JP4981375B2 - Method for extracting and separating capsinoid compounds from chili and chili extract - Google Patents
Method for extracting and separating capsinoid compounds from chili and chili extract Download PDFInfo
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- 235000002568 Capsicum frutescens Nutrition 0.000 title claims description 78
- 150000001875 compounds Chemical class 0.000 title claims description 74
- 239000000284 extract Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 25
- 238000000605 extraction Methods 0.000 claims description 149
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 128
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 239000000049 pigment Substances 0.000 claims description 31
- 235000002566 Capsicum Nutrition 0.000 claims description 26
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- 241000722363 Piper Species 0.000 claims description 25
- 235000016761 Piper aduncum Nutrition 0.000 claims description 25
- 235000017804 Piper guineense Nutrition 0.000 claims description 25
- 235000008184 Piper nigrum Nutrition 0.000 claims description 25
- 229940116257 pepper extract Drugs 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 12
- 241001247145 Sebastes goodei Species 0.000 claims description 12
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 239000003429 antifungal agent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 240000008574 Capsicum frutescens Species 0.000 claims 1
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 94
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- 239000003960 organic solvent Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 16
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- VQEONGKQWIFHMN-UHFFFAOYSA-N Nordihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O VQEONGKQWIFHMN-UHFFFAOYSA-N 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
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- 238000003828 vacuum filtration Methods 0.000 description 6
- 241001672694 Citrus reticulata Species 0.000 description 5
- AKDLSISGGARWFP-UHFFFAOYSA-N Homodihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCCC(C)C)=CC=C1O AKDLSISGGARWFP-UHFFFAOYSA-N 0.000 description 4
- XJQPQKLURWNAAH-UHFFFAOYSA-N dihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O XJQPQKLURWNAAH-UHFFFAOYSA-N 0.000 description 4
- RBCYRZPENADQGZ-UHFFFAOYSA-N dihydrocapsaicin Natural products COC1=CC(COC(=O)CCCCCCC(C)C)=CC=C1O RBCYRZPENADQGZ-UHFFFAOYSA-N 0.000 description 4
- MLJGZARGNROKAC-VQHVLOKHSA-N homocapsaicin Chemical compound CCC(C)\C=C\CCCCC(=O)NCC1=CC=C(O)C(OC)=C1 MLJGZARGNROKAC-VQHVLOKHSA-N 0.000 description 4
- JKIHLSTUOQHAFF-UHFFFAOYSA-N homocapsaicin Natural products COC1=CC(CNC(=O)CCCCCC=CC(C)C)=CC=C1O JKIHLSTUOQHAFF-UHFFFAOYSA-N 0.000 description 4
- JZNZUOZRIWOBGG-UHFFFAOYSA-N homocapsaicin-II Natural products COC1=CC(CNC(=O)CCCCC=CCC(C)C)=CC=C1O JZNZUOZRIWOBGG-UHFFFAOYSA-N 0.000 description 4
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- GOBFKCLUUUDTQE-UHFFFAOYSA-N homodihydrocapsaicin-II Natural products CCC(C)CCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 GOBFKCLUUUDTQE-UHFFFAOYSA-N 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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Description
この発明は、唐辛子からカプシノイド化合物を、色素成分とは分離して選択性良く抽出分離する方法に関する。 The present invention relates to a method for extracting and separating a capsinoid compound from chili pepper with good selectivity by separating it from a pigment component.
唐辛子には辛味成分であるカプシノイド化合物（カプサイシン等）が含まれている。近年、カプシノイド化合物は抗酸化性、抗菌性等の様々な機能を有していることが報告されている。具体的には、例えばカプシノイド化合物を摂取することで体脂肪燃焼による肥満防止効果や抗酸化作用による老化防止の効果が得られることが知られている。このようにカプシノイド化合物は様々な効用を有して有用であることから、唐辛子から抽出されたカプシノイド化合物の需要は近年急激に増大している。 The chili contains a capsinoid compound (capsaicin or the like) which is a pungent component. In recent years, it has been reported that capsinoid compounds have various functions such as antioxidant and antibacterial properties. Specifically, it is known that, for example, by taking a capsinoid compound, an obesity preventing effect by burning body fat and an aging preventing effect by antioxidant action can be obtained. Thus, since the capsinoid compound is useful with various effects, the demand for the capsinoid compound extracted from the chili pepper has increased rapidly in recent years.
従来、唐辛子からカプシノイド化合物を抽出する方法としては、唐辛子粉砕物と、水、アセトン、アルコール類、ヘキサン、エーテル及びジオキサンからなる群より選ばれる抽出溶媒とを接触させることによって、抽出溶媒中に唐辛子の中のカプシノイド化合物を抽出する方法が公知である（特許文献１参照）。この方法により唐辛子からカプシノイド化合物を容易に抽出分離することができる。
ところで、前記抽出溶媒を用いて唐辛子からカプシノイド化合物を抽出すると、唐辛子中の色素成分（カロテノイド等）も同時に抽出されるので、この抽出操作により得られたカプシノイド化合物含有唐辛子抽出物は、赤色等の有色を呈する。この色素成分が唐辛子抽出物に存在することによって、前記カプシノイド化合物による抗酸化作用、抗菌作用等を阻害するようなことはないのであるが、例えば唐辛子抽出物を合成樹脂に添加して抗菌性の合成樹脂板を製作した場合には、唐辛子抽出物中の色素成分の赤色の影響を受けて合成樹脂板が強く赤みがかった色になり、所望の美麗な色（例えば青色、緑色、黄色等）を発現させることができないことから、意匠上の制約が大きく、その適用用途は非常に限定されるという問題があった。 By the way, when the capsinoid compound is extracted from the chili pepper using the extraction solvent, the pigment component (carotenoid etc.) in the chili pepper is also extracted at the same time. It is colored. The presence of this pigment component in the pepper extract does not inhibit the antioxidant and antibacterial effects of the capsinoid compound, but for example, the pepper extract is added to a synthetic resin to give an antibacterial effect. When a synthetic resin plate is manufactured, the synthetic resin plate becomes strongly reddish under the influence of the red color of the pigment component in the pepper extract, and the desired beautiful color (for example, blue, green, yellow, etc.) Since it cannot be expressed, there is a problem that design restrictions are large and its application is very limited.
この発明は、かかる技術的背景に鑑みてなされたものであって、唐辛子からカプシノイド化合物を抽出するに際し、色素成分と分離してカプシノイド化合物を選択性良く抽出分離できる方法を提供することを目的とする。 The present invention has been made in view of such a technical background, and an object of the present invention is to provide a method capable of extracting and separating capsinoid compounds with high selectivity by separating them from pigment components when extracting capsinoid compounds from chili peppers. To do.
前記目的を達成するために、本発明は以下の手段を提供する。 In order to achieve the above object, the present invention provides the following means.
