JP4959019B2 - ヘスペリジン含有組成物 - Google Patents
ヘスペリジン含有組成物 Download PDFInfo
- Publication number
- JP4959019B2 JP4959019B2 JP2011214034A JP2011214034A JP4959019B2 JP 4959019 B2 JP4959019 B2 JP 4959019B2 JP 2011214034 A JP2011214034 A JP 2011214034A JP 2011214034 A JP2011214034 A JP 2011214034A JP 4959019 B2 JP4959019 B2 JP 4959019B2
- Authority
- JP
- Japan
- Prior art keywords
- hesperidin
- composition
- glycol
- solution
- dissolving
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 164
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 160
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 160
- 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 title claims abstract description 160
- 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 title claims abstract description 160
- 229940025878 hesperidin Drugs 0.000 title claims abstract description 160
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 title claims abstract description 160
- 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 title claims abstract description 160
- 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 title claims abstract description 159
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 48
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- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 15
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 230000002829 reductive effect Effects 0.000 claims description 11
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- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 4
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 4
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- 238000000354 decomposition reaction Methods 0.000 abstract description 9
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 20
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Description
項1.
(A)ヘスペリジン、
(B)エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブチレングリコール、及び3−メチル−1,3−ブタンジオールからなる群より選択される少なくとも1種の二価アルコール、及び
(C)糖アルコール
を含有する組成物。
項2.
(C)糖アルコールが、還元パラチノース、キシリトール、ソルビトール、マルチトール及びエリスリトールからなる群より選択される少なくとも1種である、項1に記載の組成物。
項3.
(B)二価アルコールが、ポリエチレングリコール及びプロピレングリコールからなる群より選択される少なくとも1種である、項1又は2に記載の組成物。
項4.
(A)、(B)、及び(C)を溶解して含有する液状組成物である、項1〜3のいずれかに記載の組成物。
項5.
pHが3〜10である、項4に記載の組成物。
項6.
口腔用組成物である、項1〜5のいずれかに記載の組成物。
以下の手順により、各例(ヘスペリジンを溶解して含有する液状組成物)を製造した。
