JP2020130103A - Beverage having reduced gallate type catechin-derived bitterness - Google Patents
Beverage having reduced gallate type catechin-derived bitterness Download PDFInfo
- Publication number
- JP2020130103A JP2020130103A JP2019031062A JP2019031062A JP2020130103A JP 2020130103 A JP2020130103 A JP 2020130103A JP 2019031062 A JP2019031062 A JP 2019031062A JP 2019031062 A JP2019031062 A JP 2019031062A JP 2020130103 A JP2020130103 A JP 2020130103A
- Authority
- JP
- Japan
- Prior art keywords
- beverage
- gallate
- bitterness
- present
- phenethyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 235000013361 beverage Nutrition 0.000 title claims abstract description 80
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 235000005487 catechin Nutrition 0.000 title claims abstract description 49
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 title claims abstract description 31
- 229950001002 cianidanol Drugs 0.000 title claims abstract description 31
- 235000019658 bitter taste Nutrition 0.000 title abstract description 43
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 title description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000284 extract Substances 0.000 claims description 12
- 241001122767 Theaceae Species 0.000 claims 1
- 230000035622 drinking Effects 0.000 abstract description 3
- 244000269722 Thea sinensis Species 0.000 description 24
- 150000001765 catechin Chemical class 0.000 description 18
- 235000013616 tea Nutrition 0.000 description 15
- 235000006468 Thea sinensis Nutrition 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 235000020279 black tea Nutrition 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000001603 reducing effect Effects 0.000 description 6
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 5
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 description 3
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 3
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 3
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229940030275 epigallocatechin gallate Drugs 0.000 description 3
- 235000009569 green tea Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000020333 oolong tea Nutrition 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GLRAHDCHUZLKKC-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid;hydrate Chemical compound O.CC#N.OC(=O)C(F)(F)F GLRAHDCHUZLKKC-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000000419 plant extract Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- 240000007436 Cananga odorata Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 241001632576 Hyacinthus Species 0.000 description 1
- 235000003368 Ilex paraguariensis Nutrition 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 244000174681 Michelia champaca Species 0.000 description 1
- 235000005016 Pinus halepensis Nutrition 0.000 description 1
- 241001236235 Pinus halepensis Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000020331 mate tea Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002470 solid-phase micro-extraction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
Landscapes
- Non-Alcoholic Beverages (AREA)
Abstract
Description
本発明は、飲料に存在するガレート型カテキンに由来する苦味を軽減することに関する。 The present invention relates to reducing the bitterness derived from gallate-type catechins present in beverages.
健康志向の高まりから、近年ポリフェノールの生理効果が注目され、ポリフェノールを豊富に含む飲料の需要が増大している。例えば、ポリフェノールの一種であるカテキン類は、コレステロール上昇抑制作用などの機能を有することが知られている。特にガレート型カテキンは、ヒトインフルエンザウイルスの不活化や、ＬＤＬの酸化抑制などにおいて高い生理活性を示すことが知られている。従って、ガレート型カテキンを手軽に摂取する手段として、ガレート型カテキンを含む飲料に対するニーズが存在する。しかし、ガレート型カテキンを含む飲料は、ガレート型カテキン特有の瞬間的で刺激的な苦味が強すぎて、不快感を伴うことがある。このような問題に対処するため、例えば、ガレート型カテキンを含む飲料に平均分子量２０，０００以上のコラーゲンペプチド及び／又はゼラチン、並びに増粘安定剤を含有させること（特許文献１）などが知られている。 Due to growing health consciousness, the physiological effects of polyphenols have been attracting attention in recent years, and the demand for beverages rich in polyphenols is increasing. For example, catechins, which are a type of polyphenol, are known to have a function of suppressing an increase in cholesterol. In particular, gallate-type catechins are known to exhibit high physiological activity in inactivating human influenza virus and suppressing LDL oxidation. Therefore, there is a need for beverages containing gallate-type catechins as a means for easily ingesting gallate-type catechins. However, beverages containing gallate-type catechins may be unpleasant because the momentary and pungent bitterness peculiar to gallate-type catechins is too strong. In order to deal with such a problem, for example, it is known that a beverage containing gallate-type catechin contains collagen peptide and / or gelatin having an average molecular weight of 20,000 or more, and a thickening stabilizer (Patent Document 1). ing.
一方、香り成分によっても飲料の風味を改善し得る。フェネチルアルコールは、天然に広く存在し、バラ、カーネーション、ヒヤシンス、アレッポマツ、イランイラン、ゼラニウム、ネロリ、キンコウボクなどの精油に含まれる成分である。また、フェネチルアルコールは、清酒やワインなどの酒類にも含まれることが知られている。しかし、フェネチルアルコールによる苦味軽減効果は知られていない。 On the other hand, the flavor of the beverage can also be improved by the aroma component. Phenethyl alcohol is a component that is widely present in nature and is contained in essential oils such as roses, carnations, hyacinths, aleppo pine, ylang-ylang, geranium, neroli, and champak. Phenethyl alcohol is also known to be contained in alcoholic beverages such as sake and wine. However, the bitterness-reducing effect of phenethyl alcohol is not known.
