好ましい操作温度範囲は30〜50
℃である。この反応は、大気下でも行なうことができる
が脂肪酸の劣化を防ぐために不活性ガス下、たとえば窒
素ガス、炭酸ガスの雰囲気下で行なってもよい。The reaction between the oil and fat and the alcohol can be carried out at a temperature (20 ° C. to 60 ° C.) which is almost the same as the condition of the usual enzyme reaction. If the temperature is lower than 20 ° C, the reaction rate is slow, and if it exceeds 60 ° C, the enzyme is inactivated. Particularly preferred operating temperature range is 30-50
℃. This reaction can be carried out in the air, but may be carried out in an inert gas atmosphere, for example, in an atmosphere of nitrogen gas or carbon dioxide gas in order to prevent deterioration of fatty acids.
【００１３】また、反応に際してはヘキサン、石油エー
テルなどの不活性溶剤を油脂と共存させておくのがよ
く、その使用量は油脂に対して2000％（重量％、以下同
様）以下、望ましくは 300％以下である。In the reaction, an inert solvent such as hexane or petroleum ether is preferably allowed to coexist with the fats and oils, and the amount thereof used is 2000% (% by weight, the same applies hereinafter) or less, preferably 300% of the fats and oils. % Or less.
【００１４】このようにして、１〜 240時間アルコーリ
シス反応を行なわしめる。好ましくは３〜 150時間の反
応時間で行なう。In this way, the alcoholysis reaction is carried out for 1 to 240 hours. The reaction time is preferably 3 to 150 hours.
【００１５】反応生成物よりＤＨＡ高含有グリセリドを
分取するにはクロマトグラフィー法、分子蒸留法など公
知の方法を利用できる。分取したＤＨＡ高含有グリセリ
ドはさらにアルカリ金属水酸化物や酵素などを触媒とし
て脂肪酸または脂肪酸エステルの形にすることができ
る。In order to separate the DHA-rich glyceride from the reaction product, known methods such as chromatography and molecular distillation can be used. The DHA-rich glyceride thus separated can be converted into a fatty acid or a fatty acid ester by using an alkali metal hydroxide or an enzyme as a catalyst.
【００１６】以下、本発明を実施例にもとづいて説明す
るが、本発明はこれらの実施例に限定されるものではな
い。なお、表中の脂肪酸エステルの組成は重量％を表わ
す。The present invention will be described below based on examples, but the present invention is not limited to these examples. The composition of the fatty acid ester in the table represents% by weight.
【００１７】実施例１ 20ｇの魚油（表１に脂肪酸組成を示す）に、ノボ イン
ダストリ社；デンマーク(NOVO Industri A/S;Denmark）
製のリパーゼ（商品名：リポザイム(Lipozyme)ＩＭ６
０、９６ＢＩＵ／ｇ）５ｇ、ヘキサン50ml、エタノール
20mlを加え、30℃で120hr 撹拌しながら反応させた。反
応後、生成物からシリカゲルカラムクロマトグラフィー
によりＤＨＡ高含有グリセリドを 4.5ｇ分取した。この
グリセリドをさらに0.25Ｎ−ＮａＯＨエタノール溶液で
エチルエステル化した。この脂肪酸エチルエステル混合
物の組成を表２に示す。Example 1 20 g of fish oil (fatty acid composition is shown in Table 1) was added to NOVO Industri A / S (Denmark).
Manufactured lipase (trade name: Lipozyme IM6
0,96 BIU / g) 5 g, hexane 50 ml, ethanol
20 ml was added, and the mixture was reacted at 30 ° C. for 120 hours with stirring. After the reaction, 4.5 g of a DHA-rich glyceride was collected from the product by silica gel column chromatography. The glyceride was further esterified with 0.25N-NaOH ethanol solution. The composition of this fatty acid ethyl ester mixture is shown in Table 2.
【００１８】[0018]
【表１】 [Table 1]
【００１９】[0019]
【表２】 [Table 2]
【００２０】また、表には反応基質となるエタノールの
量を種々変えて同様に行なった結果も示した。The table also shows the results obtained in the same manner by changing the amount of ethanol as a reaction substrate.
