JP2015507608A - ニトロン化合物とパーソナルケアにおけるその利用 - Google Patents
ニトロン化合物とパーソナルケアにおけるその利用 Download PDFInfo
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- JP2015507608A JP2015507608A JP2014544744A JP2014544744A JP2015507608A JP 2015507608 A JP2015507608 A JP 2015507608A JP 2014544744 A JP2014544744 A JP 2014544744A JP 2014544744 A JP2014544744 A JP 2014544744A JP 2015507608 A JP2015507608 A JP 2015507608A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- amine oxide
- propan
- oxide
- hydroxybenzylidene
- 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
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical class C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 230000003078 antioxidant effect Effects 0.000 claims description 30
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 102000008186 Collagen Human genes 0.000 claims description 13
- 108010035532 Collagen Proteins 0.000 claims description 13
- 229920001436 collagen Polymers 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 9
- 230000032683 aging Effects 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- DJHGKSPUUCMFSK-WDZFZDKYSA-N CC(C)[N+](\[O-])=C\c1ccc(O)cc1O Chemical compound CC(C)[N+](\[O-])=C\c1ccc(O)cc1O DJHGKSPUUCMFSK-WDZFZDKYSA-N 0.000 claims description 5
- VQZLTHPKDYULSZ-JYRVWZFOSA-N COc1cc(\C=[N+](/[O-])C(C)(C)C)ccc1O Chemical compound COc1cc(\C=[N+](/[O-])C(C)(C)C)ccc1O VQZLTHPKDYULSZ-JYRVWZFOSA-N 0.000 claims description 5
- LHXWBQGCYFWNSO-XFFZJAGNSA-N CC(C)[N+](\[O-])=C\c1ccccc1O Chemical compound CC(C)[N+](\[O-])=C\c1ccccc1O LHXWBQGCYFWNSO-XFFZJAGNSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- KYKCGEGLGGPHFI-GDNBJRDFSA-N C1=C(O)C(OC)=CC(\C=[N+](/[O-])C2CCCCC2)=C1 Chemical compound C1=C(O)C(OC)=CC(\C=[N+](/[O-])C2CCCCC2)=C1 KYKCGEGLGGPHFI-GDNBJRDFSA-N 0.000 claims description 3
- LGEDOTWZNSAJBS-XFFZJAGNSA-N CC(C)[N+](\[O-])=C\c1ccc(O)cc1 Chemical compound CC(C)[N+](\[O-])=C\c1ccc(O)cc1 LGEDOTWZNSAJBS-XFFZJAGNSA-N 0.000 claims description 3
- DXIASHULXBMOGV-YBEGLDIGSA-N CC1=C(O)C(C)=CC(\C=[N+](/[O-])C2CCCCC2)=C1 Chemical compound CC1=C(O)C(C)=CC(\C=[N+](/[O-])C2CCCCC2)=C1 DXIASHULXBMOGV-YBEGLDIGSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- OQPYAPULPIJSHU-QPEQYQDCSA-N CC(C)[N+](\[O-])=C\c1cc(C)c(O)c(C)c1 Chemical compound CC(C)[N+](\[O-])=C\c1cc(C)c(O)c(C)c1 OQPYAPULPIJSHU-QPEQYQDCSA-N 0.000 claims description 2
- CWFSWKSDUDORPE-YFHOEESVSA-N CC\[N+]([O-])=C\c1ccc(O)cc1 Chemical compound CC\[N+]([O-])=C\c1ccc(O)cc1 CWFSWKSDUDORPE-YFHOEESVSA-N 0.000 claims description 2
- DIMAWMHQAJMICL-GHXNOFRVSA-N COc1cc(\C=[N+](/[O-])C(C)C)ccc1O Chemical compound COc1cc(\C=[N+](/[O-])C(C)C)ccc1O DIMAWMHQAJMICL-GHXNOFRVSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- PSYHRZCRICXGJJ-WQLSENKSSA-N alpha-(4-hydroxyphenyl)-N-tert-butylnitrone Chemical compound CC(C)(C)[N+](\[O-])=C\C1=CC=C(O)C=C1 PSYHRZCRICXGJJ-WQLSENKSSA-N 0.000 claims 2
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 claims 1
- JQJBPQPOWVENRB-FLIBITNWSA-N CCC\[N+]([O-])=C\c1ccc(O)cc1 Chemical compound CCC\[N+]([O-])=C\c1ccc(O)cc1 JQJBPQPOWVENRB-FLIBITNWSA-N 0.000 claims 1
- HTTYVEISXYPRQD-GHXNOFRVSA-N COC1=CC(\C=N/C(C)C)=CC=C1O Chemical compound COC1=CC(\C=N/C(C)C)=CC=C1O HTTYVEISXYPRQD-GHXNOFRVSA-N 0.000 claims 1
