JPH028298A - Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish - Google Patents
Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefishInfo
- Publication number
- JPH028298A JPH028298A JP63150929A JP15092988A JPH028298A JP H028298 A JPH028298 A JP H028298A JP 63150929 A JP63150929 A JP 63150929A JP 15092988 A JP15092988 A JP 15092988A JP H028298 A JPH028298 A JP H028298A
- Authority
- JP
- Japan
- Prior art keywords
- internal organs
- acid
- carbon dioxide
- silver nitrate
- temperature
- 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
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound 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 title claims abstract description 20
- 210000001835 viscera Anatomy 0.000 title claims abstract description 20
- 235000020669 docosahexaenoic acid Nutrition 0.000 title claims abstract description 14
- 229940090949 docosahexaenoic acid Drugs 0.000 title claims abstract description 6
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 title claims abstract 5
- 235000020673 eicosapentaenoic acid Nutrition 0.000 title claims abstract 5
- 229960005135 eicosapentaenoic acid Drugs 0.000 title claims abstract 5
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims abstract 4
- 241000238371 Sepiidae Species 0.000 title abstract 3
- 238000000926 separation method Methods 0.000 title description 2
- 238000000746 purification Methods 0.000 title 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000002632 lipids Chemical class 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 13
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000741 silica gel Substances 0.000 claims abstract description 4
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- 241000238366 Cephalopoda Species 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 239000001569 carbon dioxide Substances 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052709 silver Inorganic materials 0.000 abstract description 2
- 239000004332 silver Substances 0.000 abstract description 2
- 210000000056 organ Anatomy 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 10
- 238000000605 extraction Methods 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、イカ内臓中より血清脂質改善作用や血液凝固
抑制作用等を有するエイコサベンクエン酸く以下ＥＰＡ
と記す）、ドコサヘキサエン酸く以下ＤＭＡと記す）を
、二酸化炭素と、その臨海温度以上及び臨界圧力以上（
以下超臨界二酸化炭素と記す）の条件で接触させ、抽出
分離を行うに際し、ＥＰＡ、ＤＮＡを変性、変質を生じ
ることなしに、効率良く、選択的に上記脂質中より抽出
分離する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention discloses the use of eicosaben citric acid, hereinafter referred to as EPA, which has serum lipid-improving effects, blood coagulation inhibiting effects, etc. from squid internal organs.
), docosahexaenoic acid (hereinafter referred to as DMA) is combined with carbon dioxide at temperatures above its critical temperature and pressure above its critical pressure (
The present invention relates to a method for efficiently and selectively extracting and separating EPA and DNA from the above-mentioned lipids without causing denaturation or alteration when contacting them under conditions of supercritical carbon dioxide (hereinafter referred to as supercritical carbon dioxide).
更に詳しくは、本発明は、凍結乾燥したイカ内臓を、該
流体と接触させ、硝酸銀を担持した粉体を充填しなカラ
ム内を通過させ、圧力、温度、硝酸銀担持量を調整して
行うＥＰＡ、ＤＨＡの選択的分離法に関する。イカ内臓
の脂質には、ＥＰＡＤＩ（Ａのほかに、ミスチリン酸、
パルミチン酸、ステアリン酸、オレイン酸、リノール酸
、アラキン酸、アラキドン酸等の多くの脂肪酸が含まれ
ており、上記高級脂肪酸が、沸点、密度などの物性及び
化学的性質が類似していることから、ＥＰＡ。More specifically, the present invention involves contacting freeze-dried squid internal organs with the fluid, passing the powder through a column not filled with silver nitrate-supported powder, and adjusting the pressure, temperature, and amount of silver nitrate supported to perform EPA. , relates to a method for selectively separating DHA. The lipids in squid internal organs include EPADI (in addition to A, mystilic acid,
It contains many fatty acids such as palmitic acid, stearic acid, oleic acid, linoleic acid, arachidic acid, and arachidonic acid, and the above higher fatty acids have similar physical and chemical properties such as boiling point and density. , E.P.A.
ＤＭＡを高選択的、高収率で上記脂質中から一つの行程
内で抽出分離することは極めて困難である。It is extremely difficult to extract and separate DMA from the above-mentioned lipids in a single process with high selectivity and high yield.
本発明は、この様な高級脂肪酸混合物から、ＥＰＡ
ＤＨＡを効率良く、操作上容易に、かつ経済的に安価に
抽出分離できる方法に関する。The present invention provides EPA from such a higher fatty acid mixture.
The present invention relates to a method for extracting and separating DHA efficiently, operationally easily, and economically at low cost.
