JP6180608B1 - Method for inhibiting production of 1-octen-3-one in citrus flavored beverages - Google Patents
Method for inhibiting production of 1-octen-3-one in citrus flavored beverages Download PDFInfo
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- JP6180608B1 JP6180608B1 JP2016208255A JP2016208255A JP6180608B1 JP 6180608 B1 JP6180608 B1 JP 6180608B1 JP 2016208255 A JP2016208255 A JP 2016208255A JP 2016208255 A JP2016208255 A JP 2016208255A JP 6180608 B1 JP6180608 B1 JP 6180608B1
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- Prior art keywords
- citrus
- octen
- chelating agent
- flavor
- beverage
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- KLTVSWGXIAYTHO-UHFFFAOYSA-N 1-Octen-3-one Chemical compound CCCCCC(=O)C=C KLTVSWGXIAYTHO-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 235000020971 citrus fruits Nutrition 0.000 title claims abstract description 84
- 241000207199 Citrus Species 0.000 title claims abstract description 78
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 21
- 235000021554 flavoured beverage Nutrition 0.000 title claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 title description 3
- 239000002738 chelating agent Substances 0.000 claims abstract description 76
- 239000000796 flavoring agent Substances 0.000 claims abstract description 68
- 235000019634 flavors Nutrition 0.000 claims abstract description 61
- 235000013361 beverage Nutrition 0.000 claims abstract description 48
- 239000000126 substance Substances 0.000 claims description 17
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 13
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 11
- 239000000467 phytic acid Substances 0.000 claims description 11
- 235000002949 phytic acid Nutrition 0.000 claims description 11
- 229940068041 phytic acid Drugs 0.000 claims description 11
- 235000005979 Citrus limon Nutrition 0.000 claims description 9
- 238000002835 absorbance Methods 0.000 claims description 5
- 230000001629 suppression Effects 0.000 claims description 5
- 239000000341 volatile oil Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229920000388 Polyphosphate Polymers 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- 229940005740 hexametaphosphate Drugs 0.000 claims description 2
- 125000005341 metaphosphate group Chemical group 0.000 claims description 2
- 239000001205 polyphosphate Substances 0.000 claims description 2
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- 230000015572 biosynthetic process Effects 0.000 claims 2
- 244000248349 Citrus limon Species 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
- 239000003205 fragrance Substances 0.000 abstract description 24
- 230000006866 deterioration Effects 0.000 abstract description 16
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract description 11
- 229910019142 PO4 Inorganic materials 0.000 abstract description 7
- 235000021317 phosphate Nutrition 0.000 abstract description 7
- 238000002156 mixing Methods 0.000 abstract description 5
- 238000012360 testing method Methods 0.000 description 51
- 230000000052 comparative effect Effects 0.000 description 29
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- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 18
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 244000131522 Citrus pyriformis Species 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 235000019640 taste Nutrition 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 5
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- 238000006731 degradation reaction Methods 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
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- 239000004571 lime Substances 0.000 description 3
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- 239000007968 orange flavor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
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- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- 244000276331 Citrus maxima Species 0.000 description 2
- 235000001759 Citrus maxima Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 235000013334 alcoholic beverage Nutrition 0.000 description 2
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- 235000013353 coffee beverage Nutrition 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- 235000019820 disodium diphosphate Nutrition 0.000 description 2
- GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 235000020124 milk-based beverage Nutrition 0.000 description 2
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 2
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
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- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
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- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
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- 240000005979 Hordeum vulgare Species 0.000 description 1
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- 239000004376 Sucralose Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000007144 ferric diphosphate Nutrition 0.000 description 1
- 239000011706 ferric diphosphate Substances 0.000 description 1
- CADNYOZXMIKYPR-UHFFFAOYSA-B ferric pyrophosphate Chemical compound [Fe+3].[Fe+3].[Fe+3].[Fe+3].[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O CADNYOZXMIKYPR-UHFFFAOYSA-B 0.000 description 1
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- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
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Landscapes
- Non-Alcoholic Beverages (AREA)
Abstract
【課題】柑橘系香味飲料における光による劣化臭を効果的にかつ低コストで簡便に抑制する柑橘系香味飲料中の1−オクテン−3−オンの生成を抑制する方法を提供すること。【解決手段】リン酸基を2個以上有するキレート剤を、柑橘系香料を含む飲料に混合することを特徴とする柑橘系香味飲料中の1−オクテン−3−オンの生成を抑制する方法である。キレート剤は縮合リン酸塩または有機リン酸エステルからなる群より選ばれる1種または2種以上のキレート剤である。リン酸基を2個以上有するキレート剤を含有することで、柑橘系香料は光の照射を受けた際に生成する劣化臭成分である1−オクテン−3−オンの生成を効果的に抑制することができる。【選択図】なしAn object of the present invention is to provide a method for suppressing the production of 1-octen-3-one in a citrus flavored beverage that effectively and easily suppresses the deterioration odor caused by light in the citrus flavored beverage. A method for suppressing the production of 1-octen-3-one in a citrus flavored beverage, comprising mixing a chelating agent having two or more phosphate groups with a beverage containing a citrus flavor. is there. The chelating agent is one or more chelating agents selected from the group consisting of condensed phosphates or organophosphates. By containing a chelating agent having two or more phosphate groups, the citrus fragrance effectively suppresses the production of 1-octen-3-one, which is a deteriorated odor component that is produced when irradiated with light. be able to. [Selection figure] None
Description
本発明は、柑橘系香料を含む柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法に関する。 The present invention relates to a method for suppressing production of 1-octen-3-one in a citrus flavored beverage containing a citrus flavor.
柑橘系香料は、レモンやライムなどの柑橘系の果物などに含まれる独特の香気・香味を有する成分であり、柑橘系香料を飲料に添加することにより柑橘系香味を付与することができる。しかし、柑橘系香料は、光の照射を受けると異性化、酸化、分解などによって化学構造が変化して劣化臭成分が生成され、柑橘系香料自体が減少し、柑橘系香味が著しく阻害されることが知られている。そのため、柑橘系香料を含有する製品は、製造、流通、保存などの各段階で光に暴露されると、本来のフレッシュ感が失われるだけでなく、生成した劣化臭により製品の品質が著しく低下する。 A citrus flavor is a component having a unique aroma and flavor contained in citrus fruits such as lemon and lime, and a citrus flavor can be imparted by adding the citrus flavor to a beverage. However, when citrus fragrances are exposed to light, their chemical structure changes due to isomerization, oxidation, decomposition, etc., and deteriorated odor components are generated, citrus fragrances themselves decrease, and citrus flavors are significantly inhibited. It is known. For this reason, products containing citrus fragrance will not only lose their original freshness when exposed to light at each stage of production, distribution, storage, etc., but the quality of the product will be significantly reduced due to the generated degraded odor. To do.
