月桂酸-2,2-d2 | 64118-39-4

• 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
• 中文名称: 月桂酸-2,2-d2
• 中文别名: 氘代2,2-D2十二烷酸
• 英文名称: 2,2-Dideuteriododanoic acid
• 英文别名: 2,2-di-2H-lauric acid；2,2-dideuterio-dodecanoic acid；2,2-Dideuterio-dodecansaeure；Dodecanoic-2,2-D2 acid；2,2-dideuteriododecanoic acid
• CAS: 64118-39-4
• 化学式: C₁₂H₂₄O₂
• 分子量: 202.305
• InChiKey: POULHZVOKOAJMA-ZWGOZCLVSA-N

物化性质

• 熔点：
  44-46 °C(lit.)
• 沸点：
  225 °C100 mm Hg(lit.)
• 闪点：
  113 °C
• 溶解度：
  DMF：30 mg/ml； DMSO：20 mg/ml；乙醇：30 mg/ml
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S28
• 危险类别码：
  R36/37/38
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  月桂酸-2,2-d2 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 4.5h， 生成 N-2,2-Dideuteriododecanoyl-L-alanine
  参考文献：
  名称：

  Investigation into the mechanism for generation of the helical axis in cholesteric lyotropic liquid crystals

  摘要：

  The molecular based process responsible for the generation of the helical axis in the cholesteric mesophase of potassium N-dodecanoyl-L-alaninate, decanol, electrolyte, and water has been investigated. The headgroup dipolar couplings have been correlated with deuterium quadruple splittings from the aliphatic chain as a function of amphiphile concentration. The results show that the change in the pitch of the helical axis with concentration is reflected by a change in preferred conformation of the amphiphile. This change in conformation is centered about the amide bonds where the aliphatic chain is joined to the alaninate headgroups. The effect presumably results from destabilization of the normally preferred rotamer in favor of others and will have its source in selective interactions between the chiral centers of adjacent amphiphiles. Studies similar to those discussed show that the variation in pitch caused by temperature changes is not correlated with similar selective changes in headgroup orientation.

  DOI：

  10.1021/j100188a058
• 作为产物：
  描述：

  2,2-Dichlor-laurinsaeure-methylester 在 alkaline solution 、 锌 作用下， 生成 月桂酸-2,2-d2
  参考文献：
  名称：

  有机氘化合物：XIX。一些氘代月桂酸及其甲酯的合成

  摘要：

  描述了在羧基、末端甲基和 α-亚甲基及其各种组合中氘化的月桂酸的合成。还制备了每种酸的甲基酯和甲基-d3 酯。报道了均裂卤化物加成到烯烃的另外两个例子。描述了烷基卤化物和乙炔化银之间的反应。假设了一种涉及新型自由基的机制。

  DOI：

  10.1139/v58-063

文献信息

• Microbial biosynthesis of medium-chain 1-alkenes by a nonheme iron oxidase
  作者：Zhe Rui、Xin Li、Xuejun Zhu、Joyce Liu、Bonnie Domigan、Ian Barr、Jamie H. D. Cate、Wenjun Zhang

  DOI：10.1073/pnas.1419701112

  日期：2014.12.23

  We have solved a long-standing mystery of the biosynthetic origin of 1-undecene, a ubiquitous hydrocarbon semivolatile metabolite of Pseudomonas . Our study revealed an unprecedented family of nonheme oxidases that specifically convert medium-chain fatty acids into the corresponding terminal olefins using an oxygen-activating, nonheme iron-dependent mechanism. Our findings unveil previously unidentified chemistry in the nonheme Fe(II) enzyme family, aid the functional study of this ubiquitous metabolite in Pseudomonas , expand the scarce enzyme inventory for the transformation of fatty acid precursors to hydrocarbons, and serve as the basis for engineering efforts to establish bioprocesses to produce medium-chain terminal olefins, useful as fuels and chemical building blocks, from renewable resources.

  《意义》 我们解决了长期存在的关于1-十一烯的生物合成起源的谜团，这是一种广泛存在的半挥发性代谢产物，来自于假单胞菌。我们的研究揭示了一类前所未见的非血红素氧化酶家族，它们通过氧活化、非血红素铁依赖机制，特异地将中链脂肪酸转化为相应的末端烯烃。我们的发现揭示了非血红素Fe（II）酶家族中以前未知的化学反应，有助于研究假单胞菌中这种普遍代谢产物的功能，扩大了转化脂肪酸前体为烃类的酶库存，为建立利用可再生资源生产中链末端烯烃的生物过程的工程努力奠定了基础，这些烃类可用作燃料和化学构建块。
• Dynamics of fatty acids in phospholipid vesicles using spin relaxation of proton-coupled carbon-13 spectra
  作者：M. M. Fuson、J. H. Prestegard

  DOI：10.1021/ja00340a004

  日期：1983.1
• NODA, MANJIRO;MIYAKE, KOJI, YUKAGAKU, 1982, 31, N 3, 154-158
  作者：NODA, MANJIRO、MIYAKE, KOJI

  DOI：——

  日期：——
• ORGANIC DEUTERIUM COMPOUNDS: XIX. SYNTHESIS OF SOME DEUTERATED LAURIC ACIDS AND THEIR METHYL ESTERS
  作者：M. Elaine Isabelle、L. C. Leitch

  DOI：10.1139/v58-063

  日期：1958.3.1

  The synthesis of lauric acids deuterated in the carboxyl, the terminal methyl, and the α-methylene groups and in various combinations of these is described. The methyl and methyl-d3 esters of each of the acids were also prepared.Two further examples of homolytic halide addition to olefins are reported.The reaction between alkyl halides and silver acetylides is described. A mechanism involving a new

  描述了在羧基、末端甲基和 α-亚甲基及其各种组合中氘化的月桂酸的合成。还制备了每种酸的甲基酯和甲基-d3 酯。报道了均裂卤化物加成到烯烃的另外两个例子。描述了烷基卤化物和乙炔化银之间的反应。假设了一种涉及新型自由基的机制。
• Investigation into the mechanism for generation of the helical axis in cholesteric lyotropic liquid crystals
  作者：Alan S. Tracey、Xin Zhang

  DOI：10.1021/j100188a058

  日期：1992.4

  The molecular based process responsible for the generation of the helical axis in the cholesteric mesophase of potassium N-dodecanoyl-L-alaninate, decanol, electrolyte, and water has been investigated. The headgroup dipolar couplings have been correlated with deuterium quadruple splittings from the aliphatic chain as a function of amphiphile concentration. The results show that the change in the pitch of the helical axis with concentration is reflected by a change in preferred conformation of the amphiphile. This change in conformation is centered about the amide bonds where the aliphatic chain is joined to the alaninate headgroups. The effect presumably results from destabilization of the normally preferred rotamer in favor of others and will have its source in selective interactions between the chiral centers of adjacent amphiphiles. Studies similar to those discussed show that the variation in pitch caused by temperature changes is not correlated with similar selective changes in headgroup orientation.