JP2007077101A - 皮膚外用剤 - Google Patents
皮膚外用剤 Download PDFInfo
- Publication number
- JP2007077101A JP2007077101A JP2005269294A JP2005269294A JP2007077101A JP 2007077101 A JP2007077101 A JP 2007077101A JP 2005269294 A JP2005269294 A JP 2005269294A JP 2005269294 A JP2005269294 A JP 2005269294A JP 2007077101 A JP2007077101 A JP 2007077101A
- Authority
- JP
- Japan
- Prior art keywords
- skin
- acid
- salt
- hyaluronic acid
- external preparation
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 68
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 63
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims abstract description 36
- -1 acetyl hyaluronic acid Chemical compound 0.000 claims description 52
- 238000004040 coloring Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 150000005846 sugar alcohols Polymers 0.000 claims description 9
- 239000002562 thickening agent Substances 0.000 claims description 9
- 239000002738 chelating agent Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 9
- 238000002845 discoloration Methods 0.000 abstract 2
- 210000003491 skin Anatomy 0.000 description 68
- 239000000306 component Substances 0.000 description 45
- 230000000694 effects Effects 0.000 description 27
- 239000002537 cosmetic Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229920002385 Sodium hyaluronate Polymers 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229940010747 sodium hyaluronate Drugs 0.000 description 9
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000002087 whitening effect Effects 0.000 description 7
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- 230000003712 anti-aging effect Effects 0.000 description 6
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- 238000002156 mixing Methods 0.000 description 6
- 230000003020 moisturizing effect Effects 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
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- 239000003963 antioxidant agent Substances 0.000 description 5
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- 235000014113 dietary fatty acids Nutrition 0.000 description 5
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- 235000011187 glycerol Nutrition 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine Chemical compound CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 4
- 238000001542 size-exclusion chromatography Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
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- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 3
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
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Abstract
【解決手段】アセチルヒアルロン酸またはその塩、平均分子量25万以下のヒアルロン酸またはその塩を含有することによって、皮膚外用剤の着色を抑制することができる。このため、アセチルヒアルロン酸またはその塩の作用をその配合量に応じて有効に発揮することができる。
【選択図】なし
Description
さらに、アセチルヒアルロン酸はヒアルロン酸の高い曳糸性などの欠点を改善しつつ、優れた皮膚柔軟化効果を発揮し得ることが知られている(特許文献2:登録3557044公報)が、アセチルヒアルロン酸について着色(特に加熱条件下)に関する報告はなされていない。
一方、GPC分析による分子量が1万以下の低分子ヒアルロン酸は、血管新生作用の増強(特許文献3:特開平11-292758号公報)、細胞死抑制剤、細胞障害抑制剤、及び細胞・組織保護剤(特許文献4:国際公開第2002/004471号パンフレット)などが知られているが、アセチルヒアルロン酸の着色に対する効果については知られていない。
このように、アセチルヒアルロン酸の着色に対しては全く検討されていないため、改善が求められている。
(1)アセチルヒアルロン酸またはその塩、および平均分子量25万以下のヒアルロン酸またはその塩を含有する皮膚外用剤。
(2)さらに、多価アルコール、グリコールエーテル、水溶性増粘剤、およびキレート剤からなる群から選択される1種または2種以上を含有する(1)記載の皮膚外用剤。
(3)さらに、美白成分、抗炎症成分、抗菌成分、細胞賦活化成分、抗酸化成分、老化防止成分および保湿成分からなる群から選択される1種または2種以上を含有する(1)または(2)記載の皮膚外用剤。
