JP6050465B1 - Method for producing 3-amino-1-ethylglutarimide - Google Patents
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine Chemical compound CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 claims abstract description 82
- 229940026510 theanine Drugs 0.000 claims abstract description 38
- 229910052751 metal Inorganic materials 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 18
- 239000003365 glass fiber Substances 0.000 claims abstract description 15
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 11
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 11
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 11
- 229910052802 copper Inorganic materials 0.000 claims abstract description 11
- 229910052709 silver Inorganic materials 0.000 claims abstract description 11
- 239000000835 fiber Substances 0.000 claims abstract description 9
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- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 239000011805 ball Substances 0.000 claims abstract description 4
- 150000002739 metals Chemical class 0.000 claims abstract description 4
- 238000003892 spreading Methods 0.000 claims description 8
- 239000011324 bead Substances 0.000 claims description 3
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- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 abstract description 12
- 229960001948 caffeine Drugs 0.000 abstract description 12
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- 238000000034 method Methods 0.000 abstract description 4
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- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
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- DATAGRPVKZEWHA-UHFFFAOYSA-N L-gamma-glutamyl-n-ethylamine Natural products CCNC(=O)CCC(N)C(O)=O DATAGRPVKZEWHA-UHFFFAOYSA-N 0.000 description 2
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- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 2
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- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 235000019583 umami taste Nutrition 0.000 description 2
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- SZQUNAOZNFKTHM-UHFFFAOYSA-N 3-ethylpiperidine-2,6-dione Chemical compound CCC1CCC(=O)NC1=O SZQUNAOZNFKTHM-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 235000019606 astringent taste Nutrition 0.000 description 1
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- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
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- Tea And Coffee (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
【課題】カフェインやカテキンを含まずに、３−アミノ−１−エチルグルタルイミドを効率的に製造できる３−アミノ−１−エチルグルタルイミドの製造方法を提供する。【解決手段】テアニンを非活性物質に展着させた後に、圧力容器内に入れ、圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で５〜５０分処理し、非活性物質が、ガラス繊維、ガラス玉、シリカゲル、金属球および金属繊維よりなる群から選ばれる１種以上であり、金属球の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であり、金属繊維の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属である３−アミノ−１−エチルグルタルイミドの製造方法である。【選択図】図１Provided is a method for producing 3-amino-1-ethylglutarimide, which can efficiently produce 3-amino-1-ethylglutarimide without containing caffeine or catechin. SOLUTION: Theanine is spread on an inactive substance, and then placed in a pressure vessel, pressurized steam is blown into the pressure vessel, and treatment is performed at 100 ° C. to 125 ° C. for 5 to 50 minutes under heating steam saturation. The inactive substance is at least one selected from the group consisting of glass fiber, glass ball, silica gel, metal sphere and metal fiber, and the metal of the metal sphere is from the group consisting of Cu, As, Sb, Bi and Ag. A process for producing 3-amino-1-ethylglutarimide, which is one or more metals selected and the metal of the metal fiber is one or more metals selected from the group consisting of Cu, As, Sb, Bi and Ag It is. [Selection] Figure 1
Description
本発明は、３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ、環状化テアニン）の製造方法に関し、特に、カフェインやカテキンを含まずに、３−アミノ−１−エチルグルタルイミドを効率的に製造できる３−アミノ−１−エチルグルタルイミドの製造方法に関する。 The present invention relates to a method for producing 3-amino-1-ethylglutarimide (3-amino-1-ethylglutarimide), and in particular, without containing caffeine or catechin, 3-amino-1-ethylglutar The present invention relates to a method for producing 3-amino-1-ethylglutarimide capable of efficiently producing imide.
食生活の多様化により、糖尿病等の患者が年々増加している。インシュリン製剤をはじめ数多くの治療薬が開発されているが、これらの薬剤には副作用がある。そのため、副作用の無い安全に利用できる糖尿病等治療に有効な食品の開発が望まれている。 Due to diversification of eating habits, the number of patients with diabetes is increasing year by year. Many therapeutic drugs have been developed, including insulin preparations, but these drugs have side effects. Therefore, development of a food effective for the treatment of diabetes and the like that can be used safely without side effects is desired.