ｐＨ５．０以上の飲料にガレート型カテキンを含有させると、ｐＨが５．０未満の飲料と比較して、ガレート型カテキン由来の苦味が一層強く感じられることが本発明者により見いだされた。本発明は、ガレート型カテキンを含有するｐＨ５．０以上の飲料において、飲用時に感じられるガレート型カテキン由来の刺激的な苦味を軽減することを目的とする。 It has been found by the present inventor that when a beverage having a pH of 5.0 or higher contains gallate-type catechin, the bitterness derived from gallate-type catechin is felt more strongly than that of a beverage having a pH of less than 5.0. An object of the present invention is to reduce the pungent bitterness derived from gallate-type catechins felt during drinking in a beverage containing gallate-type catechins having a pH of 5.0 or higher.
以上の事情に鑑み、本発明者は、飲料に関し、ガレート型カテキン由来の苦味の軽減に有効な成分を探索した。鋭意検討の結果、フェネチルアルコールが当該苦味の軽減に寄与し得ることを見出した。このような知見に基づいて、本発明を完成させた。 In view of the above circumstances, the present inventor has searched for an ingredient effective for reducing bitterness derived from gallate-type catechins in beverages. As a result of diligent studies, it was found that phenethyl alcohol can contribute to the reduction of the bitterness. Based on such findings, the present invention has been completed.
本発明により、以下が提供される。但し、本発明の範囲はこれに限定されない。
（１）（ａ）ガレート型カテキンを１〜２５０ｐｐｍ含有し、（ｂ）フェネチルアルコールを０．４ｐｐｂ以上含有し、（ｃ）ｐＨが５．０〜８．０である、飲料。
（２）Ｂｒｉｘが１以下である、（１）の飲料。
（３）茶抽出物を含有する、（１）又は（２）の飲料。
The present invention provides: However, the scope of the present invention is not limited to this.
(1) A beverage containing 1 to 250 ppm of gallate-type catechin, (b) containing 0.4 ppb or more of phenethyl alcohol, and (c) having a pH of 5.0 to 8.0.
(2) The beverage of (1) having Brix of 1 or less.
(3) The beverage of (1) or (2) containing a tea extract.
本発明の飲料及び関連する方法について、以下に説明する。
特に断りがない限り、本明細書において用いられる「ｐｐｂ」及び「ｐｐｍ」は、重量／容量（ｗ／ｖ）のｐｐｂ及びｐｐｍをそれぞれ意味する。また、本明細書において下限値と上限値によって表されている数値範囲、即ち「下限値〜上限値」は、それら下限値及び上限値を包含するものとする。例えば、「１〜２」により表される範囲は、１及び２を含む。
The beverage of the present invention and related methods will be described below.
Unless otherwise specified, "ppb" and "ppm" as used herein mean ppb and ppm in weight / volume (w / v), respectively. Further, in the present specification, the numerical range represented by the lower limit value and the upper limit value, that is, "lower limit value to upper limit value" shall include those lower limit value and upper limit value. For example, the range represented by "1-2" includes 1 and 2.
（ガレート型カテキン）
本発明の飲料は、ガレート型カテキンを含有する。本明細書において、「ガレート型カテキン」とは、エピガロカテキンガレート、ガロカテキンガレート、エピカテキンガレート及びカテキンガレートの総称を表す。従って、本発明の実施の形態では、ガレート型カテキンは、エピカテキンガレート、ガロカテキンガレート、エピガロカテキンガレート及びカテキンガレートからなる群から選択される１以上を含んでいればよい。なお、確認のために記載するが、ガレート型カテキンの含有量とは、前記４種の化合物の含有量の合計を意味するものとする。
(Gallate type catechin)
The beverage of the present invention contains gallate-type catechins. As used herein, the term "gallate-type catechin" is a general term for epigallocatechin gallate, gallocatechin gallate, epicatechin gallate, and catechin gallate. Therefore, in the embodiment of the present invention, the gallate-type catechin may contain one or more selected from the group consisting of epicatechin gallate, gallocatechin gallate, epigallocatechin gallate and catechin gallate. Although described for confirmation, the content of gallate-type catechin means the total content of the above four compounds.
