KR100305915B1 - Composition for external application to the skin - Google Patents
Composition for external application to the skin Download PDFInfo
- Publication number
- KR100305915B1 KR100305915B1 KR1019990029778A KR19990029778A KR100305915B1 KR 100305915 B1 KR100305915 B1 KR 100305915B1 KR 1019990029778 A KR1019990029778 A KR 1019990029778A KR 19990029778 A KR19990029778 A KR 19990029778A KR 100305915 B1 KR100305915 B1 KR 100305915B1
- Authority
- KR
- South Korea
- Prior art keywords
- skin
- composition
- effect
- phytosphingosine
- hexanoyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 229940106189 ceramide Drugs 0.000 claims abstract description 21
- DAAZGMWCIAIMCL-ZDXQCDESSA-N N-hexanoylphytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(=O)CCCCC DAAZGMWCIAIMCL-ZDXQCDESSA-N 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 27
- 230000003020 moisturizing effect Effects 0.000 abstract description 10
- 238000001035 drying Methods 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 3
- 210000003491 skin Anatomy 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 20
- 230000001965 increasing effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 201000004624 Dermatitis Diseases 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- 239000006071 cream Substances 0.000 description 6
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 5
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
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- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- DHFUFHYLYSCIJY-WSGIOKLISA-N CCCCCCCCCCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O Chemical compound CCCCCCCCCCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DHFUFHYLYSCIJY-WSGIOKLISA-N 0.000 description 2
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 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 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 229960001631 carbomer Drugs 0.000 description 2
- 150000001783 ceramides Chemical class 0.000 description 2
- 229940086555 cyclomethicone Drugs 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- 230000037336 dry skin Effects 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- 210000000245 forearm Anatomy 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940100460 peg-100 stearate Drugs 0.000 description 2
- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 description 2
- 229940033329 phytosphingosine Drugs 0.000 description 2
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
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- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 229940080352 sodium stearoyl lactylate Drugs 0.000 description 2
- ODFAPIRLUPAQCQ-UHFFFAOYSA-M sodium stearoyl lactylate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O ODFAPIRLUPAQCQ-UHFFFAOYSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 241000611421 Elia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
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- 238000002835 absorbance Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- DWMMZQMXUWUJME-UHFFFAOYSA-N hexadecyl octanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC DWMMZQMXUWUJME-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010487 meadowfoam seed oil Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
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- 230000009131 signaling function Effects 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 230000037067 skin hydration Effects 0.000 description 1
- 150000003410 sphingosines Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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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
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
-
- 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
Abstract
본 발명은 피부 외용제 조성물에 관한 것으로, 더욱 상세하게는 하기 구조식(I)의 N-헥사노일-파이토스핑고신(N-hexanoyl-phytosphingosine) 및 하기 구조식(II)의 네오-세라마이드(Neo-ceramides; ceradiamide 16)를 1:9 ~ 9:1의 비율로 함유하여 우수한 피부 보습 효과 및 피부 건조 방지 효과를 갖는 피부 외용제 조성물에 관한 것이다.The present invention relates to an external composition for skin, and more particularly, N-hexanoyl-phytosphingosine of the following structural formula (I) and neo-ceramides of the following structural formula (II); ceradiamide 16 ) In a ratio of 1: 9 to 9: 1, and relates to an external composition for skin having excellent skin moisturizing effect and skin drying prevention effect.
Description
본 발명은 피부 외용제 조성물에 관한 것으로, 더욱 상세하게는 하기 구조식(I)의 N-헥사노일-파이토스핑고신(N-hexanoyl-phytosphingosine) 및 하기 구조식(II)의 네오-세라마이드(Neo-ceramides; ceradiamide 16)를 1:9 ~ 9:1의 비율로 함유하여 우수한 피부 보습 효과 및 피부 건조 방지 효과를 갖는 피부 외용제 조성물에 관한 것이다.The present invention relates to an external composition for skin, and more particularly, N-hexanoyl-phytosphingosine of the following structural formula (I) and neo-ceramides of the following structural formula (II); ceradiamide 16 ) In a ratio of 1: 9 to 9: 1, and relates to an external composition for skin having excellent skin moisturizing effect and skin drying prevention effect.