また、本発明は以下の(4)に示す皮膚外用剤の着色抑制方法をも包含する。
(4)平均分子量25万以下のヒアルロン酸またはその塩による、アセチルヒアルロン酸またはその塩の着色抑制方法。
なお、本明細書中、特に言及しない限り、%は重量%を意味するものとする。
また本発明の皮膚外用剤には、アセチルヒアルロン酸の薬学的、生理学的に許容される塩を用いることもでき、このような塩としては、例えばナトリウムやカリウムなどのアルカリ金属塩、マグネシウムやカルシウム等のアルカリ土類金属塩、アンモニウム塩、モノエタノールアミン等のアルカノールアミン塩等を挙げることができ、好ましくはナトリウム塩などのアルカリ金属塩である。
本発明の皮膚外用剤で用いるアセチルヒアルロン酸またはその塩は、公知の方法、例えば粉末状ヒアルロン酸を無水酢酸溶媒に懸濁しさらに濃硫酸を加えて反応させる方法、で製造したものや、化粧品等において皮膚外用剤に通常使用されているアセチルヒアルロン酸またはその塩の市販品を利用することができる。
カラム…TSKgel GMPWXL 7.8mm×30cm
カラム温度…40℃付近の一定温度
検出器…示差屈折率計
移動相…0.2mol/L NaCl
流量…0.3mL/min
注入量…100μL
これらの水溶性増粘剤は1種又は2種以上を組み合わせて使用でき、本発明の皮膚外用剤に配合する割合は、水溶性増粘剤の合計量として、皮膚外用剤全体に対して通常0.0003〜20重量%であり、好ましくは0.01〜10重量%、特に好ましくは0.05〜5重量%であれば良い。
これらのキレート剤は1種又は2種以上を組み合わせて使用でき、本発明の皮膚外用剤に配合する割合は、キレート剤の合計量として、皮膚外用剤全体に対して通常0.0003〜20重量%であり、好ましくは0.01〜10重量%、特に好ましくは0.05〜5重量%であれば良い。
本発明の方法において、アセチルヒアルロン酸またはその塩、平均分子量25万以下のヒアルロン酸またはその塩やこれらの含有量などについては、前記皮膚外用剤で用いたものと同様である。さらに本方法にて得られた物は、用途などに応じて1日あたり1回から数回に分けて、公知あるいは慣用されている用法・用量にて使用することができる。
分子量100万のヒアルロン酸ナトリウムを、酸性条件下加熱還流を行って加水分解し、Sephadex G−10(ファルマシア社製;φ3x124)で脱塩した後、凍結乾燥した。凍結乾燥品について、以下の測定条件下でサイズ排除クロマトグラフィー法を用いて数平均分子量を算出した。
検出器…示差屈折率計
カラム…TSKgel GMPWXL 7.8mm×30cm
カラム温度…40℃付近の一定温度
移動相…0.2mol/L NaCl
流量…0.3mL/min
注入量…100μL
得られたヒアルロン酸ナトリウムのうち、サイズ排除クロマトグラフィーによる数平均分子量(極限粘度による補正後)が20万、5万、4千のヒアルロン酸ナトリウムについて下記試験および製剤に供した。
表1、2に記載の処方(重量%)に従って、アセチルヒアルロン酸、各種平均分子量25万以下のヒアルロン酸、水を混合し溶解させて、試験液を調製した。調製直後の試験液はいずれも無色透明であった。これを分光測色計CM-3500d(MINOLTA製)を用いて、国際照明委員会(CIE)のL*a*b表色系を用いて測定した。同様にして、60℃の恒温槽にて24時間および4日間保管した試験液を測定し、調製直後の試験液を基準としてΔEを算出した。また、目視で試験液の色を判定した。
結果を表1、2に示す。
このように、本発明の皮膚外用剤は、アセチルヒアルロン酸の熱による着色を平均分子量25万以下のヒアルロン酸が抑制し安定化できるという、予想外の効果があることがわかった。
Claims (3)
- アセチルヒアルロン酸またはその塩、および平均分子量25万以下のヒアルロン酸またはその塩を含有する皮膚外用剤。
- さらに、多価アルコール、グリコールエーテル、水溶性増粘剤、およびキレート剤からなる群から選択される1種または2種以上を含有する請求項1に記載の皮膚外用剤。
- 平均分子量25万以下のヒアルロン酸またはその塩による、アセチルヒアルロン酸またはその塩の着色抑制方法。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2012214418A (ja) * | 2011-03-31 | 2012-11-08 | Rohto Pharmaceutical Co Ltd | 外用組成物 |
JPWO2011129374A1 (ja) * | 2010-04-14 | 2013-07-18 | ロート製薬株式会社 | 肌質改善用外用組成物 |
KR102621083B1 (ko) * | 2023-09-08 | 2024-01-08 | 주식회사 모이스텐 | 피부 재생 기능을 갖는 생분해성 필름 및 이의 제조방법 |
Citations (5)
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JPS57185208A (en) * | 1981-05-07 | 1982-11-15 | Shiseido Co Ltd | Skin cosmetic |
JPS59219209A (ja) * | 1983-05-28 | 1984-12-10 | Kanebo Ltd | 皮膚化粧料 |
JPH01190614A (ja) * | 1988-01-21 | 1989-07-31 | Kanebo Ltd | 皮膚化粧料 |
JPH0971602A (ja) * | 1995-06-29 | 1997-03-18 | Shiseido Co Ltd | 低分子量アセチル化ヒアルロン酸及び皮膚柔軟化剤 |
JPH10279425A (ja) * | 1997-03-31 | 1998-10-20 | Shiseido Co Ltd | 皮膚外用剤 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS57185208A (en) * | 1981-05-07 | 1982-11-15 | Shiseido Co Ltd | Skin cosmetic |
JPS59219209A (ja) * | 1983-05-28 | 1984-12-10 | Kanebo Ltd | 皮膚化粧料 |
JPH01190614A (ja) * | 1988-01-21 | 1989-07-31 | Kanebo Ltd | 皮膚化粧料 |
JPH0971602A (ja) * | 1995-06-29 | 1997-03-18 | Shiseido Co Ltd | 低分子量アセチル化ヒアルロン酸及び皮膚柔軟化剤 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPWO2011129374A1 (ja) * | 2010-04-14 | 2013-07-18 | ロート製薬株式会社 | 肌質改善用外用組成物 |
JP2016104809A (ja) * | 2010-04-14 | 2016-06-09 | ロート製薬株式会社 | 肌質改善用外用組成物 |
JP2012214418A (ja) * | 2011-03-31 | 2012-11-08 | Rohto Pharmaceutical Co Ltd | 外用組成物 |
KR102621083B1 (ko) * | 2023-09-08 | 2024-01-08 | 주식회사 모이스텐 | 피부 재생 기능을 갖는 생분해성 필름 및 이의 제조방법 |
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