ＥＰＡ、Ｄ）ＩＡ等の高級不飽和脂肪酸は魚体内で形成
されず、魚類においてその餌となる海草類等から摂取さ
れることが知られている。近年、ＥＰＡ、ＤＩ−ＩＡは
血栓症、脳梗塞、心筋梗塞等の虚血性心疾患症を予防す
ることが知られ、更に、ＤＩ−ＩＡは脳に於ける代謝速
度を速めるなど、脳内に於けるその儂きに対しても大き
な注目が集められている。本発明者等は、低利用の動物
性海洋バイオマスであるイカ内臓中の脂質に、このＥＰ
Ａ。It is known that higher unsaturated fatty acids such as EPA and D)IA are not formed within the fish body, but are ingested by fish from the seaweeds and the like that they feed on. In recent years, EPA and DI-IA have been known to prevent ischemic heart diseases such as thrombosis, cerebral infarction, and myocardial infarction.Furthermore, DI-IA has effects in the brain, such as by accelerating the metabolic rate in the brain. There is also a lot of attention being paid to the person in question. The present inventors added this EP to the lipids in squid internal organs, which is an underutilized animal marine biomass.
A.
Ｄ ）［Ａか主要な構成成分として存在することを突き
止め、本発明法による抽出分離に好適な材料であること
を解明するに至った。D) [A] was found to exist as a major constituent, and it was found that it is a material suitable for extraction and separation by the method of the present invention.
−ｉに、期待と固体或いは液体を接触させた場合、常温
、常圧下に於いて気相に移行する固体或いは液体の量は
、極めて僅かである。しかし、その気体が臨界温度以上
及び臨界圧力以上の状態にあるときは、気相に移行する
固体或いは液体の量は飛躍的に増大する。また硝酸銀は
、高級脂肪酸エステル類の不飽和度が増加するにつれて
、それとの親和力は増大する。When a solid or liquid is brought into contact with -i, the amount of the solid or liquid that changes to the gas phase at normal temperature and pressure is extremely small. However, when the gas is at a temperature above the critical temperature and a pressure above the critical pressure, the amount of solid or liquid transferred to the gas phase increases dramatically. Furthermore, as the degree of unsaturation of higher fatty acid esters increases, the affinity of silver nitrate with the higher fatty acid esters increases.
本発明者は、これらの事実に着目し、イカ内臓中の脂質
に対して、二酸化炭素と、その臨界温度以上及び臨界圧
力以上の条件下で接触後、硝酸銀を担持した粉体が充填
されているカラム内を通過させ、温度、昇圧速度の調整
によって、容易に、ＥＰＡやＤＩ−ＩＡなどの高級脂肪
酸を、イカ内臓の脂質中に含まれている他のバルミチン
酸、ステアリン酸、オレイン酸等の脂肪酸から、高選択
的に抽出分離できることを見出だし、本発明に到達した
ものである。The present inventor focused on these facts, and after contacting the lipids in the internal organs of squid with carbon dioxide under conditions above its critical temperature and critical pressure, it was found that the powder supporting silver nitrate was filled. By adjusting the temperature and pressure increase rate, higher fatty acids such as EPA and DI-IA can be easily converted to other fatty acids such as valmitic acid, stearic acid, oleic acid, etc. contained in the lipids of squid internal organs. The present invention was achieved based on the discovery that it is possible to extract and separate highly selectively from fatty acids.
本発明は、当該物質を含有するイカ内臓を凍結乾燥粉末
とし、これを直接、超臨界二酸化炭素抽出を行うことに
より達成され、その他−切の前処理を必要としない。抽
出圧力については、−ａにそれが高いほど溶解力は大き
くなるが、選択性は減少する。そこで経済性も考慮して
圧力の初期設定値を７０〜９０ ｋｇ ／ ｃＡとし、
条件によって、圧力を２００ｋｇ／ｃｙＡ以上に昇圧す
る。温度は二酸化炭素の臨界温度（３Ｌ３℃）以上でな
ければならないが、臨界温度より１〜５０°Ｃ高い温度
範囲を用いる。また硝酸銀は、３２〜２００メツシユの
シリカゲル粉末を担体として用いたが、多孔性の無機粉
体であれば担体として用いることがてきる。カラム温度
は、臨界温度より１０〜５０°Ｃ高い温度範囲を用いる
。The present invention is achieved by converting squid viscera containing the substance into freeze-dried powder and directly performing supercritical carbon dioxide extraction on the powder, and does not require any other pretreatment. Regarding the extraction pressure, the higher it is in -a, the greater the solvent power becomes, but the selectivity decreases. Therefore, considering economic efficiency, the initial pressure setting was set at 70 to 90 kg/cA.
