JP2005179215A - Method for extracting taurine - Google Patents
Method for extracting taurine Download PDFInfo
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- JP2005179215A JP2005179215A JP2003420035A JP2003420035A JP2005179215A JP 2005179215 A JP2005179215 A JP 2005179215A JP 2003420035 A JP2003420035 A JP 2003420035A JP 2003420035 A JP2003420035 A JP 2003420035A JP 2005179215 A JP2005179215 A JP 2005179215A
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 title claims abstract description 120
- 229960003080 taurine Drugs 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 241000237502 Ostreidae Species 0.000 claims abstract description 24
- 235000020636 oyster Nutrition 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000284 extract Substances 0.000 claims abstract description 16
- 239000006228 supernatant Substances 0.000 claims abstract description 13
- 235000013372 meat Nutrition 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 16
- 239000002244 precipitate Substances 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000000967 suction filtration Methods 0.000 abstract description 3
- 238000003809 water extraction Methods 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000000909 electrodialysis Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Meat, Egg Or Seafood Products (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は、カキ肉を熱水抽出してカキ肉エキスを得ると共にタウリンを効率よく抽出する方法に関する。 The present invention relates to a method for efficiently extracting taurine while obtaining oyster meat extract by hot water extraction of oyster meat.
タウリンは、カキなどの貝類や軟体動物、魚類の内蔵等に多く含まれている。タウリンを抽出するには、魚介類のエキスをイオン交換法、電気透析法、有機溶剤を使用する析出法等によっている。
電気透析法でタウリンを抽出する場合、1次透析と2次透析の2段階の操作と脱塩処理を必要とすると共にグリシンやグルタミン酸などの遊離アミノ酸もタウリン分画に含まれ、タウリンの純度を50重量%以上にすることは困難で、純度を上げるには、更に精製しなければならない。
また、イオン交換法では、陽イオン交換樹脂と陰イオン交換樹脂の2本のカラムを使用すると共に脱塩操作が必要であり、イオン交換樹脂再生のために大量の酸とアルカリを用いる操作が必要である。
When taurine is extracted by electrodialysis, two steps of primary dialysis and secondary dialysis and desalting are required, and free amino acids such as glycine and glutamic acid are also included in the taurine fraction. It is difficult to make it 50% by weight or more, and in order to increase the purity, further purification is required.
In the ion exchange method, two columns of a cation exchange resin and an anion exchange resin are used, and a desalting operation is required, and an operation using a large amount of acid and alkali is necessary for regeneration of the ion exchange resin. It is.
従来の方法は、大規模な装置や高価な薬品を必要とするため、コスト高になるという欠点がある。
本発明は、カキ肉に含まれているタウリンを大がかりな設備を必要とせずに、カキ肉から簡易な手段でタウリンを抽出しようとするものである。
The conventional method requires a large-scale apparatus and expensive chemicals, and thus has a drawback of high cost.
The present invention is intended to extract taurine from oyster meat by simple means without requiring large facilities for taurine contained in oyster meat.
本発明のタウリンの抽出方法は、生カキ肉を熱水抽出して沈澱物を除去した抽出液にエタノールを添加して沈澱物を回収してカキ肉エキスを得たあとの上清を濃縮し、この濃縮液を摂氏零度以下に冷却することによりタウリンを析出させるものであり、タウリンの温度による溶解度の差が大きいことを利用したものである。 In the method for extracting taurine of the present invention, ethanol is added to an extract obtained by extracting raw oyster meat with hot water to remove the precipitate, and the precipitate is collected to obtain a oyster meat extract, and then the supernatant is concentrated. The concentrated liquid is cooled to less than zero degrees Celsius to precipitate taurine, which utilizes the large difference in solubility depending on the temperature of taurine.