【００２１】表から明らかなように、リパーゼを用いて
ＤＨＡを含む油脂をエタノールと反応させることによ
り、ＤＨＡエステルの純度が向上することがわかる。As can be seen from the table, the purity of DHA ester is improved by reacting fats and oils containing DHA with ethanol using lipase.
【００２２】比較例１ 反応基質として20ｇのエタノールを用いる本発明の方法
と比較するため、エタノールの代りに20ｇの水を用いた
加水分解反応、および別に尿素付加法（魚油：尿素：エ
タノール＝１：１：５の比率で50℃で常法に従い撹拌）
を３回用いることにより魚油から調製したＤＨＡ高含有
脂肪酸エチルエステル混合物（ＤＨＡ含有率17％）20ｇ
を用いたエステル交換反応を実施例１と同様に行なった
ときの結果を表３に示す。表中において、反応基質の脂
肪酸エステルは上述の尿素付加法により調製した脂肪酸
エステル混合物を表わし、結果の脂肪酸エステル組成は
反応生成物から分取したＤＨＡ高含有グリセリドを0.25
Ｎ−ＮａＯＨエタノールによりエチルエステル化した脂
肪酸エステルの組成をそれぞれ表わす。Comparative Example 1 In order to compare with the method of the present invention using 20 g of ethanol as a reaction substrate, a hydrolysis reaction using 20 g of water instead of ethanol and another urea addition method (fish oil: urea: ethanol = 1) Stirring at a ratio of 1: 5 at 50 ° C according to the usual method)
20 g of DHA-rich fatty acid ethyl ester mixture (DHA content 17%) prepared from fish oil by using 3 times
Table 3 shows the results when the transesterification reaction using was carried out in the same manner as in Example 1. In the table, the fatty acid ester of the reaction substrate represents the fatty acid ester mixture prepared by the above-mentioned urea addition method, and the resulting fatty acid ester composition is 0.25 for the DHA-rich glyceride separated from the reaction product.
The compositions of fatty acid esters ethyl-esterified with N-NaOH ethanol are shown.
【００２３】[0023]
【表３】 [Table 3]
【００２４】従来の方法である加水分解反応やエステル
交換反応ではＤＨＡの含有量はさほど向上しなかった。The content of DHA was not improved so much by the conventional hydrolysis reaction or transesterification reaction.
【００２５】[0025]
【発明の効果】以上の通り、本発明によれば従来の方法
に比べ操作が簡単であり、効率的にＤＨＡを多量に含有
する油脂を得ることができる。INDUSTRIAL APPLICABILITY As described above, according to the present invention, the oil and fat containing a large amount of DHA can be obtained more easily than the conventional method.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ１２Ｐ 7/64 9282−4Ｂ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location C12P 7/64 9282-4B
Claims (1)
パーゼを触媒として低級アルコールと反応させることを
特徴とするドコサヘキサエン酸またはそのエステルの濃
縮分離方法。1. A method for concentrating and separating docosahexaenoic acid or an ester thereof, which comprises reacting an oil or fat containing docosahexaenoic acid with a lower alcohol using a lipase as a catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4271781A JPH06116585A (en) | 1992-10-09 | 1992-10-09 | Method for purifying fat and oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4271781A JPH06116585A (en) | 1992-10-09 | 1992-10-09 | Method for purifying fat and oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06116585A true JPH06116585A (en) | 1994-04-26 |
Family
ID=17504767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4271781A Pending JPH06116585A (en) | 1992-10-09 | 1992-10-09 | Method for purifying fat and oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06116585A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| WO2006120120A1 (en) * | 2005-05-12 | 2006-11-16 | Proyecto Empresarial Brudy, S.L. | Use of docosahexaenoic glycerides for the treatment of tumorous diseases |
| US7179491B1 (en) | 1999-01-29 | 2007-02-20 | Ted Mag | Process of converting rendered triglyceride oil from marine sources into bland, stable oil |
| WO2008032007A1 (en) | 2006-09-14 | 2008-03-20 | Tmo Renewables Ltd | Lipase |
| WO2008110168A1 (en) * | 2007-03-15 | 2008-09-18 | Palsgaard A/S | Preparation of 2-isomers of propylene glycol monoesters |
| FR2955459A1 (en) * | 2010-01-28 | 2011-07-29 | Polaris | OIL COMPOSITION RICH IN MONOGLYCERIDES OF DHA |