一方、緑茶中には、カフェイン、渋みの主成分であるエピガロカテキン（ＥＧＣＧ等）、うま味成分のアミノ酸（テアニン、グルタミン酸等）、ビタミン（ビタミンＣ等）および無機成分が含まれている。このテアニンは、茶に含まれている特殊なアミノ酸で、茶の「うま味の指標」である。また、テアニンは、茶樹の根においてエチルアミンとグルタミン酸が結合して形成され茶葉に移行する。そして、日光の照射により茶の渋み成分であるカテキンに代謝する。そのため、茶樹への日光の照射を制限することにより、テアニンを含む高級な茶を作ることが行われ、テアニンは高級茶の指標とされている。さらに、テアニンの植物代謝経路について解明や人に対する機能、特に、脳神経系機能の改善に有効であるなど様々な研究が行われ、神経系統の調整に有効で安らぎ効果が認められているが、糖尿病等循環器系の臨床試験での効果は確認されていない。 On the other hand, green tea contains caffeine, epigallocatechin (EGCG, etc.) which is the main component of astringency, umami component amino acids (theanine, glutamic acid, etc.), vitamins (vitamin C etc.) and inorganic components. This theanine is a special amino acid contained in tea and is an “umami indicator” of tea. Theanine is formed by combining ethylamine and glutamic acid in the roots of tea tree and moves to tea leaves. And it metabolizes to catechin which is an astringent component of tea by irradiation of sunlight. Therefore, high-quality tea containing theanine is made by limiting the irradiation of sunlight to tea trees, and theanine is regarded as an index of high-quality tea. Furthermore, various studies such as elucidation of the plant metabolic pathway of theanine and its effect on humans, especially the improvement of the cranial nervous system function, have been conducted, and it has been shown to be effective in regulating the nervous system and has a calming effect. The effects in clinical trials of isocirculatory system have not been confirmed.
これに対し、茶葉中で生成したテアニンを環状化した３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ、環状化テアニン）は、糖尿病等循環器系の治療に有効であることが示唆されている。例えば、特許文献１には、茶葉より糖尿病薬を製造する方法が開示されている。また、非特許文献１には、３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ）が糖尿病等循環器系の患者に有効であることが開示されている。 In contrast, 3-amino-1-ethylglutarimide (cyclized theanine) obtained by cyclizing theanine produced in tea leaves is effective for the treatment of cardiovascular system such as diabetes. Has been suggested. For example, Patent Document 1 discloses a method for producing a diabetic drug from tea leaves. Non-Patent Document 1 discloses that 3-amino-1-ethylglutarimide is effective for patients with circulatory system such as diabetes.
また、３−アミノ−１−エチルグルタルイミドは、例えば、非特許文献２には、茶葉中に３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ、環状化テアニン）が存在することが開示されている。しかしながら、３−アミノ−１−エチルグルタルイミドは、テアニンが環状化したもので、緑茶中には１００ｇ中、５．２ｍｇと少量しか存在いていない。ここで、下記にテアニン（Ｔｈｅａｎｉｎｅ）と３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ）の構造を下記に示す。 In addition, as for 3-amino-1-ethylglutarimide, for example, Non-Patent Document 2 includes 3-amino-1-ethylglutarimide (3-amino-1-ethylglutarimide, cyclized theanine) in tea leaves. It is disclosed. However, 3-amino-1-ethylglutarimide is obtained by cyclization of theanine, and in green tea, there is only a small amount of 5.2 mg in 100 g. Here, the structures of theanine and 3-amino-1-ethylglutarimide are shown below.
さらに、３−アミノ−１−エチルグルタルイミドは、緑茶中には少量しか存在していないため、特許文献２には、茶を、圧力容器内に入れ、加圧蒸気を吹き込み、飽和蒸気圧曲線以下の液体の水を随伴しない環境下で、１００℃〜１２５℃で５〜５０分処理する、テアニンを３−アミノ−１−エチルグルタルイミドに環状化した茶の製造法が、開示されている。
Furthermore, since 3-amino-1-ethylglutarimide is present only in a small amount in green tea, Patent Document 2 discloses that a tea is placed in a pressure vessel and pressurized steam is blown into the saturated vapor pressure curve. A method for producing tea in which theanine is cyclized to 3-amino-1-ethylglutarimide, which is treated at 100 ° C. to 125 ° C. for 5 to 50 minutes in an environment not accompanied by the following liquid water, is disclosed. .