また、生カキ肉を熱水抽出した抽出液にエタノールを添加してエキスを沈澱分離した後、エタノールを含む液分の濃縮液のBrix濃度を40〜70重量%に濃縮し、その濃縮液を冷却することによりタウリンを析出させるものである。 Moreover, after adding ethanol to the extract obtained by extracting hot oyster meat with hot water and precipitating and separating the extract, the Brix concentration of the concentrate containing the ethanol is concentrated to 40 to 70% by weight. Taurine is precipitated by cooling.
図1の工程図に示すように、先ず、原料の生カキ肉に1.5〜2倍量の水を加え、100℃で約1時間煮沸して熱水抽出し、固体分をろ過によって除去した抽出液にエタノールを濃度50〜80体積%になるように添加して沈澱物と上清を得る。沈澱物は、ドラムドライヤーで乾燥させて粉末状のカキ肉エキスとする。 As shown in the process diagram of FIG. 1, first, 1.5 to 2 times the amount of water is added to raw oyster meat, boiled at 100 ° C. for about 1 hour, extracted with hot water, and the solid content is removed by filtration. Ethanol is added to the extracted solution to a concentration of 50 to 80% by volume to obtain a precipitate and a supernatant. The precipitate is dried with a drum dryer to obtain a powdery oyster meat extract.
上清を加熱濃縮法、減圧濃縮法により含有するエタノールを蒸発させて除去すると共に濃縮し、Brix濃度50重量%を超えるまで濃縮する。加熱濃縮において、加熱温度は80℃以上に保持することが望ましい。
濃縮の度合いは、生カキのタウリン含量などによって異なるが、好ましくは、Brix濃度が40〜70重量%になるまでおこなう。
Brix濃度が40重量%未満では、後の工程において濃縮液を冷却してもタウリンが効率よく析出しない場合があり、また、Brix濃度が70重量%を超えると、濃縮液の粘性が高くなりすぎて析出したタウリンを分離することが困難となる。
この濃縮液を水冷して30℃まで冷却し、更に−25℃にし、タウリンの粗結晶を析出させる。
この濃縮液は、図2にタウリンのBrix濃度と凍結温度の関係を示すように、Brix濃度が50重量%以上あると−25℃でも凍結することがなく、タウリンが効率よく析出される。
The supernatant is concentrated by evaporating and removing the ethanol contained by heating concentration method and vacuum concentration method until the Brix concentration exceeds 50% by weight. In the heat concentration, it is desirable to keep the heating temperature at 80 ° C. or higher.
The degree of concentration varies depending on the taurine content of raw oysters, etc., but is preferably performed until the Brix concentration is 40 to 70% by weight.
If the Brix concentration is less than 40% by weight, taurine may not be efficiently precipitated even if the concentrated solution is cooled in the subsequent step. If the Brix concentration exceeds 70% by weight, the viscosity of the concentrated solution becomes too high. It becomes difficult to separate the precipitated taurine.
This concentrated liquid is cooled with water, cooled to 30 ° C., and further brought to −25 ° C. to precipitate crude taurine crystals.
As shown in FIG. 2 showing the relationship between the Brix concentration of taurine and the freezing temperature, this concentrated solution does not freeze even at −25 ° C. when the Brix concentration is 50% by weight or more, and taurine is efficiently precipitated.
析出したタウリンの結晶を(吸引)ろ過によって分離する。
更に、分離したタウリンの結晶を80℃の熱水に撹拌しながら溶解し、室温まで冷却する。この溶液を2℃にし、タウリンの結晶を析出させる。タウリンの結晶が析出した濃縮液を再度(吸引)ろ過してタウリンの結晶を分離すると共に、ろ液は回収して再度の抽出工程にまわして再利用する。タウリンを溶解する際に活性炭等の吸着剤を混合することによって溶液中の不純物が吸着され、脱色されたタウリンを得ることができる。
以上の工程を経ることによって、純度70%のタウリンが得られる。
The precipitated taurine crystals are separated by (suction) filtration.
