Optimizing Curcumin Purification: Co-Crystallization and Solid-Solid-Liquid Ternary Phase Diagram-Based Approach

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题名:	Optimizing Curcumin Purification: Co-Crystallization and Solid-Solid-Liquid Ternary Phase Diagram-Based Approach
作者:	黃亞萱;Huang, Ya-Hsuan
贡献者:	化學工程與材料工程學系
关键词:	薑黃素;共晶;萃取;純化;相圖;Curcumin;Co-crystal;Extraction;Purification;Phase diagram
日期:	2025-07-21
上传时间:	2025-10-17 11:17:54 (UTC+8)
出版者:	國立中央大學
摘要:	本研究旨在運用第一晶型薑黃素（curcumin, CUR）與α型間苯二酚（resorcinol, RES）之共晶形成行為作為一種薑黃素純化策略，並結合在25°C及1 atm條件下製備的CUR-RES- Ethanol (EtOH)三元相圖，透過精準地控制系統組成於相圖中不同相區之間的轉換，以達到高效率的純化與分離。實驗中於共晶穩定存在區域內製備1:1 CUR:RES共晶，隨後僅藉由改變乙醇的含量將Q值提升(Q=(Mole of EtOH)/(Mole of CUR+Mole of RES))，使系統轉移至薑黃素單獨穩定存在之區域，進而解離共晶結構，達成純化薑黃素之目的。在此共晶系統中，薑黃素作為活性藥物成分（active pharmaceutical ingredient, API），而間苯二酚因具備良好氫鍵作用能力與形成穩定共晶結構的潛力，及能選擇性與CUR形成穩定共晶結構而非其他雜質，故被選為共構物（coformer）。完整的純化流程起始於薑黃（Curcuma longa）粉末，以溶劑萃取法獲得含薑黃素純度約為21.26 ± 0.83 wt%的油樹脂（oleoresin），其產率為5.68 ± 0.4 wt%。接著進行固液平衡，進一步製備粗製薑黃素粉末（crude curcumin powder），其純度提升至約74.74 ± 1.26 wt%，產率為16.14 ± 1.48 wt%的粗薑黃素粉末，該純度為進行後續良好結晶操作之必要條件。依據所建立之 CUR-RES-EtOH 三元相圖中共晶存在區塊，選擇對應之薑黃素莫耳分率及 Q 值進行共晶製備。經第一次共晶形成與解離後，薑黃素純度可提升至89.4 ± 2.94 wt%，產率為50.99 ± 3.13 wt%；經第二次循環後，最終可達到96.06 ± 1.19 wt%的高純度，產率為70.23 ± 3.26 wt%。整個實驗過程中共使用100公克市售薑黃粉與265.22 ± 2.15毫升乙醇，最終獲得 0.26 ± 0.03 公克純化後的薑黃素。本研究成功展示以共晶形成與解離為核心，結合三元相圖之薑黃素純化策略，為共晶導向之純化分離與藥物純化技術提供一可行性實例。;This study aims to develop a purification strategy for Form 1 curcumin (CUR) based on its co-crystal formation behavior with α-form resorcinol (RES), in conjunction with the construction and interpretation of the CUR-RES-Ethanol (EtOH) ternary phase diagram at 25°C and 1 atm. By precisely manipulating the system composition within the phase diagram, the process enables targeted transitions between phase regions to achieve efficient purification. In this study, the 1:1 CUR:RES co-crystal was prepared within the co-crystal region. Subsequently, by adjusting the EtOH content increasing the Q value (Q=(Mole of EtOH)/(Mole of CUR+Mole of RES)) the system was shifted into the curcumin dominant region, thereby disrupting the co-crystal and recovering high-purity curcumin. In this co-crystal system, curcumin serves as the active pharmaceutical ingredient (API), while resorcinol is chosen as a coformer due to its strong hydrogen bonding capability and ability to form stable co-crystal structures selectively with CUR and not other impurities. The complete purification process begins with turmeric (Curcuma longa) powder, from which an oleoresin with approximately 21.26 ± 0.83 wt% curcumin content is obtained through solvent extraction, with a yield of 5.68 ± 0.4 wt%. Solid–liquid equilibrium purification was then performed to yield crude curcumin powder with an increased purity of approximately 74.74 ± 1.26 wt% and a yield of 16.14 ± 1.48 wt%, whose purity level is suitable for further crystallization. According to the ternary phase diagram, co-crystal formation was conducted at a specific curcumin mole fraction and Q value. After the first cycle of co-crystal formation and dissociation, the curcumin purity increased to 89.4 ± 2.94 wt%, with a yield of 50.99 ± 3.13 wt%. Following a second cycle, the final purity had reached 96.06 ± 1.19 wt%, with a yield of 70.23 ± 3.26 wt%. In the entire process, 100 g of purchased turmeric powder and 265.22 ± 2.15 mL of EtOH were used, ultimately yielding 0.26 ± 0.03 g of purified curcumin. This study successfully demonstrates a curcumin purification strategy based on co-crystal formation and dissociation, guided by a ternary phase diagram, providing a feasible protocol of co-crystal purification and pharmaceutical separation.
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