本発明で用いるガレート型カテキンは、特に限定されないが、精製品の他、粗製品であっても良く、ガレート型カテキンを含有する天然物もしくはその加工品、例えば植物の抽出物やその濃縮物であってもよい。ガレート型カテキンを含有する植物の抽出物又はその濃縮物は、紅茶、緑茶、烏龍茶、プーアル茶などのカメリア・シネンシスに属する茶葉類等を原料として用い、調製することができる。中でも、本発明の効果の側面から、紅茶葉より得られる抽出物を好適に用いることができる。 The gallate-type catechin used in the present invention is not particularly limited, but may be a crude product as well as a refined product, and may be a natural product containing the gallate-type catechin or a processed product thereof, for example, a plant extract or a concentrate thereof. There may be. The extract of a plant containing gallate-type catechin or its concentrate can be prepared by using tea leaves belonging to Camellia sinensis such as black tea, green tea, oolong tea, and puer tea as raw materials. Above all, from the aspect of the effect of the present invention, an extract obtained from black tea leaves can be preferably used.
本発明の飲料中のガレート型カテキンの濃度は、１〜２５０ｐｐｍであり、好ましくは１〜１５０ｐｐｍ、より好ましくは３〜６５ｐｐｍ、さらに好ましくは５〜３０ｐｐｍである。飲料中のガレート型カテキンの濃度が１ｐｐｍ以上の場合、飲料における苦味が強く感じられるため、本発明による苦味の軽減効果を得る上で好ましい。また、飲料中のカレート型カテキンの濃度が２５０ｐｐｍを超える場合、本発明による苦味の軽減効果は得られるが、苦味が十分に軽減しないことがある。 The concentration of gallate-type catechin in the beverage of the present invention is 1 to 250 ppm, preferably 1 to 150 ppm, more preferably 3 to 65 ppm, still more preferably 5 to 30 ppm. When the concentration of gallate-type catechin in the beverage is 1 ppm or more, the bitterness in the beverage is strongly felt, which is preferable in obtaining the effect of reducing the bitterness according to the present invention. Further, when the concentration of curate-type catechin in the beverage exceeds 250 ppm, the bitterness reducing effect according to the present invention can be obtained, but the bitterness may not be sufficiently reduced.
飲料中のガレート型カテキンの濃度は、高速液体クロマトグラフィー（ＨＰＬＣ）を用いて測定することができる。測定条件は、例えば以下のように設定することができる。
・ＨＰＬＣ装置：ＴＯＳＯＨ ＨＰＬＣシステム ＬＣ８０２０ ｍｏｄｅｌ Ｉ
・カラム：ＴＳＫｇｅｌ ＯＤＳ８０Ｔ ｓＱＡ（４．６ｍｍ×１５０ｍｍ）
・カラム温度：４０℃
・移動相Ａ：水−アセトニトリル−トリフルオロ酢酸（９０：１０：０．０５）
・移動相Ｂ：水−アセトニトリル−トリフルオロ酢酸（２０：８０：０．０５）
・検出：ＵＶ２７５ｎｍ
・注入量：２０μＬ
・流速：１．０ｍＬ／ｍｉｎ．
・グラジエントプログラム（体積％）：
時間（分） ％Ａ ％Ｂ
０ １００ ０
５ ９２ ８
１１ ９０ １０
２１ ９０ １０
２２ ０ １００
２９ ０ １００
３０ １００ ０
・標準物質：カテキンガレート、エピカテキンガレート、ガロカテキンガレートおよびエピガロカテキンガレート（栗田工業株式会社、高純度試薬）。
The concentration of gallate-type catechins in beverages can be measured using high performance liquid chromatography (HPLC). The measurement conditions can be set as follows, for example.
-HPLC device: TOSOH HPLC system LC8020 model I
-Column: TSKgel ODS80T sQA (4.6 mm x 150 mm)
-Column temperature: 40 ° C
Mobile phase A: water-acetonitrile-trifluoroacetic acid (90:10: 0.05)
Mobile phase B: water-acetonitrile-trifluoroacetic acid (20: 80: 0.05)
-Detection: UV275nm
・ Injection amount: 20 μL
-Flow velocity: 1.0 mL / min.
・ Gradient program (% by volume):
Hours (minutes)% A% B
0 100 0
5 928
11 90 10
21 90 10
22 0 100
290 100
30 100 0
-Standard substances: catechin gallate, epicatechin gallate, galocatechin gallate and epigallocatechin gallate (Kurita Water Industries, Ltd., high-purity reagent).