- XIFCTXIAWCLBCV-YVLHZVERSA-N COc1cc(\C=[N+](/[O-])C(C)(C)CC(C)(C)C)ccc1O Chemical compound COc1cc(\C=[N+](/[O-])C(C)(C)CC(C)(C)C)ccc1O XIFCTXIAWCLBCV-YVLHZVERSA-N 0.000 claims 1
- UGLDFIVEDDBNQQ-UVTDQMKNSA-N OC1=CC=CC=C1\C=[N+](/[O-])C1CCCCC1 Chemical compound OC1=CC=CC=C1\C=[N+](/[O-])C1CCCCC1 UGLDFIVEDDBNQQ-UVTDQMKNSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- HGLLGCIZHHMQDE-WQLSENKSSA-N chembl2160210 Chemical compound CC(C)(C)[N+](\[O-])=C\C1=CC=CC=C1O HGLLGCIZHHMQDE-WQLSENKSSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 2
- 235000006708 antioxidants Nutrition 0.000 description 39
- 210000003491 skin Anatomy 0.000 description 32
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 19
- 230000011382 collagen catabolic process Effects 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 6
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 5
- 229930003427 Vitamin E Natural products 0.000 description 5
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 5
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- 229940046009 vitamin E Drugs 0.000 description 5
- 230000006378 damage Effects 0.000 description 4
- 210000004207 dermis Anatomy 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
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- UTCFOFWMEPQCSR-UHFFFAOYSA-N 5-formylsalicylic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1O UTCFOFWMEPQCSR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000004678 hydrides Chemical class 0.000 description 1
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- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
- 229960004705 kojic acid Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
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- 239000011619 pantothenol Substances 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008288 physiological mechanism Effects 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
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- 239000000341 volatile oil Substances 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本出願は、参照によりその全体が本明細書に援用される2011年11月30日に出願された仮出願第61/564,920号に基づき優先権を主張する。
(Z)−N−(4−ヒドロキシベンジリデン)−2−メチルプロパン−2−アミン(pHBz−tBHA)の合成
(Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)プロパン−2−アミンオキシド(DMHBZ−IPHA)
(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)プロパン−2−アミンオキシド(VAN−IPHA)の合成
(Z)−N−(2−ヒドロキシベンジリデン)プロパン−2−アミンオキシド(SAL−IPHA)の合成
(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)−2−メチルプロパン−2−アミンオキシド(VAN−tBHA)の合成
(Z)−N−(4−ヒドロキシベンジリデン)プロパン−2−アミンオキシド(pHBz−IPHA)の合成
ナトリウム(Z)−2−ヒドロキシ−5−((イソプロピルオキシドイミノ)メチル)ベンゾエート(FSANa−IPHA)の合成
(Z)−N−(2,4−ジヒドロキシベンジリデン)プロパン−2−アミンオキシド(DHBz−IPHA)の合成
ナトリウム(Z)−N−(4−ヒドロキシ−2−オキソベンジリデン)プロパン−2−アミンオキシド(DHBzNa−IPHA)の合成
抗酸化力
酸素ラジカル吸収能(Oxygen Radical Absorbance Capacity、ORAC)プロトコルを用いて抗酸化力が評価される。ORACは、水素原子移動(hydrogen atom transfer、HAT)機構を基にしたインビトロな化学的手法である。ORACはペルオキシルラジカルによって引き起こされる酸化の抗酸化的抑制を測定し、それにより、原子移動による、古典的なラジカル連鎖停止の抗酸化活性を反映する。この試験において、ペルオキシルラジカルは蛍光プローブと反応して非蛍光反応物を生成する。これを蛍光測定によって定量化する。抗酸化力は経時的に生成された反応物の減少率及び量によって決定される。この試験は、蛍光プローブのフリーラジカルによる損傷の結果としての蛍光強度の変化に依存する。蛍光強度の変化は、フリーラジカルによる損傷の程度の指標である。抗酸化剤の存在下で、フリーラジカルによる損傷の抑制は、より強い蛍光強度によって反映され、フリーラジカルに対する抗酸化力として測定可能である。ORAC試験の独自性は、反応が完了まで行われることである。これにより、曲線化面積(area under the curve、AUC)の算出が可能になり、他の数多くの試験法における相対的測定とは異なり、抗酸化力の絶対的な定量化がなされる。