인간의 피부를 구성하는 표피층에 존재하는 수분의 양은 표피내 깊이에 따라 다양하다. 기저층에 거의 70의 수분이 존재하며 각질층에는 10~13정도의 수분이 존재한다. 정상적인 표피층의 가장 바깥층인 각질층은 Elias 모델에 의하면 여러 단백질로 구성된 무핵세포인 각질세포와 주로 세라마이드로 구성된 세포간 지질로 구성되어 있는데, 최근 과도한 세안, 빈번한 목욕, 잦은 빈도의 색조화장 및 그 색조화장의 부적절한 제거, 건조한 생활환경 및 계절적인 요인과 아토피성 피부, 노인성 건조피부, 주부의 건조습진, 접촉피부염으로 인하여 건조피부 증상을 호소하는 사람의 수가 증가하고 있다.The amount of moisture present in the epidermal layer of human skin varies with the depth within the epidermis. Nearly 70 moisture is present in the basal layer and 10-13 moisture is present in the stratum corneum. The outermost layer of the normal epidermal layer, the Elias model, consists of keratinocytes, which are nucleated cells composed of several proteins, and intercellular lipids, mainly composed of ceramides. Recently, excessive face washing, frequent bathing, frequent color cosmetics and their color cosmetics The number of people complaining of dry skin is increasing due to inadequate removal, dry living conditions and seasonal factors, atopic dermatitis, senile dry skin, dry housewife's eczema and contact dermatitis.
따라서, 피부의 수분을 유지하기 위하여 외부에서 수분을 공급하거나, 수분의 손실을 방지하고자 하였다. 그 예로 글리세린 등과 같은 보습성분을 외부에서 공급하여 스케일링(scaling) 및 피부 거칠음이 일어나는 현상을 완화하고자 하였으며, 바셀린(petrolatum) 등을 피부에 도포하여 도포막을 형성시킴으로써 수분의 손실을 방지하고자 하였으나 효과는 일시적인 것이다.Therefore, in order to maintain the moisture of the skin to provide moisture or to prevent the loss of moisture. For example, it tried to alleviate the phenomenon of scaling and roughness by supplying moisturizing ingredients such as glycerin from the outside, and tried to prevent loss of moisture by forming a coating film by applying petrolatum to skin. It is temporary.
한편, 최적의 피부 수분을 유지하기 위한 가장 중요한 요소는 적절한 수분공급과 더불어 각질형성세포에 의한 적절한 양과 속도로 각질층을 형성시키는 것과, 피부내 지질의 합성을 증가시키는 것인데, 현재 피부내 지질의 합성을 증가시키는 세라마이드에 대한 연구는 활발히 진행되고 있으나, 각질층 형성에 대해서는 그 연구가 미흡한 상태이다. 즉, 각질층의 형성은 열, 태양자외선, 화학물질, 피부 미생물 등과 같은 여러 스트레스, 노화 등에 의해 지연되는데, 이러한 각질형성에 영향을 주는 요인들을 통제할 수 있는 성분에 대하여 그 연구가 미흡한 상태이다.On the other hand, the most important factor for maintaining optimal skin hydration is to form a stratum corneum at the proper amount and speed by keratinocytes and to increase the synthesis of lipids in the skin, along with proper hydration. Studies on ceramides to increase the amount of cellulose have been actively conducted, but studies on the formation of stratum corneum are insufficient. In other words, the formation of the stratum corneum is delayed by various stresses and aging, such as heat, solar ultraviolet rays, chemicals, skin microorganisms, etc., and the study on the ingredients that can control the factors affecting the keratinogenesis is insufficient.