| JP2012211147A (en) * | 2003-12-19 | 2012-11-01 | Pronova Biopharma Norge As | Use of fatty acid composition containing at least either one or combination of epa and dha |
| JP2014168412A (en) * | 2013-03-04 | 2014-09-18 | Ikeda Shokken Kk | Manufacturing method of enzyme treated kelp extract |
-
1992
- 1992-10-09 JP JP4271781A patent/JPH06116585A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| US7179491B1 (en) | 1999-01-29 | 2007-02-20 | Ted Mag | Process of converting rendered triglyceride oil from marine sources into bland, stable oil |
| JP2012211147A (en) * | 2003-12-19 | 2012-11-01 | Pronova Biopharma Norge As | Use of fatty acid composition containing at least either one or combination of epa and dha |
| US9282760B2 (en) | 2003-12-19 | 2016-03-15 | Pronova Biopharma Norge As | Use of a fatty acid composition comprising at least one of EPA and DHA or any combinations thereof |
| WO2006120120A1 (en) * | 2005-05-12 | 2006-11-16 | Proyecto Empresarial Brudy, S.L. | Use of docosahexaenoic glycerides for the treatment of tumorous diseases |
| WO2008032007A1 (en) | 2006-09-14 | 2008-03-20 | Tmo Renewables Ltd | Lipase |
| WO2008110168A1 (en) * | 2007-03-15 | 2008-09-18 | Palsgaard A/S | Preparation of 2-isomers of propylene glycol monoesters |
| FR2955459A1 (en) * | 2010-01-28 | 2011-07-29 | Polaris | OIL COMPOSITION RICH IN MONOGLYCERIDES OF DHA |
| WO2011092299A1 (en) * | 2010-01-28 | 2011-08-04 | Polaris | Oily composition rich in dha monoglycerides |
| JP2014168412A (en) * | 2013-03-04 | 2014-09-18 | Ikeda Shokken Kk | Manufacturing method of enzyme treated kelp extract |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2362212C (en) | Lipase-catalysed esterification of marine oil | |
| AU686348B2 (en) | Refining oil compositions | |
| EP0191217B2 (en) | Process for producing glycerides in the presence of lipases | |
| JP3720194B2 (en) | Method for producing partial glycerides | |
| EP0307154B1 (en) | Preparation of diglycerides | |
| JP2002027995A (en) | Method for producing glyceride with lipase | |
| RU96118495A (en) | REFINING OIL COMPOSITIONS | |
| WO1991016441A1 (en) | Stereoselective synthesis of 1,2-diglycerides and triglycerides | |
| US5897994A (en) | Fatty acid fractionation for polyunsaturated fatty acid fraction enrichment | |
| JPH06116585A (en) | Method for purifying fat and oil | |
| JP3072022B2 (en) | Diglyceride production method | |
| JP2007070486A (en) | Glyceride and method for producing the same | |
| JP2005287511A (en) | Method for enzymatically synthesizing triglyceride of unsaturated fatty acid | |
| JPH08214891A (en) | Production of oil and fat containing highly unsaturated fatty acid-containing triglyceride | |
| JPH0533988B2 (en) | ||
| JP3773315B2 (en) | Method for purifying omega-3 highly unsaturated fatty acid ester | |
| JP3734905B2 (en) | Method for purifying omega-3 polyunsaturated fatty acids | |
| JPH07163382A (en) | Production of diglycerin-1-ester | |
| JPH07163381A (en) | Production of diglycerin-1,2-diester | |
| KR100385625B1 (en) | The isolation and purification method of high purity diglyceride | |
| JP3853181B2 (en) | Method for separating steryl esters | |
| JP3995409B2 (en) | Process for producing glycerides containing 5,8,11-eicosatrienoic acid and / or 6,9-octadecadienoic acid in high concentration | |
| JPH01187089A (en) | Production of palmitoleic acid and glyceride thereof | |
| JP2004305155A (en) | Method for producing tocopherol and tocotrienol | |
| JPH09121878A (en) | Preparation of ethyl trans-2,cis-4-decadienate ester |