6-Hydroxyoctanoic acid, bis(trimethylsilyl) derivative

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-Hydroxyoctanoic acid, bis(trimethylsilyl) derivative
• 英文别名: trimethylsilyl 6-trimethylsilyloxyoctanoate
• 化学式: C₁₄H₃₂O₃Si₂
• 分子量: 304.577
• InChiKey: IMVSEVRFAKHCSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 6-羟基辛酸 在 吡啶 、 N,N-bis(trimethylethylsilyl)trifluoroacetamide 作用下， 反应 0.5h， 生成 6-Hydroxyoctanoic acid, bis(trimethylsilyl) derivative
  参考文献：
  名称：

  3-, 6- and 7-Hydroxyoctanoic Acids are Metabolites of Medium-Chain Triglycerides and Excreted in Urine as Glucuronides

  摘要：

  Three new metabolites of medium-chain fatty acid oxidation, 3-, 6- and 7-hydroxyoctanoyl beta-D-glucuronide, were identified in the urine of six infants who were fed a diet enriched in medium-chain triglycerides (MCT), Glucuronides were extracted from the urine by organic solvent extraction with ethyl acetate and by solid-phase extraction on Sep-Pak C-18 cartridges. The compounds of interest were also purified from the organic solvent extract by preparative one-dimensional thin-layer chromatography. Cleavage of the glucuronides was achieved by either alkaline hydrolysis or enzymatic hydrolysis with beta-D-glucuronidase. The analyses of the trimethylsilylated derivatives were performed both by gas chromatography with dame ionization detection (GC/FID) and by gas chromatography/mass spectrometry (GC/MS). The structure of the hydroxyoctanoic acids was proved by comparison of their mass spectra with those of reference substances. Authentic 6-hydroxyoctanoic acid was synthesized. The presence of 6-hydroxyoctanoyl glucuronide shows that in addition to beta-oxidation, omega-oxidation and (omega - 1)-hydroxylation, medium-chain fatty acids can be oxidized at the omega-2 position, The conjugation of medium-chain hydroxymonocarboxylic acids with glucuronic acid has not been described in humans before.

  DOI：

  10.1002/(sici)1096-9888(199606)31:6<633::aid-jms332>3.0.co;2-l

文献信息

• Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
  作者：Ana C. Ebrecht、Thato M. Mofokeng、Frank Hollmann、Martha S. Smit、Diederik J. Opperman

  DOI：10.1021/acs.orglett.3c01601

  日期：2023.7.14

  γ- and δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8–C12 fatty acids to yield after lactonization the corresponding γ- and δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones

  γ-和δ-内酯是有价值的香料和香料化合物。它们的合成取决于合适的羟基脂肪酸前体的可用性。鉴定出三种短的非特异性过氧化酶，它们选择性羟基化 C8-C12 脂肪酸的 C4 和 C5 位置，在内酯化后产生相应的 γ- 和 δ-内酯。 C4 羟基化优先于 C5 羟基化，产生 γ-内酯作为主要产物。通过在双酶级联反应中使用醇脱氢酶还原所得含氧酸来解决羟基脂肪酸的过度氧化。