［１］水と有機溶媒を含有してなる混合抽出溶媒、唐辛子粉砕物、及び活性炭を相互に接触させることによって、前記混合抽出溶媒中に唐辛子中のカプシノイド化合物を抽出すると共に、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめることを特徴とする唐辛子からカプシノイド化合物を抽出分離する方法。 [1] A mixed extraction solvent containing water and an organic solvent, a pulverized pepper, and activated carbon are contacted with each other to extract a capsinoid compound in the pepper into the mixed extraction solvent, and the mixed extraction solvent A method for extracting and separating a capsinoid compound from chili, which comprises adsorbing a pigment component derived from chili to the activated carbon.
［２］唐辛子粉砕物と、水及び有機溶媒を含有してなる混合抽出溶媒とを接触させることによって、該混合抽出溶媒中に唐辛子中のカプシノイド化合物を抽出する工程と、
前記抽出カプシノイド化合物を含有した混合抽出溶媒と、活性炭とを接触させることによって、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめる工程とを包含することを特徴とする唐辛子からカプシノイド化合物を抽出分離する方法。
[2] A step of extracting a capsinoid compound in chili from the mixed extract solvent by bringing the ground pepper into contact with a mixed extract solvent containing water and an organic solvent;
A step of adsorbing the pepper-derived pigment component in the mixed extraction solvent to the activated carbon by bringing the mixed extraction solvent containing the extracted capsinoid compound into contact with activated carbon. A method for extracting and separating compounds.
［３］前記混合抽出溶媒における水と有機溶媒の混合モル比が、水／有機溶媒＝１０／９０〜９０／１０の範囲である前項１または２に記載の唐辛子からカプシノイド化合物を抽出分離する方法。
[3] A method for extracting and separating a capsinoid compound from chili as described in the preceding
［４］前記混合抽出溶媒を構成する有機溶媒としてエタノールを用いる前項１〜３のいずれか１項に記載の唐辛子からカプシノイド化合物を抽出分離する方法。
[4] The method for extracting and separating a capsinoid compound from chili according to any one of
［５］前記混合抽出溶媒を構成する有機溶媒としてアセトンを用いる前項１〜３のいずれか１項に記載の唐辛子からカプシノイド化合物を抽出分離する方法。
[5] A method for extracting and separating a capsinoid compound from chili according to any one of
［６］前項１〜５のいずれか１項に記載の方法によって得られたカプシノイド化合物含有抽出溶媒から活性炭を分離除去した後、溶媒留去操作を行うことによって粘稠液体又は固形状態で回収された唐辛子抽出物。 [6] After separating and removing activated carbon from the capsinoid compound-containing extraction solvent obtained by the method described in any one of 1 to 5 above, the solvent is distilled off and recovered in a viscous liquid or solid state. Pepper extract.
［７］前項６に記載の唐辛子抽出物を含有してなることを特徴とする防カビ剤。 [7] An antifungal agent comprising the chili extract according to item 6 above.
［８］前項６に記載の唐辛子抽出物を含有してなることを特徴とする抗菌剤。 [8] An antibacterial agent comprising the pepper extract as described in 6 above.
［１］［２］の発明では、混合抽出溶媒として水及び有機溶媒を含有したものを用いているから、即ち混合抽出溶媒として水系のものを用いているから、この混合抽出溶媒に抽出されたカプシノイド化合物は、活性炭に殆ど吸着されることなく該混合抽出溶媒中に安定して存在する。即ち、水系混合溶媒という環境下においてカプシノイド化合物は活性炭には殆ど吸着されない。一方、混合抽出溶媒に抽出された色素成分は活性炭に効率良く吸着されて分離される。従って、本抽出分離方法によれば、唐辛子から、色素成分とは分離してカプシノイド化合物を選択性良く抽出分離することができる。 In the inventions of [1] and [2], since a solvent containing water and an organic solvent is used as the mixed extraction solvent, that is, an aqueous solvent is used as the mixed extraction solvent, the mixture is extracted into this mixed extraction solvent. The capsinoid compound is stably present in the mixed extraction solvent with almost no adsorption to the activated carbon. That is, the capsinoid compound is hardly adsorbed on the activated carbon in an environment of an aqueous mixed solvent. On the other hand, the pigment component extracted into the mixed extraction solvent is efficiently adsorbed and separated by the activated carbon. Therefore, according to the present extraction / separation method, capsinoid compounds can be extracted and separated with high selectivity from chili and separated from the pigment component.
［３］の発明では、混合抽出溶媒における水と有機溶媒の混合モル比が、水／有機溶媒＝１０／９０〜９０／１０の範囲であるから、カプシノイド化合物の抽出効率をより高めることができると共に、カプシノイド化合物の抽出分離の選択性もさらに向上させることができる（色素成分を活性炭により効率良く吸着させることができる）。 In the invention of [3], since the mixing molar ratio of water and organic solvent in the mixed extraction solvent is in the range of water / organic solvent = 10/90 to 90/10, the extraction efficiency of the capsinoid compound can be further increased. At the same time, the selectivity of extraction and separation of capsinoid compounds can be further improved (the dye component can be efficiently adsorbed by activated carbon).
［４］の発明では、水及びエタノールを含有してなる混合抽出溶媒を用いることで特異的な抽出挙動が発現してカプシノイド化合物の抽出効率をより高めることができる。 In the invention of [4], by using a mixed extraction solvent containing water and ethanol, a specific extraction behavior is expressed and the extraction efficiency of the capsinoid compound can be further increased.
［５］の発明では、水及びアセトンを含有してなる混合抽出溶媒を用いることで特異的な抽出挙動が発現してカプシノイド化合物の抽出効率をより高めることができる。 In the invention of [5], by using a mixed extraction solvent containing water and acetone, a specific extraction behavior is expressed and the extraction efficiency of the capsinoid compound can be further increased.
［６］の発明の唐辛子抽出物は、上記抽出分離方法によって得られたカプシノイド化合物含有抽出溶媒から活性炭を分離除去した後、溶媒留去操作を行うことによって粘稠液体又は固形状態で回収された唐辛子抽出物であり、この唐辛子抽出物は色素成分を含有しないか又は殆ど含有しないので、赤色等の色素成分由来の色を呈することがなく、例えば従来の色彩上、意匠上の制約が一挙に解消され、この唐辛子抽出物の適用用途は大きく拡大され得る。 The pepper extract of the invention of [6] was recovered in a viscous liquid or solid state by separating and removing activated carbon from the capsinoid compound-containing extraction solvent obtained by the extraction and separation method, and then performing a solvent distillation operation. It is a chili extract, and since this chili extract contains little or no pigment component, it does not exhibit a color derived from a pigment component such as red. For example, conventional color and design restrictions are all at once. Eliminating, the application of this pepper extract can be greatly expanded.
