β-sitosteryl linolenate | 3177-92-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: β-sitosteryl linolenate
• 英文别名: sitosterol linolenate；18:3 Sitosteryl ester；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 3177-92-2
• 化学式: C₄₇H₇₈O₂
• 分子量: 675.135
• InChiKey: VQUUVZGVBPYGJU-RSWKHDOOSA-N

物化性质

• 熔点：
  36 °C
• 沸点：
  695.8±44.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  存在于烟叶和烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  49
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Γ-十八碳三烯酸 、 豆甾醇 反应 166.67h， 以91%的产率得到β-sitosteryl linolenate
  参考文献：
  名称：

  METHOD OF PROCESSING TALL OIL

  摘要：

  在制浆过程中生成的木油的处理方法。该方法中，在木油分离阶段的早期向木油中添加约占木油数量（重量）0.5-5.0%的低分子量羧酸，以便通过所述酸酯化木油中存在的醇基。根据本发明的保护酯化可以防止木油中天然存在的脂肪酸对醇基的酯化。

  公开号：

  US20100152478A1

文献信息

• Highly efficient synthesis of phytosterol linolenate in the presence of Bronsted acidic ionic liquid
  作者：Wen-Sen He、Ling-Ling Li、Qiu-Jin Huang、Ji Yin、Xue-Chen Cao

  DOI：10.1016/j.foodchem.2018.04.107

  日期：2018.10

  melting point and a poor oil solubility, thereby limiting their practical application in foods. The present study was to establish a green and highly efficient method to synthesize phytosterol linolenate for the first time by employing Bronsted acidic ionic liquid (IL) as a catalyst in order to improve its oil solubility. The product was separated, analyzed and subsequently characterized using thin layer

  植物甾醇可有效降低血浆胆固醇。然而，游离形式的植物甾醇具有一些缺点，因为它们具有高熔点和差的油溶性，从而限制了它们在食品中的实际应用。本研究旨在建立一种绿色高效的方法，首次采用布朗斯台德酸性离子液体（IL）作为催化剂来合成植物甾醇亚油酸酯，以提高其油溶性。分离，分析并随后使用薄层色谱，傅立叶变换红外光谱和质谱对产物进行表征。在以下最佳条件下，植物甾醇的转化率可在极短的时间内（30分钟）达到96％以上：3％的1-丁基磺酸盐-3-甲基咪唑鎓三氟甲磺酸盐（[BSO3HMim] OTf），植物固醇与亚油酸乙酯的比例为110°C和1：1.75M。本方法证明[BSO3HMim] OTf将是植物甾醇酯合成的潜在催化剂。最重要的是植物甾醇亚油酸酯的油溶解度比其相应的游离植物甾醇大得多。
• Ultrasonic pretreatment for lipase-catalyed synthesis of phytosterol esters with different acyl donors
  作者：Ming-Ming Zheng、Lian Wang、Feng-Hong Huang、Ling Dong、Ping-Mei Guo、Qian-Chun Deng、Wen-Lin Li、Chang Zheng

  DOI：10.1016/j.ultsonch.2012.02.004

  日期：2012.9

  This study is focused on the enzymatic esterification of phytosterols with different acyl donors to produce the corresponding phytosterol esters catalyzed by Canadia sp. 99-125 lipase under ultrasound irradiation. An ultrasonic frequency of 35 kHz, power of 200 W and time of 1 h was determined to guarantee satisfactory degree of esterification and lipase activity. The influence of temperature, substrates concentration and molar ratio was investigated subsequently. The optimum production was achieved in isooctane system at 60 degrees C with phytosterol concentration of 150 mu mol/mL and phytosterol to fatty acid molar ratio of 1:1.5, resulting in a phytosterol esters conversion of above 85.7% in short reaction time (8 h). Phytosterols esters could also be converted in high yields to the corresponding long-chain acyl esters via transesterification with triacylglycerols (above 90.3%) under ultrasound irradiation. In optimum conditions, the overall esterification reaction rate using the ultrasonic pretreatment process was above 2-fold than that of mechanical stirring process without damage the lipase activity. (C) 2012 Elsevier B.V. All rights reserved.