10-Hydroxycaprate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 10-Hydroxycaprate
• 英文别名: 10-hydroxydecanoate
• 化学式: C₁₀H₁₉O₃
• 分子量: 187.259
• InChiKey: YJCJVMMDTBEITC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-Hydroxycaprate 、 nicotinamide adenine dinucleotide 生成 10-oxodecanoate 、 氢(+1)阳离子 、 NADH
  参考文献：
  名称：

  Studies on ω-Oxidation of Fatty Acids in vitro

  摘要：

  ω-羟基脂肪酸：从兔肝丙酮粉中部分纯化了NAD氧化还原酶。该酶对11-羟基十一烷酸、11-羟基癸酸和9-羟基苄酸具有高度底物特异性，对6-羟基己酸没有活性。乙醇也不作为底物。ω-羟基脂肪酸：NAD氧化还原酶需要NAD，而NAD不能替代NAD。ω-氧代脂肪酸是由ω-羟基脂肪酸脱氢形成的。该酶的最佳pH值约为10.5（25°C）。该酶不稳定，被对氯苯甲酸汞完全抑制。

  DOI：

  10.1093/oxfordjournals.jbchem.a127961
• 作为产物：
  描述：

  10-羟基癸酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 生成 10-Hydroxycaprate
  参考文献：
  名称：

  Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations

  摘要：

  The enthalpies of hydrolysis of the monocyclic lactones from gamma-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl esters having the same number of atoms were studied in the same fashion. The enthalpies of reduction of the lactones to the corresponding alpha,omega-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the cases of gamma-butyrolactone and delta-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of gamma-butyrolactone and delta-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.

  DOI：

  10.1021/ja00020a036

文献信息

• Retinoids, ω-hydroxyfatty acids and cytotoxic aldehydes as physiological substrates, and H₂-receptor antagonists as pharmacological inhibitors, of human class IV alcohol dehydrogenase
  作者：Abdellah Allali-Hassani、Josep M Peralba、Sı́lvia Martras、Jaume Farrés、Xavier Parés

  DOI：10.1016/s0014-5793(98)00374-3

  日期：1998.4.24

  Kinetic constants of human class IV alcohol dehydrogenase (σσ‐ADH) support a role of the enzyme in retinoid metabolism, fatty acid ω‐oxidation, and elimination of cytotoxic aldehydes produced by lipid peroxidation. Class IV is the human ADH form most efficient in the reduction of 4‐hydroxynonenal (k cat/K m: 39 500 mM−1 min−1). Class IV shows high activity with all‐trans‐retinol and 9‐cis‐retinol,

  人类 IV 类酒精脱氢酶 (σσ-ADH) 的动力学常数支持该酶在类视黄醇代谢、脂肪酸 ω-氧化和消除脂质过氧化产生的细胞毒性醛中的作用。IV 类是还原 4-羟基壬烯醛最有效的人类 ADH 形式（k cat/K m：39 500 mM-1 min-1）。IV类对全反式-视黄醇和9-顺-视黄醇显示出高活性，而13-顺-视黄醇不是底物而是抑制剂。全反式视黄酸和 13-顺式视黄酸都是视黄醇氧化的有效竞争性抑制剂 (K i: 3–10 μM)，可作为调节视黄酸生成和 13 -顺式异构体。乙醇对 IV 类视黄醇氧化的抑制 (K i: 6-10 mM) 可能是乙醇毒性和致畸作用的起源。
• Omega hydroxy fatty acid dehydrogenase
  作者：M.A. Mitz、R.L. Heinrikson

  DOI：10.1016/0006-3002(61)90644-8

  日期：1961.1