［７］の発明は、前記［６］の唐辛子抽出物を含有してなる防カビ剤であり、優れた防カビ効果を発揮すると共に、赤色等の色素成分由来の色を呈しないから適用用途は幅広いものとなる。 The invention of [7] is an antifungal agent comprising the chili extract of [6], and exhibits an excellent antifungal effect and does not exhibit a color derived from a pigment component such as red. Will be broad.
［８］の発明は、前記［６］の唐辛子抽出物を含有してなる抗菌剤であり、優れた抗菌効果を発揮すると共に、赤色等の色素成分由来の色を呈しないから適用用途は幅広いものとなる。 [8] The invention of [8] is an antibacterial agent comprising the chili extract of [6], and exhibits an excellent antibacterial effect and does not exhibit a color derived from a pigment component such as red, and thus has a wide range of applications. It will be a thing.
この発明に係る唐辛子からカプシノイド化合物を抽出分離する方法は、水と有機溶媒を含有してなる混合抽出溶媒、唐辛子粉砕物、及び活性炭を混合したものを相互に接触させることによって、前記混合抽出溶媒中に唐辛子中のカプシノイド化合物を抽出すると共に、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめることを特徴とするものである。この抽出分離方法によれば、混合抽出溶媒として水及び有機溶媒を含有したものを用いているから、即ち混合抽出溶媒として水系のものを用いているから、この混合抽出溶媒に抽出されたカプシノイド化合物は、活性炭に殆ど吸着されることなく該混合抽出溶媒中に安定して存在する一方、混合抽出溶媒に抽出された色素成分（唐辛子由来）は活性炭に効率良く吸着分離されるので、唐辛子から、色素成分とは分離してカプシノイド化合物を選択性良く抽出分離することができる。 The method for extracting and separating a capsinoid compound from chili according to the present invention is a mixed extraction solvent comprising water and an organic solvent, a mixture of chili pulverized product, and activated carbon, and the mixed extraction solvent The capsinoid compound in the chili pepper is extracted therein, and the pigment component derived from the chili pepper in the mixed extraction solvent is adsorbed on the activated carbon. According to this extraction / separation method, since a solvent containing water and an organic solvent is used as the mixed extraction solvent, that is, an aqueous solvent is used as the mixed extraction solvent, the capsinoid compound extracted into the mixed extraction solvent. Is stably present in the mixed extraction solvent with almost no adsorption to the activated carbon, while the pigment component extracted from the mixed extraction solvent (derived from chili) is efficiently adsorbed and separated by the activated carbon. Capsinoid compounds can be extracted and separated with high selectivity by separating from the pigment component.
この発明に係る抽出分離方法は、水と有機溶媒を含有してなる混合抽出溶媒、即ち水系混合溶媒という環境下においてはカプシノイド化合物は活性炭には殆ど吸着されないのに対し、色素成分（カロテノイド等）は活性炭に効率良く吸着されるという性質を見出すに至り、このような性質を利用することによって、唐辛子から、色素成分とは分離してカプシノイド化合物を選択性良く抽出分離することができるものである。 In the extraction / separation method according to the present invention, a capsinoid compound is hardly adsorbed on activated carbon in a mixed extraction solvent containing water and an organic solvent, that is, an aqueous mixed solvent, whereas a pigment component (such as a carotenoid). Has been found to be efficiently adsorbed on activated carbon, and by using such properties, capsinoid compounds can be extracted and separated with high selectivity from chili and separated from pigment components. .
なお、上記抽出分離方法では、水と有機溶媒を含有してなる混合抽出溶媒、唐辛子粉砕物、及び活性炭を混合したものを相互に接触させることによって、前記混合抽出溶媒中へのカプシノイド化合物の抽出と、色素成分の活性炭への吸着を同時並行的に行わしめているが、特にこのような方法に限定されるものではなく、混合抽出溶媒中へのカプシノイド化合物の抽出と、色素成分の活性炭への吸着を別工程で行うようにしても良い。即ち、この発明に係る別の、唐辛子からカプシノイド化合物を抽出分離する方法は、唐辛子粉砕物と、水及び有機溶媒を含有してなる混合抽出溶媒とを接触させることによって、該混合抽出溶媒中に唐辛子中のカプシノイド化合物を抽出する工程と、前記抽出カプシノイド化合物を含有した混合抽出溶媒と、活性炭とを接触させることによって、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめる工程とを包含することを特徴とする。 In the extraction and separation method, the capsinoid compound is extracted into the mixed extraction solvent by bringing the mixed extraction solvent containing water and an organic solvent into contact with each other, and a mixture of the ground pepper and activated carbon. In addition, the adsorption of the dye component to the activated carbon is performed simultaneously, but it is not particularly limited to such a method, and the extraction of the capsinoid compound into the mixed extraction solvent and the adsorption of the dye component to the activated carbon are performed. You may make it perform adsorption | suction by another process. That is, another method for extracting and separating a capsinoid compound from chili according to the present invention involves bringing a ground pepper into contact with a mixed extraction solvent containing water and an organic solvent, thereby bringing the capsinoid compound into the mixed extraction solvent. A step of extracting a capsinoid compound in chili, a step of adsorbing the pigment component derived from chili in the mixed extraction solvent to the activated carbon by contacting the mixed extraction solvent containing the extracted capsinoid compound with activated carbon; It is characterized by including.
この発明において、前記混合抽出溶媒における水と有機溶媒の混合モル比は、水／有機溶媒＝１０／９０〜９０／１０の範囲に設定するのが好ましい。水の混合モル比を上記下限又は下限以上に設定することでカプシノイド化合物の抽出分離の選択性をより向上させることができる（即ち色素成分を活性炭により効率良く吸着させることができる）と共に、水の混合モル比を上記上限又は上限以下に設定することでカプシノイド化合物の抽出効率をより高めることができる。中でも、前記混合抽出溶媒における水と有機溶媒の混合モル比は、水／有機溶媒＝４０／６０〜８０／２０の範囲に設定するのがより好ましく、特に好ましい範囲は水／有機溶媒＝４５／５５〜７５／２５であり、さらに最好適範囲は水／有機溶媒＝５０／５０〜６５／３５である。 In the present invention, the mixing molar ratio of water and organic solvent in the mixed extraction solvent is preferably set in the range of water / organic solvent = 10/90 to 90/10. By setting the mixing molar ratio of water to the above lower limit or above the lower limit, the selectivity of extraction and separation of capsinoid compounds can be further improved (that is, the dye component can be adsorbed efficiently by activated carbon) and the water The extraction efficiency of the capsinoid compound can be further increased by setting the mixing molar ratio to the above upper limit or lower limit. Among them, the mixing molar ratio of water and organic solvent in the mixed extraction solvent is more preferably set to a range of water / organic solvent = 40/60 to 80/20, and a particularly preferable range is water / organic solvent = 45 / It is 55-75 / 25, and the most suitable range is water / organic solvent = 50 / 50-65 / 35.