（フェネチルアルコール）
本発明の飲料は、2-Phenylethanol（以下、本明細書では「フェネチルアルコール」という）を特定量で含有する。これにより、ガレート型カテキン由来の苦味を軽減することができる。本発明の飲料中のフェネチルアルコールの含有量は、０．４ｐｐｂ以上であり、好ましくは０．４〜５ｐｐｂ、好ましくは０．５〜４ｐｐｂ、より好ましくは０．６〜３ｐｐｂ、さらに好ましくは０．７〜２ｐｐｂである。飲料中のフェネチルアルコールの含有量が０．４ｐｐｂより小さいとガレート型カテキン由来の苦味の軽減効果が不十分になることがある。一方、飲料中のフェネチルアルコールの含有量が５ｐｐｂを超えるとフェネチルアルコールの風味が強くなりすぎて飲料自体の味が損なわれるおそれがある。
(Phenethyl alcohol)
The beverage of the present invention contains 2-Phenylethanol (hereinafter referred to as "phenethyl alcohol" in the present specification) in a specific amount. This makes it possible to reduce the bitterness derived from gallate-type catechins. The content of phenethyl alcohol in the beverage of the present invention is 0.4 ppb or more, preferably 0.4 to 5 ppb, preferably 0.5 to 4 ppb, more preferably 0.6 to 3 ppb, still more preferably 0. It is 7 to 2 ppb. If the content of phenethyl alcohol in the beverage is less than 0.4 ppb, the effect of reducing the bitterness derived from gallate-type catechins may be insufficient. On the other hand, if the content of phenethyl alcohol in the beverage exceeds 5 ppb, the flavor of phenethyl alcohol may become too strong and the taste of the beverage itself may be impaired.
本発明の飲料においては、ガレート型カテキン含有量に対するフェネチルアルコール含有量の比率（フェネチルアルコール含有量／ガレート型カテキン含有量）は、特に限定されないが、例えば０．００００８以上であってよく、好ましくは０．０００１４以上であってもよい。 In the beverage of the present invention, the ratio of the phenethyl alcohol content to the gallate-type catechin content (phenethyl alcohol content / gallate-type catechin content) is not particularly limited, but may be, for example, 0.00008 or more, preferably 0.00008 or more. It may be 0.00014 or more.
本発明の飲料中のフェネチルアルコールの含有量は、公知のＧＣ−ＭＳ法にて測定できる。ただし、本発明においては、カラムに高極性カラム（アジレントテクノロジーズ社製、ＤＢ−ＷａｘＵＩ）、抽出法に固相マイクロ抽出法（ＣＴＣアナリティクス社製、ＳＰＭＥ−ＡｒｒｏｗＣａｒｂｏｎ ＷＲ／ＰＤＭＳ）、検出器に高分解能質量分析装置（サーモフィッシャーサイエンティフィック社製、Ｑ Ｅｘａｃｔｉｖｅ ＧＣ Ｏｒｂｉｔｒａｐ）を用いるのがよい。 The content of phenethyl alcohol in the beverage of the present invention can be measured by a known GC-MS method. However, in the present invention, the column is a highly polar column (manufactured by Azilent Technologies, DB-WaxUI), the extraction method is a solid-phase microextraction method (manufactured by CTC Analytics, SPME-ArrowCarbon WR / PDMS), and the detector is high resolution. It is preferable to use a mass spectrometer (Q Active GC Orbitrap manufactured by Thermo Fisher Scientific Co., Ltd.).
本発明で用いるフェネチルアルコールは、特に限定されないが、精製品の他、粗製品であってもよい。例えば、フェネチルアルコールを含有する天然物又はその加工品（植物抽出物、精油、植物の発酵物、これらの濃縮物等）であってもよい。より具体的な例として、フェネチルアルコールを含有する香料の他、果汁やエキス等を挙げることができる。飲料への添加が少量で済むことから、香料が好ましい一例である。 The phenethyl alcohol used in the present invention is not particularly limited, but may be a crude product or a crude product. For example, it may be a natural product containing phenethyl alcohol or a processed product thereof (plant extract, essential oil, fermented plant product, concentrate thereof, etc.). More specific examples include fruit juices and extracts in addition to flavors containing phenethyl alcohol. Perfume is a preferred example because it requires only a small amount to be added to the beverage.
（ｐＨ）
本発明の飲料のｐＨは５．０〜８．０であり、好ましくは５．５〜７．５である。飲料のｐＨが５．０未満である場合は、飲料中の酸味成分により、苦味がマスキングされることがある。しかし、飲料のｐＨが５．０以上である場合は、マスキング成分として作用する酸味成分が少ないために苦味が顕著に知覚され得るため、本発明による苦味の軽減効果を得る上で好ましい。飲料のｐＨ調整は、クエン酸ナトリウム、水酸化ナトリウム、重曹等のｐＨ調整剤を用いて適宜行うことができる。飲料のｐＨは市販のｐＨメーターを使用して容易に測定することができる。
(PH)
The pH of the beverage of the present invention is 5.0 to 8.0, preferably 5.5 to 7.5. If the pH of the beverage is less than 5.0, the sourness component in the beverage may mask the bitterness. However, when the pH of the beverage is 5.0 or more, bitterness can be remarkably perceived because there are few sour components acting as masking components, which is preferable in obtaining the effect of reducing bitterness according to the present invention. The pH of the beverage can be appropriately adjusted by using a pH adjusting agent such as sodium citrate, sodium hydroxide, or baking soda. The pH of the beverage can be easily measured using a commercially available pH meter.