最近では、透明ガラス容器や透明プラスチック容器入りの飲料が増加しており、更にこれらの飲料をコンビニエンスストア、スーパーなどでは長時間、蛍光灯または日光の下に陳列する販売形態が一般的になっている。また、柑橘系香料を含有する飲料のなかでも透明な飲料は、白濁または混濁した飲料に比べて香気成分が光の影響を受けやすいため、異臭や異味の原因となる物質が増加しやすく、光劣化による異臭が目立ちやすいことが知られている。その結果、柑橘系香料の減少と劣化臭の生成に起因する柑橘系香味飲料の品質低下や劣化臭の発生の問題が頻繁に生じており、その早期の解決が望まれている。 Recently, beverages in clear glass containers and clear plastic containers are increasing, and moreover, sales forms of these beverages in convenience stores, supermarkets, etc. are displayed for a long time under fluorescent light or sunlight. Yes. In addition, transparent beverages that contain citrus fragrances are more susceptible to light than turbid or turbid beverages, so the substances that cause off-flavors and tastes tend to increase. It is known that nasty odor due to deterioration is conspicuous. As a result, problems such as a decrease in the quality of citrus flavored beverages and the generation of deteriorated odors due to a decrease in citrus flavors and the generation of deteriorated odors frequently occur, and an early solution is desired.
そこで、光による柑橘系香料の劣化に対して、酸化防止剤として植物の溶媒抽出物の添加(特許文献1)、複数のアミノ酸の混合(特許文献2)、活性炭による光劣化物質の除去(特許文献3)などの対策が検討されている。また、バニリンなどを加えて異臭を目立たなくする(特許文献4)対策が検討されている。 Therefore, for the deterioration of citrus fragrances due to light, addition of a plant solvent extract as an antioxidant (Patent Document 1), mixing of a plurality of amino acids (Patent Document 2), removal of photo-degrading substances by activated carbon (Patent Measures such as literature 3) are being studied. In addition, measures are taken to add vanillin or the like to make the off-flavor inconspicuous (Patent Document 4).
特許文献1および2には、光の照射により生成する劣化臭の原因物質として、シトラールから生成するフォトシトラールに関して記載されている。フォトシトラールは、シトラールが光照射をうけることにより、光化学反応が生じて生成される物質であり、rel-2α-(1-メチルエテニル)-5β-メチルシクロペンタン-1α-カルボアルデヒドなど複数の種類が知られている。 Patent Documents 1 and 2 describe photocitral generated from citral as a causative substance of a deteriorated odor generated by light irradiation. Photocitral is a substance produced by photochemical reaction when citral is exposed to light, and there are several types such as rel-2α- (1-methylethenyl) -5β-methylcyclopentane-1α-carbaldehyde. Are known.
特許文献1では、植物の溶媒抽出物の添加により光による香料の減少とフォトシトラールの生成が抑制されている。また、特許文献2では、アミノ酸を4種類混合することによりフォトシトラールの生成が抑制されている。 In patent document 1, the reduction | decrease of the fragrance | flavor by light and the production | generation of a photocitral are suppressed by addition of the solvent extract of a plant. Moreover, in patent document 2, the production | generation of a photocitral is suppressed by mixing four types of amino acids.
また、特許文献3には、光照射により生成する劣化臭の原因物質は不揮発性物質や植物蝋から生成するカビ臭としており、柑橘系香味が著しく阻害される原因物質であることについて記載されている。不揮発性物質や植物蝋から生成するカビ臭は一般的には1-オクテン-3-オンであることが知られているが、1-オクテン-3-オンは、マッシュルーム臭とも金属臭とも称される匂いを持ち、0.03〜1.12μg/m3とごく低濃度でも劣化臭として敏感に知覚される。 In addition, Patent Document 3 describes that the causative substance of a deteriorated odor generated by light irradiation is a mold odor generated from a nonvolatile substance or vegetable wax, and is a causative substance that significantly inhibits citrus flavor. Yes. Mold odor generated from non-volatile substances and vegetable wax is generally known to be 1-octen-3-one, but 1-octen-3-one is also called mushroom odor or metal odor. It is perceived as a deteriorated odor even at very low concentrations of 0.03 to 1.12 μg / m 3 .
そこで、特許文献3では、香料に活性炭を接触させ、植物蝋に含まれる原因物質(β−シトステリルエステル類、コレステリルエステル類等)を除去し、カビ臭の生成が抑制されている。 Therefore, in Patent Document 3, activated carbon is brought into contact with the fragrance to remove causative substances (β-sitosteryl esters, cholesteryl esters, etc.) contained in the plant wax, and generation of mold odor is suppressed.
特許文献4には、透明飲料に乳性飲料に含まれる香気成分として、バニリン、マルトール、オクタン酸エチル、2−ウンデカノン、エチルマルトールなどを加えることで光劣化物質の異臭を目立たなくするマスキング方法が記載されている。 Patent Document 4 discloses a masking method for making the odor of a photodegradable material inconspicuous by adding vanillin, maltol, ethyl octoate, 2-undecanone, ethyl maltol, or the like as an aroma component contained in a milk beverage to a transparent beverage. Have been described.
しかしながら、特許文献1に記載の発明は、植物から溶媒抽出を行う必要があるため手間と時間がかかり、かつ高コストである。さらに、十分な劣化抑制を行うには大量の抽出物を使用する必要があり香味が損なわれるという問題が生じている。 However, the invention described in Patent Document 1 requires labor and time since it is necessary to perform solvent extraction from plants, and is expensive. Furthermore, in order to sufficiently suppress deterioration, it is necessary to use a large amount of extract, which causes a problem that the flavor is impaired.
また、特許文献2に記載の発明は、アミノ酸を4種類混合するために調合に手間がかかるうえに、十分な劣化抑制を行うには大量にアミノ酸を必要としており、香味が損なわれかつ高コストとなる。 In addition, the invention described in Patent Document 2 requires a lot of time for preparation because four kinds of amino acids are mixed, and also requires a large amount of amino acids to sufficiently suppress deterioration, resulting in loss of flavor and high cost. It becomes.
さらに、フォトシトラールはいずれも劣化臭が弱く、柑橘系香味が著しく阻害されることがないため、フォトシトラールの生成を抑制する方法では効果的に柑橘系香味飲料の光劣化臭を抑制することはできない。 Furthermore, since all of the photocitrals have a weak deterioration odor and the citrus flavor is not significantly inhibited, the method for suppressing the generation of photocitral effectively suppresses the light deterioration odor of the citrus flavored beverage. Can not.
一方、特許文献3に記載の発明は、光劣化臭である1-オクテン-3-オンの生成の抑制を目的としているものの、活性炭で完全に1-オクテン-3-オンの原因物質を除去するには吸着処理やろ過にかなりの工数がかかるため時間とコストが増加し、かつ使用済み活性炭の廃棄物が発生するなどの問題を生じている。 On the other hand, although the invention described in Patent Document 3 aims to suppress the production of 1-octen-3-one which is a photodegradation odor, the causative substance of 1-octen-3-one is completely removed with activated carbon. Has a considerable amount of man-hours for adsorption treatment and filtration, resulting in increased time and cost, and waste of used activated carbon.