前記混合抽出溶媒を構成する有機溶媒としては、特に限定されるものではないが、例えばエタノール、アセトン、メタノール、１−プロパノール、２−プロパノール等の親水性有機溶媒などが挙げられる。 Although it does not specifically limit as an organic solvent which comprises the said mixed extraction solvent, For example, hydrophilic organic solvents, such as ethanol, acetone, methanol, 1-propanol, 2-propanol, etc. are mentioned.
中でも、前記混合抽出溶媒を構成する有機溶媒としてはエタノールを用いるのが好ましい。水及びエタノールを含有してなる混合抽出溶媒を用いることで特異的な抽出挙動が発現してカプシノイド化合物の抽出効率をより高めることができる。 Among them, it is preferable to use ethanol as the organic solvent constituting the mixed extraction solvent. By using a mixed extraction solvent containing water and ethanol, a specific extraction behavior is exhibited, and the extraction efficiency of the capsinoid compound can be further increased.
図１は、水及びエタノールからなる混合抽出溶媒におけるエタノールのモル分率とカプサイシン抽出量との関係を調べたグラフであるが、このグラフから、エタノール（グラフではエタノールのモル分率が１のケースに相当する）はカプサイシンをある程度抽出できるのに対し、水（グラフではアセトンのモル分率が０のケースに相当する）はカプサイシンを殆ど抽出しないことがわかる。このような２つの溶媒（エタノール・水）を混合して混合抽出溶媒とした場合、その混合モル比率を変化させていった時のグラフは一般的には図１の破線のようになると推定される。実際その他の多くの混合溶媒系ではこのようになることが知られている。しかしながら、唐辛子からカプサイシンを溶媒で抽出するに際し、水及びエタノールからなる混合溶媒系では、図１の実線で示すように、一般的な予測曲線（破線）で求められる抽出量よりも格段に多くの量のカプサイシンを抽出できることがわかった。即ち、唐辛子からカプサイシンを溶媒で抽出するに際し、抽出溶媒として、水及びエタノールを含有してなる混合抽出溶媒を用いた場合には、図１の実線で示すような特異的な抽出挙動を示して高い抽出効率でカプサイシンを抽出することができるのである。 FIG. 1 is a graph in which the relationship between the molar fraction of ethanol and the amount of capsaicin extracted in a mixed extraction solvent composed of water and ethanol is examined. From this graph, ethanol (the case where the molar fraction of ethanol is 1 in the graph) is shown. It can be seen that capsaicin can be extracted to some extent, while water (corresponding to the case where the molar fraction of acetone is 0 in the graph) hardly extracts capsaicin. When two such solvents (ethanol and water) are mixed to form a mixed extraction solvent, the graph when the mixing molar ratio is changed is generally estimated to be as shown by the broken line in FIG. The In fact, many other mixed solvent systems are known to do this. However, when capsaicin is extracted from chili pepper with a solvent, the mixed solvent system consisting of water and ethanol, as shown by the solid line in FIG. It was found that an amount of capsaicin could be extracted. That is, when extracting capsaicin from chili with a solvent, when a mixed extraction solvent containing water and ethanol is used as the extraction solvent, the specific extraction behavior as shown by the solid line in FIG. Capsaicin can be extracted with high extraction efficiency.
なお、図１のグラフは次のようにして得られたものである。即ち、ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、表１に示す組成からなる抽出溶媒１００ｇを加えた後、恒温横型振とう機で温度３３０Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行った後、濾液５ｍＬを採取して天日で十分に乾燥させた。乾燥物（抽出物）を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１００ｇによって抽出されたカプサイシン量（カプサイシン抽出量）を算出した。これらの結果を表１に示す。表１の１１点の結果をグラフにプロットして纏めたものが図１である。 The graph of FIG. 1 is obtained as follows. That is, after adding 100 g of an extraction solvent having the composition shown in Table 1 to 10 g of pulverized pepper (powder) placed in a beaker, the mixture was shaken for 30 minutes using a constant temperature horizontal shaker at a temperature of 330 K and 130 rpm. Stirred. Subsequently, qualitative filter paper No. After performing vacuum filtration using 131, 5 mL of the filtrate was collected and sufficiently dried in the sun. The amount of capsaicin extracted by 100 g of the extraction solvent by quantifying a dry product (extract) dissolved in 10 mL of eluent (methanol: pure water = 8 parts by volume: 2 parts by volume) using a high performance liquid chromatograph. (Capsaicin extraction amount) was calculated. These results are shown in Table 1. FIG. 1 summarizes the results of 11 points in Table 1 plotted on a graph.
或いは、前記混合抽出溶媒を構成する有機溶媒としてはアセトンを用いるのが好ましい。水及びアセトンを含有してなる混合抽出溶媒を用いることで特異的な抽出挙動が発現してカプシノイド化合物の抽出効率をより高めることができる。 Alternatively, acetone is preferably used as the organic solvent constituting the mixed extraction solvent. By using a mixed extraction solvent containing water and acetone, a specific extraction behavior is exhibited, and the extraction efficiency of the capsinoid compound can be further increased.
図２は、水及びアセトンからなる混合抽出溶媒におけるアセトンのモル分率とカプサイシン抽出量との関係を調べたグラフであるが、このグラフから、アセトン（グラフではアセトンのモル分率が１のケースに相当する）はカプサイシンをある程度抽出できるのに対し、水（グラフではアセトンのモル分率が０のケースに相当する）はカプサイシンを殆ど抽出しないことがわかる。このような２つの溶媒（アセトン・水）を混合して混合抽出溶媒とした場合、その混合モル比率を変化させていった時のグラフは一般的には図２の破線のようになると推定される。実際その他の多くの混合溶媒系ではこのようになることが知られている。しかしながら、唐辛子からカプサイシンを溶媒で抽出するに際し、水及びアセトンからなる混合溶媒系では、図２の実線で示すように、一般的な予測曲線（破線）で求められる抽出量よりも格段に多くの量のカプサイシンを抽出できることがわかった。即ち、唐辛子からカプサイシンを溶媒で抽出するに際し、抽出溶媒として、水及びアセトンを含有してなる混合抽出溶媒を用いた場合には図２の実線で示すような特異的な抽出挙動を示して高い抽出効率でカプサイシンを抽出することができるのである。 FIG. 2 is a graph in which the relationship between the molar fraction of acetone and the amount of capsaicin extracted in a mixed extraction solvent composed of water and acetone is examined. From this graph, acetone (the case where the molar fraction of acetone is 1 in the graph) is shown. It can be seen that capsaicin can be extracted to some extent, while water (corresponding to the case where the molar fraction of acetone is 0 in the graph) hardly extracts capsaicin. When these two solvents (acetone / water) are mixed to form a mixed extraction solvent, it is estimated that the graph when the mixing molar ratio is changed is generally as shown by the broken line in FIG. The In fact, many other mixed solvent systems are known to do this. However, when capsaicin is extracted from chili with a solvent, the mixed solvent system consisting of water and acetone is much more than the amount of extraction required by a general prediction curve (dashed line) as shown by the solid line in FIG. It was found that an amount of capsaicin could be extracted. That is, when extracting capsaicin from chili with a solvent, when a mixed extraction solvent containing water and acetone is used as the extraction solvent, a specific extraction behavior as shown by the solid line in FIG. Capsaicin can be extracted with the extraction efficiency.