（Ｂｒｉｘ）
本発明の飲料のＢｒｉｘ（ブリックス）は、特に限定されないが、１以下であることが好ましい。理論に拘束されないが、Ｂｒｉｘが１以下である場合、苦味のマスキング成分として作用する可溶性固形分が少ないために、ガレート型カテキンの苦味が顕著に感じられることが考えられるため、本発明による苦味の軽減効果を得る上で好ましい。Ｂｒｉｘは、糖度計や屈折計などを用いて得られるＢｒｉｘ値によって評価することができる。ブリックス値は、２０℃で測定された屈折率を、ＩＣＵＭＳＡ（国際砂糖分析統一委員会）の換算表に基づいてショ糖溶液の質量／質量パーセントに換算した値である。単位は「°Ｂｘ」、「％」または「度」で表示される。
(Brix)
The Brix of the beverage of the present invention is not particularly limited, but is preferably 1 or less. Although not bound by theory, when Brix is 1 or less, the bitterness of gallate-type catechins may be noticeably felt due to the small amount of soluble solids acting as a masking component for bitterness. It is preferable to obtain a mitigation effect. Brix can be evaluated by the Brix value obtained by using a sugar content meter, a refractometer, or the like. The Brix value is a value obtained by converting the refractive index measured at 20 ° C. into the mass / mass percent of the sucrose solution based on the conversion table of ICUMSA (International Sugar Analysis Unified Committee). The unit is displayed in "° Bx", "%" or "degree".
（その他原料）
本発明の飲料には、上記に示した各種成分に加えて、飲料に一般的に用いられる成分を配合することができる。例えば、限定されないが、香料、糖類、酸味料、栄養強化剤、酸化防止剤、乳化剤、保存料、エキス類、食物繊維、品質安定剤などを、本発明の効果を損なわない範囲で添加することができる。
(Other raw materials)
In addition to the various ingredients shown above, the beverage of the present invention can contain ingredients generally used in beverages. For example, but not limited to, flavors, sugars, acidulants, nutritional enhancers, antioxidants, emulsifiers, preservatives, extracts, dietary fiber, quality stabilizers, etc. are added as long as the effects of the present invention are not impaired. Can be done.
（飲料）
本発明の飲料は、清涼飲料であれば特に限定されない。例えば、栄養飲料、機能性飲料、フレーバードウォーター（ニアウォーター）系飲料、茶系飲料（紅茶、ウーロン茶、緑茶等）、コーヒー飲料、炭酸飲料などいずれであってもよい。本発明の飲料は、一実施形態において、茶飲料であることが好ましい。ここで「茶飲料」とは、茶葉の抽出物や穀類の抽出物を主成分として含有する飲料であり、具体的には、緑茶、ほうじ茶、ブレンド茶、麦茶、マテ茶、ジャスミン茶、紅茶、ウーロン茶、杜仲茶などが挙げられる。本発明において特に好ましい茶飲料は、紅茶飲料である。
(Beverage)
The beverage of the present invention is not particularly limited as long as it is a soft drink. For example, it may be any of nutritional drinks, functional drinks, flavored water (near water) drinks, tea drinks (black tea, oolong tea, green tea, etc.), coffee drinks, and carbonated drinks. In one embodiment, the beverage of the present invention is preferably a tea beverage. Here, the "tea beverage" is a beverage containing an extract of tea leaves or an extract of grains as a main component, and specifically, green tea, roasted tea, blended tea, barley tea, mate tea, jasmine tea, black tea, etc. Examples include oolong tea and tochu tea. A particularly preferred tea beverage in the present invention is a black tea beverage.
本発明の飲料は、加熱殺菌され、容器に詰められた状態の容器詰飲料であることが好ましい。飲料が加熱されることにより、ガレート型カテキンの苦味がより強くなる可能性があるからである。加熱殺菌の手段は特に限定されないが、例えばＵＨＴ殺菌及びレトルト殺菌等、公知のいずれの手段を用いることができる。飲料を充填する容器は、特に限定されないが、例えば、ＰＥＴボトル、アルミ缶、スチール缶、紙パック、チルドカップ、瓶などを用いることができる。手軽ないし利便性の側面からみれば、軽量で持ち運びが容易であり、かつ再栓が可能である容器、例えば、ＰＥＴボトルのような容器が好ましい。 The beverage of the present invention is preferably a packaged beverage in a state of being heat sterilized and packed in a container. This is because the bitterness of gallate-type catechins may become stronger as the beverage is heated. The means of heat sterilization is not particularly limited, but any known means such as UHT sterilization and retort sterilization can be used. The container for filling the beverage is not particularly limited, and for example, PET bottles, aluminum cans, steel cans, paper packs, chilled cups, bottles and the like can be used. From the viewpoint of convenience or convenience, a container that is lightweight, easy to carry, and can be re-plugged, for example, a container such as a PET bottle is preferable.
