(R)-α-hydroxymyristic acid | 2507-55-3

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: (R)-α-hydroxymyristic acid
• 英文别名: (R)-2-hydroxy-tetradecanoic acid；(R)-2-Hydroxy-tetradecansaeure；(2R)-2-hydroxytetradecanoic acid
• CAS: 2507-55-3；37639-48-8；67253-09-2；26632-17-7
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: JYZJYKOZGGEXSX-CYBMUJFWSA-N

物化性质

• 熔点：
  70-72°C
• 沸点：
  377.5±15.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  5.150 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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

• WGK Germany：
  3
• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (R)-α-hydroxymyristic acid 生成 (R)-methyl 2-hydroxytetradecanoate
  参考文献：
  名称：

  Horn et al., Journal of the Chemical Society, 1954, p. 177,179

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]tetradecanamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (R)-α-hydroxymyristic acid
  参考文献：
  名称：

  Cerebrosides fromfomitopsis pinicola (Sw. Ex Fr.) Karst.

  摘要：

  A cerebroside fraction was obtained from the fruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC. The sugar component of all cerebrosides was D-glucose. The major fatty acids were 2-hydroxyfatty acids (C-14-C-18), the long chain base was identified as 9-methyl-C-18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi. Based on degradation studies, fast atom bombardment mass spectrometry, and different H-1 and C-13 NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-beta-D-glucopyranosyl-9-methyl-4,8-sphingadienine.

  DOI：

  10.1007/bf00817267

文献信息

• α Hydroxylation of Carboxylic Acids with Molecular Oxygen Catalyzed by the α Oxidase of Peas (<i>Pisum </i><i>s</i><i>ativum</i>):  A Novel Biocatalytic Synthesis of Enantiomerically Pure (<i>R</i>)-2-Hydroxy Acids
  作者：Waldemar Adam、Wilhelm Boland、Jenny Hartmann-Schreier、Hans-Ulrich Humpf、Michael Lazarus、Alexander Saffert、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1021/ja981252r

  日期：1998.11.1

  the α oxidation of saturated, unsaturated, and heteroatom-containing (oxygen, sulfur) carboxylic acids 1 by the enzyme extract of peas (Pisum sativum) indicate that this biotransformation proceeds highly enantioselectively. For the first time, the synthesis of optically pure 2-hydroxy acids 2 has been achieved on the semipreparative scale (1 mmol) by α hydroxylation of long-chain carboxylic acids with

  豌豆 (Pisum sativum) 的酶提取物对饱和、不饱和和含杂原子（氧、硫）羧酸 1 进行 α 氧化的底物选择性表明，这种生物转化具有高度的对映选择性。在豌豆的α氧化酶的催化下，通过长链羧酸与分子氧的α羟基化，首次在半制备规模（1 mmol）上合成了光学纯的2-羟基酸2。对于链中带有硫原子的衍生物，没有观察到亚砜化。官能团（碳双键和三键、氧和硫原子）必须距离羧酸基团至少三个碳原子才能实现有效的不对称羟基化。2-羟基酸 2 的绝对构型是通过将气相色谱数据与真实参考化合物的数据进行比较并通过应用激子耦合圆二色性 (ECCD) 方法来确定的。这种前所未有的不对称...
• Enantioselective α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidation enzyme system of young pea leaves (Pisum sativum): A substrate selectivity study
  作者：Waldemar Adam、Michael Lazarus、Chantu R. Saha-Mǒller、Peter Schreier

  DOI：10.1016/0957-4166(96)00283-2

  日期：1996.8

  The substrate selectivity of the a oxidation of carboxylic acids I by crude homogenate of young pea leaves was investigated. Saturated fatty acids with 7 to 16 carbon atoms and oleic acid were transformed to the enantiomerically pure (R)-2-hydroxy acids 2 in the presence of molecular oxygen. Copyright (C) 1996 Elsevier Science Ltd
• Crystal Structure of H2O2-dependent Cytochrome P450SPα with Its Bound Fatty Acid Substrate
  作者：Takashi Fujishiro、Osami Shoji、Shingo Nagano、Hiroshi Sugimoto、Yoshitsugu Shiro、Yoshihito Watanabe

  DOI：10.1074/jbc.m111.245225

  日期：2011.8

  Cytochrome P450(SP alpha) (CYP152B1) isolated from Sphingomonas paucimobilis is the first P450 to be classified as a H2O2-dependent P450. P450(SP alpha) hydroxylates fatty acids with high alpha-regioselectivity. Herein we report the crystal structure of P450(SP alpha) with palmitic acid as a substrate at a resolution of 1.65 angstrom. The structure revealed that the C-alpha of the bound palmitic acid in one of the alternative conformations is 4.5 angstrom from the heme iron. This conformation explains the highly selective alpha-hydroxylation of fatty acid observed in P450(SP alpha). Mutations at the active site and the F-G loop of P450(SP alpha) did not impair its regioselectivity. The crystal structures of mutants (L78F and F288G) revealed that the location of the bound palmitic acid was essentially the same as that in the WT, although amino acids at the active site were replaced with the corresponding amino acids of cytochrome P450(BS alpha) (CYP152A1), which shows beta-regioselectivity. This implies that the high regioselectivity of P450(SP alpha) is caused by the orientation of the hydrophobic channel, which is more perpendicular to the heme plane than that of P450(BS alpha)
• Keratin fiber strengthening agent and method for strengthening keratin fiber
  申请人：Takasago International Corporation

  公开号：EP0920852B1

  公开（公告）日：2005-06-01
• US6379659B1
  申请人：——

  公开号：US6379659B1

  公开（公告）日：2002-04-30