Depending on the conditions, the pressure may be increased to 200 kg/cyA or more. The temperature must be above the critical temperature of carbon dioxide (3L3°C), but a temperature range of 1 to 50°C higher than the critical temperature is used. Furthermore, although 32 to 200 mesh silica gel powder was used as a carrier for silver nitrate, any porous inorganic powder can be used as a carrier. The column temperature used is a temperature range 10 to 50°C higher than the critical temperature.
本発明法によって得られるＥＰＡ、ＤＩ−ＩＡの濃度は
、ヘキサンなどを用いた有機溶媒抽出法に比べ、２〜３
倍に濃縮され、しかも変性の主な原因であるリンの含有
量はｌｐｐｍ以下の製品となる。The concentration of EPA and DI-IA obtained by the method of the present invention is 2 to 3
The result is a product that is twice as concentrated and contains less than 1 ppm of phosphorus, which is the main cause of denaturation.
尚、ヘキサン抽出法によるイカ内臓中の脂質に含まれる
構成脂肪酸組成を表１に示す。Table 1 shows the composition of fatty acids contained in the lipids in squid viscera obtained by the hexane extraction method.
発明の効果
本発明法によって、血栓症、脳梗塞、心筋梗塞等の虚血
性心疾患症の予防や、プロスタグランジンの前駆体とし
て利用される高機能性油脂のＥＰＡ、ＤＨＡを、これま
でほとんど利用されていなかったイカ内臓より、常温で
、短時間、低コストで効率よく製造することかでるうえ
、装置は流通系なので、連続的に、且つ一行程でＥＰＡ
、ＤＨＡが抽出できるので、本発明法はＥＰＡ、ＤＩ−
ＩＡの工業的製法として好適である。以下に実施例を例
示するが、本発明は、これらの実施例に限定されるもの
ではない。Effects of the Invention By the method of the present invention, EPA and DHA, which are highly functional fats and oils that are used for the prevention of ischemic heart diseases such as thrombosis, cerebral infarction, and myocardial infarction, and as precursors of prostaglandin, have been almost completely eliminated. It can be produced efficiently at room temperature, in a short time, at low cost, using unused squid internal organs, and since the equipment is a distribution system, EPA can be produced continuously and in one process.
, DHA can be extracted, so the method of the present invention can extract EPA, DI-
This is suitable as an industrial method for producing IA. Examples are illustrated below, but the present invention is not limited to these examples.
実施例−１
イカ内臓３００〜５００ｇを、−４０°Ｃで凍結した後
、凍結乾燻しな。凍結乾燥試斜約１ｇを抽出器に仕込み
、流通系装置を用い、恒温槽の温度を６０°Ｃ２二酸化
炭素を９０ ｋＩｒ／ ｃＡ、流量３０ｎ１／ｈの条件
で試料と接触させた。これにより、容易に、イカ内臓中
の脂質は、硝酸銀を担持したシリカゲル粉体を充填した
カラム内に導かれた。Example-1 After freezing 300 to 500 g of squid internal organs at -40°C, freeze-dry and smoke them. Approximately 1 g of the freeze-dried sample was placed in an extractor, and brought into contact with the sample using a flow system device under the conditions of a constant temperature bath of 60°C, carbon dioxide of 90 kIr/cA, and a flow rate of 30 n1/h. As a result, the lipids in the squid internal organs were easily guided into a column filled with silica gel powder supporting silver nitrate.
ここでカラム長さは２５０ｍ５、内径４．６目、カラム
温度は、恒温槽温度と同じである。上記条件でカラムを
通過した該流体は、フィルター、圧力調整弁を経て、常
圧、温度７０℃の分離器に導かれ、上記脂質中から、パ
ルミチン酸、オレイン酸を主成分とする黄色の脂質が分
離された。上記条件下での抽出物の平均抽出速度、脂肪
酸組成は、表２．３にそれぞれ示すとおりである。上記
脂質の主成分は、パルミチン酸、オレイン酸などの不飽
和度の少ない脂肪酸であり、はとんどＥＰＡ。Here, the column length is 250 m5, the inner diameter is 4.6 mm, and the column temperature is the same as the constant temperature bath temperature. The fluid that has passed through the column under the above conditions is guided through a filter and a pressure regulating valve to a separator at normal pressure and a temperature of 70°C. was separated. The average extraction rate and fatty acid composition of the extract under the above conditions are shown in Table 2.3. The main components of the above lipids are fatty acids with a low degree of unsaturation, such as palmitic acid and oleic acid, and are mostly EPA.