（発明の効果）
本発明によれば、ガレート型カテキン由来の苦味が軽減されたｐＨが５．０以上の飲料を提供することができる。本明細書において「苦味」というときは、飲用時に瞬間的に感じる、舌を刺すような刺激的な苦味を意味する。
(The invention's effect)
According to the present invention, it is possible to provide a beverage having a pH of 5.0 or more in which the bitterness derived from gallate-type catechins is reduced. As used herein, the term "bitterness" means a pungent bitterness that pierces the tongue, which is felt momentarily when drinking.
以下、実験例を示して本発明の詳細を具体的に説明するが、本発明はこれに限定されるものではない。また、本明細書においては、特に記載しない限り、数値範囲はその端点を含むものとして記載される。 Hereinafter, the details of the present invention will be specifically described with reference to experimental examples, but the present invention is not limited thereto. Further, in the present specification, unless otherwise specified, the numerical range is described as including the end points thereof.
［実施例１］ｐＨの苦味に対する影響
ガレート型カテキンとして、チャ抽出物（サンフェノンＥＧＣ−ＯＰ；太陽化学株式会社；ガレート型カテキン含有量９４％）を用いた。飲料中のガレート型カテキン濃度が５ｐｐｍとなるように水にチャ抽出物を添加し飲料を調製した。クエン酸又は水酸化ナトリウムを用いて飲料のｐＨを表１に示すように調整した（サンプル１〜５）。また、このように調製した飲料に、さらにフェネチルアルコールを１ｐｐｂとなるように添加した飲料も調製した。Ｂｒｉｘは全ての飲料で１以下であった。
[Example 1] Effect of pH on bitterness As a gallate-type catechin, a tea extract (Sanphenon EGC-OP; Taiyo Kagaku Co., Ltd .; Galate-type catechin content 94%) was used. A tea extract was added to water so that the concentration of gallate-type catechin in the beverage was 5 ppm to prepare a beverage. The pH of the beverage was adjusted with citric acid or sodium hydroxide as shown in Table 1 (Samples 1-5). In addition, a beverage prepared by adding phenethyl alcohol to 1 ppb to the beverage prepared in this manner was also prepared. Brix was 1 or less for all beverages.
それぞれの飲料について、苦味の評価を行った。以下の基準に沿って、専門パネル３名が各自で苦味を評価した後、パネル全員で協議して最終的な評価を決定した。
○：苦味をほとんど感じない
△：苦味を少し感じる
×：苦味を強く感じる
結果を表１に示す。フェネチルアルコールを添加していない飲料の評価結果より、ガレート型カテキン由来の不快な苦味は、飲料のｐＨが５．０以上のときに知覚されることがわかった。これらの飲料にフェネチルアルコールを添加すると、不快な苦味が軽減されることが示された。
The bitterness of each beverage was evaluated. After each of the three expert panels evaluated the bitterness according to the following criteria, all the panels discussed and decided the final evaluation.
◯: Almost no bitterness △: Slight bitterness ×: Strong bitterness The results are shown in Table 1. From the evaluation results of the beverage to which phenethyl alcohol was not added, it was found that the unpleasant bitterness derived from gallate-type catechin was perceived when the pH of the beverage was 5.0 or higher. The addition of phenethyl alcohol to these beverages has been shown to reduce unpleasant bitterness.
一方、ｐＨ３．５の飲料では、ガレート型カテキン由来の不快な苦味はあまり問題にならないことがわかった。また、この飲料にフェネチルアルコールを添加しても苦味の強さは変わらないこともわかった。 On the other hand, it was found that the unpleasant bitterness derived from gallate-type catechins was not so problematic for beverages having a pH of 3.5. It was also found that the intensity of bitterness did not change even when phenethyl alcohol was added to this beverage.
［実施例２］ガレート型カテキンとフェネチルアルコールの含有量の苦味に対する影響
水にチャ抽出物とフェネチルアルコールを添加し、ガレート型カテキンとフェネチルアルコールの濃度を表２の濃度となるように調整し、各飲料を調製した。調製した飲料を５００ｍｌ容量のＰＥＴ容器に充填した。調製した飲料のｐＨは５．９であった。Ｂｒｉｘは全ての飲料で１以下であった。
[Example 2] Effect of content of gallate-type catechin and phenethyl alcohol on bitterness Cha extract and phenethyl alcohol were added to water, and the concentrations of gallate-type catechin and phenethyl alcohol were adjusted to the concentrations shown in Table 2. Each beverage was prepared. The prepared beverage was filled in a PET container having a capacity of 500 ml. The pH of the prepared beverage was 5.9. Brix was 1 or less for all beverages.
