JP6572242B2 - 柑橘類由来の液体組成物 - Google Patents
柑橘類由来の液体組成物 Download PDFInfo
- Publication number
- JP6572242B2 JP6572242B2 JP2016566377A JP2016566377A JP6572242B2 JP 6572242 B2 JP6572242 B2 JP 6572242B2 JP 2016566377 A JP2016566377 A JP 2016566377A JP 2016566377 A JP2016566377 A JP 2016566377A JP 6572242 B2 JP6572242 B2 JP 6572242B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid composition
- citrus
- limonene
- peel
- naringin
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 66
- 239000007788 liquid Substances 0.000 title claims description 64
- 235000020971 citrus fruits Nutrition 0.000 title claims description 58
- 241000207199 Citrus Species 0.000 title claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Natural products CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 25
- 229940087305 limonene Drugs 0.000 claims description 24
- 235000001510 limonene Nutrition 0.000 claims description 24
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- 239000002994 raw material Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 17
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 claims description 16
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 claims description 16
- 229940052490 naringin Drugs 0.000 claims description 16
- 229930019673 naringin Natural products 0.000 claims description 16
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims description 15
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- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 claims description 15
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 claims description 15
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- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 claims description 15
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 claims description 15
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 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
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000220225 Malus Species 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
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- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
- A23L2/04—Extraction of juices
- A23L2/06—Extraction of juices from citrus fruits
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
- A23L19/03—Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
- A23L19/07—Fruit waste products, e.g. from citrus peel or seeds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/68—Acidifying substances
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
- A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C5/00—Other raw materials for the preparation of beer
- C12C5/02—Additives for beer
- C12C5/026—Beer flavouring preparations
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G3/00—Preparation of other alcoholic beverages
- C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
- C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
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- Alcoholic Beverages (AREA)
Description
〔1〕 0.5〜5.0mmの切れ込み間隔を表面に有する柑橘類の果皮部を溶媒中で抽出して得られ、前記柑橘類の芳香成分と苦味成分を含有してなる液体組成物。
〔2〕 前記〔1〕記載の液体組成物を飲料用原料と混合して得られる、容器詰めの飲料。
〔3〕 0.5〜5.0mmの切れ込み間隔を表面に有する柑橘類の果皮部を溶媒中で抽出し、前記柑橘類の芳香成分と苦味成分を含有する液体組成物を調製する工程を含む、液体組成物の製造方法。
試料となる液体組成物を59%アルコール水溶液にて10倍に希釈後、フィルター(0.45μm)でろ過し、HPLC分析に供する。HPLCの分析条件は以下のとおり。