コラーゲン劣化の抑制
皮膚中に典型的に多く見られるI型コラーゲンが、様々な処理に先立って、0.04M、pH4.3の酢酸に溶解される。ラジカルによって引き起こされるコラーゲンの劣化として、水性のラジカル開始剤2,2’−アゾビス−2−メチル−プロパンイミドアミドジヒドロクロリド(AAPH)を用いる。コラーゲン試料をAAPHと共に、同濃度のVAN−IPHA(実施例3)、pHBz−IPHA(実施例6)、及びビタミンE(比較例)の存在下でインキュベートし、これらの抗酸化剤についてコラーゲン劣化防止の有効性を求める。50℃で90分インキュベートした後、コラーゲン試料はSDS−PAGEによって分析され、コラーゲンの共有結合架橋三量体であるγ帯の残存量によって劣化の程度を求める。図1に示されるとおり、コラーゲン劣化の程度は、pHBz−IPHA、ビタミンE、又は抗酸化剤を含まないコントロール溶液に比べ、VAN−IPHAの存在下で顕著に低い。
Claims (10)
- パーソナルケア組成物であって、
(a)式Iの抗酸化化合物であって、
R1、R2、R3、R4、及びR5は独立してH、C1−C10アルキル、ヒドロキシ、C1−C6アルコキシ、−COOH、−COO−M+、又は−O−M+であり、ここで、R1、R2、R3、R4、及びR5のうち1以上がヒドロキシであり、R6がH、C1−C10アルキル、C3−C12シクロアルキル又はフェニルである場合、M+はナトリウム又はカリウム又はアンモニウムイオンである抗酸化化合物と、
(b)皮膚科学上許容されるキャリアと、を含むパーソナルケア組成物。 - 請求項1に記載の組成物であって、RはC1−C10アルキル、C3−C12シクロアルキルである、組成物。
- 請求項1又は2に記載の組成物であって、R3はOHである、組成物。
- 請求項1乃至3のいずれかに記載の組成物であって、R2はH、C1−C10アルキル、ヒドロキシ、C1−C6アルコキシ、−COOH、又は−COO−M+であり、M+はナトリウムである、組成物。
- 請求項1に記載の組成物であって、式Iの化合物は
(Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)シクロヘキサンアミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)−2−メチルプロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)−2,4,4−トリメチルペンタン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)シクロヘキサンアミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)エタンアミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)プロパン−1−アミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)−2−メチルプロパン−2−アミンオキシド、(Z)−N−(2−ヒドロキシベンジリデン)プロパン−2−アミンオキシド、ナトリウム(Z)−2−ヒドロキシ−5−((イソプロピルオキシドイミノ)メチル)ベンゾエート、(Z)−N−(2,4−ジヒドロキシベンジリデン)プロパン−2−アミンオキシド、ナトリウム(Z)−N−(4−ヒドロキシ−2−オキシドベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(2−ヒドロキシベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)−2−メチルプロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)−2,4,4−トリメチルペンタン−2−アミンオキシド、(Z)−N−(2−ヒドロキシベンジリデン)−2−メチルプロパン−2−アミンオキシド、又は(Z)−N−(2−ヒドロキシベンジリデン)シクロヘキサンアミンオキシドである、組成物。 - 請求項1に記載の組成物であって、式Iの化合物は
(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)プロパン−2−アミン、又は(Z)−N−(4−ヒドロキシベンジリデン)プロパン−2−アミンオキシドである、組成物。 - 皮膚を手入れする美容法であって、請求項1乃至6のいずれかに記載の組成物を前記皮膚に塗布する手順を含む美容法。
- 皮膚中のコラーゲンの劣化を抑制する方法であって、有効量の請求項1乃至6のいずれかに記載の組成物を、前記皮膚に局所的に投与することを含む方法。
- 加齢の可視的な兆候を軽減させる方法であって、このような処置を必要とする皮膚に、請求項1乃至6のいずれかに記載の組成物を塗布することを含む、方法。
- (Z)−N−(4−ヒドロキシ−3,5−ジメチルベンジリデン)シクロヘキサンアミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)−2−メチルプロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)−2,4,4−トリメチルペンタン−2−アミンオキシド、(Z)−N−(4−ヒドロキシ−3−メトキシベンジリデン)シクロヘキサンアミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)エタンアミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)プロパン−1−アミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)プロパン−2−アミンオキシド、(Z)−N−(4−ヒドロキシベンジリデン)−2−メチルプロパン−2−アミンオキシド、(Z)−N−(2−ヒドロキシベンジリデン)プロパン−2−アミンオキシド、ナトリウム(Z)−2−ヒドロキシ−5−((イソプロピルオキシドイミノ)メチル)ベンゾエート、(Z)−N−(2,4−ジヒドロキシベンジリデン)プロパン−2−アミンオキシド、又はナトリウム(Z)−N−(4−ヒドロキシ−2−オキシドベンジリデン)プロパン−2−アミンオキシドである、化合物。
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US10064804B2 (en) | 2014-06-30 | 2018-09-04 | Dow Global Technologies Llc | Polymeric nitrones and their use in personal care |
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