公开(公告)号：KR100437102B1

公开(公告)日：2004-06-23

申请号：KR1020020001178

申请日：2002-01-09

Applicant: (주)케비젠

Inventor： 신홍식 ,  박시호 ,  노영쇠 ,  엄수종 ,  권윤자 ,  박명순 ,  한혜숙 ,  정민숙 ,  김소미 ,  김동명 ,  오덕근 ,  박종섭

IPC: C07K5/00

Abstract: PURPOSE: Provided are a novel retinol derivative, its preparation method in higher yield, and its use. The novel retinol has excellent light-stability, and shows high reactivity to retinoic acid receptor α, while showing low reactivity to retinoic receptor β and γ. It can applied to medical products, cosmetics, soap, shampoo, functional foods, etc., for the prevention and improvement of skin aging. CONSTITUTION: The novel retinol derivative is characterized by carboester bond of a peptide material having COOH group, wherein the peptide material having COOH group is selected from -di, -tri, -poly peptide including N-L- α-aspartyl-L-phenylalanine 1-methylester(AMP;aspartame), N-protection group-aspartame, neotame and the like. Its manufacturing method comprises the steps of: reacting retinylacetate with methanolic solvent and inorganic slat at 25-40 deg.C in a dark room then extracting the reaction product with ether solvent; removing the solvent then followed by mixing a compound having OH group, natural or separated and purified retinol, diethylazodicarboxylate and triphenylphosphate with methylenechloride solvent, and reacting them at room temperature to obtain the ester derivative of retinol; and performing chromatography with reverse-phase, Merck Silicagel 60 RP 18(40-63) micro meter to separate pure ester derivative of retinol.

Abstract translation: 目的：提供一种新颖的视黄醇衍生物及其制备方法，其收率较高，并且其用途。 该新型视黄醇具有优异的光稳定性，并且对视黄酸受体α具有高反应性，而对视黄酸受体β具有低反应性; 和＆amp; gamma ;. 它可以应用于医疗产品，化妆品，肥皂，洗发水，功能性食品等，以预防和改善皮肤老化。 构成：新颖的视黄醇衍生物的特征在于具有COOH基团的肽材料的羧基酯键，其中具有COOH基团的肽材料选自包括NL-和α-天冬氨酰-L- 苯丙氨酸1-甲酯（AMP;天冬甜素），N-保护基 - 阿斯巴甜，纽甜等。 其制造方法包括以下步骤：在25-40℃，在黑暗的房间内将乙酸视黄醇酯与甲醇溶剂和无机薄片反应，然后用乙醚溶剂萃取反应产物; 然后除去溶剂，然后将具有OH基团的化合物，天然或分离纯化的视黄醇，偶氮二羧酸二乙酯和磷酸三苯酯与二氯甲烷溶剂混合，并在室温下反应，得到视黄醇的酯衍生物; 并用反相色谱（Merck Silicagel 60 RP 18（40-63）微米）进行色谱分离以分离视黄醇的纯酯衍生物。

公开(公告)号：KR1020020060598A

公开(公告)日：2002-07-18

申请号：KR1020020001178

申请日：2002-01-09

Applicant: (주)케비젠

Inventor： 신홍식 ,  박시호 ,  노영쇠 ,  엄수종 ,  권윤자 ,  박명순 ,  한혜숙 ,  정민숙 ,  김소미 ,  김동명 ,  오덕근 ,  박종섭

IPC: C07K5/00

CPC classification number: C07C403/08 ,  A23L33/155 ,  A61K8/671 ,  A61K31/07 ,  A61Q5/02 ,  A61Q19/005 ,  A61Q19/008 ,  A61Q19/10 ,  C07K5/04 ,  C07K19/00

Abstract: PURPOSE: Provided are a novel retinol derivative, its preparation method in higher yield, and its use. The novel retinol has excellent light-stability, and shows high reactivity to retinoic acid receptor α, while showing low reactivity to retinoic receptor β and γ. It can applied to medical products, cosmetics, soap, shampoo, functional foods, etc., for the prevention and improvement of skin aging. CONSTITUTION: The novel retinol derivative is characterized by carboester bond of a peptide material having COOH group, wherein the peptide material having COOH group is selected from -di, -tri, -poly peptide including N-L- α-aspartyl-L-phenylalanine 1-methylester(AMP;aspartame), N-protection group-aspartame, neotame and the like. Its manufacturing method comprises the steps of: reacting retinylacetate with methanolic solvent and inorganic slat at 25-40 deg.C in a dark room then extracting the reaction product with ether solvent; removing the solvent then followed by mixing a compound having OH group, natural or separated and purified retinol, diethylazodicarboxylate and triphenylphosphate with methylenechloride solvent, and reacting them at room temperature to obtain the ester derivative of retinol; and performing chromatography with reverse-phase, Merck Silicagel 60 RP 18(40-63) micro meter to separate pure ester derivative of retinol.

Abstract translation: 目的：提供一种新型视黄醇衍生物，其制备方法较高产率及其用途。 该新型视黄醇具有优异的光稳定性，对视黄酸受体α具有高反应性，而对视黄酸受体β和γ的反应性低。 适用于医疗用品，化妆品，肥皂，洗发水，功能性食品等，用于预防和改善皮肤老化。 构成：新型视黄醇衍生物的特征在于具有COOH基团的肽材料的碳键，其中具有COOH基团的肽材料选自-di，-tri， - 多肽，包括NL-α-天冬氨酰-L-苯丙氨酸1- 甲基酯（AMP;阿斯巴甜），N-保护基 - 阿斯巴甜，neotame等。 其制造方法包括以下步骤：将黑醋酸乙烯酯与甲醇溶剂和无机条板在25-40℃下在暗室中反应，然后用乙醚溶剂萃取反应产物; 除去溶剂，然后将具有OH基团的化合物，天然或分离的纯化的视黄醇，偶氮二甲酸二乙酯和磷酸三苯酯与二氯甲烷溶剂混合，并在室温下使其反应，得到视黄醇的酯衍生物; 并用反相色谱法，Merck Silicagel 60 RP 18（40-63）微米分离纯化的视黄醇酯衍生物。