Further, the separated taurine crystals are dissolved in hot water at 80 ° C. with stirring, and cooled to room temperature. The solution is brought to 2 ° C. to precipitate taurine crystals. The concentrated solution in which the taurine crystals are deposited is filtered again (suction) to separate the taurine crystals, and the filtrate is recovered and reused by being reused in the extraction process. When taurine is dissolved, an adsorbent such as activated carbon is mixed to adsorb impurities in the solution, and decolored taurine can be obtained.
Through the above steps, taurine having a purity of 70% is obtained.
純度90%以上のタウリンを得る場合には、前述の純度70%のタウリン結晶を多めの70℃の熱水に溶解し、活性炭を加えて撹拌し、ろ過助剤プリコートしたブフナー漏斗を使用して吸引ろ過することによって80%以上の純度のタウリンの結晶が得られる。更に、純度を上げる必要がある場合は、このタウリンの結晶に少量の水を加え、80℃以上で加熱溶解した後、再結晶させれば良い。この操作により、純度90%のタウリンを得ることができる。 When obtaining taurine having a purity of 90% or more, dissolve the above-mentioned 70% purity taurine crystals in a large amount of hot water at 70 ° C., add activated carbon, stir, and use a Buchner funnel pre-coated with a filter aid. A taurine crystal having a purity of 80% or more is obtained by suction filtration. Further, when it is necessary to increase the purity, a small amount of water is added to the taurine crystals, dissolved by heating at 80 ° C. or higher, and then recrystallized. By this operation, taurine having a purity of 90% can be obtained.
タウリン結晶を分離した母液は、多くの種類の遊離アミノ酸を高濃度に含む呈味性の高い液であるため、調味料の原料またはそのまま調味料として利用することが可能である。 The mother liquor from which taurine crystals have been separated is a highly tasteful liquid containing many types of free amino acids at high concentrations, and therefore can be used as a raw material for seasonings or as it is as a seasoning.
凍結生カキ肉1.3kgに蒸留水2.0リットルを加え、100℃で40分間加熱抽出し、固体分を除去してカキ肉の抽出液を得た。この濃縮液にエタノールを最終濃度が75%(体積)となるように添加して沈澱を生じさせ、2〜4日間そのまま常温で放置した。
沈澱物を分離し、この沈澱物をドラムドライヤーで140℃において乾燥して粉末化し、カキ肉エキスパウダーを得た。生カキ肉中のタウリンの60〜70%が沈澱物中に、即ちカキ肉エキスパウダーに含まれており、残りの30〜40%が上清に含まれている。
2.0 liters of distilled water was added to 1.3 kg of frozen raw oyster meat, and the mixture was heated and extracted at 100 ° C. for 40 minutes to remove the solid content, thereby obtaining an extract of oyster meat. Ethanol was added to the concentrate to a final concentration of 75% (volume) to cause precipitation, and the mixture was allowed to stand at room temperature for 2 to 4 days.
The precipitate was separated, and the precipitate was dried with a drum dryer at 140 ° C. to be powdered to obtain oyster meat extract powder. 60-70% of taurine in raw oyster meat is contained in the precipitate, that is, in the oyster meat extract powder, and the remaining 30-40% is contained in the supernatant.
このエタノールを高濃度に含有する上清は、Brix濃度が12重量%であり、この上清を加熱して5〜6倍に濃縮してBrix濃度を60重量%にした。エタノールは、加熱によって蒸発飛散して上清から除去された。加熱濃縮に際し、減圧することにより濃縮効率が向上する。
この濃縮液体を−20℃の冷凍庫に10時間いれて冷却してタウリンを析出させ、ブフナー漏斗によって吸引ろ過してタウリンの結晶を分離した。
The supernatant containing ethanol at a high concentration had a Brix concentration of 12% by weight. The supernatant was heated and concentrated 5 to 6 times to a Brix concentration of 60% by weight. Ethanol was removed from the supernatant by evaporation and evaporation by heating. Concentration efficiency is improved by reducing the pressure during the heat concentration.
The concentrated liquid was placed in a freezer at −20 ° C. for 10 hours to cool to precipitate taurine, and suction filtered through a Buchner funnel to separate taurine crystals.