上記のように、茶葉中で生成したテアニンを環状化した３−アミノ−１−エチルグルタルイミド（３−Ａｍｉｎｏ−１−ｅｔｈｙｌｇｌｕｔａｒｉｍｉｄｅ、環状化テアニン）は、糖尿病等循環器系の治療に有効であることが示唆されているが、動物および人間による臨床試験を行うためには、カフェイン、カテキン等を含まないことが必要であり、そのため、カフェインやカテキンを含まずない「３−アミノ−１−エチルグルタルイミドの製造方法」が求められていた。しかしながら、特許文献２記載の技術は、原料の茶中に含まれるカフェイン等を含み、さらに３−アミノ−１−エチルグルタルイミドの収率が低いという問題があった。 As described above, 3-amino-1-ethylglutarimide (cyclized theanine) obtained by cyclizing theanine produced in tea leaves is effective for the treatment of cardiovascular system such as diabetes. However, in order to carry out clinical trials with animals and humans, it is necessary not to contain caffeine, catechin, etc. Therefore, “3-amino-1 which does not contain caffeine or catechin” is required. -"Method for producing ethylglutarimide" has been demanded. However, the technique described in Patent Document 2 includes caffeine and the like contained in the raw tea, and further has a problem that the yield of 3-amino-1-ethylglutarimide is low.
また、非特許文献１，２および特許文献１記載の技術もカフェイン、カテキン等の除去ができず、３−アミノ−１−エチルグルタルイミドを効率的に製造できるものではなかった。 In addition, the techniques described in Non-Patent Documents 1 and 2 and Patent Document 1 cannot remove caffeine, catechin and the like, and cannot efficiently produce 3-amino-1-ethylglutarimide.
そこで、本発明の目的は、前記の従来技術の問題を解決し、カフェインやカテキンを含まずに、３−アミノ−１−エチルグルタルイミドを効率的に製造できる３−アミノ−１−エチルグルタルイミドの製造方法を提供することにある。 Accordingly, an object of the present invention is to solve the above-mentioned problems of the prior art and to produce 3-amino-1-ethylglutarimide efficiently without containing caffeine or catechin. It is providing the manufacturing method of an imide.
本発明者らは、前記課題を解決すべく鋭意検討を行った結果、テアニンを特定の非活性物質に展着することにより、前記目的を達成し得ることを見出し、本発明を完成するに至った。
As a result of intensive studies to solve the above problems, the present inventors have found that the object can be achieved by spreading theanine on a specific inactive substance, and have completed the present invention. It was.
即ち、本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、テアニンを非活性物質に展着させた後に、圧力容器内に入れ、
前記圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で５〜５０分処理し、
前記非活性物質が、ガラス繊維、ガラス玉、シリカゲル、金属球および金属繊維よりなる群から選ばれる１種以上であり、
前記金属球の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であり、
前記金属繊維の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であることを特徴とするものである。
That is, in the method for producing 3-amino-1-ethylglutarimide of the present invention, theanine is spread on an inactive substance and then placed in a pressure vessel.
Pressurized steam is blown into the pressure vessel, and is heated at 100 ° C. to 125 ° C. for 5 to 50 minutes under heated steam saturation,
The inactive substance is at least one selected from the group consisting of glass fiber, glass ball, silica gel, metal sphere and metal fiber;
The metal of the metal sphere is at least one metal selected from the group consisting of Cu, As, Sb, Bi and Ag;
The metal of the metal fiber is one or more metals selected from the group consisting of Cu, As, Sb, Bi, and Ag .
また、本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、前記非活性物質が、ガラス繊維、ガラス玉およびシリカゲルよりなる群から選ばれる１種以上であることが好ましい。
In the method for producing 3-amino-1-ethylglutarimide of the present invention, the inactive substance is preferably at least one selected from the group consisting of glass fibers, glass beads, and silica gel .
本発明によると、カフェインやカテキンを含まずに、３−アミノ−１−エチルグルタルイミドを効率的に製造できる３−アミノ−１−エチルグルタルイミドの製造方法を提供することができる。 According to the present invention, it is possible to provide a method for producing 3-amino-1-ethylglutarimide, which can efficiently produce 3-amino-1-ethylglutarimide without containing caffeine or catechin.