なお、図２のグラフは次のようにして得られたものである。即ち、ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、表２に示す組成からなる抽出溶媒１００ｇを加えた後、恒温横型振とう機で温度３３０Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行った後、濾液５ｍＬを採取して天日で十分に乾燥させた。乾燥物（抽出物）を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１００ｇによって抽出されたカプサイシン量（カプサイシン抽出量）を算出した。これらの結果を表２に示す。表２の１１点の結果をグラフにプロットして纏めたものが図２である。 The graph of FIG. 2 is obtained as follows. That is, after adding 100 g of an extraction solvent having the composition shown in Table 2 to 10 g of pulverized pepper (powder) placed in a beaker, the mixture was shaken for 30 minutes using a constant temperature horizontal shaker at a temperature of 330 K and 130 rpm. Stirred. Subsequently, qualitative filter paper No. After performing vacuum filtration using 131, 5 mL of the filtrate was collected and sufficiently dried in the sun. The amount of capsaicin extracted by 100 g of the extraction solvent by quantifying a dry product (extract) dissolved in 10 mL of eluent (methanol: pure water = 8 parts by volume: 2 parts by volume) using a high performance liquid chromatograph. (Capsaicin extraction amount) was calculated. These results are shown in Table 2. FIG. 2 summarizes the results of 11 points in Table 2 plotted on a graph.
前記活性炭としては、特に限定されるものではなく、どのようなものでも使用できる。例えば、粉末状、粒状、繊維状等いずれの形状であっても良い。また、活性炭の細孔径、表面積等の性状も特に限定されない。 The activated carbon is not particularly limited, and any activated carbon can be used. For example, any shape such as powder, granule, or fiber may be used. Further, properties such as pore diameter and surface area of the activated carbon are not particularly limited.
また、前記唐辛子粉砕物としては、唐辛子を粉砕したものであればどのようなものでも使用できる。中でも、長径０．５ｍｍ以下の唐辛子粉砕物を用いるのが好ましく、特に好ましいのは唐辛子粉末である。 Further, as the pulverized pepper, any pulverized pepper can be used. Among them, it is preferable to use a pulverized pepper having a major axis of 0.5 mm or less, and particularly preferable is a pepper powder.
この発明の抽出分離方法において、前記各成分の混合比は、特に限定されないが、次のような混合比範囲に設定するのが好ましい。即ち、前記唐辛子粉砕物１０質量部に対して前記混合抽出溶媒を５０〜３００質量部混合するのが好ましい。混合抽出溶媒を５０質量部以上混合することでカプシノイド化合物の抽出効率をさらに向上させることができると共に、３００質量部以下とすることで高い濃度のカプシノイド化合物を含有した抽出溶液を得ることができる。また、前記唐辛子粉砕物１０質量部に対して前記活性炭を２〜８質量部混合するのが好ましい。活性炭を２質量部以上混合することで色素成分の吸着効率をさらに向上させることができると共に、８質量部以下とすることで活性炭の使用量を低減できて経済的である。 In the extraction / separation method of the present invention, the mixing ratio of the respective components is not particularly limited, but is preferably set within the following mixing ratio range. That is, it is preferable to mix 50 to 300 parts by mass of the mixed extraction solvent with respect to 10 parts by mass of the pulverized pepper. By mixing 50 parts by mass or more of the mixed extraction solvent, the extraction efficiency of the capsinoid compound can be further improved, and when it is 300 parts by mass or less, an extraction solution containing a high concentration of capsinoid compound can be obtained. Moreover, it is preferable to mix 2-8 mass parts of said activated carbon with respect to 10 mass parts of said pulverized peppers. By mixing 2 parts by mass or more of activated carbon, the adsorption efficiency of the pigment component can be further improved, and by using 8 parts by mass or less, the amount of activated carbon used can be reduced, which is economical.
また、唐辛子粉砕物と混合抽出溶媒との接触は、特に限定されるものではないが、攪拌により行うのが好ましい。この攪拌操作としては、特に限定されないが、例えば攪拌翼による攪拌、振とう機による振とう攪拌、超音波による攪拌などが挙げられる。 In addition, the contact between the pulverized pepper and the mixed extraction solvent is not particularly limited, but is preferably performed by stirring. The stirring operation is not particularly limited, and examples thereof include stirring with a stirring blade, shaking stirring with a shaker, and stirring with ultrasonic waves.
また、前記抽出操作を行う際の混合抽出溶媒の温度は、抽出効率への影響はあまり無いものの、３０〜６０℃に設定するのが好ましい。 Moreover, although the temperature of the mixed extraction solvent at the time of performing said extraction operation does not have much influence on extraction efficiency, it is preferable to set to 30-60 degreeC.
前記抽出分離操作を行うための抽出分離装置としては、特に限定されるものではないが、例えば特開２００４−６６２２７号公報に記載の装置を挙げることができる。勿論、一般的なミキサー・セトラー装置を用いても良いし、その他の設備を用いても良く、特に限定されない。 The extraction / separation apparatus for performing the extraction / separation operation is not particularly limited, and examples thereof include an apparatus described in JP-A-2004-66227. Of course, a general mixer / settler apparatus may be used, and other equipment may be used, and is not particularly limited.
なお、上記抽出分離方法によって抽出され得るカプシノイド化合物としては、特に限定されるものではないが、例えばカプサイシン、ジヒドロカプサイシン、ノルジヒドロカプサイシン、ホモカプサイシン、ホモジヒドロカプサイシン等が挙げられる。 The capsinoid compound that can be extracted by the extraction and separation method is not particularly limited, and examples thereof include capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin, and homodihydrocapsaicin.
しかして、この発明の抽出分離方法によって得られたカプシノイド化合物含有抽出溶媒から活性炭を分離除去した後、抽出溶媒を留去することによって唐辛子抽出物（カプシノイド化合物含有）を回収する。この唐辛子抽出物は、粘稠液体又は固形状態（粉体、粒体等）で回収される。このような溶媒蒸発法により回収するのが一般的であるが、特にこの手法に限定されるものではなく、例えば吸着剤（多孔性樹脂等）を用いる吸着法により唐辛子抽出物の回収を行うものとしても良い。また、これら唐辛子抽出物から、各個別成分（カプサイシン、ジヒドロカプサイシン、ノルジヒドロカプサイシン、ホモカプサイシン、ホモジヒドロカプサイシン等）に単離して利用するものとしても良い。 Thus, after separating and removing the activated carbon from the capsinoid compound-containing extraction solvent obtained by the extraction and separation method of the present invention, the chili extract (capsinoid compound-containing) is recovered by distilling off the extraction solvent. This chili extract is recovered in a viscous liquid or solid state (powder, granules, etc.). Although it is common to collect by such a solvent evaporation method, it is not particularly limited to this method. For example, a chili extract is recovered by an adsorption method using an adsorbent (porous resin or the like). It is also good. Moreover, it is good also as what isolates and uses for each individual component (Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, a homocapsaicin, a homodihydrocapsaicin, etc.) from these pepper extracts.