이에, 본 발명자들은 피부에 수분을 효과적으로 공급할 수 있으면서, 각질형성에 영향을 주는 요인들을 효과적으로 통제할 수 있는 활성성분을 찾고자 하였다. 그 결과, 스핑고이드 베이스에 지방산 사슬이 결합된 형태가 피부 세포 내에서 특정한 신호전달 기능을 수행한다는 사실로부터, 파이토스핑고신에 짧은 지방산 사슬을 결합시킨 형태를 연구하게 되었고, 이로부터 헥사노익산과 파이토스핑고신을 결합한 상기 구조식(I)의 N-헥사노일-파이토스핑고신의 각질 형성 촉진효과가 우수하다는 것을 알게 되었으며, 상기 구조식(II)의 네오-세라마이드를 N-헥사노일-파이토스핑고신(I)과 혼합 사용한다면, 각질형성촉진 효과가 상승될 뿐만 아니라 피부보습효과 또한 상승된다는 것을 발견하고 본 발명을 완성하게 되었다.Accordingly, the present inventors have been trying to find an active ingredient that can effectively supply moisture to the skin and can effectively control the factors that affect keratinogenesis. As a result, from the fact that the fatty acid chains bound to the sphingoid base perform specific signaling functions in skin cells, we studied the form of binding short fatty acid chains to phytosphingosine, from which hexanoic acid and phytosphingosine were derived. It was found that the effect of promoting the formation of keratin formation of the N-hexanoyl-phytosphingosine of the structural formula (I) combined with the above, and using the neo-ceramide of the structural formula (II) mixed with N-hexanoyl-phytosphingosine (I), It was found that not only the exfoliation promoting effect is increased, but also the skin moisturizing effect is increased, thereby completing the present invention.
따라서, 본 발명의 목적은 각질형성촉진효과에 의한 우수한 피부 건조 방지 효과 및 우수한 피부보습효과를 갖는 피부 외용제 조성물을 제공하는 것이다. 본 발명의 상기한 목적 및 다른 목적들은 하기 발명의 구성 및 작용으로부터 당업자들에게 명백해질 것이다.Accordingly, an object of the present invention is to provide an external composition for skin having excellent skin drying prevention effect and excellent skin moisturizing effect by the keratinogenesis promoting effect. The above and other objects of the present invention will become apparent to those skilled in the art from the construction and function of the following invention.
도 1은 본 발명의 조성물에 의한 피부염의 개선효과를 확인하기 위하여, SLS 처치부위에 실시예 4 ~ 6의 크림연고제와 비교예 4 ~ 6의 크림연고제를 도포할 경우와 아무 것도 도포하지 않을 경우의 피부염 유발 후 회복력을 나타내는 그래프이다.1 is a case of applying the cream ointment of Examples 4 to 6 and the cream ointment of Comparative Examples 4 to 6 to the SLS treatment site in order to confirm the improvement effect of the dermatitis by the composition of the present invention This graph shows the recovery after dermatitis.
상기한 목적을 달성하기 위해서, 본 발명에 따른 피부 외용제 조성물은 구조식(I)의 N-헥사노일-파이토스핑고신과 구조식(II)의 네오-세라마이드를 1:9 내지 9:1의 비율로 함유하는 것을 특징으로 한다.In order to achieve the above object, the external preparation composition for skin according to the present invention contains N-hexanoyl-phytosphingosine of formula (I) and neo-ceramide of formula (II) in a ratio of 1: 9 to 9: 1. It features.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에 사용된 N-헥사노일-파이토스핑고신은 하기 구조식 1로 표현되며, 분자량(Molecular Weight)은 415.55이고, N-카프로일-파이토스핑고신(N-Caproyl-phytospingosine), N-카프로일-4D-하이드록시스핑개닌(N-Caproyl-4D-hydroxysphinganine) 또는 (2S, 3S, 4R)-2-카프로일아미도-1,3,4-옥타데칸트리올((2S,3S,4R0-2-Caproylamido-1,3,4-octadecanetriol)이라고도 불린다.N-hexanoyl-phytosphingosine used in the present invention is represented by the following structural formula 1, the molecular weight (Molecular Weight) is 415.55, N-caproyl-phytospingosine (N-Caproyl-phytospingosine), N-caproyl-4D-hydro N-Caproyl-4D-hydroxysphinganine or (2S, 3S, 4R) -2-caproylamido-1,3,4-octadecanetriol ((2S, 3S, 4R0-2-Caproylamido -1,3,4-octadecanetriol).