調製した飲料の苦味の強さに関して官能評価を行った。専門パネル３名が、ガレート型カテキンを１ｐｐｍ、フェネチルアルコールを添加していない飲料をコントロール（サンプル１）として、以下の基準に沿って評価を行った。３名の専門パネルの点数の平均を算出し、３．０点以下を合格とした。官能評価結果を表２に示した。
５点：コントロールと比較して苦味が強い。
４点：コントロールと同等の苦味がある。
３点：コントロールと比較して、苦味が少ない。
２点：コントロールと比較して、苦味がかなり少ない。
１点：苦味を感じない。
A sensory evaluation was performed on the strength of the bitterness of the prepared beverage. Three expert panels evaluated the beverage according to the following criteria, using 1 ppm of gallate-type catechin and a beverage to which phenethyl alcohol was not added as a control (Sample 1). The average score of the three specialized panels was calculated, and a score of 3.0 or less was passed. The sensory evaluation results are shown in Table 2.
5 points: Bitterness is stronger than control.
4 points: Has the same bitterness as control.
3 points: Less bitter than control.
2 points: Compared to the control, the bitterness is considerably less.
1 point: I do not feel bitterness.
ガレート型カテキンを１〜２５０ｐｐｍ含有する飲料に対して、フェネチルアルコールを０．４ｐｐｂ以上、０．４〜５ｐｐｂ添加すると、ガレート型カテキンに由来する不快な苦味が軽減され、飲みやすくなった。 When phenethyl alcohol was added at 0.4 ppb or more and 0.4 to 5 ppb to a beverage containing 1 to 250 ppm of gallate-type catechin, the unpleasant bitterness derived from gallate-type catechin was reduced and it became easier to drink.
［実施例３］
紅茶抽出液に、フェネチルアルコールを飲料中の濃度が０．１ｐｐｂ及び１．０ｐｐｂとなるように添加し、紅茶飲料を調製した。これを加熱殺菌した後、５００ｍｌ容量のＰＥＴ容器に充填した。得られた紅茶飲料は、ガレート型カテキンの濃度が５ｐｐｍ、フェネチルアルコールの濃度が０．１ｐｐｂ又は１．０ｐｐｂ、ｐＨが６．０、Ｂｒｉｘが０．３であった。
[Example 3]
Phenethyl alcohol was added to the black tea extract so that the concentrations in the beverage were 0.1 ppb and 1.0 ppb to prepare a black tea beverage. After heat sterilizing this, it was filled in a PET container having a capacity of 500 ml. The obtained black tea beverage had a gallate-type catechin concentration of 5 ppm, a phenethyl alcohol concentration of 0.1 ppb or 1.0 ppb, a pH of 6.0, and a Brix of 0.3.
これら飲料の苦味を、実施例２に記載の方法に従って官能で評価した。フェネチルアルコールの濃度が０．１ｐｐｂである飲料は、評価が４．３点（専門パネルの平均）であり、苦味が強く飲みにくかった。一方、フェネチルアルコールの濃度が１．０ｐｐｂである飲料は、苦味がほとんど感じられず飲みやすいことが示された。
The bitterness of these beverages was sensually evaluated according to the method described in Example 2. The beverage having a phenethyl alcohol concentration of 0.1 ppb had a rating of 4.3 points (average of the specialized panel), and had a strong bitter taste and was difficult to drink. On the other hand, it was shown that the beverage having a phenethyl alcohol concentration of 1.0 ppb was easy to drink with almost no bitterness.
Claims (3)
（ｂ）フェネチルアルコールを０．４ｐｐｂ以上含有し、
（ｃ）ｐＨが５．０〜８．０である、
飲料。 (A) Contains 1 to 250 ppm of gallate-type catechin,
(B) Contains 0.4 ppb or more of phenethyl alcohol,
(C) The pH is 5.0-8.0,
Beverage.