以下、本発明の３−アミノ−１−エチルグルタルイミドの製造方法ついて具体的に説明する。
本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、テアニンを非活性物質に展着させた後に、圧力容器内に入れ、前記圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で５〜５０分処理し、前記非活性物質が、ガラス繊維、ガラス玉、シリカゲル、金属球および金属繊維よりなる群から選ばれる１種以上であり、前記金属球の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であり、前記金属繊維の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であることを特徴とするものである。テアニンを非活性物質に展着させることで、カフェイン、カテキン等を含まないテアニンとすることができる。また、展着後のテアニンを圧力容器内に入れ、前記圧力容器内に加圧蒸気を吹き込み、前記圧力容器内の空気を加圧蒸気に置換することで、テアニンを含む茶原料の好ましくない香気を排気とともに除去することができ、加熱水蒸気飽和により酵素の失活を図ることができる。なお、本発明において「展着」とは、テアニンを物質の表面に広げて付着させることを示す。
Hereinafter, the method for producing 3-amino-1-ethylglutarimide of the present invention will be specifically described.
In the method for producing 3-amino-1-ethylglutarimide of the present invention, theanine is spread on an inactive substance, and then placed in a pressure vessel, and pressurized steam is blown into the pressure vessel, And the non-active substance is at least one selected from the group consisting of glass fiber, glass ball, silica gel, metal sphere, and metal fiber, The metal is at least one metal selected from the group consisting of Cu, As, Sb, Bi and Ag, and the metal of the metal fiber is one type selected from the group consisting of Cu, As, Sb, Bi and Ag It is the above metal . By spreading theanine on an inactive substance, theanine containing no caffeine or catechin can be obtained. Also, the theanine after spreading is put into a pressure vessel, pressurized steam is blown into the pressure vessel, and the air in the pressure vessel is replaced with pressurized steam, thereby unfavorable aroma of the tea material containing theanine Can be removed together with the exhaust gas, and the enzyme can be deactivated by heating steam saturation. In the present invention, “spreading” refers to spreading and attaching theanine to the surface of a substance.
本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、１００℃〜１２５℃の範囲で設定した温度に到達後、前記圧力容器内の空気が加圧水蒸気と置換が完了したことを確認し、排気弁を閉じ、設定した温度とその温度にあわせた所定の圧力で、５〜５０分の設定時間で加熱処理を行い、テアニンを環状化させ、３−アミノ−１−エチルグルタルイミドに転換させる。 The method for producing 3-amino-1-ethylglutarimide according to the present invention confirms that the air in the pressure vessel is completely replaced with pressurized steam after reaching a temperature set in the range of 100 ° C to 125 ° C. The exhaust valve is closed, heat treatment is performed at a set temperature and a predetermined pressure according to the set temperature for a set time of 5 to 50 minutes, theanine is cyclized and converted to 3-amino-1-ethylglutarimide Let
また、本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、テアニンを非活性物質に展着させた後に、圧力容器内に入れ、前記圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で１０〜５０分処理することが好ましく、２５〜５０分処理することがより好ましい。これにより、３−アミノ−１−エチルグルタルイミドをより効率的に製造できる。 Further, in the method for producing 3-amino-1-ethylglutarimide of the present invention, theanine is spread on an inactive substance, and then placed in a pressure vessel, pressurized steam is blown into the pressure vessel, and heated steam Under saturation, the treatment is preferably performed at 100 ° C. to 125 ° C. for 10 to 50 minutes, more preferably 25 to 50 minutes. Thereby, 3-amino-1-ethyl glutarimide can be manufactured more efficiently.