····(I) (I)
그리고, 본 발명에 사용된 네오-세라마이드는 하기 구조식(II)로 표시되는 것이다.In addition, the neo-ceramide used in the present invention is represented by the following structural formula (II).
본 발명에 따른 외용제 조성물은 상기한 N-헥사노일-파이토스핑고신(I)과 네오-세라마이드(II)를 각각 조성물 총 중량에 대하여 0.0001~40중량, 바람직하게는 0.001~5중량의 양으로 함유하며, 혼합비는 1:9 내지 9:1, 바람직하게는 1:3 내지 3:1이다.The external preparation composition according to the present invention contains the above-mentioned N-hexanoyl-phytosphingosine (I) and neo-ceramide (II) in an amount of 0.0001 to 40 weight, preferably 0.001 to 5 weight, based on the total weight of the composition, respectively. The mixing ratio is 1: 9 to 9: 1, preferably 1: 3 to 3: 1.
본 발명의 피부 건조방지 효과 및 피부보습효과를 갖는 외용제 조성물은 그 제형에 있어서 특별히 한정되는 바가 없으며, 예를 들면, 유연화장수, 영양화장수, 마사지크림, 영양크림, 팩, 젤 또는 점착타입의 제형을 갖는 화장료 조성물일 수 있으며, 또한, 로션, 연고, 겔, 크림, 패취 또는 분무제의 제형을 갖는 의약제제일 수 있다. 또한, 각 제형의 외용제 조성물에 있어서, 상기한 N-헥사노일-파이토스핑고신(I)과 네오-세라마이드(II) 이외의 다른 성분들은 기타 외용제의 제형 또는 사용목적 등에 따라 당업자가 어려움없이 적의 선정하여 배합할 수 있다.The external preparation composition having an anti-drying effect and a skin moisturizing effect of the present invention is not particularly limited in the formulation, for example, softening longevity, nourishing longevity, massage cream, nourishing cream, pack, gel or adhesive type formulation It may be a cosmetic composition having, and may also be a pharmaceutical formulation having a formulation of a lotion, ointment, gel, cream, patch or spray. In addition, in the external composition of each formulation, components other than the above-mentioned N-hexanoyl-phytosphingosine (I) and neo-ceramide (II) are appropriately selected by those skilled in the art without difficulty according to the formulation or purpose of use of other external preparations. can do.
이하, 본 발명의 시험예 및 실시예를 들어 본 발명의 구성 및 작용효과를 보다 구체적으로 설명한다. 그러나, 본 발명이 이들 예로만 한정되는 것은 아니다.Hereinafter, the configuration and effect of the present invention will be described in more detail with reference to Examples and Examples of the present invention. However, the present invention is not limited only to these examples.