ＤＨＡが含まれていないことが分かる。このことから、
上記繰作条件下では、カラム内にＥＰＡ。It can be seen that DHA is not included. From this,
Under the above operating conditions, EPA was added to the column.
ＤＨＡは、高濃度で保持されたままであることが分かる
。It can be seen that DHA remains retained at high concentrations.
実施ＰＡ−２
実施例−１で処理した後、抽出圧力を１５（Ｈｔｇ／−
に昇圧すると、実施例−１で得な抽出物とは異なる白色
の抽出物を得た。この抽出物の脂肪酸組成を、ＧＣ，Ｇ
Ｃ−ＭＳによって分析した結果を表４に、抽出速度を表
５に示しな。本発明法により、ＥＰＡとＤ）ＩＡを合わ
せた濃度は、９０重量％にもたつすることが分がる。特
に、ＤＨＡの濃度が高く、それは７０重量％を越えた。Implementation PA-2 After the treatment in Example-1, the extraction pressure was increased to 15 (Htg/-
When the pressure was increased to , a white extract different from the extract obtained in Example-1 was obtained. The fatty acid composition of this extract was determined by GC, G
The results of analysis by C-MS are shown in Table 4, and the extraction rates are shown in Table 5. It can be seen that by the method of the present invention, the combined concentration of EPA and D)IA is as high as 90% by weight. In particular, the concentration of DHA was high, exceeding 70% by weight.
これは、表１に示した原料中に含まれるＥＰＡとＤＨＡ
の合計濃度の３．２倍の濃縮率である。また、抽出速度
も大きく、上記で示したような温和な条件でありながら
、１時間に約１５０ｍｇの抽出物が得られることが分か
った。This is due to the EPA and DHA contained in the raw materials shown in Table 1.
This is a concentration factor of 3.2 times the total concentration of . It was also found that the extraction rate was high, and approximately 150 mg of extract could be obtained per hour even under the mild conditions shown above.
Claims (1)
イカ内臓を、凍結乾燥し、それに対して、化学的に不活
性である二酸化炭素と、その臨界温度以上および臨界圧
力以上の条件下で接触させ、イカ内臓に含まれている脂
質を上記二酸化炭素中へ移行させたうえで、硝酸銀を担
持した粉体を充填したカラム内を通過させることにより
、実質上効率よく、選択的に上記エイコサペンタエン酸
、ドコサヘキサエン酸をイカ内臓の脂質中から分離する
方法。 ２ 凍結乾燥したイカ内臓と二酸化炭素の接触を、二酸
化炭素の臨界温度より１〜５０℃高い温度条件下で行う
特許請求の範囲の第（１）項記載の方法。 ３ 凍結乾燥したイカ内臓と二酸化炭素の接触を、二酸
化炭素の臨界圧力より１〜１５０ｋｇ／ｃｍ＾２高い条
件下で行う特許請求の範囲第（１）項又は第（２）項記
載の方法。４ 硝酸銀を担持した粉体がシリカゲル又は
アルミナのような多孔性無機粉体である特許請求の範囲
第（１）項、第（２）項、又は第（３）項記載の方法。 ５ 硝酸銀の担持量が、１〜２０重量％である特許請求
の範囲第（１）項、第（２）項、第（３）項又は第（４
）項記載の方法。[Scope of Claims] 1 Squid internal organs containing eicosapentaenoic acid and docosahexaenoic acid are freeze-dried and treated with carbon dioxide, which is chemically inert, under conditions of a temperature above its critical temperature and a pressure above its critical pressure. The lipids contained in the squid internal organs are transferred to the carbon dioxide, and then passed through a column filled with powder supporting silver nitrate, thereby effectively and selectively transferring the lipids contained in the squid internal organs into the carbon dioxide. A method for separating icosapentaenoic acid and docosahexaenoic acid from the lipids of squid internal organs. 2. The method according to claim (1), wherein the freeze-dried squid internal organs are brought into contact with carbon dioxide at a temperature 1 to 50°C higher than the critical temperature of carbon dioxide. 3. The method according to claim (1) or (2), wherein the freeze-dried squid internal organs are brought into contact with carbon dioxide under conditions that are 1 to 150 kg/cm^2 higher than the critical pressure of carbon dioxide. 4. The method according to claim (1), (2), or (3), wherein the powder supporting silver nitrate is a porous inorganic powder such as silica gel or alumina. 5 Claims (1), (2), (3), or (4) in which the supported amount of silver nitrate is 1 to 20% by weight.
