11-hydroxytetradecanoic acid methyl ester | 460082-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-hydroxytetradecanoic acid methyl ester
• 英文别名: 11-Hydroxy-tetradecansaeuremethylester；Methyl 11-hydroxytetradecanoate
• CAS: 460082-45-5
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: GIXQATLUZYOKKT-UHFFFAOYSA-N

物化性质

• 熔点：
  39.5-40.5 °C
• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  11-hydroxytetradecanoic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 11-羟基十四烷酸
  参考文献：
  名称：

  Die bestandteile des Giftigen glykosidharzes aus Ipomoea fistulosa mart。等等。

  摘要：

  摘要 从 Ipomoea fistulosa (Convolvulaceae) 的叶子中分离出一种树脂状的高分子量酯糖苷，类似于在其他旋花科地下器官中发现的树脂。它由 7-羟基癸酸、11-羟基十四烷酸、11-羟基十六烷酸和 3,11-二羟基十四烷酸与 d-葡萄糖、d-岩藻糖、d-奎诺糖和 l-的几个残基糖苷结合组成鼠李糖形成糖苷酸，当量重量为 800 至 1300。一部分 7-羟基癸酸被分离为 β-d-喹诺酮苷。糖苷酸相互酯化，形成平均分子量约为 25,000 的密切相关聚酯的混合物，在超速离心机中显示出宽分布曲线。

  DOI：

  10.1016/s0031-9422(00)86143-9
• 作为产物：
  描述：

  10-十一烯-1-醇 在 sodium tetrahydroborate 、 dimethyl sulfide borane 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 11-hydroxytetradecanoic acid methyl ester
  参考文献：
  名称：

  Products of Cytochrome P450_BioI (CYP107H1)-Catalyzed Oxidation of Fatty Acids

  摘要：

  [GRAPHICS]Oxidation of tetradecanoic and hexadecanoic acids by cytochrome P450(Biol) (CYP107H1) produces mainly the 11-, 12-, and 13-hydroxy C-14 fatty acids and the 11- to 15-hydroxy C-16 fatty acids, respectively. In contrast to previous reports, terminal hydroxylation is not observed. The enantiospecificity of fatty acid hydroxylation by P450(Biol) was also determined, and the enzyme was shown to be moderately selective for production of the (R)-alcohols.

  DOI：

  10.1021/ol035254e

文献信息

• CYP505E3: A Novel Self‐Sufficient ω‐7 In‐Chain Hydroxylase
  作者：Mpeyake Jacob Maseme、Alizé Pennec、Jacqueline Marwijk、Diederik Johannes Opperman、Martha Sophia Smit

  DOI：10.1002/anie.202001055

  日期：2020.6.22

  The self‐sufficient cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus catalyzes the regioselective in‐chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the ω‐7 position. It is the first reported P450 to give regioselective in‐chain ω‐7 hydroxylation of C10–C16 n ‐alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5‐dodecanol and 7‐tetradecanol

  来自土曲霉的自给自足的细胞色素P450单加氧酶CYP505E3催化ω-7位烷烃，脂肪醇和脂肪酸的区域选择性链内羟化反应。这是第一个报道的P450，具有C10–C16 n的区域选择性链内ω-7羟基化作用链烷烃，从而一步一步生物催化合成稀有醇（如5-十二烷醇和7-十四烷醇）。它显示出一个甲基末端对第八个碳原子的区域选择性超过70％，并且对癸烷（TTN≈8000）和十二烷（TTN≈2000）的活性很高。CYP505E3可用于通过两种途径合成高价值风味化合物δ-十二内酯：1）将十二烷酸转化为5-羟基十二烷酸（区域选择性为24％），在低pH内酰胺酶下可转化为δ-十二内酯，以及2）转化将1-十二烷醇转化为1,5-十二烷二醇（55％的区域选择性），可以通过马肝醇脱氢酶将其转化为δ-十二烷内酯。
• The CYPome of Sorangium cellulosum So ce56 and Identification of CYP109D1 as a New Fatty Acid Hydroxylase
  作者：Yogan Khatri、Frank Hannemann、Kerstin M. Ewen、Dominik Pistorius、Olena Perlova、Norio Kagawa、Alexander O. Brachmann、Rolf Müller、Rita Bernhardt