<시험예 1> 사람의 각질형성세포의 분화 유도 효과Test Example 1 Induction of Differentiation of Human Keratinocytes
사람의 각질형성세포를 배양용 플라스크에 넣고 약 80정도 자랄 때까지 배양하였다. 하기 표 1의 조성물을 4일간 처리한 후 요소(Urea)나 SDS 같은 변성제(denaturant)와 DTT나 β-메캅토에탄올(β-mecaptoethanol) 같은 환원제를 혼합하여 녹아나는 단백질을 제거한 후 남는 각질층의 펩타이드 농도를 310nm에서 측정하여 그 흡광도값을 비교하였다. 이때 조성물을 처리하지 않은 저농도 칼슘(0.05 mM) 처리군을 대조군으로 하였고, 그 결과를 표 2에 나타내었다.Human keratinocytes were placed in a culture flask and cultured until about 80. After treating the composition of Table 1 for 4 days, a peptide of the stratum corneum remaining after removing the dissolved protein by mixing a denaturant such as urea or SDS and a reducing agent such as DTT or β-mecaptoethanol The concentration was measured at 310 nm and the absorbance values were compared. At this time, the low calcium (0.05 mM) treated group was not treated with the composition as a control group, the results are shown in Table 2.
표 2로부터 각질 분화 유도효과는 주로 N-헥사노일-파이토스핑고신(I)에 의한 것이라는 것을 알 수 있으며, 조성물 B에서와 같이 네오-세라마이드(II)의 혼합에 의해 그 효과가 상승하는 것으로 나타났다.It can be seen from Table 2 that the effect of inducing keratin differentiation is mainly due to N-hexanoyl-phytosphingosine (I), and the effect was increased by mixing neo-ceramide (II) as in composition B.
<시험예 2> 표피세포의 이상과분열 억제효과Experimental Example 2 Inhibitory Effect of Epidermal Cells
각 군당 5마리의 무모생쥐(hairless mouse) 피부에 TPA(포볼12-미리스테이트 13-아세테이트; Phorbol 12-myristate 13-acetate) 10 nmol과 표 1의 조성물 20 mmol을 1회 처리하였고, 3일 경과 후 물질 도포 부위를 생검하여 파라핀에 고정한 후 헤마톡실린-에오신 염색법으로 염색하였다. 이때 현미경 상에서 표피의 두께를 무작위로 20 군데를 측정해 그 평균값을 기준으로 하고 TPA만 단독 처리한 군을 대조군으로 하여 하기의 수학식 1에 의하여 계산하고, 그 결과를 표 3에 나타내었다.Five hairless mouse skins from each group were treated with 10 nmol of TPA (Phorbol 12-myristate 13-acetate) and 20 mmol of the composition of Table 1 once, followed by 3 days. The material application site was then biopsied, fixed in paraffin and stained by hematoxylin-eosin staining. At this time, the thickness of the epidermis was randomly measured 20 places on the microscope, and the average value was calculated, and the TPA alone-treated group was calculated by the following Equation 1, and the results are shown in Table 3 below.
표 3으로부터 이상과분열 억제효과는 N-헥사노일-파이토스핑고신(I)에 의한 것이란 것을 알 수 있으며, 조성물 B에서와 같이 네오-세라마이드(II)의 혼합에 의해 그 효과가 상승하는 것으로 나타났다.It can be seen from Table 3 that the effect of inhibiting abnormal hyperdivision is due to N-hexanoyl-phytosphingosine (I), and the effect was increased by mixing neo-ceramide (II) as in composition B.
<시험예 3> 항염증 효과<Test Example 3> anti-inflammatory effect
쥐의 귀에 TPA를 처리하여 부종을 유발한 후, 15분 경과 후 표 1의 조성물을 귀에 도포하고 6시간 경과 후 시료를 1회 더 도포하였다. 최초 TPA 도포 후 24시간 뒤, 쥐 귀의 일정부분을 펀치로 도려내어 무게를 측정하고, MPO(마이엘로퍼옥시다제; Myeloperoxidase) 축적억제(neutrophil 수 평가) 정도를 평가하였다. 이때 조성물이 함유되지 않은 군을 음성대조군으로, 아스피린을 양성대조군으로 사용하였고, 그 결과를 표 4에 나타내었다.After treatment with TPA to induce edema in the ears of rats, the composition of Table 1 was applied to the ears after 15 minutes and the sample was applied once more after 6 hours. 24 hours after the initial TPA application, a portion of the rat's ear was punched out and weighed, and the degree of MPO (Myeloperoxidase) accumulation inhibition (neutrophil number evaluation) was evaluated. At this time, the group containing no composition was used as a negative control group and aspirin as a positive control group, and the results are shown in Table 4.