実施例1で調整したタウリン結晶6.0 gに水10ミリリットルを加え、80℃以上に加熱してタウリンを溶解した後、この溶液の温度を80℃以上に保持した状態でろ過し、このろ液を実施例1と同様の条件で冷却した。析出したタウリン結晶を吸引ろ過して分離して乾燥したところ、純度80.1重量%のタウリン結晶2.8g を得た。タウリン以外のその他の遊離アミノ酸は含まれなかった。 After adding 10 ml of water to 6.0 g of taurine crystals prepared in Example 1 and heating to 80 ° C. or higher to dissolve taurine, the solution was filtered while maintaining the temperature of the solution at 80 ° C. or higher. The liquid was cooled under the same conditions as in Example 1. The precipitated taurine crystals were separated by suction filtration and dried to obtain 2.8 g of taurine crystals having a purity of 80.1% by weight. Other free amino acids other than taurine were not included.
本発明のタウリンの抽出方法は、カキ肉を熱水抽出したエキスにエタノールを添加して沈澱物を得た後、上清を濃縮して濃縮液を冷却することにより、タウリンを結晶として析出させるものであるから、従来のような電気透析、イオン交換、分取クロマトグラフィーに比較し、大規模で高価な設備を必要とせず、タウリンの溶解度特性を利用する簡易な方法によって低コストでタウリンを抽出することができる。
また、カキ肉を熱水抽出したエキスにエタノールを添加して沈澱物を得た後の上清は、利用分野が限定されていたものであるが、本発明によってタウリンを効率よく低コストで得ることができ、利用価値を高めることができた。
In the method for extracting taurine of the present invention, after adding ethanol to an extract obtained by extracting oyster meat with hot water to obtain a precipitate, the supernatant is concentrated and the concentrated solution is cooled to precipitate taurine as crystals. Therefore, compared with conventional electrodialysis, ion exchange, and preparative chromatography, taurine can be produced at low cost by a simple method that uses the solubility characteristics of taurine without requiring large-scale and expensive equipment. Can be extracted.
In addition, the supernatant after obtaining ethanol by adding ethanol to an extract obtained by extracting oyster meat with hot water has a limited field of application, but according to the present invention, taurine can be obtained efficiently and at low cost. It was possible to increase the utility value.
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CN102807511A (en) * | 2012-06-18 | 2012-12-05 | 浙江省海洋开发研究院 | Method for extracting taurine from mussel |
CN103570593A (en) * | 2013-10-29 | 2014-02-12 | 张苗 | Method for extracting taurine from oysters |
CN103848763B (en) * | 2014-03-20 | 2015-08-12 | 天津大学 | Organic carboxyl acid or organic carboxyl acid salt additives is adopted to change the method for taurine crystal habit |
CN103848763A (en) * | 2014-03-20 | 2014-06-11 | 天津大学 | Method for changing morphology of taurine crystals by adopting organic carboxylic acid or organic carboxylate additives |
US20170165211A1 (en) * | 2014-12-16 | 2017-06-15 | Jonghyun BYUN | Modified taurine, and pharmaceutical composition for preventing or treating metabolic diseases containing same |
US9877938B2 (en) * | 2014-12-16 | 2018-01-30 | Jonghyun BYUN | Modified taurine, and pharmaceutical composition for preventing or treating metabolic diseases containing same |
CN104829501A (en) * | 2015-03-24 | 2015-08-12 | 辽宁双增生物工程有限公司 | A method of extracting taurine from a mactra chinensis water decoction |
CN104788348A (en) * | 2015-04-30 | 2015-07-22 | 邓鑫 | Method for extracting natural taurine from pearl shells |
CN109476590A (en) * | 2016-06-15 | 2019-03-15 | 边钟贤 | Modified taurine and preparation method thereof |
CN113200889A (en) * | 2020-12-18 | 2021-08-03 | 浙江经贸职业技术学院 | Method for preparing taurine from mussels |
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