  DOI：10.1016/j.chembiol.2010.10.010

  日期：2010.12

  studies on the characterization of fatty acid hydroxylases. Three novel potential fatty acid hydroxylases (CYP109D1, CYP264A1, and CYP266A1) were used for detailed characterization. One of them, CYP109D1 was able to perform subterminal hydroxylation of saturated fatty acids with the support of two autologous and one heterologous electron transfer system(s). The kinetic parameters for the product hydroxylation

  提出了对纤维素酶Soce56的完整细胞色素P450补体（CYPome）进行的首次系统研究，该酶是重要的次生代谢产物的生产者，具有迄今为止最大的细菌基因组序列。我们描述了由21个推定的P450基因组成的Soce56细胞色素P450补体的生物信息学分析。由于脂肪酸在黏菌的复杂生命周期中起着关键作用，因此我们将研究重点放在了脂肪酸羟化酶的表征上。三种新颖的潜在脂肪酸羟化酶（CYP109D1，CYP264A1和CYP266A1）用于详细表征。其中之一，CYP109D1能够在两个自体和一个异源电子转移系统的支持下进行饱和脂肪酸的亚末端羟基化反应。
• A new β-d-quinovoside from commercial Ipomoea purga
  作者：Sukhdev Singh、Bernard Ellis Stacey

  DOI：10.1016/0031-9422(73)80390-5

  日期：1973.7

  Abstract Treatment of convolvulin (the ether insoluble portion of purified jalap resin) with sodium methoxide in methanol has yielded a new β- d -quinovoside. Periodate oxidation and methylation studies together with chemical and spectroscopic analyses have shown this fragment to consist of one molecule of d -quinovose glycosidically linked to a molecule of methyl 11-hydroxytetradecanoate.

  摘要 用甲醇钠在甲醇中处理旋花素（纯化的墨西哥胡椒树脂的醚不溶部分）产生了一种新的 β-d-喹诺酮苷。高碘酸盐氧化和甲基化研究以及化学和光谱分析表明，该片段由一个 d-奎诺糖分子与一个 11-羟基十四酸甲酯分子糖苷连接而成。
• Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides
  作者：Shigeru Kobayashi、Jun-ichi Furukawa、Tomoko Sakai、Nobuo Sakairi

  DOI：10.1016/s0008-6215(02)00092-7

  日期：2002.6

  The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its H-1 NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Facile determination of the absolute stereochemistry of hydroxy fatty acids by GC: application to the analysis of fatty acid oxidation by a P450BM3 mutant
  作者：Max J. Cryle、James J. De Voss

  DOI：10.1016/j.tetasy.2007.01.034

  日期：2007.3

  The determination of the absolute stereochemistry of hydroxy fatty acid methyl esters as their (S)-ibuprofen esters is possible via standard gas chromatographic techniques. Analyses of various racemic and nonracemic standards and mixtures from enzymic oxidation show excellent resolution of the resultant diastereomers, with the (S,S)-diastereomers eluting first in all cases studied. The stereochemistry of the oxidation of dodecanoic acid by P450(BM3), which has not been previously reported, was determined by this method and indicated a preference for (R)-hydroxylation. The sensitivity of this technique allows the analysis of very small quantities of product, which has revealed that the oxidation of dodecanoic and hexadecanoic acids by the T268A mutant of P450(BM3) display the same stereochemical efficiency and produce (R)-hydroxy fatty acids in the same manner as wildtype P450(BM3), despite the poor coupling efficiency of these substrates. This stereochemistry implies that hydroxylation catalysed by the T268A mutant of P450(BM3) occurs through residual levels of the normal hydroxylating species. (c) 2007 Elsevier Ltd. All rights reserved.