上記製造例で調製した各実施例及び各比較例を、それぞれ80mLづつ透明ボトルに入れ、5℃又は55℃で3週間暗室で放置した。また、これとは別に、各実施例及び各比較例を調製した直後、これらをフィルターで濾過した後HPLCで解析を行い、各例のヘスペリジンを示すピークを測定した。当該ピークを調製初期ピークとする。
<フィルター>
使用濾過フィルター:ミニザルトRC15(孔径0.45μm;膜材質はセルロースアセテート)(ザルトリウス・メカトロニクス・ジャパン株式会社)
<HPLC>
使用HPLC機器:LC-10AS(島津製作所)
検出器:紫外吸光光度計(測定波長:284nm)
カラム:内径約5mm、長さ約15cmのステンレス管に約5μmの液体クロマトグラフ用オクタデシルシリル化シリカゲルを充填したもの(GL Sciences社製、Inertsil(登録商標) ODS-2 5μm 4.6×150mm)。
カラム温度:40℃付近の一定温度
移動相:0.03mol/Lリン酸二水素カリウム試薬/メタノール/アセトニトリル混液(7:2:1)。
流量:ヘスペリジンの保持時間が約10分になるように調整(約1mL/分)。
表2に記載される成分を混合し、各組成物(実施例#16、#17、及び比較例#18、#19)を製造した。#18及び#19については、表2に記載される成分を一度に混合して各組成物を製造した。ただし、#18のみ、精製水の代わりに0.05M炭酸ナトリウム水溶液を用いた。#16及び#17については、以下のようにして製造した。
実施例#16、#17、及び比較例#18、#19につき、安定性試験1と同様にしてHPLC解析を行った。また、検量線作成用標準溶液を調製し、これも同様にHPLC解析を行って、ヘスペリジンの濃度(mg/L)を横軸に、それぞれのヘスペリジン濃度に対応するピーク面積(μV・sec)を縦軸にプロットして検量線を作成した。次に、測定した各実施例及び比較例の溶液のピーク面積(μV・sec)から、検量線の直線回帰式を用いて各実施例及び比較例溶液のヘスペリジン濃度(mg/L)を算出した。なお、検量線作成用標準溶液は、超音波照射により、ヘスペリジンをメタノールに溶解させた溶液であり、これを順次希釈して検量線作成に用いた。
成分 配合量
セラック 10.0
ソルビトール 10.0
エチルアルコール 40.0
ポリエチレングリコール 4.0
炭酸ナトリウム 0.2
ヘスペリジン 0.002
香料 1.5
クエン酸 適量
精製水 残部
合計 100.0
成分 配合量
エタノール 10.0
還元パラチノース 10.0
ポリエチレングリコール 3.0
グリセリン 5.0
炭酸ナトリウム 0.2
クエン酸ナトリウム 0.1
パラオキシ安息香酸メチル 0.1
ビタミンE 0.05
ビタミンC 0.01
ヘスペリジン 0.002
香料 0.2
クエン酸 適量
精製水 残部
合計 100.0
成分 配合量
グリセリン 30.0
ソルビトール 13.0
プロピレングリコール 4.0
カルボキシメチルセルロース 0.2
ビタミンE 0.05
ヘスペリジン 0.001
香料 0.2
水酸化ナトリウム 適量
クエン酸 適量
精製水 残部
合計 100.0
成分 配合量
グリセリン 10.0
還元パラチノース 5.0
エタノール 10.0
トレハロース 5.0
ポリエチレングリコール 5.0
塩化セチルピリジニウム 0.3
ステビアエキス 0.1
ヘスペリジン 0.002
香料 0.2
水酸化ナトリウム 適量
クエン酸 適量
精製水 残部
合計 100.0
成分 配合量
還元パラチノース 5.0
第2リン酸カルシウム・2水和物 20.0
カルボキシメチルセルロース 3.0
硝酸カリウム 5.0
フッ化ナトリウム 1.05
プロピレングリコール 5.0
ヘスペリジン 0.1
パラオキシ安息香酸メチル 0.2
ポリオキシエチレン硬化ヒマシ油 0.4
香料 0.3
サッカリンナトリウム 0.1
リン酸2水素ナトリウム 適量
リン酸水素2ナトリウム 適量
精製水 残部
合計 100.0
成分 配合量
還元パラチノース 10.0
ソルビトール 10.0
カルボキシメチルセルロース 2.0
キサンタンガム 1.0
硝酸カリウム 5.0
フッ化ナトリウム 0.21
プロピレングリコール 0.2
ヘスペリジン 0.002
パラオキシ安息香酸メチル 0.2
ポリオキシエチレン硬化ヒマシ油 0.4
香料 0.3
リン酸2水素ナトリウム 適量
リン酸水素2ナトリウム 適量
精製水 残部
合計 100.0
成分 配合量
ソルビトール 10.0
還元パラチノース 10.0
グリセリン 1.0
グルコン酸カルシウム 0.15
モノフルオロリン酸ナトリウム 0.7
プロピレングリコール 3.0
ヘスペリジン 0.02
パラオキシ安息香酸メチル 0.1
ポリオキシエチレン硬化ヒマシ油 0.2
香料 1.0
炭酸水素ナトリウム 適量
炭酸2ナトリウム 適量
精製水 残部
合計 100.0
成分 配合量
グリセリン 10.0
ソルビトール 10.0
フッ化ナトリウム 0.3
プロピレングリコール 2.0
ヘスペリジン 0.02
パラオキシ安息香酸メチル 0.1
ポリオキシエチレン硬化ヒマシ油 0.2
香料 0.1
グリシン 適量
水酸化ナトリウム 適量
精製水 残部
合計 100.0
Claims (9)