표 4로부터 국소 항염증 효과는 주로 N-헥사노일-파이토스핑고신(I)에 의한 것이라는 것을 알 수 있으며, 조성물 B에서와 같이 네오-세라마이드(II)의 혼합에 의해 그 효과가 상승하는 것으로 나타났다.It can be seen from Table 4 that the topical anti-inflammatory effect is mainly due to N-hexanoyl-phytosphingosine (I), which was shown to be enhanced by the mixing of neo-ceramide (II) as in composition B.
<시험예 4> 동물실험을 통한 장벽손상 후 회복력 효과<Test Example 4> resilience effect after barrier damage through animal experiment
무모생쥐에 아세톤을 반복적으로 도포하여 장벽기능을 손상시킨다. 표피수분손실량(TEWL, transepidermal water loss)을 스웨덴 서바메드(servomed)사의 증발계(evaporimeter)인 EP1으로 측정하여 4.0g/m2/h 에 도달하면 하기 표 5의 조성물이 함유된 시료를 5cm2면적에 도포하여 표피수분손실양을 측정하여 감소되는 정도를 평가함으로써 장벽기능이 회복되는 정도를 평가하였다. 각각 1시간, 2시간, 4시간, 8시간 경과 후에 측정하고, 그 결과를 표 6에 나타내었다.Acetone is repeatedly applied to hairless mice to impair barrier function. Epidermal water loss (TEWL, transepidermal water loss) The Swedish seoba Med (servomed)'s jeungbalgye (evaporimeter) is measured by the EP1 4.0g / m 2 / h when to 5cm 2 area of the sample contained the composition shown in Table 5 reaches the The extent to which barrier function was restored was evaluated by measuring the amount of epidermal moisture loss applied to the skin. It measured after 1 hour, 2 hours, 4 hours, and 8 hours, respectively, and shows the result in Table 6.
<실험결과><Experiment Result>
손상된 장벽상태를 100으로 하여 TEWL 변화를 측정하였다. 측정결과 하기 표 6에서와 같이 비교예 1, 2, 3에 비해 실시예 1, 2, 3에서 보다 우수한 회복효과를 보였다. 이러한 장벽기능 회복효과는 주로 네오-세라마이드(II)에 의한 것으로 보이며 실시예에서 N-헥사노일-파이토스핑고신(I)의 혼합에 의해 그 효과가 상승하는 것으로 나타났다.TEWL changes were measured with a damaged barrier state of 100. As a result of the measurement, as shown in Table 6, Comparative Examples 1, 2, and 3 showed better recovery effects in Examples 1, 2, and 3, respectively. This barrier function recovery effect appears to be mainly due to neo-ceramide (II), and the effect was increased by mixing N-hexanoyl-phytosphingosine (I) in the examples.
<시험예 5-1> 인체실험을 통한 피부보습력 증가효과 측정<Test Example 5-1> Measurement of the effect of increasing skin moisturizing power through human testing
상기 표 5에 의해 제조된 화장수에 대하여 피부 보습력 개선 효과를 비교하였다. 피부 보습력 개선 효과는 20 - 30대 200명을 대상으로 4개조로 나누어 측정하였다. 시험 방법은 하기와 같다.The skin moisturizing improvement effect was compared with respect to the lotion prepared by Table 5. The effect of improving skin moisturizing power was divided into four groups of 200 people in their 20s to 30s. The test method is as follows.