HPLC装置:Agilent Technologies 1200Series
カラム:Shimadzu phenomenex kinetex 2−6μ C18 100A 150×2.10mm
カラム温度:40℃
移動相A:水−0.1%ギ酸
移動相B:水−12%アセトニトリル
移動相C:水−70%メタノール
検出:UV 280nm
注入量:1μL
標準物質:ナリンギン、ヘスペリジン
試料となる液体組成物を以下の条件にて、ガスクロマトグラフィー質量分析(GC−MS)に供する。分析条件は以下のとおり。
GC装置:Agilent Technologies GC−MSD
GCオーブン温度条件:40℃(5分)− 6℃/min − 240℃
質量分析(MS)条件
四重極設定値:150 イオン源設定値:230
面積値算出条件
トータルイオンモード 質量(LOW):35 質量(HIGH):550
カラム:DB−WAXETR 60m 内径320μm、膜厚0.25μm
試料前処理条件:試料80μLと内部標準物質(デカン酸メチルエステル20ppmアルコール水溶液)20μLを20mLスクリューキャップバイアル瓶中で混合
ダイナミックヘッドスペース条件
装置:ゲステル社MPS
吸着剤:TENAX
試料気化温度:80℃
試料気化用ガス供給量:3000ml
試料気化用ガス供給速度 100ml/min
試料気化用ガス種類 窒素
ピーク保持時間:MSの解析によって成分および濃度の同定を行った。
標準物質:リモネン
グレープフルーツの液体組成物を下記のように調製した。果肉を除去して、カットした1cm×5cm程度の果皮(フラベド、アルベドを含む)を準備し、厚さ0.1mmの刃物にて、フラベド側の果皮表面に0.5〜5.0mm幅で切れ込みを入れた。切れ込みの深さは、フラベド表面から0.5〜3.0mmまでいれた。
レモンの液体組成物を下記のように調製した。果肉を除去して、カットした1cm×5cm程度の果皮(フラベド、アルベドを含む)を準備し、厚さ0.1mmの刃物にて、フラベド側の果皮表面に表3に示す幅と深さで切れ込みを入れた。切れ込みを入れた後は、果皮3.5gに対し、15mLの59v/v%のエタノール水溶液に1分浸し、抽出を行った。果皮は1分後に除去し、これを液体組成物とした。ゆず、オレンジ、みかんに関しては、フラベドの厚み相当分までフラべド側の果皮表面から切れ込みを同様の幅と深さで入れた(表4〜6参照)。
Claims (14)
- 0.5〜5.0mmの切れ込み間隔を表面に有する柑橘類の果皮部を溶媒中で抽出して得られ、前記柑橘類の芳香成分と苦味成分を含有してなる液体組成物であって、芳香成分がリモネンであり、苦味成分がナリンギン及び/又はヘスペリジンであり、リモネンとナリンギンの含有質量比(リモネン/ナリンギン)が1.7以上であるか、又はリモネンとヘスペリジンの含有質量比(リモネン/ヘスペリジン)が1.7以上であり、抽出に用いる溶媒が20%〜60%(容積/容積)濃度のエタノール水溶液である、液体組成物。
- 刃による切れ込みの幅は0.04〜0.1mmであり、果皮部の表面(横幅)100mm×(奥行き)100mmあたり、その刃による切れ込み面積が80mm2〜2000mm2である、請求項1記載の液体組成物。
- 切れ込みの深さがフラベド側の果皮部表面から0.1〜3.0mmの深さである、請求項1又は2記載の液体組成物。
- 切れ込み間隔が0.5〜3.0mmである、請求項1〜3いずれかに記載の液体組成物。
- 抽出溶媒を除去してなる請求項1〜4いずれかに記載の液体組成物。
- 柑橘類の果皮部が果皮のみあるいは果皮と果肉を含む状態である請求項1〜5いずれかに記載の液体組成物。
- 柑橘類がグレープフルーツ、レモン、ゆず、みかん、及びオレンジからなる群から選ばれる1種又は2種以上である、請求項1〜6いずれかに記載の液体組成物。
- 請求項1〜7いずれかに記載の液体組成物を飲料用原料と混合して得られる、容器詰めの飲料。
- 0.5〜5.0mmの切れ込み間隔を表面に有する柑橘類の果皮部を溶媒中で抽出し、前記柑橘類の芳香成分と苦味成分を含有する液体組成物を調製する工程を含む、液体組成物の製造方法であって、芳香成分がリモネンであり、苦味成分がナリンギン及び/又はヘスペリジンであり、リモネンとナリンギンの含有質量比(リモネン/ナリンギン)が1.7以上であるか、又はリモネンとヘスペリジンの含有質量比(リモネン/ヘスペリジン)が1.7以上であり、抽出に用いる溶媒が20%〜60%(容積/容積)濃度のエタノール水溶液である、液体組成物の製造方法。
- 切れ込みの深さがフラベド側の果皮部表面から0.1〜3.0mmの深さである、請求項9記載の製造方法。
- 切れ込み間隔が0.5〜3.0mmである、請求項9又は10記載の製造方法。
- 更に、抽出溶媒を除去する工程を含む請求項9〜11いずれかに記載の製造方法。
- 柑橘類の果皮部が果皮のみあるいは果皮と果肉を含む状態である請求項9〜12いずれかに記載の製造方法。
- 柑橘類がグレープフルーツ、レモン、ゆず、みかん、及びオレンジからなる群から選ばれる1種又は2種以上である、請求項9〜13いずれかに記載の製造方法。
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PCT/JP2015/085782 WO2016104481A1 (ja) | 2014-12-26 | 2015-12-22 | 柑橘類由来の液体組成物 |
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JP7127961B2 (ja) * | 2017-02-10 | 2022-08-30 | アサヒビール株式会社 | アルコール飲料及びその製造方法 |
JP7174527B2 (ja) * | 2018-03-29 | 2022-11-17 | サッポロビール株式会社 | アルコール飲料、アルコール飲料の製造方法、及び、アルコール飲料の香味向上方法 |
US20210235727A1 (en) * | 2018-04-25 | 2021-08-05 | Carlsberg A/S | Barley Based Beverages |
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US3826855A (en) * | 1972-03-27 | 1974-07-30 | J Fiorella | Citrus fruit peels for alcoholic beverages |
US4497838A (en) * | 1982-02-17 | 1985-02-05 | Tropicana Products, Inc. | Process for the production of useful products from orange peel |
JP2000014322A (ja) * | 1998-07-02 | 2000-01-18 | Shigeo Horimizu | 梅のエキス入り飴 |
JP4117717B2 (ja) * | 1999-04-05 | 2008-07-16 | 宝ホールディングス株式会社 | アルコール含有香味液及びアルコール飲料 |
US20060204624A1 (en) * | 2005-03-14 | 2006-09-14 | Cargill, Inc. | Process and apparatus for enhancing peel oil extraction |
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