特許文献4に記載の発明は、光劣化臭の生成を抑制するものではなく、異臭をマスキングして緩和するためのものであり、生成した光劣化臭が強い場合にはマスキングしきれず光劣化臭を抑制できないという問題がある。 The invention described in Patent Document 4 does not suppress the generation of a photodegraded odor, but is for masking and mitigating a strange odor. When the generated photodegraded odor is strong, it cannot be completely masked and the photodegraded odor There is a problem that cannot be suppressed.
本発明は、前記の不具合を解消するためになされたものであって、柑橘系香味飲料の光による劣化を効果的にかつ低コストで簡便に抑制する柑橘系香味飲料中の1−オクテン−3−オンの生成を抑制する方法を提供することを目的とする。 This invention was made | formed in order to eliminate the said malfunction, Comprising : 1-octene-3 in the citrus flavor drink which suppresses deterioration by the light of a citrus flavor drink simply and effectively at low cost -It aims at providing the method of suppressing production | generation of ON .
本発明に係る柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法は、柑橘類の天然精油を原料として得られる不揮発性物質を含有する柑橘系香料を含有する柑橘系香味飲料に、フィチン酸、ヘキサメタリン酸塩、メタリン酸塩、ポリリン酸塩、ピロリン酸塩からなる群より選ばれる1種または2種以上のキレート剤を混合し、前記キレート剤の水溶液中の濃度が0.2〜100ppmであり、前記柑橘系飲料の波長660nmの吸光度が0.06以下であり、前記キレート剤により1−オクテン−3−オンの生成を抑制することを特徴とする。 The method for suppressing the production of 1-octen-3-one in the citrus flavored beverage according to the present invention is a citrus flavored beverage containing a citrus flavor containing a non-volatile substance obtained from a natural essential oil of citrus fruits. One or more chelating agents selected from the group consisting of phytic acid, hexametaphosphate, metaphosphate, polyphosphate and pyrophosphate are mixed, and the concentration of the chelating agent in the aqueous solution is 0.2 to The absorbance at a wavelength of 660 nm of the citrus beverage is 0.06 or less, and the chelating agent suppresses production of 1-octen-3-one .
前記柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法において、前記柑橘系香料がレモンを原料としていることを特徴とする。 In the method for suppressing the production of 1-octen-3-one in the citrus flavored beverage , the citrus flavor is made from lemon.
前記柑橘系香味飲料において、前記柑橘系飲料が、透明又は半透明な容器に充填されていることを特徴とする。 In the citrus flavor beverage, the citrus beverage, characterized in that it is filled in transparency or semi-transparent container.
本発明の柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法では、リン酸基を2個以上有するキレート剤を、柑橘系香料を含む飲料に混合することにより、柑橘系香味飲料の光による劣化を効果的にかつ低コストで簡便に抑制することができる。 In citrus method oct-1-en-3- one product inhibition flavor beverage of the present invention, a chelating agent having a phosphoric acid group two or more, by mixing the drink containing citrus flavors, citrus flavors beverage Deterioration due to light can be effectively suppressed at low cost and easily.
また、柑橘系香味飲料が光照射により1-オクテン-3-オンを生成することを効果的に抑制できる。さらに、添加するキレート剤は少量でも効果が高いために低コストであり、かつ柑橘系香味飲料にキレート剤を通常の方法で混合するだけであるため簡便に製造することができる。 Moreover, it can suppress effectively that a citrus flavor drink produces | generates 1-octen-3-one by light irradiation. Furthermore, the amount of the chelating agent to be added is low because it is highly effective, and the chelating agent can be simply produced by simply mixing the chelating agent into the citrus flavored beverage by an ordinary method.
本発明の実施形態に係る柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法は、リン酸基を2個以上有するキレート剤と、柑橘系香料とを含む。柑橘系香味飲料は、糖分、酸、香料を所定の量加え調合した後、原液または5〜50%水溶液としたキレート剤を加えても良いし、あるいはキレート剤を前記香料と混合製剤として加えて調整されても良いが、これに限定されるものではない。 The production | generation suppression method of 1-octen-3-one in the citrus flavor drink which concerns on embodiment of this invention contains the chelating agent which has two or more phosphate groups, and a citrus flavor. The citrus flavored beverage may be prepared by adding a predetermined amount of sugar, acid, and fragrance, and then adding a chelating agent that is an undiluted solution or 5 to 50% aqueous solution, or adding a chelating agent as a mixed preparation with the fragrance. Although it may be adjusted, it is not limited to this.
柑橘系香料とは、柑橘類の天然精油または天然精油を原料として得られるエッセンス香料などである。原料である柑橘類は、ミカン科ミカン亜科に属するもので特に限定されないが、植物の果実または果実由来の残渣物、花、葉、茎、根、木部等があげられる。また柑橘類と非柑橘類の混合物や、天然に限らず合成の香料原料として使用されるものも含まれる。 Citrus fragrances are citrus natural essential oils or essence fragrances obtained from natural essential oils as raw materials. Citrus which is a raw material belongs to the citrus family Citrus subfamily and is not particularly limited, and examples thereof include plant fruits or fruit-derived residues, flowers, leaves, stems, roots, xylem and the like. Also included are mixtures of citrus and non-citrus fruits and those used as raw materials for synthetic fragrances as well as natural ones.
飲料中の柑橘系香料の濃度に特に限定はなく、それぞれの飲料に応じた濃度を適宜設定することができるが、通常は、100〜5000ppm程度が用いられている。 There is no limitation in particular in the density | concentration of the citrus-type fragrance | flavor in a drink, Although the density | concentration according to each drink can be set suitably, Usually, about 100-5000 ppm is used.
柑橘系香料としては、以下のようなものがある。例えば、ミカン類としては、マンダリンオレンジ、ウンシュウミカン、ポンカン、タチバナ、カラマンシー等がある。オレンジ類としては、バレンシアオレンジ、ネーブルオレンジ、ブラッドオレンジ、ベルガモット等がある。グレープフルーツ類としては、グレープフルーツ、オランジェロ等がある。香酸柑橘類としては、ユズ、ダイダイ、カボス、スダチ、レモン、シークヮーサー、ライム、シトロン、ブッシュカン、三宝柑等がある。 Examples of citrus fragrances include the following. For example, mandarin oranges include mandarin orange, Satsuma mandarin, Ponkan, Tachibana, and Karamanshi. Examples of oranges include Valencia orange, Navel orange, Blood orange and Bergamot. Examples of grapefruits include grapefruit and orangelo. Examples of perfume citrus include yuzu, daidai, kabosu, sudachi, lemon, shikwasa, lime, citron, bushcan, and sanpokan.
また、雑柑類としては、ナツミカン、ハッサク、ヒュウガナツ、ジャバラ、スウィーティー等があげられる。タンゴール類としては、イヨカン、清見、タンカン、マーコット、シラヌヒ、せとか等がある。タンゼロ類としては、セミノール、サマーフレッシュ、スイートスプリング、タンジェロ等があげられる。ブンタン類としては、ブンタン、晩白柚、河内晩柑等があげられる。さらに、その他としては、カラタチ類とキンカン類があげられる。なお、柑橘系香料はこれらに限定されるものではない。 Examples of miscellaneous citrus fruits include nutmican, hassaku, hyuganatsu, bellows, and sweeties. Examples of tongues include Iyokan, Kiyomi, Tankan, Markot, Shiranuhi, and Setoko. Examples of tan zeros include seminole, summer fresh, sweet spring, and tangelo. Examples of Buntans include Buntan, Banpaku, and Kawachi Bankan. Other examples include Karachi and kumquats. In addition, a citrus fragrance | flavor is not limited to these.