- (α)ヘスペリジンをアルカリ性溶液に溶解させる工程、
(β)エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブチレングリコール、及び3−メチル−1,3−ブタンジオールからなる群より選択される少なくとも1種の二価アルコールを溶液に溶解させる工程、及び
(γ)糖アルコールを溶液に溶解させる工程、
(ただし、(α)〜(γ)工程は行う順序は制限されず、ヘスペリジン、上記二価アルコール、及び上記糖アルコールは同一溶液に溶解される)
を含み、(α)〜(γ)工程後に、
(δ)該溶液のpHを3〜10に調整する工程
をさらに含む(ただし、(α)〜(γ)工程を終えた段階で該溶液のpHが3〜10である場合は(δ)工程は省く)、
ヘスペリジン、上記二価アルコール、及び上記糖アルコールを溶解したpH3〜10の液状組成物の製造方法。 - (α)ヘスペリジンをアルカリ性溶液に溶解させる工程、
(β)エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブチレングリコール、及び3−メチル−1,3−ブタンジオールからなる群より選択される少なくとも1種の二価アルコールを溶液に溶解させる工程、及び
(γ)糖アルコールを溶液に溶解させる工程、
(ただし、(α)〜(γ)工程は、行う順序は制限されず、(α)〜(γ)工程に記載の成分は同一溶液に溶解される)
を含み、(α)〜(γ)工程後に、
(δ)該溶液のpHを3〜10に調整する工程
をさらに含む、
請求項1に記載の製造方法。 - (α)ヘスペリジンをアルカリ性溶液に溶解させる工程、
(β)エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブチレングリコール、及び3−メチル−1,3−ブタンジオールからなる群より選択される少なくとも1種の二価アルコールを該溶液に溶解させる工程、及び
(γ)糖アルコールを該溶液に溶解させる工程、
を含み、(α)〜(γ)工程後に、
(δ)該溶液のpHを3〜10に調整する工程
をさらに含む(ただし、(α)〜(γ)工程を終えた段階で該溶液のpHが3〜10である場合は(δ)工程は省く)、
請求項1に記載の製造方法。 - (α)ヘスペリジンをアルカリ性溶液に溶解させる工程、
(β)エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブチレングリコール、及び3−メチル−1,3−ブタンジオールからなる群より選択される少なくとも1種の二価アルコールを該溶液に溶解させる工程、及び
(γ)糖アルコールを該溶液に溶解させる工程、
を含み、(α)〜(γ)工程後に、
(δ)該溶液のpHを3〜10に調整する工程
をさらに含む、
請求項1に記載の製造方法。 - ヘスペリジンを溶解させるアルカリ性溶液のpHが11以上である、請求項1〜4のいずれかに記載の製造方法。
- 糖アルコールが、還元パラチノース、キシリトール、ソルビトール、マルチトール及びエリスリトールからなる群より選択される少なくとも1種である、請求項1〜5のいずれかに記載の製造方法。
- 二価アルコールが、ポリエチレングリコール及びプロピレングリコールからなる群より選択される少なくとも1種である、請求項1〜6のいずれかに記載の製造方法。
- 液状組成物が口腔用組成物である、請求項1〜7のいずれかに記載の製造方法。
- 口腔用組成物が液状歯磨又は洗口剤である、請求項8に記載の製造方法。
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JP2009256341A (ja) | 2008-03-27 | 2009-11-05 | Sunstar Inc | う蝕予防剤 |
JP2011073970A (ja) | 2009-09-29 | 2011-04-14 | Sunstar Inc | 口腔用又は咽喉用組成物 |
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US20110288038A1 (en) | 2011-11-24 |
JP4959006B2 (ja) | 2012-06-20 |
WO2010090236A1 (ja) | 2010-08-12 |
SG173193A1 (en) | 2011-09-29 |
EP2394634A4 (en) | 2012-08-29 |
CA2751304C (en) | 2016-08-02 |
CA2751304A1 (en) | 2010-08-12 |
US8507452B2 (en) | 2013-08-13 |
JP2012041352A (ja) | 2012-03-01 |
ES2707775T3 (es) | 2019-04-05 |
JPWO2010090236A1 (ja) | 2012-08-09 |
CN102300552A (zh) | 2011-12-28 |
KR20110116194A (ko) | 2011-10-25 |
EP2394634B1 (en) | 2018-11-21 |
EP2394634A1 (en) | 2011-12-14 |
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