また、本発明の３−アミノ−１−エチルグルタルイミドの製造方法は、前記非活性物質が、ガラス繊維、ガラス玉、シリカゲル、非活性金属（Ｃｕ、Ａｓ、Ｓｂ、Ｂｉ、Ａｇ等）球および非活性金属（Ｃｕ、Ａｓ、Ｓｂ、Ｂｉ、Ａｇ等）繊維よりなる群から選ばれる１種以上であることが好ましく、特に、ガラス繊維、ガラス玉であることが好ましい。前記非活性物質にテアニンを展着することで、カフェイン、カテキン等を含まないテアニンとすることができ、カフェインやカテキンを含まずに、３−アミノ−１−エチルグルタルイミドを効率的に製造できる。ここで、前記ガラス繊維としては、例えば、ジーエルサイエンス株式会社製の「ガラスウール」等を挙げることができる。さらに、前記非活性金属としては、例えば、Ｃｕ、Ａｓ、Ｓｂ、Ｂｉ、Ａｇ等である。なお、３−アミノ−１−エチルグルタルイミドは、極めて吸湿性が高く安定性に欠けるため、保存する場合は、前記非活性物質に展着した状態で保存することが、好ましい。 Further, in the method for producing 3-amino-1-ethylglutarimide of the present invention, the inactive substance includes glass fiber, glass ball, silica gel, inactive metal (Cu, As, Sb, Bi, Ag, etc.) sphere It is preferably at least one selected from the group consisting of non-active metal (Cu, As, Sb, Bi, Ag, etc.) fibers, particularly preferably glass fibers and glass beads. By spreading theanine on the inactive substance, it can be made theanine free of caffeine, catechin, etc., and 3-amino-1-ethylglutarimide can be efficiently added without containing caffeine or catechin. Can be manufactured. Here, examples of the glass fiber include “glass wool” manufactured by GL Sciences Inc. Furthermore, examples of the inactive metal include Cu, As, Sb, Bi, and Ag. Since 3-amino-1-ethylglutarimide is extremely hygroscopic and lacks stability, it is preferable to store the 3-amino-1-ethylglutarimide in a state of spreading on the inactive substance.
本発明において、テアニンは、茶由来のもの等を使用でき、食品等に使用できるものであれば限定されないが、例えば、太陽化学株式会社製のサンテアニン（商品名）等を使用することができる。なお、グルタミンとエチルアミンと酵素を原料としてテアニンを製造している場合は、テアニン中に前記グルタミン等が残留しているため、精製等を行って、残留物を除去して純度を高めることが好ましい。 In the present invention, theanine is not limited as long as it can be used for tea or the like, and for example, suntheanine (trade name) manufactured by Taiyo Kagaku Co., Ltd. can be used. . In the case where theanine is produced using glutamine, ethylamine and an enzyme as raw materials, it is preferable that purification is performed to remove the residue to increase purity because the glutamine and the like remain in theanine. .
本発明において、本発明の製造方法を行うための装置としては、圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で５〜５０分処理することができれば、特に限定されないが、例えば、第１種圧力容器（株式会社サムスン製：ＳＧＣ ６０／１０ＳＡＮ）を使用するこができる。具体的には、例えば、操作盤を操作することで、外部に設置されたボイラーにより、加圧水蒸気が作られ、前記第１種圧力容器に供給し、操作盤で、処理温度１２５℃に設定し、圧力を飽和蒸気圧０．２３２１ＭＰａ、処理時間は５０分を設定することで、本発明の製造方法を行うことができる。 In the present invention, as an apparatus for carrying out the production method of the present invention, if pressurized steam is blown into a pressure vessel and treatment can be performed at 100 ° C. to 125 ° C. for 5 to 50 minutes under heating steam saturation, Although it is not limited, for example, a first type pressure vessel (manufactured by Samsung Co., Ltd .: SGC 60 / 10SAN) can be used. Specifically, for example, by operating the operation panel, pressurized steam is produced by a boiler installed outside and supplied to the first type pressure vessel, and the processing temperature is set to 125 ° C. on the operation panel. The production method of the present invention can be performed by setting the saturated vapor pressure to 0.2321 MPa and the processing time to 50 minutes.
以下、本発明について、実施例を用いてさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although this invention is demonstrated further in detail using an Example, this invention is not limited to these Examples.