また、柑橘系香料の原料である天然精油は、果実原料から圧搾、溶媒抽出などを行うことにより得られ、これにはテルペン炭化水素、アルコール、アルデヒドなどの揮発性香気成分と、クマリン類、フロクマリン類、フラボノイド、配糖体、植物蝋などの不揮発性成分が含まれている。 Natural essential oil, which is a raw material for citrus fragrances, is obtained by pressing, solvent extraction, etc. from fruit raw materials, which include volatile aromatic components such as terpene hydrocarbons, alcohols, aldehydes, and coumarins, furocoumarins. Non-volatile components such as flavonoids, flavonoids, glycosides and vegetable waxes are included.
リン酸基を2個以上有するキレート剤としては、縮合リン酸塩または有機リン酸エステルが用いられる。 As the chelating agent having two or more phosphate groups, condensed phosphates or organic phosphates are used.
リン酸基を2個以上有する縮合リン酸塩としては、ヘキサメタリン酸ナトリウム、酸性メタリン酸ナトリウム、メタリン酸カリウム、ポリリン酸ナトリウム、ポリリン酸カリウム、ピロリン酸四ナトリウム、ピロリン酸二水素二ナトリウム、ピロリン酸四カリウム、ピロリン酸二水素カルシウム、ピロリン酸第二鉄などがあるが、これらに限定されるものではない。 Examples of condensed phosphates having two or more phosphate groups include sodium hexametaphosphate, acidic sodium metaphosphate, potassium metaphosphate, sodium polyphosphate, potassium polyphosphate, tetrasodium pyrophosphate, disodium dihydrogen pyrophosphate, pyrophosphoric acid Examples include, but are not limited to, tetrapotassium, calcium dihydrogen pyrophosphate, and ferric pyrophosphate.
また、リン酸基を2個以上有する有機リン酸エステルは、フィチン酸があげられる。フィチン酸は生体物質の1種で、myo−イノシトールの六リン酸エステル、myo−イノシトール−1,2,3,4,5,6−六リン酸とも言う。種子など多くの植物組織に存在する主要なリンの貯蔵形態であり、キレート作用が強く、多くの金属イオンを強く結合する特徴がある。 An organic phosphate having two or more phosphate groups is phytic acid. Phytic acid is a kind of biological material and is also called myo-inositol hexaphosphate, myo-inositol-1,2,3,4,5,6-hexaphosphate. It is a major phosphorus storage form present in many plant tissues such as seeds, has a strong chelating action, and has a feature of strongly binding many metal ions.
また、キレート剤としては、縮合リン酸塩または有機リン酸エステルからなる群より1種類のキレート剤が用いられるが、2種類以上のキレート剤を組み合わせて用いてもよい。 Further, as the chelating agent, one type of chelating agent is used from the group consisting of condensed phosphates or organic phosphates, but two or more types of chelating agents may be used in combination.
リン酸基を2個以上有するキレート剤の柑橘系香味飲料中における含有量は、0.2〜1000ppm、好ましくは1〜100ppmである。キレート剤が0.2ppmよりも少ないと光劣化物の抑制効果がみられず、また1000ppmよりも多いとキレート剤の呈味により柑橘系香味が損なわれる。 Content in the citrus flavor drink of the chelating agent which has 2 or more of phosphoric acid groups is 0.2-1000 ppm, Preferably it is 1-100 ppm. When the amount of the chelating agent is less than 0.2 ppm, the effect of suppressing photodegradation is not observed, and when it is more than 1000 ppm, the citrus flavor is impaired due to the taste of the chelating agent.
キレート剤は、飲料中にそのまま添加したものであっても、柑橘系香料(レモン香料、オレンジ香料、ライム香料、グレープフルーツ香料など)に含まれる形で添加されてもよいし、非柑橘系香料およびそれらの混合物や、天然に限らず合成の香料原料として使用されるものに含まれる形で添加されてもよい。 The chelating agent may be added as it is in the beverage, or may be added in a form contained in a citrus flavor (lemon flavor, orange flavor, lime flavor, grapefruit flavor, etc.), non-citrus flavor and You may add in the form contained in those mixtures, and what is used not only as a natural thing but as a synthetic | combination fragrance | flavor raw material.
本発明の実施形態に係る柑橘系香味飲料は、柑橘系香料を含有しかつ酸性である飲料であれば、特に限定がされず、非アルコール飲料およびアルコール飲料のいずれも含む。非アルコール飲料としては、例えば、炭酸飲料、ミネラルウォーター(硬水・軟水)、スポーツドリンク、ニアーウォーター、茶飲料(緑茶飲料・紅茶飲料・ウーロン茶飲料・麦茶飲料)、コーヒー飲料、乳飲料、果汁入り飲料(特に、柑橘果汁および/または柑橘果肉入り飲料)、野菜汁入り飲料、果汁および野菜汁飲料などがあげられる。また、アルコール飲料としては、例えば、ビール、発泡酒、酎ハイ、ウイスキー、バーボン、スピリッツ、リキュール、ワイン、果実酒、日本酒、中国酒、焼酎などがあげられる。 The citrus flavored beverage according to the embodiment of the present invention is not particularly limited as long as it contains a citrus flavor and is acidic, and includes both non-alcoholic beverages and alcoholic beverages. Non-alcoholic beverages include, for example, carbonated beverages, mineral water (hard water / soft water), sports drinks, near water, tea beverages (green tea beverages / tea beverages / oolong tea beverages / barley tea beverages), coffee beverages, milk beverages, fruit juice beverages (In particular, citrus fruit juice and / or citrus fruit-containing beverages), vegetable juice-containing beverages, fruit juices and vegetable juice beverages. Examples of alcoholic beverages include beer, sparkling liquor, strawberry high, whiskey, bourbon, spirits, liqueur, wine, fruit liquor, Japanese sake, Chinese liquor, and shochu.
本発明の飲料は透明でもよく、「透明な飲料」とは紫外可視分光光度計(Thermo SCIENTIFIC社製GENESYS 10S UV-Visなど)を用いて測定した波長660nmにおける吸光度が0.06以下であるものを「透明」と呼ぶことができる。なお、飲料の色は特に限定されず、上述の透明さを保持していれば、有色であってもかまわない。 The beverage of the present invention may be transparent, and the “transparent beverage” is one having an absorbance at a wavelength of 660 nm of 0.06 or less measured using an ultraviolet-visible spectrophotometer (such as GENESYS 10S UV-Vis manufactured by Thermo SCIENTIFIC). Can be called “transparent”. In addition, the color of a drink is not specifically limited, As long as the transparency mentioned above is hold | maintained, it may be colored.