각 조에 실시예 1 - 3과 비교예 1 - 3를 주고 매일 2회 1개월간 얼굴 및 전박부 부위에 도포하게 하면서 도포 시작 전 항온·항습조건 (24℃, 습도 40)에서 코니오미터(corneometer; CM820 courage+Khazaka elctronic GmbH, Germany)를 이용하여 피부전도도를 측정하여 기본 값을 삼고, 1주, 2주, 4주 경과 후 및 도포중지 후 2주 경과(6주 경과)후 피부수분양의 변화를 측정하여 객관적인 효과를 평가하게하고 그 결과를 표 7에 나타내었다. 또한 시험대상자에 대한 설문지를 통하여 주관적인 효능 평가를 시행하고, 그 결과를 표 8에 나타내었다.Each group was given Examples 1 to 3 and Comparative Examples 1 to 3 and applied to the face and forearm area twice daily for 1 month, at a constant temperature / humidity condition (24 ° C., 40 humidity) prior to the start of application. CM820 courage + Khazaka elctronic GmbH, Germany) was used to measure skin conductivity and change skin moisture content after 1 week, 2 weeks, 4 weeks, and 2 weeks after application stop (6 weeks). Was measured to evaluate the objective effect and the results are shown in Table 7. In addition, subjective efficacy evaluation was conducted through a questionnaire for the test subjects, and the results are shown in Table 8.
표 7과 같이 피부수분증가에 있어서 네오-세라마이드(II)와 N-헥사노일-파이토스핑고신(I)의 혼합조성에 의해 그 효과가 상승하는 것으로 나타났다.As shown in Table 7, the effect was increased by the mixed composition of neo-ceramide (II) and N-hexanoyl-phytosphingosine (I) in skin moisture increase.
<실험예 5-2> 접촉성 피부염 개선 효과 측정Experimental Example 5-2 Measurement of Contact Dermatitis Improvement Effect
하기 표 9의 실시예 4 ~ 6 및 비교예 4 ~ 6에서 제조된 크림형 의약료에 대하여 계면활성제에 의해 유발된 피부염 개선 효과를 비교하였다.For the cream-type medicines prepared in Examples 4 to 6 and Comparative Examples 4 to 6 of Table 9, the dermatitis improvement effect caused by the surfactant was compared.
피부염 개선 효과는 20-30대 30명을 대상으로 홍반의 개선정도를 측정하였다. 시험 방법은 하기와 같다.The effect of improving dermatitis was measured in 30 patients in their 20s and 30s. The test method is as follows.
팔 전박부 4개소에 3SLS 용액을 24시간 첩포하여 계면활성제에 의한 접촉피부염을 유발하였다. 각 사람에게 실시예 4 ~ 6과 비교예 4 ~ 6를 6개소에 매일 2회 3주간 도포하였고 SLS 처치부위를 음성대조군으로 미처치부위를 양성대조군으로 삼아 평가하였다. 효능평가는 도포시작 1, 2, 3주 후 및 도포중지 1주 후에 하기 기준에 의해 평가하고, 그 결과를 도 1에 나타내었다.A 3SLS solution was applied to 4 arm forearms for 24 hours to induce contact dermatitis by a surfactant. Each person was applied to Examples 4 to 6 and Comparative Examples 4 to 6 twice daily for 3 weeks, and the SLS treatment site was evaluated as a negative control and the untreated site as a positive control. Efficacy evaluation was evaluated by the following criteria 1, 2, 3 weeks after the start of the application and 1 week after the stop application, the results are shown in FIG.
<평가기준><Evaluation Criteria>
도 1에서 알 수 있듯이 SLS에 의한 피부염 유발 후 회복력에 있어서 네오-세라마이드(II)와 N-헥사노일-파이토스핑고신(II)의 함유시 베이스 및 미도포 부위에 비하여 회복이 빨랐으며 특히 실시예의 혼합조성에 의해 그 효과가 상승하는 것으로 나타났다.As can be seen in Figure 1 in the recovery after the dermatitis induced by SLS, the recovery was faster compared to the base and uncoated site when containing neo-ceramide (II) and N-hexanoyl- phytosphingosine (II), especially the composition of the embodiment It was found that the effect is increased.
