[(2S)-2-[(2R)-4,5-二羟基-3-氧代呋喃-2-基]-2-羟基乙基](Z)-十八碳-9-烯酸酯 | 2495-84-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: [(2S)-2-[(2R)-4,5-二羟基-3-氧代呋喃-2-基]-2-羟基乙基](Z)-十八碳-9-烯酸酯
• 英文名称: 6-ascorbyl oleate
• 英文别名: 6-O-oleoyl L-ascorbate；ascorbyl oleate；6-O-ascorbyl oleate；[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] (Z)-octadec-9-enoate
• CAS: 2495-84-3
• 化学式: C₂₄H₄₀O₇
• 分子量: 440.577
• InChiKey: JPBAVLUULZJFFO-JENHRLMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三棕榈酸甘油酯 、 维生素 C 在 Lipozyme TL IM 作用下， 以 2-甲基-2-丁醇 为溶剂， 以50%的产率得到[(2S)-2-[(2R)-4,5-二羟基-3-氧代呋喃-2-基]-2-羟基乙基](Z)-十八碳-9-烯酸酯
  参考文献：
  名称：

  甘油三酸酯为酰基供体的Lipozyme TL IM催化合成抗坏血酸酯

  摘要：

  AbstractEsters of l‐ascorbic acid with long‐chain fatty acids (E‐304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida antarctica as biocatalyst and free fatty acids or activated esters as acyl donors. In order to diminish the cost of the process, we have investigated the synthesis of ascorbyl oleate and ascorbyl palmitate esters with the immobilized Thermomyces lanuginosus lipase Lipozyme TL IM—which is significantly less expensive than Novozym 435—and triglycerides as source of fatty acids. Lipozyme TL IM gave rise to a lower yield of 6‐O‐ascorbyl oleate than Novozym 435 when using triolein (64 vs. 84%) and olive oil (27 vs. 33%) as acyl donors. Both 6‐O‐ascorbyl oleate and 6‐O‐ascorbyl palmitate displayed excellent surfactant and antioxidant properties. The Trolox Equivalent Antioxidant Capability values for the oleate and palmitate were 71 and 84%, respectively, of those obtained with l‐ascorbic acid; however, both derivatives were able to stabilize soybean oil towards peroxide formation.

  DOI：

  10.1007/s11746-010-1643-5

文献信息

• Enzymatic synthesis and anti-oxidative activities of plant oil-based ascorbyl esters in 2-methyltetrahydrofuran-containing mixtures
  作者：Ying-Dan Hu、Min-Hua Zong、Ning Li

  DOI：10.1080/10242422.2016.1247820

  日期：2016.7.3

  Abstract Ascorbyl fatty acid esters are commercially interesting fat-soluble antioxidants. In this work, enzymatic synthesis of ascorbyl esters from less expensive and readily available plant oils, and their anti-oxidative activities are described. Among the immobilized lipases tested, Candida antarctica lipase B was the best for the synthesis of plant oil-based ascorbyl esters. The enzyme showed much

  摘要 抗坏血酸脂肪酸酯是具有商业价值的脂溶性抗氧化剂。在这项工作中，描述了从较便宜且容易获得的植物油中酶促合成抗坏血酸酯及其抗氧化活性。在测试的固定化脂肪酶中，南极假丝酵母脂肪酶 B 是合成植物油基抗坏血酸酯的最佳选择。该酶在基于生物质的 2-甲基四氢呋喃 (MeTHF) 和叔丁醇的二元混合物中表现出比以前优选的叔丁醇更好的催化性能。在最佳反应条件下，24 小时后转化率为 70-73%，主要产物为不饱和脂肪酸酯（油酸酯和亚油酸酯，80-90%）。固定化脂肪酶在含 MeTHF 系统中重复使用 6 批后，相对活性仍保持 80%。
• Continuous production of acyl l-ascorbates using a packed-bed reactor with immobilized lipase
  作者：Ko Kuwabara、Yoshiyuki Watanabe、Shuji Adachi、Kazuhiro Nakanishi、Ryuichi Matsuno

  DOI：10.1007/s11746-003-0791-0

  日期：2003.9

  AbstractSaturated acyl (6‐O‐caproyl, lauroyl, and myristoyl) and unsaturated acyl (6‐O‐oleoyl, linoleoyl, and arachidonoyl) l‐ascorbates were continuously synthesized at 50°C using a system where a column packed with ascorbic acid powder and a packed‐bed reactor with an immobilized lipase from Candida antarctica were connected in series. A productivity of 1.6–1.9 kg/L reactor·d was achieved for at least 11 d. The surface tension of the caproyl or lauroyl l‐ascorbate in aqueous solution was measured at various temperatures and pH to estimate the critical micelle concentration (CMC) of the acyl l‐ascorbate. The CMC values were independent of temperature but dependent on the pH. The value of the caproyl ascorbate increased with an increase in pH.
• Antioxidative properties and enzymatic synthesis of ascorbyl FA esters
  作者：Fredrik Viklund、Jari Alander、Karl Hult

  DOI：10.1007/s11746-003-0774-1

  日期：2003.8

  AbstractEfficient synthesis of unsaturated FA esters of ascorbic acid is possible with only a small excess of one of the reactants in t‐amyl alcohol using Candida antarctica lipase as biocatalyst. Using free acids, we obtained yields that were comparable to yields reached using vinyl‐activated acyl donors (71, 80, and 86% yields of esters with FA excesses of 1∶1, 1∶1.5, and 1∶2, respectively). As very low water activity is needed to achieve sufficiently high yields of product, molecular sieves were used to improve the ascorbyl ester yields. Ascorbyl oleate is more amorphous and has a much lower m.p. and lower enthalpy of fusion than ascorbyl palmitate. This leads to a higher solubility of ascorbyl oleate in oil, resulting in an increased antioxidant effect compared to that of the palmitate. In an accelerated storage test using deodorized rapeseed oil, samples incubated with ascorbyl palmitate showed noticeable oxidation after 1 wk of storage, whereas samples incubated with ascorbyl oleate displayed negligible oxidation for 9 and 4 wk at 30 and 40°C, respectively.
• CONVENIENTLY INJECTABLE OR IMPLANTABLE SUSTAINED-RELEASE ANTIOXIDANT FORMULATIONS FOR THERAPIES OF OCULAR MALADIES OR CANCER
  申请人：Ramscor, Inc.

  公开号：EP2717866A2

  公开（公告）日：2014-04-16
• ANTIOXIDANT-RELEASING VITREOUS SUBSTITUTES AND USES THEREOF
  申请人：Ohio State Innovation Foundation

  公开号：EP3920986A1

  公开（公告）日：2021-12-15