JP5695355B2 - ビタミンa類の安定化方法 - Google Patents
ビタミンa類の安定化方法 Download PDFInfo
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- JP5695355B2 JP5695355B2 JP2010151460A JP2010151460A JP5695355B2 JP 5695355 B2 JP5695355 B2 JP 5695355B2 JP 2010151460 A JP2010151460 A JP 2010151460A JP 2010151460 A JP2010151460 A JP 2010151460A JP 5695355 B2 JP5695355 B2 JP 5695355B2
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- 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 title claims description 88
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 title claims description 64
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- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 title claims description 40
- 235000019155 vitamin A Nutrition 0.000 title claims description 40
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- 238000000034 method Methods 0.000 title claims description 24
- 230000000087 stabilizing effect Effects 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- 150000002430 hydrocarbons Chemical group 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 12
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 11
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- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
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- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
- XWCYDHJOKKGVHC-UHFFFAOYSA-N Vitamin A2 Chemical compound OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C XWCYDHJOKKGVHC-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005015 aryl alkynyl group Chemical group 0.000 description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- YYVJAABUJYRQJO-UHFFFAOYSA-N isomyristic acid Chemical compound CC(C)CCCCCCCCCCC(O)=O YYVJAABUJYRQJO-UHFFFAOYSA-N 0.000 description 2
- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 description 1
- 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 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- LBPNCQGSZHRGME-UHFFFAOYSA-N 2,2,3,3,4,4-hexahydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)(O)C(O)(O)C(O)(O)C(O)=O LBPNCQGSZHRGME-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- XMMODWGMKHUZQW-UHFFFAOYSA-N 2-hydroxy-16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCC(O)C(O)=O XMMODWGMKHUZQW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
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- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
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- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
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Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
[1]ビタミンA類を含有する組成物に下記式(1)で表される化合物を含有させるビタミンA類の安定化方法。
[2]上記式(2)中、nは3〜8、YはR−CO−基であってRは水酸基を有するアルキル基、Z 1 及びZ 3 は−(CH 2 )mで表される炭素数が5〜15の二価の炭化水素基、Z 2 及びZ 4 は炭素数が−(CH 2 )mで表される4〜10の一価の炭化水素基である[1]記載のビタミンA類の安定化方法。
[3]R1〜R6の2以上がR−CO−基である[1]又は[2]記載のビタミンA類の安定化方法。
[4]上記式(1)で表される化合物の分子量が1,000〜10,000である[1]乃至[3]のいずれかに記載のビタミンA類の安定化方法。
[5]上記式(1)で表される化合物の含有量が0.5〜5質量%である[1]乃至[4]のいずれかに記載のビタミンA類の安定化方法。
[6]上記ビタミンA類と上記式(1)で表される化合物との割合(重量比)が1:(1〜100)である[1]乃至[5]のいずれかに記載のビタミンA類の安定化方法。
本発明では、ビタミンA類を含有する組成物に化合物(1)を含有させる。本発明では、化合物(1)を1種単独で含有させてもよく、2種以上の異なる構造の化合物(1)を含有させてもよい。
以下に記載の処方に基づいて化粧料組成物1〜6(実施例;化粧料組成物1、比較例;化粧料組成物2〜6)を調製した。
得られた化粧料組成物1〜6を、各々エアレス容器に充填後、25℃の条件で保管した。その後、6週間経過時(化粧料組成物1〜6)、10週間経過時(化粧料組成物5)、12週間経過時(化粧料組成物1〜4)、16週間経過時(化粧料組成物6)の各経過時における化粧料組成物中に残存されたレチノール残存率(%)を測定した。当初添加量したレリノール量に対する残存されたレチノール量の割合を測定し、その結果を表1及び図1に示した。
上記HPLCに際しては、以下の分析条件とした。即ち、カラムにナーゲル社製「Nucleosil C18 100−7μm(長さ250mm、内径4mm)」を用い、カラム温度は35℃とし、移動相としてメタノール90体積%及び水10体積%の混合液を用いた。更に、検知には波長325nmの紫外線光を利用した。
レチノール;0.1質量%
化合物(1)として下記化合物A〜Dのいずれか;2.00質量%
トリ(カプリル/カプリン酸)グリセリル;6.00質量%
グリセリン;5.00質量%
(アクリル酸ヒドロキシエチル/アクリロイルジメチルタウリンNa)コポリマ
;4.50質量%
ホホバ油;4.00質量%
1,3−ブチルグリコール;3.50質量%
スクワラン;1.50質量%
ペンチレングリコール;1.50質量%
グリコシルトレハロース;1.20質量%
バチルス/(コメヌカエキス/ダイズエキス)発酵液;1.00質量%
ヒアルロン酸Na;0.01質量%
ポリソルベート60;0.50質量%
加水分解水添デンプン;0.90質量%
フェノキシエタノール;0.60質量%
水;残部
(1)化粧料組成物1;トリポリヒドロキシステアリン酸ジペンタエリスリチル
式(1)に示すR1〜R6として、「式(3)に示す基(但し、n≒4)」と「水素原子」とを、3:3で有する化合物(以下、表及び図において「化合物A」という)。
式(1)に示すR1〜R6として、R1〜R6の全てに「12−ヒドロキシステアリン酸のエステル残基」を有する化合物(以下、表及び図において「化合物B」という)。
式(1)に示すR1〜R6として、「12−ヒドロキシステアリン酸のエステル残基」と「イソステアリン酸のエステル残基」と「水素原子」とを、3:1:2で有する化合物(以下、表及び図において「化合物C」という)。
式(1)に示すR1〜R6として、「12−ヒドロキシステアリン酸のエステル残基」と「ステアリン酸のエステル残基」と「ロジン酸のエステル残基」とを、4:1.5:0.5で有する化合物(以下、表及び図において「化合物D」という)。
一方、化合物(1)を配合した化粧料組成物1〜4では、12週経過時点で90%前後の残存率を達成している。このことから、化合物(1)を配合することにより、上記化粧料組成物中のレチノールが安定化されていることが分かる。
Claims (6)
- 上記式(2)中、nは3〜8、YはR−CO−基であってRは水酸基を有するアルキル基、Z 1 及びZ 3 は−(CH 2 )mで表される炭素数が5〜15の二価の炭化水素基、Z 2 及びZ 4 は炭素数が−(CH 2 )mで表される4〜10の一価の炭化水素基である請求項1記載のビタミンA類の安定化方法。
- R1〜R6の2以上がR−CO−基である請求項1又は2記載のビタミンA類の安定化方法。
- 上記式(1)で表される化合物の分子量が1,000〜10,000である請求項1乃至3のいずれかに記載のビタミンA類の安定化方法。
- 上記式(1)で表される化合物の含有量が0.5〜5質量%である請求項1乃至4のいずれかに記載のビタミンA類の安定化方法。
- 上記ビタミンA類と上記式(1)で表される化合物との割合(重量比)が1:(1〜100)である請求項1乃至5のいずれかに記載のビタミンA類の安定化方法。
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