前記カプシノイド化合物含有抽出溶媒から活性炭を分離除去する方法としては、特に限定されるものではないが、例えばフィルター濾過による分離、遠心分離などが挙げられる。 A method for separating and removing activated carbon from the capsinoid compound-containing extraction solvent is not particularly limited, and examples thereof include separation by filter filtration and centrifugation.
なお、前記抽出溶媒留去操作後に液−液抽出操作を実施して唐辛子抽出物を回収するようにしても良い。例えば、前記抽出溶媒留去操作後に水を添加し、さらにｎ−ヘキサン等の有機溶媒を加えて攪拌することによって液−液抽出を行わしめた後、静置して水相と油相（ｎ−ヘキサン等）とに分離せしめ、該油相から溶媒を留去することによって唐辛子抽出物（カプシノイド化合物含有）を回収するようにしても良い。 In addition, you may make it collect a chili extract by performing liquid-liquid extraction operation after the said extraction solvent distillation operation. For example, water is added after the extraction solvent evaporating operation, liquid-liquid extraction is performed by adding and stirring an organic solvent such as n-hexane, and the mixture is allowed to stand to leave an aqueous phase and an oil phase (n -Hexane etc.) and the chili extract (capsinoid compound-containing) may be recovered by distilling off the solvent from the oil phase.
前記唐辛子抽出物は、色素成分を含有しないか又は殆ど含有しないので、赤色等の色素成分由来の色を呈することがなくて、様々な用途に利用することが可能であり、例えば防カビ剤、防虫剤、抗菌剤等として好適に用いられる。例えば、前記唐辛子抽出物を合成樹脂に添加することにより、所望の美麗な色（例えば青色、緑色、黄色、パステル調色等）を呈する抗菌性樹脂成形品を提供することができる。 The pepper extract contains no or almost no pigment component, so it does not exhibit a color derived from a pigment component such as red, and can be used for various purposes, for example, an antifungal agent, It is suitably used as an insect repellent and antibacterial agent. For example, an antibacterial resin molded product exhibiting a desired beautiful color (for example, blue, green, yellow, pastel toning, etc.) can be provided by adding the chili extract to a synthetic resin.
なお、この発明において、唐辛子粉砕物と混合抽出溶媒とを接触させる前に、予め唐辛子粉砕物と水とを接触せしめて唐辛子中の水溶性物質を溶解除去しておいても良い。こうすることによって、カプシノイド化合物含有抽出溶媒や唐辛子抽出物における水溶性物質の含有比率を大きく低減することができ、その分カプシノイド化合物含有抽出溶媒や唐辛子抽出物におけるカプシノイド化合物含有比率を顕著に増大させることができる。 In addition, in this invention, before making a chili ground material and a mixed extraction solvent contact, you may make a chili ground material and water contact previously, and dissolve and remove the water-soluble substance in a chili. By doing so, the content ratio of the water-soluble substance in the capsinoid compound-containing extraction solvent and the pepper extract can be greatly reduced, and the capsinoid compound content ratio in the capsinoid compound-containing extraction solvent and the pepper extract is significantly increased accordingly. be able to.
次に、この発明の具体的実施例について説明するが、本発明はこれら実施例のものに特に限定されるものではない。 Next, specific examples of the present invention will be described, but the present invention is not particularly limited to these examples.
＜実施例１＞
ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、水／エタノール＝５８／４２（モル比）の組成からなる混合抽出溶媒１００ｇ及び活性炭０．５ｇを加えた後、恒温横型振とう機で温度３１８Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行って活性炭を分離除去した後、濾液５ｍＬを採取して天日で十分に乾燥させることによって、唐辛子抽出物を得た。この唐辛子抽出物を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。この結果を表３に示す。
<Example 1>
After adding 100 g of mixed extraction solvent having a composition of water / ethanol = 58/42 (molar ratio) and 0.5 g of activated carbon to 10 g of pulverized pepper (powder) put in a beaker, constant temperature horizontal shaking. The mixture was shaken and stirred for 30 minutes at a temperature of 318 K and 130 rpm. Subsequently, qualitative filter paper No. After performing a vacuum filtration using 131 to separate and remove the activated carbon, 5 mL of the filtrate was collected and sufficiently dried in the sun to obtain a chili extract. The amount of capsaicin extracted per 10 g of extraction solvent was calculated by quantifying a solution obtained by dissolving this chili extract in 10 mL of an eluent (methanol: pure water = 8 volumes: 2 volumes) using a high performance liquid chromatograph. . The results are shown in Table 3.
なお、天日で乾燥させて得た前記唐辛子抽出物を液体クロマトグラフ−質量分析装置（ＬＣ−ＭＳ）で分析した結果、抽出物は少なくともカプサイシン・ジヒドロカプサイシン・ノルジヒドロカプサイシン・ホモカプサイシン・ホモジヒドロカプサイシンこれら５種類のカプシノイド化合物を含有していることを確認できた。 In addition, as a result of analyzing the said pepper extract obtained by drying with the sun with a liquid chromatograph-mass spectrometer (LC-MS), an extract is at least capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin, homodihydro. It was confirmed that capsaicin contained these five capsinoid compounds.
＜実施例２＞
活性炭の添加量を１．０ｇとした以外は、実施例１と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 2>
A chili extract was obtained in the same manner as in Example 1 except that the amount of activated carbon added was 1.0 g, and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
＜実施例３＞
活性炭の添加量を２．０ｇとした以外は、実施例１と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 3>
A chili extract was obtained in the same manner as in Example 1 except that the amount of activated carbon added was 2.0 g, and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
＜実施例４＞
活性炭の添加量を５．０ｇとした以外は、実施例１と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 4>
A chili extract was obtained in the same manner as in Example 1 except that the amount of activated carbon added was 5.0 g, and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
＜比較例１＞
活性炭の添加量を０ｇとした（活性炭を添加しない）以外は、実施例１と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Comparative Example 1>
A chili extract was obtained in the same manner as in Example 1 except that the amount of activated carbon added was 0 g (no activated carbon was added), and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
表３から明らかなように、この発明の抽出分離方法を適用した実施例１〜４では、唐辛子から、色素成分とは分離してカプシノイド化合物を選択性良く且つ高い抽出効率で抽出分離することができた。なお、色素成分の活性炭による吸着除去は、抽出溶媒の液の色（色種、濃淡）により確認した（以下、同様）。 As is apparent from Table 3, in Examples 1 to 4 to which the extraction and separation method of the present invention is applied, capsinoid compounds can be extracted and separated from chili by separating them from pigment components with high selectivity and high extraction efficiency. did it. In addition, adsorption removal by activated carbon of a pigment | dye component was confirmed by the color (color kind, light and shade) of the liquid of an extraction solvent (hereinafter the same).
