ε-hydroxycaproate | 15216-15-6

• 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: ε-hydroxycaproate
• 英文别名: 6-hydroxyhexanoate；6-hydroxycaproate；e-hydroxycaproate；hydroxyhexaneate；hydroxyhexanoate；hydroxycaproate
• CAS: 15216-15-6
• 化学式: C₆H₁₁O₃
• 分子量: 131.152
• InChiKey: IWHLYPDWHHPVAA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ε-hydroxycaproate 、 NADP⁺ 生成 adipate semialdehyde 、 氢(+1)阳离子 、 NADPH(4-)
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  6-羟基己酸 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.42h， 生成 ε-hydroxycaproate
  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

• The Metabolism of Cyclohexanol by Acinetobacter NCIB 9871
  作者：Nuala A. DONOGHUE、Peter W. TRUDGILL

  DOI：10.1111/j.1432-1033.1975.tb20968.x

  日期：1975.12

  Acinetobacter NCIB 9871 was isolated by elective culture on cyclohexanol and grows with this compound as sole source of carbon. It displays a restricted growth spectrum, being unable to grow on a wide range of alternative alicyclic alcohols and ketones. Cyclohexanol‐grown cells oxidize the growth substrate at a rate of 230 μl of O2/h per mg dry wt with the consumption of 5.65 μmot of O2/μmol substrate. Cyclohexanone is oxidized at a similar rate with the consumption of 4.85 μmol of O2/μmol. 1 ‐Oxa‐2‐oxocycloheptane and 6‐hydroxyhexanoate are both oxidized at the same slow rate of 44 μl of O2/h per mg dry wt and adipate is not oxidized.Studies with cell extracts reveal the presence of inducible dehydrogenases for cyclohexanol, 6‐hydroxyhexanoate and 6‐oxohexanoate and a monooxygenase, that in conjunction with a lactonase converts cyclohexanone to 6‐hydroxyhexanoate. The monooxygenase is therefore presumed to be of the lactone‐forming type and the pathway for conversion of cyclohexanol to adipate; cyclohexanol → cyclohexanone → 1‐oxa‐2‐oxocycloheptane → 6‐hydroxyhexanoate → 6‐oxohexanoate → adipate; for which key intermediates have been identified chromatographically, is identical with the route for the oxidation of cyclohexanol by Nocardia globerula CL1.

  Acinetobacter NCIB 9871 通过选择性培养基在环己醇上分离出来，并且仅以该化合物为唯一的碳源来源生长。其生长谱系有限，无法在各种替代的环烷醇和酮类上生长。以环己醇为生长底物的细胞，其底物的氧化速率为每毫克干重每小时 230 μl 的 O2，同时消耗 5.65 μmol 的 O2/μmol 底物。环己酮的氧化速率相似，但每个 μmol 消耗 4.85 μmol 的 O2。1-oxa-2-oxocycloheptane 和 6-羟基己酸的氧化速率相同，均为每毫克干重每小时 44 μl 的 O2，而己二酸未被氧化。细胞提取物的研究揭示了环己醇、6-羟基己酸和 6-氧代己酸的诱导型脱氢酶的存在，以及一种单加氧酶，其与一种乳酸苷酶结合，将环己酮转化为 6-羟基己酸。因此，该单加氧酶被推测为形成内酯的类型，而将环己醇转化为己二酸的途径；环己醇 → 环己酮 → 1-oxa-2-oxocycloheptane → 6-羟基己酸 → 6-氧代己酸 →己二酸；其中的关键中间体已通过色谱法鉴定，与 Nocardia globerula CL1 氧化环己醇的途径相同。
• Formation of ε-hydroxycaproate and ε-aminocaproate from N-nitrosohexamethyleneimine: Evidence that microsomal α-hydroxylation of cyclic nitrosamines may not always involve the insertion of molecular oxygen into the substrate
  作者：Lanny I. Hecker、Yves Tondeur、James G. Farrelly

  DOI：10.1016/0009-2797(84)90064-4

  日期：1984.4

  derived from molecular oxygen into NO-HEX. All of the oxygen atoms in epsilon-aminocaproate (EAC) were derived from water. Approximately half of the molecules of epsilon- hydroxycaproate ( EHC ) contain an 18O atom; thus, half of the alpha-hydroxy-NO-HEX formed incorporates a hydroxyl group derived from molecular oxygen with the remainder of the hydroxyls being from water. To account for the above

  研究了环亚硝胺，亚硝基六亚甲基亚胺（NO-HEX）微粒体代谢产物的形成。通过在18O2气氛中使用微粒体代谢该化合物来获得有关NO-HEX四种主要代谢物中氧原子来源的信息，由于插入了N-HEX，形成了β-和γ-羟基-NO-HEX。分子氧衍生成NO-HEX的羟基 ε-氨基己酸酯（EAC）中的所有氧原子均来自水。ε-羟基己酸酯（EHC）分子中大约有一半包含18O原子；因此，形成的一半α-羟基-NO-HEX掺入了源自分子氧的羟基，其余的羟基则来自水。
• Barton, Patrick; Laws, Andrew P.; Page, Michael I., Journal of the Chemical Society. Perkin transactions II, 1994, # 9, p. 2021 - 2030
  作者：Barton, Patrick、Laws, Andrew P.、Page, Michael I.

  DOI：——

  日期：——
• Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations
  作者：Kenneth B. Wiberg、Roy F. Waldron

  DOI：10.1021/ja00020a036

  日期：1991.9

  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.