（実施例１〜２、比較例１）
図１および２に示すように、１００ｍＬのビーカーに、ガラス繊維（ジーエルサイエンス株式会社製の「ガラスウール」）を入れ、太陽化学株式会社製のサンテアニン（（商品名）１ｇ、５ｇ、１０ｇ）を入れて、展着した。１種圧力容器（株式会社サムスン製：ＳＧＣ ６０／１０ＳＡＮ）を使用して、温度を１２５℃に設定し、排気弁を閉じ、圧力を飽和蒸気圧０．２３２１ＭＰａで、それぞれの処理時間で製造を行った。次いで、常圧に戻して取り出し、ガラス繊維から溶出して乾燥して、３−アミノ−１−エチルグルタルイミドを得た。得られた３−アミノ−１−エチルグルタルイミドを下記高速液体クロマトグラフィー法により、定量分析した。なお、３−アミノ−１−エチルグルタルイミドは、極めて吸湿性が高く安定性に欠けるため、保存する場合は、ガラス繊維（非活性物質）に展着した状態で保存した。
(Examples 1-2, Comparative Example 1)
As shown in FIGS. 1 and 2, glass fiber (“Glass Wool” manufactured by GL Science Co., Ltd.) is put into a 100 mL beaker, and Suntheanine ((trade name) 1 g, 5 g, 10 g) manufactured by Taiyo Kagaku Co., Ltd. And put it on. Using a type 1 pressure vessel (Samsung Co., Ltd .: SGC 60 / 10SAN), set the temperature to 125 ° C, close the exhaust valve, and make the pressure at a saturated vapor pressure of 0.2321 MPa at each treatment time. went. Subsequently, it returned to normal pressure, took out, eluted from the glass fiber, and dried to obtain 3-amino-1-ethylglutarimide. The obtained 3-amino-1-ethylglutarimide was quantitatively analyzed by the following high performance liquid chromatography method. Since 3-amino-1-ethylglutarimide is extremely hygroscopic and lacks stability, when stored, it was stored in a state of being spread on a glass fiber (inactive substance).
処理条件は、比較例１は、テアニンをガラス繊維（ジーエルサイエンス株式会社製の「ガラスウール」）に展着処理後、実施例１は、テアニンをガラス繊維（ジーエルサイエンス株式会社製の「ガラスウール」）に展着処理後、上記１種圧力容器で２５分処理、実施例２は、テアニンをガラス繊維（ジーエルサイエンス株式会社製の「ガラスウール」）に展着処理後、上記１種圧力容器で５０分処理、を行い、各々の条件で、処理後の主要遊離アミノ酸、３−アミノ−１−エチルグルタルイミドにつき、下記高速液体クロマトグラフィーにより、定量分析した。テアニン１ｇの場合の結果を下記表１、テアニン５ｇの場合の結果を下記表２、テアニン１０ｇの場合の結果を下記表３に示す。表１〜３中、単位は、ｍｇ／１００ｇである。 The treatment conditions were as follows: Comparative Example 1 was used to spread theanine on glass fiber (“Glass Wool” manufactured by GL Science Co., Ltd.), and Example 1 was prepared by applying theanine to glass fiber (“Glass Wool” manufactured by GL Science Co., Ltd.). )) And then treated with the above-mentioned one type pressure vessel for 25 minutes. In Example 2, the theanine was spread on glass fiber (“Glass Wool” manufactured by GL Sciences Inc.), and then the above one type pressure vessel. The main free amino acid after treatment, 3-amino-1-ethylglutarimide, was quantitatively analyzed by the following high performance liquid chromatography under each condition. The results in the case of 1 g of theanine are shown in Table 1, the results in the case of 5 g of theanine are shown in Table 2, and the results in the case of 10 g of theanine are shown in Table 3 below. In Tables 1 to 3, the unit is mg / 100 g.
（高速液体クロマトグラフィー（ＨＰＬＣ）による測定）
高速液体クロマトグラフとして株式会社島津製作所製のＬＣ−２０ＡＤ、検出器として株式会社島津製作所製のＲＦ−１０Ａｘｓ、カラムとしてＯＤＳ系カラムを使用し、オーブン温度４０℃、注入量１０μＬで分析した。操作は、試料サンプル１０ｍｇを採取し、精製水で抽出後、内部標準液を添加して５０ｍＬとして、ＨＰＬＣ用サンプルとした。また、和光純薬工業株式会社製のＬ−アスパラギン酸、Ｌ−グルタミン酸、Ｌ−セリン、Ｌ−グルタミン、Ｌ−アルギニン、フナコシ社製のＬ−テアニン、静岡県立大学（衛藤氏）所有の既知の３−アミノ−１−エチルグルタルイミドを用いて、検量線を作成して分析を行った。
(Measurement by high performance liquid chromatography (HPLC))
The analysis was performed at an oven temperature of 40 ° C. and an injection amount of 10 μL using LC-20AD manufactured by Shimadzu Corporation as a high performance liquid chromatograph, RF-10Axs manufactured by Shimadzu Corporation as a detector, and an ODS column as a column. For the operation, 10 mg of a sample sample was collected and extracted with purified water, and then an internal standard solution was added to make 50 mL, thereby preparing a sample for HPLC. In addition, L-aspartic acid, L-glutamic acid, L-serine, L-glutamine, L-arginine manufactured by Wako Pure Chemical Industries, Ltd., L-theanine manufactured by Funakoshi Co., Ltd., known by Shizuoka Prefectural University (Mr. Eto) A calibration curve was prepared and analyzed using 3-amino-1-ethylglutarimide.