이상의 실시예 및 시험예에서 볼 수 있는 바와 같이, 본 발명에 의해 제공 되는 피부외용제 조성물은 N-헥사노일-파이토스핑고신(I)과 네오-세라마이드(II)를 복합 사용하는 것에 의해 단독 사용시 보다 각질세포 분화유도 효과, 표피세포 이상과분열 억제효과, 국소항염증 효과, 장벽손상 후 회복력 효과, 인체시험에서의 피부보습력 증가 및 유지효과에 있어 상승효과가 있음을 알 수 있다.As can be seen in the above examples and test examples, the external skin composition provided by the present invention is more keratinocytes when used alone by using a combination of N-hexanoyl-phytosphingosine (I) and neo- ceramide (II) There is a synergistic effect on the differentiation-inducing effect, epidermal aberration and division inhibition effect, local anti-inflammatory effect, resilience effect after barrier damage, increase and maintenance of skin moisturizing effect in human test.
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| KR100429404B1 (en) * | 2001-03-31 | 2004-04-29 | 엔프라니 주식회사 | Cosmetic composition for lowering stimulation of the skin and enhancing moisturization of the skin |
| KR101461625B1 (en) | 2012-07-30 | 2014-11-20 | 동국대학교 산학협력단 | Composition for ameliorating or treating skin barrier damage, or for improving or reinforcing skin barrier function comprising 16-hydroxyhexadecanoic phytosphingosine |
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| KR100919731B1 (en) * | 2006-05-11 | 2009-09-29 | 재단법인서울대학교산학협력재단 | Chitosan microsheres for vaccine delivery containing polyether as stabilizer |
| KR101006693B1 (en) * | 2009-03-26 | 2011-01-11 | (주)지앤지 | Cosmetic compositions improving atopic dermatitis by complex function of damaged skin barrier repairing by lipid exchange and desensitizing, anti-inflammation and its manufacturing method thereof |
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| WO1995011881A1 (en) * | 1993-10-28 | 1995-05-04 | Gist-Brocades N.V. | Phytosphingosine-based ceramide i analogs |
| EP0774249A2 (en) * | 1995-10-27 | 1997-05-21 | Unilever Plc | Topical composition containing specific flavanones |
| US5667770A (en) * | 1996-03-25 | 1997-09-16 | Elizabeth Arden Company, Division Of Conopco, Inc. | Long wearing lipstick |
| US5693677A (en) * | 1994-09-30 | 1997-12-02 | Gist-Brocades N.V. | Ceramide 3 derivatives based on monounsaturated fatty acids |
| KR19980053299A (en) * | 1996-12-26 | 1998-09-25 | 이능희 | Ceramide-like compound and preparation method thereof |
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| WO1995011881A1 (en) * | 1993-10-28 | 1995-05-04 | Gist-Brocades N.V. | Phytosphingosine-based ceramide i analogs |
| US5693677A (en) * | 1994-09-30 | 1997-12-02 | Gist-Brocades N.V. | Ceramide 3 derivatives based on monounsaturated fatty acids |
| EP0774249A2 (en) * | 1995-10-27 | 1997-05-21 | Unilever Plc | Topical composition containing specific flavanones |
| US5667770A (en) * | 1996-03-25 | 1997-09-16 | Elizabeth Arden Company, Division Of Conopco, Inc. | Long wearing lipstick |
| KR19980053299A (en) * | 1996-12-26 | 1998-09-25 | 이능희 | Ceramide-like compound and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100429404B1 (en) * | 2001-03-31 | 2004-04-29 | 엔프라니 주식회사 | Cosmetic composition for lowering stimulation of the skin and enhancing moisturization of the skin |
| KR101461625B1 (en) | 2012-07-30 | 2014-11-20 | 동국대학교 산학협력단 | Composition for ameliorating or treating skin barrier damage, or for improving or reinforcing skin barrier function comprising 16-hydroxyhexadecanoic phytosphingosine |
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