11-羟基十四烷酸 | 2034-56-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 11-羟基十四烷酸
• 中文别名: 11-羟基十四酸
• 英文名称: 11-hydroxymyristic acid
• 英文别名: (+/-)-11-hydroxy-tetradecanoic acid；(+/-)-11-Hydroxy-tetradecansaeure；11-Hydroxytetradecansaeure；Convolvulinolsaeure；11-Hydroxytetradecanoic acid
• CAS: 2034-56-2
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: DMCZWEUMVOFXBT-UHFFFAOYSA-N

物化性质

• LogP：
  3.729 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  11-羟基十四烷酸 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (R)-1-(methoxycarbonyl)tridec-10-yl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-β-D-glucopyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(02)00092-7
• 作为产物：
  描述：

  10-十一烯醛 在 sodium chlorite 、 N-氯代丁二酰亚胺 、 2,2,6,6-四甲基哌啶氧化物 、 硼烷 、 四丁基氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 5.0h， 生成 11-羟基十四烷酸
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(02)00092-7

文献信息

• Regioselective Hydroxylation of C₁₂-C₁₅Fatty Acids with Fluorinated Substituents by Cytochrome P450 BM3
  作者：Chih-Hsiang Chiang、Ravirala Ramu、Yi-Jung Tu、Chung-Ling Yang、Kok Yaoh Ng、Wen-I Luo、Charles H. Chen、Yu-Ying Lu、Chen-Lun Liu、Steve S.-F. Yu

  DOI：10.1002/chem.201302402

  日期：2013.10.4

  control of the regioselectivity by the fluorinated terminal methyl groups of the C12–C15 fatty acids has been noted. Despite the fact that residues Arg47/Tyr51/Ser72 exert significant control over the hydroxylation of the subterminal carbon atoms toward the hydrocarbon tail, the fluorine substituent(s) at the ω‐position affects the regioselective hydroxylation. For substrate hydroxylation, we have found

  我们在这里证明野生型细胞色素P450 BM3可以识别非天然底物，例如氟化的C 12 –C 15链长脂肪酸，并对它们的有效转化表现出更好的催化作用。尽管P450 BM3袋中氟化底物的结合亲和力略低于非氟化底物的结合亲和力，但自旋位移测量表明ω位的氟取代基可促进内部重整水网络动态结构的重排。通过微去溶剂化过程将疏水囊袋排出，以排出处于静止状态的血红素铁的水配体。Michaelis-Menten常数（K m），但表明与非氟代脂肪酸相比，氟代脂肪酸确实是更好的底物。周转频率（的增强ķ猫），用于从NADPH电子转移到血红素铁和对C 由化合物I（CPD I），得到产物H键氧化表明，与来自酶-底物去相关联的活化能在氟化基板的情况下，对于两个步骤，从（ES状态）到相应的过渡状态（ES ≠状态）的活性均显着降低。通过C 12 –C 15的氟化末端甲基精确控制区域选择性已经注意到脂肪酸。尽管残基Arg47 /
• Catalytic Hydroxylation in Biphasic Systems using CYP102A1 Mutants
  作者：Steffen C. Maurer、Katja Kühnel、Leonard A. Kaysser、Sabine Eiben、Rolf D. Schmid、Vlada B. Urlacher

  DOI：10.1002/adsc.200505044

  日期：2005.6

  isolated P450 enzymes is believed to be impractical due to their low stability, stoichiometric need of the expensive cofactor NAD(P)H and low solubility of most substrates in aqueous media. We investigated the behaviour of an isolated bacterial monooxygenase (mutants of CYP102A1) in a biphasic reaction system supported by cofactor recycling with the NADP+-dependent formate dehydrogenase from Pseudomonas

  细胞色素P450单加氧酶是可将多种疏水性有机底物羟化或环氧化的生物催化剂。但是，它们的技术应用仅限于少数几个全细胞过程。由于分离的P450酶的低稳定性，昂贵的辅因子NAD（P）H的化学计量需要以及大多数底物在水性介质中的低溶解度，因此认为使用分离的P450酶是不切实际的。我们调查了分离的细菌单加氧酶（CYP102A1突变体）在双相反应系统中的行为，该系统由辅因子循环与假单胞菌NADP +依赖性甲酸脱氢酶支持101.使用该实验装置，将环己烷，辛烷和肉豆蔻酸羟化。为降低工艺成本，设计了一种新的依赖NADH的CYP102A1突变体。为了回收NADH，使用了NAD +依赖性的FDH。在双相系统的反应条件下，单加氧酶突变体的稳定性非常高，这在NADPH依赖性环己烷羟基化反应中高达12,850，而在NADH依赖性肉豆蔻酸氧化中则高达30,000。
• Die bestandteile des giftigen glykosidharzes aus Ipomoea fistulosa mart. et chois.
  作者：Günter Legler

  DOI：10.1016/s0031-9422(00)86143-9

  日期：1965.2

  Abstract From the leaves of Ipomoea fistulosa (Convolvulaceae) a resinous high-molecular-weight ester glycoside has been isolated, similar to the resins found in the underground organs of other convolvulaceae. It consists of 7-hydroxy decanoic acid, 11-hydroxy tetradecanoic acid, 11-hydroxy hexadecanoic acid, and 3,11-dihydroxy tetradecanoic acid glycosidically bound to several residues of d -glucose

  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。
• [EN] DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT
  申请人：UNIV MISSOURI

  公开号：WO2009158633A1

  公开（公告）日：2009-12-30

  Conjugated compounds comprising a therapeutic or diagnostic agent linked to a substrate for a cell membrane transporter or receptor by lipophilic linker are provided.

  提供了包含治疗或诊断药物与细胞膜转运体或受体的底物通过亲脂性连接剂连接的共轭化合物。
• The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3
  作者：Max J. Cryle、Nick J. Matovic、James J. De Voss

  DOI：10.1016/j.tetlet.2006.10.136

  日期：2007.1

  The stereochemical preference for the cytochrome P450BM3-catalysed hydroxylation of tetradecanoic and pentadecanoic acids has been determined via comparison with authentic non-racemic standards utilising enantioselective HPLC. The sub-terminal hydroxylation of these fatty acids by P450BM3 is highly selective for the formation of the R-alcohols. This is the same enantioselectivity as is seen for hexadecanoic

  通过与对映选择性HPLC的可靠非外消旋标准品进行比较，确定了细胞色素P450 BM3催化的十四烷酸和十五烷酸羟基化的立体化学偏好。这些脂肪酸通过P450 BM3的亚末端羟基化对于R-醇的形成具有高度选择性。这与十六烷酸氧化反应的对映选择性相同，但与先前报道的P450 BM3对十五烷酸进行S-羟基化反应相反。