（処理前後の比較）
上記実施例１または実施例２で得られた３−アミノ−１−エチルグルタルイミドを（ｍｏｌ／ｍｏｌ）に変換し、その値をＡとし、上記比較例１で得られた３−アミノ−１−エチルグルタルイミドを（ｍｏｌ／ｍｏｌ）に変換し、その値をＢとし、上記比較例１のＬ−テアニンを（ｍｏｌ／ｍｏｌ）に変換し、その値をＣとし、実施例１および実施例２の３−アミノ−１−エチルグルタルイミドの変化率を、下記式、
変化率（％）＝（Ａ−Ｂ）／Ｃ×１００
で求め、結果を下記表４に示す。表４中、単位は、％である。
(Comparison before and after processing)
The 3-amino-1-ethylglutarimide obtained in Example 1 or Example 2 was converted to (mol / mol), and the value was A, and 3-amino-1 obtained in Comparative Example 1 was used. -Ethyl glutarimide is converted to (mol / mol), the value is B, L-theanine of Comparative Example 1 is converted to (mol / mol), the value is C, and Example 1 and Example 2, the change rate of 3-amino-1-ethylglutarimide in the following formula:
Rate of change (%) = (A−B) / C × 100
The results are shown in Table 4 below. In Table 4, the unit is%.
表１〜４の結果から、比較例１と比較して、本発明を実施した実施例１および２では、いずれも３−アミノ−１−エチルグルタルイミドが大幅に増加していた。
From the results of Tables 1 to 4, as compared with Comparative Example 1, in Examples 1 and 2 in which the present invention was carried out, 3-amino-1-ethylglutarimide was significantly increased.
Claims (2)
前記圧力容器内に加圧蒸気を吹き込み、加熱水蒸気飽和下で、１００℃〜１２５℃で５〜５０分処理し、
前記非活性物質が、ガラス繊維、ガラス玉、シリカゲル、金属球および金属繊維よりなる群から選ばれる１種以上であり、
前記金属球の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であり、
前記金属繊維の金属が、Ｃｕ、Ａｓ、Ｓｂ、ＢｉおよびＡｇよりなる群から選ばれる１種以上の金属であることを特徴とする３−アミノ−１−エチルグルタルイミドの製造方法。 After spreading theanine to an inactive substance, put it in a pressure vessel,
Pressurized steam is blown into the pressure vessel, and is heated at 100 ° C. to 125 ° C. for 5 to 50 minutes under heated steam saturation,
The inactive substance is at least one selected from the group consisting of glass fiber, glass ball, silica gel, metal sphere and metal fiber;
The metal of the metal sphere is at least one metal selected from the group consisting of Cu, As, Sb, Bi and Ag;
The method for producing 3-amino-1-ethylglutarimide, wherein the metal of the metal fiber is one or more metals selected from the group consisting of Cu, As, Sb, Bi, and Ag .
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| JP5778876B1 (en) * | 2014-11-28 | 2015-09-16 | 清水 敏子 | Process for producing tea containing 3-amino-1-ethylglutarimide and tea |
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| JP5778876B1 (en) * | 2014-11-28 | 2015-09-16 | 清水 敏子 | Process for producing tea containing 3-amino-1-ethylglutarimide and tea |
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| JPN6016039449; 科学・技術研究 Ｖｏｌ．３, 2014, ｐ．４５-４８ * |
| JPN6016039455; '亜臨界水抽出による茶の味および香りに関する化学的研究' 静岡大学博士論文 , 2013 * |
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