本発明の実施形態に係る柑橘系香味飲料は、適量の柑橘系香料と、前記所定範囲の量のキレート剤を含有させる以外は、その飲料の種類に応じた原料を用い、その飲料の製造で通常用いられている方法及び条件に従って製造することが出来る。上記キレート剤を含有させる方法は、たとえば上記キレート剤を飲料に直接添加する方法があげられるが、これに限定されるものではない。 The citrus flavored beverage according to the embodiment of the present invention is produced by using a raw material corresponding to the type of the beverage, except for containing an appropriate amount of the citrus flavor and the amount of the chelating agent in the predetermined range. It can be produced in accordance with commonly used methods and conditions. Examples of the method of containing the chelating agent include a method of directly adding the chelating agent to a beverage, but are not limited thereto.
柑橘系香味飲料のpHは、pH7未満の酸性であればいずれのpHでもよいが、酸味を強く感じるpH2.5〜4が通常よく用いられている。 The pH of the citrus flavored beverage may be any pH as long as it is acidic at a pH of less than 7, but pH 2.5 to 4 that strongly feel the acidity is usually used.
本発明の実施形態に係る柑橘系香味飲料は、クエン酸、リンゴ酸、酒石酸等の酸味料とショ糖、ブドウ糖、果糖、果糖ブドウ糖液糖、オリゴ糖類などの糖類を基本処方とする酸性飲料に、上記キレート剤を含有させたものであるが、飲料において許容され、通常使用される果汁や茶、コーヒーなどの植物抽出物および添加物、例えば、アスパルテーム、スクラロース、ステビア等の甘味料、ビタミン類、着色料、安定剤、酸化防止剤、pH調整剤、乳化剤、保存料、防腐剤、防かび剤、発色剤などを含有してもよい。 The citrus flavored beverage according to the embodiment of the present invention is an acidic beverage having a basic prescription of sucrose, glucose, fructose, fructose glucose liquid sugar, saccharides such as oligosaccharides, and sour agents such as citric acid, malic acid and tartaric acid The above-mentioned chelating agent is contained, but it is acceptable in beverages and is commonly used in plant extracts and additives such as fruit juice, tea, and coffee, for example, sweeteners such as aspartame, sucralose, stevia, vitamins , Colorants, stabilizers, antioxidants, pH adjusters, emulsifiers, preservatives, preservatives, fungicides, color formers and the like.
本発明の実施形態に係る柑橘系香味飲料は、PETボトル、ガラスビンなど光透過性を有する透明容器又は半透明容器に充填した形態で提供するのが好ましく、充填される容量は特に制限されない。 The citrus flavored beverage according to the embodiment of the present invention is preferably provided in a form filled in a transparent or translucent container having light transmittance such as a PET bottle or a glass bottle, and the capacity to be filled is not particularly limited.
以下、実施例によって光照射試験を行い、官能評価と、1-オクテン-3-オンの生成量の測定により光劣化の程度を評価したが、これらの実施例は本発明を限定するものでない。 Hereinafter, although the light irradiation test was done by the Example and the degree of photodegradation was evaluated by sensory evaluation and the measurement of the production amount of 1-octen-3-one, these Examples do not limit the present invention.
光劣化についての実験は、柑橘系香料を用いて飲料を調整し、光劣化抑制物質であるキレート剤を加えた後、人工気象器を用いて光照射を行い、光劣化の程度を官能試験と1-オクテン-3-オンの生成量を測定することで光劣化抑制物質を加えていない飲料と比較した。1-オクテン-3-オンの生成量の比較は、実験誤差を抑えるためにキレート剤が無添加の場合の1-オクテン-3-オンの生成量を100とし、各キレート剤を添加した場合の1-オクテン-3-オンの生成量を測定し、相対値を算出しておこなった。 The experiment on photodegradation is to prepare a beverage using citrus fragrance, add a chelating agent that is a photodegradation inhibitor, and then irradiate light using an artificial meteor, and determine the degree of photodegradation as a sensory test. The amount of 1-octen-3-one produced was measured and compared with a beverage to which no photodegradation inhibitor was added. Comparison of the production amount of 1-octen-3-one shows that the production amount of 1-octen-3-one in the case where no chelating agent is added is 100 in order to suppress experimental error, and each chelating agent is added. The amount of 1-octen-3-one produced was measured, and the relative value was calculated.
〔飲料の調合〕
グラニュー糖5g、クエン酸0.1g、香料0.1gの割合で混合し、水を加えて全体で100gとした後加熱殺菌をして、透明な100mlのペットボトル容器に飲料を注入した。
[Beverage preparation]
The mixture was mixed at a ratio of 5 g of granulated sugar, 0.1 g of citric acid, and 0.1 g of fragrance, and water was added to make a total of 100 g, followed by heat sterilization.
〔光照射試験〕
容器を密閉した後、人工気象器((株)日本医化器械製作所NC−220/350S〈C〉)を用いて6000ルクス(3波長形昼白色:40W×8本)にて7日間、10℃下で光照射し、光劣化試験を行った。
(Light irradiation test)
After sealing the container, 7 days at 6000 lux (3-wavelength daylight white: 40W × 8) using an artificial meteorological device (Nippon Medical Instruments Co., Ltd. NC-220 / 350S <C>) for 10 days A light deterioration test was conducted by irradiating with light at ℃.
〔官能評価〕
光劣化試験後、10名の熟練したパネラーで官能評価を行った。官能評価の点数は「異味・異臭を非常に強く感じる」を5点、「異味・異臭を強く感じる」を4点、「異味・異臭を感じるが許容範囲内」を3点、「異味・異臭を若干感じる」を2点、「異味・異臭を感じない」を1点とした。点数はパネラーの平均点を結果として示し、どの程度柑橘系香味飲料が光劣化しているか評価を行った。
〔sensory evaluation〕
After the light deterioration test, sensory evaluation was performed by 10 skilled panelists. The sensory evaluation score is 5 points for "I feel a very strong taste and smell", 4 points for "I feel a strong taste and smell", 3 points for "I feel a strange taste and a bad smell but within an acceptable range", and "A taste and strange smell""Slightlyfeel" was given 2 points and "I don't feel a strange taste / odour" was given 1 point. The score shows the average score of the panelists as a result, and evaluated how much the citrus flavored beverage was photo-degraded.
〔異臭物質測定評価〕
光劣化試験後に飲料の5gの試料中にポリジメチルシロキサンをコーティングした攪拌子を浸し1時間攪拌しながら目的成分を抽出した。その後、抽出された成分をガスクロマトグラフィー(Agilent7890A(GC),Agilent5975C(MS))に接続した加熱脱着装置を使用した直接導入法により異臭物質である1-オクテン-3-オンの生成量を測定した。
[Measurement and evaluation of off-flavor substances]
After the light deterioration test, a stirrer coated with polydimethylsiloxane was immersed in a 5 g sample of the beverage, and the target component was extracted while stirring for 1 hour. Thereafter, the amount of 1-octen-3-one, which is an off-flavor substance, is measured by a direct introduction method using a heat desorption apparatus in which the extracted components are connected to gas chromatography (Agilent 7890A (GC), Agilent 5975C (MS)). did.
