近年來對利用大豆除臭油 (SODD) 之興趣主要是由於其所含具經濟價值的生物活性化合物，如 鯊烯、FASEs、生育酚及游離植物固醇。現行商業化分離這些生物活性物質之製程仍有許多改善之空間。Gunawan (2008)利用創新及改良之分離方法，如修正索式提取法 (MSE) 及修正矽膠管柱層析法 (MSC) 成功地從SODD中分離出 角鯊烯和FASEs。經由一簡單的兩步驟法，本研究可得到高 回收率和高總含量的生育酚和游離植物固醇。首先， 經由MSE操作將SODD成兩部分：含有鯊烯 (100％之回收率) 和FASEs (約90％之回收率)之非極性脂質 (NPLF)和含有生育酚 (> 90％之回收率) 和游離植物固醇 (> 95％之回收率)之極性脂質 (PLF)。經低溫皂化可將生育酚和游離植物固醇最後隔離在不可皂化部分中。生育酚和游離植物固醇之總含量約95 wt％，其總回收率為 95％以上。使用不可皂化部分為起始原料，本研究探討如何分離生育酚和游離植物固醇。本研究採用溶劑結晶法以分離生育酚和游離植物固醇。最終產物包括兩部分：其一為含微量生育酚的游離植物固醇細微晶體；另一為粘稠黃色 液體，含有高純度的生育酚及少量的游離植物固醇。利用氣相色譜、質譜和薄層色譜法 本研究分析並鑑定不可皂化部分中所含之其他成份。
另一方面，在分離鯊烯及FASEs時得到未鑑定/未知之碳氫化合物(約為NPLF之30 wt%)。本研究也分離並鑑定大部分這些未知碳氫化合物。根據極性之差異，這些未知碳氫化合物可區分成脂肪族碳氫化合物、類固醇碳氫化合物及sesquiterpene碳氫化合物。類固醇碳氫化合物之分離係透過MSE、MSC及真空蒸餾達成，而鑑定及定量則是利用GC、GC–MS及TLC。經由鑑定油中所含之類固醇碳氫化合物，可追溯其形成之根源；此為一偵測油品掺假之有效方法。脂肪族碳氫化合物之分離係透過MSE、MSC及傳統矽膠管柱層析達成，而鑑定及定量則是利用FT-IR、GC、GC–MS及TLC。在以GC及GC–MS分析脂肪族碳氫化合物時會遭遇出現波峰無法區分之複雜脂肪族碳氫化合物，此或許可經由鹵化某些脂肪族碳氫化合物標準品並與脂肪族碳氫化合物之結果比較而得到解決。

Recent interest in the exploitation of soybean oil deodorizer distillate (SODD) is due to its content of economically-valuable bioactive compounds, such as squalene, FASEs, tocopherols, and free phytosterols. There is still room for improvement in the commercial isolation of these bioactive compounds. Gunawan (2008) succeeded in isolating respective squalene and FASEs from SODD via newly innovated methods such as modified soxhlet extraction (MSE) and modified silica gel column chromatography (MSC). The isolation of both tocopherols and free phytosterols in high recovery and high total content via a simple two-step method was carried out in this study. Firstly, SODD was subjected to a MSE to separate the non polar lipid fraction (NPLF) containing squalene (100% recovery) and FASEs (ca. 90% recovery) from the polar lipid fraction (PLF) containing tocopherols (> 90% recovery) and free phytosterols (> 95% recovery). Both tocopherols and free phytosterols were finally isolated in the unsaponifiable fraction via cold saponification of the PLF. The total content of both tocopherols and free phytosterols was about 95 wt% with a corresponding total recovery of about 95%. Using unsaponifiable matters as the starting material, the investigation of the separation between tocopherols and free phytosterols was carried out in this study. Solvent crystallization was employed for the separation of tocopherols and free physterols. The final product consists of two parts. The first one is a fine crystal of free phytosterols (purity ca. 90 wt%) with trace amount of tocopherols and the second part is a viscous yellow liquid containing high purity tocopherols (ca. 85 wt%) with small amount of free phytosterols. Identification of other compounds in the unsaponifiable matters was investigated via GC, GC–MS, and TLC analyses.
On the other hand, unidentified/unknown hydrocarbons (ca. 30 wt% of NPLF) were found in the isolation of squalene and FASEs. The majority of those unknown hydrocarbons (HCs) were isolated and identified in this study. Based on their polarity difference, unknown HCs can be classified as aliphatic, steroidal, and sesquiterpene HCs. The isolation of steroidal HCs was achieved via MSE, MSC, and vacuum distillation; meanwhile its identification and quantification was accomplished by using GC, GC–MS, and TLC analyses. From the identification of steroidal HCs, the origin of their formation can be traced back and this is a useful tool to detect adulteration of oils. Isolation of aliphatic HCs was attained by using MSE, MSC, and conventional silica gel column chromatography; while its identification was accomplished via FT-IR, GC, GC–MS, and TLC analyses. Difficulty in the appearance of unresolved complex mixture of aliphatic HCs in GC and GC–MS was encountered and this might be solved by carrying out halogenation of some standards of aliphatic HCs and comparing the results with those of aliphatic HCs.

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