これに対し、比較例１では、抽出溶媒は、赤色を呈しており、カプシノイド化合物と共に色素成分も抽出含有したものとなっていた。 On the other hand, in Comparative Example 1, the extraction solvent exhibited a red color, and the pigment component was extracted and contained together with the capsinoid compound.
＜実施例５＞
ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、水／アセトン＝４５／５５（モル比）の組成からなる混合抽出溶媒１００ｇ及び活性炭０．５ｇを加えた後、恒温横型振とう機で温度３１８Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行って活性炭を分離除去した後、濾液５ｍＬを採取して天日で十分に乾燥させることによって、唐辛子抽出物を得た。この唐辛子抽出物を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。この結果を表４に示す。
<Example 5>
After adding 100 g of mixed extraction solvent having a composition of water / acetone = 45/55 (molar ratio) and 0.5 g of activated carbon to 10 g of pulverized pepper (powder) placed in a beaker, constant temperature horizontal shaking. The mixture was shaken and stirred for 30 minutes at a temperature of 318 K and 130 rpm. Subsequently, qualitative filter paper No. After performing a vacuum filtration using 131 to separate and remove the activated carbon, 5 mL of the filtrate was collected and sufficiently dried in the sun to obtain a chili extract. The amount of capsaicin extracted per 10 g of extraction solvent was calculated by quantifying a solution obtained by dissolving this chili extract in 10 mL of an eluent (methanol: pure water = 8 volumes: 2 volumes) using a high performance liquid chromatograph. . The results are shown in Table 4.
なお、天日で乾燥させて得た前記唐辛子抽出物を液体クロマトグラフ−質量分析装置（ＬＣ−ＭＳ）で分析した結果、抽出物は少なくともカプサイシン・ジヒドロカプサイシン・ノルジヒドロカプサイシン・ホモカプサイシン・ホモジヒドロカプサイシンこれら５種類のカプシノイド化合物を含有していることを確認できた。 In addition, as a result of analyzing the said pepper extract obtained by drying with the sun with a liquid chromatograph-mass spectrometer (LC-MS), an extract is at least capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin, homodihydro. It was confirmed that capsaicin contained these five capsinoid compounds.
＜実施例６＞
活性炭の添加量を１．０ｇとした以外は、実施例５と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 6>
A chili extract was obtained in the same manner as in Example 5 except that the amount of activated carbon added was 1.0 g, and the amount of extracted capsaicin per 10 g of the extraction solvent was similarly calculated.
＜実施例７＞
活性炭の添加量を２．０ｇとした以外は、実施例５と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 7>
A chili extract was obtained in the same manner as in Example 5 except that the amount of activated carbon added was 2.0 g, and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
＜実施例８＞
活性炭の添加量を５．０ｇとした以外は、実施例５と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Example 8>
A chili extract was obtained in the same manner as in Example 5 except that the amount of activated carbon added was 5.0 g, and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
＜比較例２＞
活性炭の添加量を０ｇとした（活性炭を添加しない）以外は、実施例５と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Comparative example 2>
A chili extract was obtained in the same manner as in Example 5 except that the amount of activated carbon added was 0 g (no activated carbon was added), and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
表４から明らかなように、この発明の抽出分離方法を適用した実施例５〜８では、唐辛子から、色素成分とは分離してカプシノイド化合物を選択性良く且つ高い抽出効率で抽出分離することができた。 As is clear from Table 4, in Examples 5 to 8 to which the extraction and separation method of the present invention was applied, capsinoid compounds were extracted and separated from chili by separating them from pigment components with high selectivity and high extraction efficiency. did it.
これに対し、比較例２では、抽出溶媒は、赤色を呈しており、カプシノイド化合物と共に色素成分も抽出含有したものとなっていた。 On the other hand, in Comparative Example 2, the extraction solvent exhibited a red color, and the pigment component was extracted and contained together with the capsinoid compound.
＜比較例３＞
ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、エタノール（抽出溶媒）１００ｇ及び活性炭５．０ｇを加えた後、恒温横型振とう機で温度３１８Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行って活性炭を分離除去した後、濾液５ｍＬを採取して天日で十分に乾燥させることによって、唐辛子抽出物を得た。この唐辛子抽出物を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。この結果を表５に示す。
<Comparative Example 3>
After adding 100 g of ethanol (extraction solvent) and 5.0 g of activated carbon to 10 g of pulverized pepper (powder) in a beaker, the mixture is shaken for 30 minutes with a constant temperature horizontal shaker at a temperature of 318 K and 130 rpm. Stir. Subsequently, qualitative filter paper No. After performing a vacuum filtration using 131 to separate and remove the activated carbon, 5 mL of the filtrate was collected and sufficiently dried in the sun to obtain a chili extract. The amount of capsaicin extracted per 10 g of extraction solvent was calculated by quantifying a solution obtained by dissolving this chili extract in 10 mL of an eluent (methanol: pure water = 8 volumes: 2 volumes) using a high performance liquid chromatograph. . The results are shown in Table 5.
＜比較例４＞
活性炭の添加量を０ｇとした（活性炭を添加しない）以外は、比較例３と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Comparative example 4>
A chili extract was obtained in the same manner as in Comparative Example 3 except that the amount of activated carbon added was 0 g (no activated carbon was added), and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
表５における比較例３と比較例４の抽出溶媒中のカプサイシン含有量の対比から明らかなように、水を含有しない抽出溶媒（エタノールのみ）を用いた比較例３では、抽出されたカプサイシンは活性炭に吸着される量がかなり多くなっており、このためにカプサイシンの抽出効率は低かった。 As is clear from the comparison of capsaicin contents in the extraction solvents of Comparative Example 3 and Comparative Example 4 in Table 5, the extracted capsaicin was activated carbon in Comparative Example 3 using an extraction solvent not containing water (ethanol only). Therefore, the amount of capsaicin extracted was low.