〔紫外可視分光光度計による測定〕
光劣化試験前の飲料を紫外可視分光光度計(Thermo SCIENTIFIC社製GENESYS 10S UV-Vis)を用いて、波長660nmにおける吸光度を測定した。その結果、実施例1〜21及び比較例1〜8のいずれの飲料も吸光度は0.06以下であり、透明であった。
[Measurement with UV-visible spectrophotometer]
The beverage before the light degradation test was measured for absorbance at a wavelength of 660 nm using an ultraviolet-visible spectrophotometer (GENESYS 10S UV-Vis manufactured by Thermo SCIENTIFIC). As a result, all the beverages of Examples 1 to 21 and Comparative Examples 1 to 8 had an absorbance of 0.06 or less and were transparent.
<レモン風味香料及びキレート剤を1種類用いた場合の光劣化試験>
以下に、レモン風味香料を用いて飲料を作成し、光劣化抑制物質であるキレート剤を加えた後、人工気象器を用いて光照射を行なった光劣化試験の結果を示す。
<Photodegradation test when using one lemon-flavored flavor and chelating agent>
Below, after making a drink using a lemon flavoring fragrance | flavor, adding the chelating agent which is a photodegradation inhibitory substance, the result of the photodegradation test which performed light irradiation using the artificial weather device is shown.
(実施例1)
試験料飲料にはレモン風味香料を調合した。また、飲料中にキレート剤としてヘキサメタリン酸ナトリウムを250ppmとなるように調整し、その後光劣化試験を行い、官能試験および1-オクテン-3-オンの測定を行った。
Example 1
A lemon-flavored flavor was prepared in the test beverage. In addition, sodium hexametaphosphate was adjusted to 250 ppm as a chelating agent in the beverage, and then a photo-degradation test was performed, and a sensory test and a measurement of 1-octen-3-one were performed.
(実施例2)
キレート剤としてピロリン酸二水素二ナトリウムを250ppmに調整した他は実施例1と同様に試験を行った。
(Example 2)
The test was conducted in the same manner as in Example 1 except that disodium dihydrogen pyrophosphate was adjusted to 250 ppm as a chelating agent.
(実施例3)
キレート剤としてピロリン酸四ナトリウムを350ppmに調整した他は実施例1と同様に試験を行った。
(Example 3)
The test was conducted in the same manner as in Example 1 except that tetrasodium pyrophosphate was adjusted to 350 ppm as a chelating agent.
(実施例4)
キレート剤としてトリポリリン酸ナトリウムを400ppmに調整した他は実施例1と同様に試験を行った。
Example 4
The test was conducted in the same manner as in Example 1 except that sodium tripolyphosphate was adjusted to 400 ppm as a chelating agent.
(実施例5)
キレート剤としてピロリン酸四カリウムを450ppmに調整した他は実施例1と同様に試験を行った。
(Example 5)
The test was conducted in the same manner as in Example 1 except that tetrapotassium pyrophosphate was adjusted to 450 ppm as a chelating agent.
(実施例6)
キレート剤としてフィチン酸を67ppmに調整した他は実施例1と同様に試験を行った。
(Example 6)
The test was conducted in the same manner as in Example 1 except that phytic acid was adjusted to 67 ppm as a chelating agent.
(比較例1)
比較例として飲料中にキレート剤を加えずに実施例1と同様に試験を行った。
(Comparative Example 1)
As a comparative example, a test was conducted in the same manner as in Example 1 without adding a chelating agent to the beverage.
(比較例2)
キレート剤としてリン酸三ナトリウムを250ppmに調整した他は実施例1と同様に試験を行った。リン酸三ナトリウムはリン酸基を1つだけもつキレート剤である。
(Comparative Example 2)
The test was conducted in the same manner as in Example 1 except that trisodium phosphate was adjusted to 250 ppm as a chelating agent. Trisodium phosphate is a chelating agent with only one phosphate group.
(比較例3)
キレート剤としてリン酸水素二ナトリウムを300ppmに調整した他は実施
例1と同様に試験を行った。試験の評価は1-オクテン-3-オンの生成量(相対値)の測定のみ実施した。リン酸水素二ナトリウムはリン酸基を1つだけもつキレート剤である。
(Comparative Example 3)
A test was conducted in the same manner as in Example 1 except that disodium hydrogen phosphate was adjusted to 300 ppm as a chelating agent. In the evaluation of the test, only the production amount (relative value) of 1-octen-3-one was measured. Disodium hydrogen phosphate is a chelating agent having only one phosphate group.
官能試験の結果を表1に示す
表1に示す通り、実施例1〜6はキレート剤を加えていない比較例1と比較して点数が低く、光照射後でも異味・異臭を効果的に抑えることができた。一方、比較例2では光照射後の点数が比較例1と同程度であり、異味・異臭を強く感じる結果となった。 As shown in Table 1, Examples 1 to 6 had a lower score than Comparative Example 1 in which no chelating agent was added, and were able to effectively suppress off-flavors and odors even after light irradiation. On the other hand, in Comparative Example 2, the score after light irradiation was about the same as in Comparative Example 1, and the result was a strong sense of taste and odor.
1-オクテン-3-オンの測定結果を表2に示す。表中の数字はキレート剤を加えていない比較例1を100とした場合の相対値である。
表2に示すとおり、実施例1〜6の相対値は比較例1より小さく、効果的に1-オクテン-3-オンの生成を抑制することができた。一方、比較例2および比較例3の相対値は比較例1より大きく、1-オクテン-3-オンが多く生成していることがわかる。 As shown in Table 2, the relative values of Examples 1 to 6 were smaller than those of Comparative Example 1, and the production of 1-octen-3-one could be effectively suppressed. On the other hand, the relative values of Comparative Example 2 and Comparative Example 3 are larger than those of Comparative Example 1, and it can be seen that a large amount of 1-octen-3-one is generated.
表1及び表2の結果より、リン酸基を2個以上有するキレート剤は効果的に1-オクテン-3-オンの生成を抑え、その結果劣化臭を抑制できることが分かった。しかし比較例2及び3より、リン酸基を1個のみ有するキレート剤(リン酸三ナトリウム、リン酸水素二ナトリウム)はキレート能力があるにもかかわらず、1-オクテン-3-オンの生成を促進させ劣化臭を増大させる結果であった。これから、単にキレート能の強弱だけで劣化臭が抑制されないことがわかる。 From the results of Tables 1 and 2, it was found that a chelating agent having two or more phosphate groups effectively suppressed the production of 1-octen-3-one, and as a result, the deterioration odor could be suppressed. However, from Comparative Examples 2 and 3, a chelating agent having only one phosphate group (trisodium phosphate, disodium hydrogen phosphate) has the ability to chelate, but produces 1-octen-3-one. This was a result of promoting the deterioration odor. From this, it can be seen that the deterioration odor is not suppressed only by the strength of the chelating ability.