) Method described in section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63150929A JPH028298A (en) | 1988-06-17 | 1988-06-17 | Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63150929A JPH028298A (en) | 1988-06-17 | 1988-06-17 | Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH028298A true JPH028298A (en) | 1990-01-11 |
Family
ID=15507496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63150929A Pending JPH028298A (en) | 1988-06-17 | 1988-06-17 | Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH028298A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05287295A (en) * | 1992-04-10 | 1993-11-02 | Shiseido Co Ltd | Method for separating and purifying highly unsaturated fatty acid and its homologue |
| JPH0625694A (en) * | 1992-03-02 | 1994-02-01 | Kd Pharma Gmbh | Production of unsaturated fatty acid |
| JPH06247893A (en) * | 1993-02-23 | 1994-09-06 | Agency Of Ind Science & Technol | Production of octadecatetraenoic acid |
| EP1065196A1 (en) * | 1999-06-28 | 2001-01-03 | Nisshin Flour Milling Co., Ltd. | Process of selectively separating and purifying eicosapentaenoic and docosahexaenoic acids or their esters |
| US6346276B1 (en) | 1997-10-24 | 2002-02-12 | Asahi Kasei Kabushiki Kaisha | Composition containing useful substances originating in fishes and shellfishes and process for the preparation of the substances |
| WO2010010364A2 (en) * | 2008-07-24 | 2010-01-28 | Pharma Marine As | Process for the purification of oils |
| ES2684178A1 (en) * | 2017-03-30 | 2018-10-01 | Universidad Autónoma de Madrid | Obtaining phospholipids from cephalopods by sequential extraction with supercritical fluids (Machine-translation by Google Translate, not legally binding) |
| US10246663B2 (en) | 2015-03-18 | 2019-04-02 | Ihi Corporation | Lipid composition and method for producing same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5484519A (en) * | 1977-12-16 | 1979-07-05 | Kagakuhin Kensa Kiyoukai | Method of purifying longgchained and highly unsaturated fatty acids |
| JPS6055096A (en) * | 1983-09-06 | 1985-03-29 | 岩谷産業株式会社 | Manufacture of neutral lipid from fishes and shells |
| JPS6259697A (en) * | 1985-09-10 | 1987-03-16 | 昭和炭酸株式会社 | Method of extracting, purifying and separating oily components from plant seed |
-
1988
- 1988-06-17 JP JP63150929A patent/JPH028298A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5484519A (en) * | 1977-12-16 | 1979-07-05 | Kagakuhin Kensa Kiyoukai | Method of purifying longgchained and highly unsaturated fatty acids |
| JPS6055096A (en) * | 1983-09-06 | 1985-03-29 | 岩谷産業株式会社 | Manufacture of neutral lipid from fishes and shells |
| JPS6259697A (en) * | 1985-09-10 | 1987-03-16 | 昭和炭酸株式会社 | Method of extracting, purifying and separating oily components from plant seed |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0625694A (en) * | 1992-03-02 | 1994-02-01 | Kd Pharma Gmbh | Production of unsaturated fatty acid |
| JPH05287295A (en) * | 1992-04-10 | 1993-11-02 | Shiseido Co Ltd | Method for separating and purifying highly unsaturated fatty acid and its homologue |
| JPH06247893A (en) * | 1993-02-23 | 1994-09-06 | Agency Of Ind Science & Technol | Production of octadecatetraenoic acid |
| US6346276B1 (en) | 1997-10-24 | 2002-02-12 | Asahi Kasei Kabushiki Kaisha | Composition containing useful substances originating in fishes and shellfishes and process for the preparation of the substances |
| EP1065196A1 (en) * | 1999-06-28 | 2001-01-03 | Nisshin Flour Milling Co., Ltd. | Process of selectively separating and purifying eicosapentaenoic and docosahexaenoic acids or their esters |
| WO2010010364A2 (en) * | 2008-07-24 | 2010-01-28 | Pharma Marine As | Process for the purification of oils |
| WO2010010364A3 (en) * | 2008-07-24 | 2010-03-25 | Pharma Marine As | Process for the purification of oils |
| US10246663B2 (en) | 2015-03-18 | 2019-04-02 | Ihi Corporation | Lipid composition and method for producing same |
| US10844317B2 (en) | 2015-03-18 | 2020-11-24 | Ihi Corporation | Lipid composition and method for producing same |
| ES2684178A1 (en) * | 2017-03-30 | 2018-10-01 | Universidad Autónoma de Madrid | Obtaining phospholipids from cephalopods by sequential extraction with supercritical fluids (Machine-translation by Google Translate, not legally binding) |
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