6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde | 113348-75-7

• 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: 6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde
• 英文别名: 5-formyl-α-tocopherol；5-formyl-γ-tocopherol；5-formyl-7,8-dimethyltocol；tocopeduncunal；(2R)-6-hydroxy-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromene-5-carbaldehyde
• CAS: 113348-75-7
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: PLMNVVZQVNZDDC-IEOSBIPESA-N

物化性质

• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以75%的产率得到天然维生素E
  参考文献：
  名称：

  Witkowski; Poplawski, Polish Journal of Chemistry, 1996, vol. 70, # 11, p. 1448 - 1452

  摘要：

  DOI：
• 作为产物：
  描述：

  天然维生素E 在 1,4-dioxane dibromide 作用下， 以 乙醚 为溶剂， 反应 48.05h， 生成 6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde
  参考文献：
  名称：

  Witkowski; Poplawski, Polish Journal of Chemistry, 1996, vol. 70, # 11, p. 1448 - 1452

  摘要：

  DOI：

文献信息

• Copper(II)-Catalyzed Oxidation of d-.ALPHA.-Tocopherol by Oxygen in Aqueous Solution.
  作者：Yoshiko NAGATA、Chie MIYAMOTO、Yoshikazu MATSUSHIMA、Shigenobu MATSUMOTO

  DOI：10.1248/cpb.48.71

  日期：——

  solutions using 13 solubilizing agents and the products of oxidation by oxygen in the presence and the absence of Cu(II) were analyzed by HPLC. In the presence of Cu(II), the oxidation was accelerated and 5-formyl-7,8-dimethyltocol and alpha-tocoquinone were the major oxidation products. Their yields greatly increased in the presence of Cu(II). The yields and the rates of formation of the products were

  使用13种增溶剂将α-生育酚（α-Toc）溶解在水溶液中，并通过HPLC分析在存在和不存在Cu（II）的情况下氧的氧化产物。在Cu（II）的存在下，氧化被加速，并且5-甲酰基-7,8-二甲基生育酚和α-生育酚是主要的氧化产物。在Cu（II）的存在下，它们的产率大大提高。产物的产率和形成速率取决于增溶剂的性质和其他条件以及Cu（II）或其他金属离子的存在。建议增溶剂结构的轻微变化会影响反应过程。
• Identification of α-Tocopherol and Its Oxidation Products by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry
  作者：Chuanhui Tang、Guanjun Tao、Yue Wang、Yuanfa Liu、Jinwei Li

  DOI：10.1021/acs.jafc.9b06544

  日期：2020.1.15

  This study aimed to determine α-tocopherol (α-T) and its thermal oxidation products simultaneously. A novel method based on an ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) was developed. This approach was achieved by means of a BEH C18 analytical column under gradient elution conditions with eluents of acetonitrile/isopropanol (1:9

  本研究旨在同时测定α-生育酚（α-T）及其热氧化产物。开发了一种基于超高效液相色谱结合四极杆飞行时间质谱（UPLC-Q-TOF-MS）的新方法。通过BEH C18分析柱在梯度洗脱条件下使用乙腈/异丙醇（1：9，v / v）和乙腈/水（4：6，v / v）的洗脱液实现该方法。通过从Q-TOF-MS检测器获得的确切分子量和碎片离子来阐明化合物。鉴定了两种氧化产物，即α-生育酚醌和5-甲酰基-γ-生育酚，并确定了一种新的化合物。这种方法提供了一种简单，精确和可靠的方法来确定α-T的氧化产物，
• Synthesis and antioxidant properties of novel α-tocopherol glycoconjugates
  作者：Anil K. Singh、K. Gopu

  DOI：10.1016/j.tetlet.2009.12.078

  日期：2010.2

  Glycoconjugates of alpha-tocopherol (1), synthesized using click chemistry between alpha-tocopherol-azide and glyco-alkynes are solids, have enhanced water solubility and exhibit radical-scavenging activities comparable to 1, as determined by DPPH and lipid peroxidation assay methods. (C) 2009 Elsevier Ltd. All rights reserved.
• Photolysis of α-Tocopherol in Olive Oils and Model Systems
  作者：Filippo M. Pirisi、Alberto Angioni、Giovanni Bandino、Paolo Cabras、Claude Guillou、Elisabetta Maccioni、Fabiano Reniero

  DOI：10.1021/jf980239n

  日期：1998.11.1

  The photolysis of a-tocopherol (I) in olive oil (O) acid in some model systems (n-hexane = H; anhydrous n-hexane = KA, and triolein = T) was studied under sunlight and under artificial light (lambda > 290 nm) by HPLC and GC/MS. In O and T, I disappeared linearly to 50% of the starting concentration, reached a constant value, and finally disappeared rapidly from the medium. In the model system, photolysis followed a pseudo-first-order kinetics. Although no peaks attributable to photoproducts were found in O, a main product identified by H-1 and C-13 NMR and GC/MS as 5-formyltocopherol (II) was found in the model systems. Irradiation of compound II led to species undetectable by HPLC in agreement with a slower consecutive kinetic process than that of I. In the HA and T systems, the formation of II occurred at lower levels than in H. The possible behavior of photodegradation is discussed.
• Development of Novel Antioxidants:  Design, Synthesis, and Reactivity
  作者：Helmi H. Hussain、Gordana Babic、Tony Durst、James S. Wright、Mihaela Flueraru、Alexandru Chichirau、Leonid L. Chepelev

  DOI：10.1021/jo0301090

  日期：2003.9.1

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.