<レモン風味香料及び2種のキレート剤を用いた光劣化試験>
以下に2種類のキレート剤を用いた光劣化試験の結果を示す。
<Photodegradation test using lemon-flavored flavor and two chelating agents>
The results of a photodegradation test using two types of chelating agents are shown below.
(実施例7)
飲料にはレモン風味香料を用いた。また、飲料中にキレート剤としてヘキサメタリン酸ナトリウムを250ppm、フィチン酸を67ppmとなるように加えた。その後光劣化試験を行い、1-オクテン-3-オンの測定を行った。
(Example 7)
Lemon-flavored flavor was used for the beverage. Further, sodium hexametaphosphate was added to the beverage as a chelating agent at 250 ppm and phytic acid was added at 67 ppm. Thereafter, a photo-degradation test was performed, and 1-octen-3-one was measured.
(実施例8)
キレート剤としてヘキサメタリン酸ナトリウムを125ppm、フィチン酸を33ppmに調整した他は実施例7と同様に試験を行った。
(Example 8)
The test was conducted in the same manner as in Example 7 except that sodium hexametaphosphate was adjusted to 125 ppm and phytic acid was adjusted to 33 ppm as the chelating agent.
(実施例9)
キレート剤としてヘキサメタリン酸ナトリウムを60ppm、フィチン酸を15ppmに調整した他は実施例7と同様に試験を行った。
Example 9
The test was conducted in the same manner as in Example 7 except that sodium hexametaphosphate was adjusted to 60 ppm and phytic acid was adjusted to 15 ppm as the chelating agent.
(実施例10)
キレート剤としてヘキサメタリン酸ナトリウムを30ppm、フィチン酸を7ppmに調整した他は実施例7と同様に試験を行った。
(Example 10)
The test was conducted in the same manner as in Example 7 except that sodium hexametaphosphate was adjusted to 30 ppm and phytic acid was adjusted to 7 ppm as the chelating agent.
(実施例11)
キレート剤としてヘキサメタリン酸ナトリウムを15ppm、フィチン酸を3ppmに調整した他は実施例7と同様に試験を行った。
(Example 11)
The test was conducted in the same manner as in Example 7 except that sodium hexametaphosphate was adjusted to 15 ppm and phytic acid was adjusted to 3 ppm as the chelating agent.
(比較例4)
比較例として飲料中にキレート剤を加えずに実施例7と同様に試験を行った。
(Comparative Example 4)
As a comparative example, a test was conducted in the same manner as in Example 7 without adding a chelating agent to the beverage.
1-オクテン-3-オン生成量(相対値)の測定結果を表3に示す
表3に示すとおり、実施例7〜11の相対値は比較例4よりも小さく、効果的に1-オクテン-3-オンの生成を抑制することができた。 As shown in Table 3, the relative values of Examples 7 to 11 were smaller than those of Comparative Example 4, and production of 1-octen-3-one could be effectively suppressed.
<レモン風味香料及びキレート剤を1種類用いて濃度を変化させた場合の光劣化試験>
飲料中のキレート剤濃度を0.1〜1000ppmまで変化させた場合の光劣化試験の結果を以下に示す。
<Light degradation test when the concentration is changed using one type of lemon flavoring and chelating agent>
The result of the photodegradation test when the chelating agent concentration in the beverage is changed from 0.1 to 1000 ppm is shown below.
(実施例12)
飲料にはレモン風味香料を用いた。また飲料中にキレート剤としてヘキサメタリン酸ナトリウムを1000ppmに調整した。その後光劣化試験を行い、1-オクテン-3-オンの測定を行った。
(Example 12)
Lemon-flavored flavor was used for the beverage. Moreover, sodium hexametaphosphate was adjusted to 1000 ppm as a chelating agent in the beverage. Thereafter, a photo-degradation test was performed, and 1-octen-3-one was measured.
(実施例13)
キレート剤としてヘキサメタリン酸ナトリウムを100ppmに調整した他は実施例12と同様に試験を行った。
(Example 13)
The test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 100 ppm as a chelating agent.
(実施例14)
キレート剤としてヘキサメタリン酸ナトリウムを10ppmに調整した他は実施例12と同様に試験を行った。
(Example 14)
The test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 10 ppm as a chelating agent.
(実施例15)
キレート剤としてヘキサメタリン酸ナトリウムを1ppmに調整した他は実施例12と同様に試験を行った。
(Example 15)
A test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 1 ppm as a chelating agent.
(実施例16)
キレート剤としてヘキサメタリン酸ナトリウムを0.5ppmに調整した他は実施例12と同様に試験を行った。
(Example 16)
The test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 0.5 ppm as a chelating agent.
(実施例17)
キレート剤としてヘキサメタリン酸ナトリウムを0.3ppmに調整した他は実施例12と同様に試験を行った。
(Example 17)
The test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 0.3 ppm as a chelating agent.
(実施例18)
キレート剤としてヘキサメタリン酸ナトリウムを0.2ppmに調整した他は実施例12と同様に試験を行った。
(Example 18)
A test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 0.2 ppm as a chelating agent.
(比較例5)
キレート剤としてヘキサメタリン酸ナトリウムを0.1ppmに調整した他は実施例12と同様に試験を行った。
(Comparative Example 5)
A test was conducted in the same manner as in Example 12 except that sodium hexametaphosphate was adjusted to 0.1 ppm as a chelating agent.
(比較例6)
比較例として飲料中にキレート剤を加えずに実施例12と同様に試験を行った。
(Comparative Example 6)
As a comparative example, a test was conducted in the same manner as in Example 12 without adding a chelating agent to the beverage.
光劣化試験後の1-オクテン-3-オン生成量(相対値)測定結果を表4に示す。
表4に示す通り、ヘキサメタリン酸ナトリウム濃度が0.2ppm以上の場合(実施例12〜18)に相対値が比較例6よりも小さくなり、効果的に1-オクテン-3-オンの生成を抑制することがわかる。しかし、ヘキサメタリン酸ナトリウム濃度が0.1ppmの時(比較例5)にはキレート剤を加えない場合と同程度の1-オクテン-3-オンが生成しており、1-オクテン-3-オンの抑制効果がないことがわかる As shown in Table 4, when the sodium hexametaphosphate concentration is 0.2 ppm or more (Examples 12 to 18), the relative value is smaller than that of Comparative Example 6 and effectively suppresses the production of 1-octen-3-one. I understand that However, when the concentration of sodium hexametaphosphate was 0.1 ppm (Comparative Example 5), 1-octen-3-one was produced in the same degree as when no chelating agent was added. It turns out that there is no suppression effect
<レモン風味香料以外の柑橘系香料及びキレート剤を1種類用いた場合の光劣化試験>
以下に、レモン風味香料以外の香料として、オレンジ風味香料、グレープフルーツ風味香料、ミカン風味香料、ユズ風味香料を用いて飲料を作成し、光劣化抑制物質であるキレート剤を加えた後、人工気象器を用いて光照射を行なった光劣化試験の結果を示す。
<Light degradation test in the case of using one kind of citrus flavor and chelating agent other than lemon flavor flavor>
Below, create a beverage using orange flavor, grapefruit flavor, tangerine flavor, yuzu flavor as flavors other than lemon flavor, and add a chelating agent that is a photodegradation-inhibiting substance. The result of the light deterioration test which performed light irradiation using is shown.