The beverage according to claim 1 or 2, which contains a tea extract.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019031062A JP7300847B2 (en) | 2019-02-22 | 2019-02-22 | Beverage with reduced bitterness derived from gallated catechins |
| PCT/JP2020/007142 WO2020171214A1 (en) | 2019-02-22 | 2020-02-21 | Beverage having reduced bitterness from gallate-type catechins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019031062A JP7300847B2 (en) | 2019-02-22 | 2019-02-22 | Beverage with reduced bitterness derived from gallated catechins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020130103A true JP2020130103A (en) | 2020-08-31 |
| JP7300847B2 JP7300847B2 (en) | 2023-06-30 |
Family
ID=72261527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019031062A Active JP7300847B2 (en) | 2019-02-22 | 2019-02-22 | Beverage with reduced bitterness derived from gallated catechins |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP7300847B2 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005143467A (en) * | 2003-11-20 | 2005-06-09 | Kiyomitsu Kawasaki | Green tea flavored composition |
| JP2007167004A (en) * | 2005-12-22 | 2007-07-05 | Ogawa & Co Ltd | Additive for tea beverage |
| JP2008148605A (en) * | 2006-12-15 | 2008-07-03 | Kirin Beverage Corp | Tea beverage additive |
| JP2008148604A (en) * | 2006-12-15 | 2008-07-03 | Kirin Beverage Corp | Tea beverage additive |
| JP2013252128A (en) * | 2012-03-16 | 2013-12-19 | Shizuoka Industrial Foundation | Method for improving quality of low-grade tea and green tea with improved quality |
| JP2016015924A (en) * | 2014-07-09 | 2016-02-01 | 味の素ゼネラルフーヅ株式会社 | Composition for tea beverage, manufacturing method of composition for tea beverage, manufacturing method of tea beverage, and method for improving flavor of tea beverage |
-
2019
- 2019-02-22 JP JP2019031062A patent/JP7300847B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005143467A (en) * | 2003-11-20 | 2005-06-09 | Kiyomitsu Kawasaki | Green tea flavored composition |
| JP2007167004A (en) * | 2005-12-22 | 2007-07-05 | Ogawa & Co Ltd | Additive for tea beverage |
| JP2008148605A (en) * | 2006-12-15 | 2008-07-03 | Kirin Beverage Corp | Tea beverage additive |
| JP2008148604A (en) * | 2006-12-15 | 2008-07-03 | Kirin Beverage Corp | Tea beverage additive |
| JP2013252128A (en) * | 2012-03-16 | 2013-12-19 | Shizuoka Industrial Foundation | Method for improving quality of low-grade tea and green tea with improved quality |
| JP2016015924A (en) * | 2014-07-09 | 2016-02-01 | 味の素ゼネラルフーヅ株式会社 | Composition for tea beverage, manufacturing method of composition for tea beverage, manufacturing method of tea beverage, and method for improving flavor of tea beverage |
Non-Patent Citations (4)
| Title |
|---|
| "名糖 スティックメイト Fアソート 24袋入", よろずやマルシェ, JPN6023008349, 2016, ISSN: 0005003321 * |
| 日本食品工業学会誌，1987，VOL.34，P.20-27, JPN6022038559, ISSN: 0005003323 * |
| 長野県工技センター研報，2006，NO.1，P.F20-F23, JPN6022038562, ISSN: 0005003324 * |
| 静岡県環境衛生科学研究所報告，2004，NO.47，P.41-45, JPN6022038557, ISSN: 0005003322 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7300847B2 (en) | 2023-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6629483B1 (en) | Drink with reduced bitterness derived from gallate-type catechin | |
| JP6630020B1 (en) | Drinks with reduced bitterness derived from catechins | |
| JP7282544B2 (en) | Beverage with reduced bitterness derived from tannin | |
| JP7300847B2 (en) | Beverage with reduced bitterness derived from gallated catechins | |
| JP6648333B1 (en) | Drinks with reduced bitterness derived from gallate catechin | |
| JP6648334B1 (en) | Drinks with reduced bitterness derived from catechins | |
| JP2020130106A (en) | Beverage having reduced gallate type catechin-derived bitterness | |
| JP7296742B2 (en) | Beverage with reduced bitterness derived from catechins | |
| JP2020130104A (en) | Beverage having reduced gallate type catechin-derived bitterness | |
| JP6758466B2 (en) | Furaneol-derived off-flavour-reduced beverage | |
| JP2020130111A (en) | Beverage having reduced catechin-derived bitterness | |
| JP2020130112A (en) | Beverage having reduced catechin-derived bitterness | |
| JP7125904B2 (en) | Beverage with reduced bitterness derived from tannin | |
| WO2020171214A1 (en) | Beverage having reduced bitterness from gallate-type catechins | |
| JP6676817B1 (en) | Beverage with reduced off-flavor derived from furaneol | |
| JP7156971B2 (en) | Beverage with reduced bitterness derived from tannin | |
| WO2020171218A1 (en) | Beverage having reduced bitterness from catechins | |
| JP7134899B2 (en) | Beverage with reduced bitterness derived from caffeine | |
| JP7267768B2 (en) | Beverage with reduced bitterness derived from caffeine | |
| JP2020130117A (en) | Beverage having reduced furaneol-derived off-flavor | |
| JP6289773B1 (en) | Tea drink | |
| JP7211847B2 (en) | Beverage with reduced bitterness derived from caffeine | |
| WO2020171213A1 (en) | Beverage with reduced bitter taste originating from tannin | |
| JP2020130119A (en) | Beverage having reduced furaneol-derived off-flavor | |
| JP2020130118A (en) | Beverage having reduced furaneol-derived off-flavor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210819 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220913 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20221110 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230302 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230417 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230616 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230620 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 7300847 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |