Journal of the Society of Cosmetic Scientists of Korea (대한화장품학회지)

Society of Cosmetic Scientists of Korea (대한화장품학회)
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Preparation and Properties of Phytosphingosine Ascorbate with Retaining Skin Development Effects

피부 활성을 갖는 Phytosphingosine Ascorbate의 합성

  • Published : 2004.09.01
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Abstract

In the human skin, vitamin C (L -ascorbic acid) that is well known as the activated materials has effects that is skin anti-aging and wrinkle repair by giving impetus to collagen biosynthesis and anti-oxidation, and that is the sun screen, a wound recovering, inhibition melanogenesis and so on. In spite of its effects, vitamin C has the defects of the skin stimulation and easily oxidized instability by water, air, heat and light. For solving their matters, many investigation is advanced and its results are synthesized the various vitamin C derivatives. And yet they have not solved the unstable property of vitamin C and were still insufficient for the comparing with the effect of the pure vitamin C itself. In this study, in order to prepare vitamin C derivative of being improved the stability and to apply vitamin C effect in the skin, we prepared new vitamin C derivative, phytosphingosine ascorbate, by using phytosphingosine, one of sphingolipids, which have a distinguished skin affinity. Phytosphingosine ascorbate can be prepared as the ionic bond between amine group (-NH$_2$) of phytosphingosine and hydroxy group (-OH) of vitamin C by way of the relatively simple reaction. So the structure and properties of the synthesized phytosphingosine ascorbate was confirmed the use of elemental analysis (C 58.3 : H 9.3 : N 2.8 : O 29.5), MALDI TOF-MS (Mw=492.58), Ultraviolet spectra (268.5nm), lH NMR, FT-IR spectra, thermal analysis (m.p=l54$^{\circ}C$), HPLC and so on. And we could confirm the anti-bacterial and anti-oxidation effects. Based on these results, we could confirm to prepare a new material that was expected of both effects of vitamin C and phytosphingosine and that is improved properties of vitamin C.

피부 활성 물질로 넓이 알려져 있는 vitamin C (L-Ascorbic acid)는 콜라겐 생합성 촉진과 강한 항산화 작용으로 피부 항노화 및 주름 개선 효과 있을 뿐만 아니라 멜라닌 세포 활성 억제, 자외선 차단, 상처치유 등의 효능을 갖고 있다. 그러나 물성 면에서 피부 자극과 수분 및 공기, 빛에 불안정하여 쉽게 산화된다는 단점을 갖고 있다 이러한 문제점을 해결하기 위해 많은 연구가 진행되어 왔고, 그 결과 다양한 vitamin C 유도체가 개발되었다. 그러나 아직까지도 vitamin C의 불안정한 물성을 해결하면서 그 자체의 효능을 피부에 적용시키기에는 미흡한 점이 많다는 평을 받고 있다. 본 연구에서는 이러한 vitamin C의 불안정한 물성을 개선시키고 그 효능을 피부에 적용시킬 수 있는 vitamin C 유도체를 개발하기 위해, 피부 친화성이 우수한 스핑고지질류 중 하나인 phytosphingosine을 이용하여 산염기 반응에 의한 vitamin C의 OH기와 phytosphingosine의 -NH$_2$이온 결합시킨 새로운 vitamin C 유도체인 phytosphingosine ascorbate (SP-VC)를 합성하였다. 이렇게 합성된 phytosphingosine ascorbate (SP-VE)는 원소 분석(C58.3 : H9.3 : N2.8 : 029.5) 및 mass spectrosocopy (Maldi TOF-MS), UV/vis spectra (268.5nm), $^1$H NMR, FT-IR, 열분석 (m.p=154$^{\circ}C$), HPLC 등을 통하여 구조 및 물성을 확인하였다 또한 효능면에서는 우선적으로 phytosphingosine ascorbate(SP-VC)의 항균 및 항산화 효과를 확인하였다. 이러한 결과를 토대로 vitamin C와 phytosphingosine의 효능을 동시에 갖으며 불안정한 물성과 자극을 개선시킬 것이라 예상되는 새로운 소재를 합성하였다.

Keywords

References

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