(実施例19)
飲料には香料としてオレンジ風味香料、グレープフルーツ風味香料、ミカン風味香料、ユズ風味香料をそれぞれ用いて4種類の飲料を作成した。
(Example 19)
Four types of beverages were prepared using orange flavor, grapefruit flavor, tangerine flavor, and yuzu flavor as the flavor.
上記4種類の飲料中にキレート剤としてピロリン酸四ナトリウムを350ppmとなるように加えた。その後光劣化試験を行い、官能試験及び1-オクテン-3-オンの測定を行った。 Tetrasodium pyrophosphate as a chelating agent was added to the above four types of beverages so as to be 350 ppm. Thereafter, a photo-degradation test was performed, and a sensory test and a measurement of 1-octen-3-one were performed.
(実施例20)
キレート剤としてヘキサメタリン酸ナトリウムを250ppmに調整した他は実施例19と同様に試験を行った。
(Example 20)
The test was conducted in the same manner as in Example 19 except that sodium hexametaphosphate was adjusted to 250 ppm as a chelating agent.
(実施例21)
キレート剤としてフィチン酸を67ppmに調整した他は実施例19と同様に試験を行った。
(Example 21)
A test was conducted in the same manner as in Example 19 except that phytic acid was adjusted to 67 ppm as a chelating agent.
(比較例7)
比較例として飲料中にキレート剤を加えずに実施例19と同様に試験を行った。
(Comparative Example 7)
As a comparative example, a test was conducted in the same manner as in Example 19 without adding a chelating agent to the beverage.
(比較例8)
キレート剤としてリン酸三ナトリウムを250ppmに調整した他は実施例19と同様に試験を行った。測定は1-オクテン-3-オン生成量(相対値)のみ実施した。
(Comparative Example 8)
The test was conducted in the same manner as in Example 19 except that trisodium phosphate was adjusted to 250 ppm as a chelating agent. The measurement was carried out only for the amount of 1-octen-3-one produced (relative value).
官能試験の結果を表5に示す
表5に示す通り、いずれの柑橘系香料の場合も実施例19〜21は比較例7より点数が低く、光照射後に異味・異臭を抑制できる結果となった。 As shown in Table 5, in any citrus fragrance, Examples 19 to 21 had a lower score than Comparative Example 7, and it was possible to suppress off-flavors and odors after light irradiation.
1-オクテン-3-オン生成量(相対値)の測定結果を表6に示す
表6に示すとおり、いずれの柑橘系香料の場合も実施例19〜21の相対値は比較例7の値より小さく、効果的に1-オクテン-3-オンの生成を抑制することができた。一方、比較例8の相対値は比較例7よりも大きく、リン酸三ナトリウムは1-オクテン-3-オンの生成を抑制することができないばかりか、むしろ生成を促進していることがわかる。 As shown in Table 6, the relative values of Examples 19 to 21 were smaller than those of Comparative Example 7 for any citrus fragrance, and the production of 1-octen-3-one could be effectively suppressed. . On the other hand, the relative value of Comparative Example 8 is larger than that of Comparative Example 7, indicating that trisodium phosphate can not only suppress the production of 1-octen-3-one, but rather promotes the production.
本発明は、柑橘系香料を含有する飲料において透明な包装容器を用い、かつ光の当たる場所に長時間保存する場合の光劣化を抑制する分野において利用できる。 INDUSTRIAL APPLICATION This invention can be utilized in the field | area which suppresses photodegradation when using a transparent packaging container in the drink containing a citrus type fragrance | flavor, and preserve | saves for a long time in the place where light hits.
Claims (3)
前記キレート剤の水溶液中の濃度が0.2〜100ppmであり、
前記柑橘系飲料の波長660nmの吸光度が0.06以下であり、
前記キレート剤により1−オクテン−3−オンの生成を抑制することを特徴とする柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法。 Citrus flavored beverages containing citrus flavors containing non-volatile substances obtained from citrus natural essential oils are selected from the group consisting of phytic acid, hexametaphosphate, metaphosphate, polyphosphate, pyrophosphate Mix one or more chelating agents,
The concentration of the chelating agent in the aqueous solution is 0.2 to 100 ppm,
The absorbance at a wavelength of 660 nm of the citrus beverage is 0.06 or less,
The method suppressing the formation of 1-octene-3-one citrus flavor beverage characterized that you suppress the formation of 1-octen-3-one by the chelating agent.
前記柑橘系香料がレモンを原料としていることを特徴とする柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法。 Oite the generation suppression method 1-octen-3-one in claim 1 citrus flavor beverage according,
The method for suppressing the production of 1-octen-3-one in a citrus flavored drink, wherein the citrus flavor is made from lemon.
前記柑橘系香味飲料が、透明又は半透明な容器に充填されていることを特徴とする柑橘系香味飲料中の1−オクテン−3−オンの生成抑制方法。 Oite the generation suppression method 1-octen-3-one in citrus flavored beverages according to claim 1 or 2,
The said citrus flavor drink is filled in the transparent or translucent container, The production | generation suppression method of 1-octen-3-one in the citrus flavor drink characterized by the above-mentioned .
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JPS5411259A (en) * | 1977-06-25 | 1979-01-27 | Toyo Seikan Kaisha Ltd | Treating of vegetables and 1 or fruits |
JPS5513017A (en) * | 1978-07-13 | 1980-01-29 | Ikeda Touka Kogyo Kk | Improvement of taste of carbonated beverage |
JPH04169173A (en) * | 1990-10-31 | 1992-06-17 | Wakayama Pref Gov Nousanbutsu Kako Kenkyusho | Method for preventing citrus fruit juice from clarifying |
JPH08224071A (en) * | 1995-02-20 | 1996-09-03 | Dot Onotsukusu Kk | Aromatic fruit juice and its production |
JP2011120479A (en) * | 2009-12-08 | 2011-06-23 | Kirin Holdings Co Ltd | Basic amino acid-containing packaged beverage |
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JPS5411259A (en) * | 1977-06-25 | 1979-01-27 | Toyo Seikan Kaisha Ltd | Treating of vegetables and 1 or fruits |
JPS5513017A (en) * | 1978-07-13 | 1980-01-29 | Ikeda Touka Kogyo Kk | Improvement of taste of carbonated beverage |
JPH04169173A (en) * | 1990-10-31 | 1992-06-17 | Wakayama Pref Gov Nousanbutsu Kako Kenkyusho | Method for preventing citrus fruit juice from clarifying |
JPH08224071A (en) * | 1995-02-20 | 1996-09-03 | Dot Onotsukusu Kk | Aromatic fruit juice and its production |
JP2011120479A (en) * | 2009-12-08 | 2011-06-23 | Kirin Holdings Co Ltd | Basic amino acid-containing packaged beverage |
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