＜比較例５＞
ビーカー内に入れた唐辛子粉砕物（粉末状）１０ｇに対して、アセトン（抽出溶媒）１００ｇ及び活性炭５．０ｇを加えた後、恒温横型振とう機で温度３１８Ｋ、１３０ｒｐｍの条件で３０分間振とう攪拌した。次いで、定性濾紙Ｎｏ．１３１を使用して減圧濾過を行って活性炭を分離除去した後、濾液５ｍＬを採取して天日で十分に乾燥させることによって唐辛子抽出物を得た。この唐辛子抽出物を溶離液（メタノール：純水＝８体積部：２体積部）１０ｍＬに溶解したものを高速液体クロマトグラフを用いて定量することによって、抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。この結果を表６に示す。
<Comparative Example 5>
After adding 100 g of acetone (extraction solvent) and 5.0 g of activated carbon to 10 g of pulverized pepper (powder) in a beaker, shake it for 30 minutes with a constant temperature horizontal shaker at a temperature of 318 K and 130 rpm. Stir. Subsequently, qualitative filter paper No. After carrying out vacuum filtration using 131 to separate and remove activated carbon, 5 mL of the filtrate was collected and dried sufficiently in the sun to obtain a chili extract. The amount of capsaicin extracted per 10 g of extraction solvent was calculated by quantifying a solution obtained by dissolving this chili extract in 10 mL of an eluent (methanol: pure water = 8 volumes: 2 volumes) using a high performance liquid chromatograph. . The results are shown in Table 6.
＜比較例６＞
活性炭の添加量を０ｇとした（活性炭を添加しない）以外は、比較例４と同様にして唐辛子抽出物を得、同様に抽出溶媒１０ｇ当たりの抽出カプサイシン量を算出した。
<Comparative Example 6>
A chili extract was obtained in the same manner as in Comparative Example 4 except that the amount of activated carbon added was 0 g (no activated carbon was added), and the amount of extracted capsaicin per 10 g of extraction solvent was similarly calculated.
表６における比較例５と比較例６の抽出溶媒中のカプサイシン含有量の対比から明らかなように、水を含有しない抽出溶媒（アセトンのみ）を用いた比較例５では、抽出されたカプサイシンは活性炭に吸着される量がかなり多くなっており、このためにカプサイシンの抽出効率は低かった。 As is clear from the comparison of capsaicin contents in the extraction solvents of Comparative Example 5 and Comparative Example 6 in Table 6, in Comparative Example 5 using an extraction solvent not containing water (only acetone), the extracted capsaicin was activated carbon. Therefore, the amount of capsaicin extracted was low.
＜唐辛子抽出物の防カビ性の評価＞
実施例１で得られた唐辛子抽出物の防カビ性を下記のようにして評価した。まず、シャーレに接着剤を塗布した後、塗布面の中央位置に四角形に切り出した夏蜜柑（１ｃｍ×１ｃｍ角）を載せて接着固定し、これを評価用試料とした。前記評価用試料の夏蜜柑に、実施例１で得られた唐辛子抽出物の１倍希釈液を０．５ｍＬ含浸せしめたものを「試料Ｘ」とし、前記評価用試料に液を特に含浸せしめなかったものを「試料Ｙ」とし、これら両試料を２５℃の条件下で９日間放置したところ、前記試料Ｙでは夏蜜柑の全面がカビで完全に覆われると共に接着剤表面にもカビが広がっていたのに対し、前記試料Ｘでは夏蜜柑の一部に少しカビが発生した程度であった。また、前記角形夏蜜柑の裏面をシャーレの透明底面ごしに観察したところ、前記試料Ｙではカビが密集して付着していたのに対し、前記試料Ｘではカビは殆ど付着していなかった。このように、本発明の唐辛子抽出物は、優れた防カビ性（抗菌性）を有している。
<Evaluation of mold resistance of pepper extract>
The antifungal property of the chili extract obtained in Example 1 was evaluated as follows. First, after applying an adhesive to the petri dish, a summer mandarin orange (1 cm × 1 cm square) cut out in a square shape was placed on the center of the coating surface and adhered and fixed, and this was used as a sample for evaluation. A sample obtained by impregnating the sample for summer mandarin orange with 0.5 mL of the 1-fold diluted solution of the pepper extract obtained in Example 1 is referred to as “sample X”, and the sample for evaluation is not particularly impregnated with the solution. When these samples were left for 9 days at 25 ° C., the entire surface of summer mandarin orange was completely covered with mold and the mold also spread on the adhesive surface. On the other hand, in the sample X, a little mold was generated in a part of summer mandarin orange. Further, when the back surface of the square summer mandarin orange was observed through the transparent bottom surface of the petri dish, molds were densely adhered in the sample Y, whereas molds were hardly adhered in the sample X. Thus, the chili pepper extract of the present invention has excellent antifungal properties (antibacterial properties).
Claims (7)
前記抽出カプシノイド化合物を含有した混合抽出溶媒と、活性炭とを接触させることによって、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめる工程とを包含することを特徴とする唐辛子からカプシノイド化合物を抽出分離する方法。 And pepper ground product, contains water and ethanol, by mixing molar ratio of water and ethanol, brought into contact with water / ethanol = 10 / 90-90 / 10 range der of Ru mixed extraction solvent, the mixture extracted Extracting a capsinoid compound from chili in a solvent;
A step of adsorbing the pepper-derived pigment component in the mixed extraction solvent to the activated carbon by bringing the mixed extraction solvent containing the extracted capsinoid compound into contact with activated carbon. A method for extracting and separating compounds.
前記抽出カプシノイド化合物を含有した混合抽出溶媒と、活性炭とを接触させることによって、前記混合抽出溶媒中の唐辛子由来の色素成分を前記活性炭に吸着せしめる工程とを包含することを特徴とする唐辛子からカプシノイド化合物を抽出分離する方法。 A step of adsorbing the pepper-derived pigment component in the mixed extraction solvent to the activated carbon by bringing the mixed extraction solvent containing the extracted capsinoid compound into contact with activated carbon. A method for extracting and separating compounds.
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| KR101837823B1 (en) | 2016-02-17 | 2018-03-13 | 경남대학교 산학협력단 | Method for Producing Hot Pepper Extract |
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| JP6066622B2 (en) * | 2012-08-15 | 2017-01-25 | 日清丸紅飼料株式会社 | Additives used for meat chicken feed and feed containing the same |
| JP7020265B2 (en) * | 2018-04-18 | 2022-02-16 | 味の素株式会社 | Capsinoid extraction method |
| CN111054307B (en) * | 2019-11-28 | 2022-07-05 | 海南大学 | Modified pepper stem adsorbing material and preparation method and application thereof |
| CN112098553B (en) * | 2020-09-11 | 2023-06-09 | 安徽中创食品检测有限公司 | Method for detecting capsaicin compounds in duck necks |
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| JPH10251112A (en) * | 1997-03-07 | 1998-09-22 | Aramitsuku:Kk | Air-permeable insecticidal sheet, air-permeable insecticidal packing bag and their production |
| JP3133708B2 (en) * | 1997-07-18 | 2001-02-13 | アルプス薬品工業株式会社 | Industrial purification method of capsaicin |
| JP4637377B2 (en) * | 2001-02-01 | 2011-02-23 | 長谷川香料株式会社 | Extraction method of capsaicinoid-like substance from pepper |
| JP2004066227A (en) * | 2002-06-13 | 2004-03-04 | Hayaji Shibata | Extraction-separating apparatus and extraction-separating method of capsinoid compound from red pepper and extracted capsinoid compound |
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