malonaldehyde sodium salt | 24382-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: malonaldehyde sodium salt
• 英文别名: sodium malondialdehyde；sodiomalondialdehyde；sodio-malonaldehyde
• CAS: 24382-04-5
• 化学式: C₃H₃NaO₂
• 分子量: 94.0454
• InChiKey: IYOZELODQNHIPW-UHFFFAOYSA-N

物化性质

• 熔点：
  246° (dec)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 malonaldehyde sodium salt 在 sodium hydroxide 、 sodium dihydrogenphosphate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以67%的产率得到四甲基(1R,4S,5R,8S)-3,7-二羟基双环[3.3.1]壬-2,6-二烯-2,4,6,8-四羧酸酯
  参考文献：
  名称：

  Series on chemistry under physiological conditions. Part 7. Tetramethyl 3,7-dihydroxybicyclo[3.3.1]nona-2,6-diene-2,4,6,8-tetracarboxylate: a useful companion to Meerwein's ester. Topological analysis of bicyclo[3.3.1]nonane synthesis

  摘要：

  DOI：

  10.1021/jo00219a027

文献信息

• Reaction of malonaldehyde with nucleic acid. IV. Formation of pyrimido(1,2-a)purin-10(3H)-one nucleoside by thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine.
  作者：Hiroshi SETO、Takako SETO、Tomoko OHKUBO、Ikue SAITOH

  DOI：10.1248/cpb.39.515

  日期：——

  The reaction of 1, 1, 3, 3-tetraethoxypropane with guanosine under strongly acidic conditions resulted in the formation of diastereomeric oxadiazabicyclononene residues linked to guanine base. The diastereomers were decomposed by heat, giving changed pyrimido[1, 2-a]purin-10(3H)-one nucleoside (3) in a good yield. A convenient method for the preparation of 3, which includes the thermal decomposition process of the diastereomers, was developed.

  在强酸性条件下，1, 1, 3, 3-四乙氧基丙烷与鸟嘌呤核苷反应，形成与鸟嘌呤碱相连的非对映氧二氮杂环壬烯残基。非对映异构体受热分解后，得到了嘧啶并[1, 2-a]嘌呤-10(3H)-酮核苷（3），收率很高。开发出了一种制备 3 的简便方法，其中包括非对映异构体的热分解过程。
• Synthetic studies on nogalamycin : stereospecific C-5 alkylations of a sugar derivative via claisen rearrangement and a new route to 1,1,4-trialkoxybuta-1,3-dienes
  作者：J.-M. Vatele

  DOI：10.1016/s0040-4020(01)87284-7

  日期：1986.1

  Claisen rearrangement of the 4-methoxybutadienylether of the allylic alcohol 13, which was made in 15 steps from D-glucose, afforded one major aldehyde 17 or 18 in good yield. All attempts to oxidize this aldehyde to an acid were unsuccessful. The model compound 24 and compound 13 were converted respectively to the α ,β -unsaturated esters 25 and 26. Compound 25 was further transformed into the 1,1

  由D-葡萄糖以15个步骤制得的烯丙醇13的4-甲氧基丁二烯基醚的克莱森重排以良好的产率提供了一种主要的醛17或18。将这种醛氧化为酸的所有尝试均未成功。将模型化合物24和化合物13分别转化为α，β-不饱和酯25和26。将化合物25进一步转化为1,1,4-三烷氧基丁-1,3-二烯27，发现其对醌没有反应性。
• Redox-active, functionalised [3]- and [4]-dendralenes
  作者：Malcolm A. Coffin、Martin R. Bryce、Andrei S. Batsanov、Judith A. K. Howard

  DOI：10.1039/c39930000552

  日期：——

  A series of [3]- and [4]-dendralenes, functionalised with 1,3-dithiole groups, are synthesised and shown by cyclic voltammetry to undergo reversible multi-stage redox reactions to yield tri- and tetra-cation species, respectively; the X-ray crystal structure of a [3]-dendralene derivative is reported.

  合成了一系列具有 1,3 二硫代官能团的 [3]- 和 [4]- 树枝烯，并通过循环伏安法显示其发生了可逆的多级氧化还原反应，分别生成了三阳离子和四阳离子物种；报告了一种 [3]- 树枝烯衍生物的 X 射线晶体结构。
• Protein Modification by Adenine Propenal
  作者：Sarah C. Shuck、Orrette R. Wauchope、Kristie L. Rose、Philip J. Kingsley、Carol A. Rouzer、Steven M. Shell、Norie Sugitani、Walter J. Chazin、Irene Zagol-Ikapitte、Olivier Boutaud、John A. Oates、James J. Galligan、William N. Beavers、Lawrence J. Marnett

  DOI：10.1021/tx500218g

  日期：2014.10.20

  Base propenals are products of the reaction of DNA with oxidants such as peroxynitrite and bleomycin. The most reactive base propenal, adenine propenal, is mutagenic in Escherichia coli and reacts with DNA to form covalent adducts; however, the reaction of adenine propenal with protein has not yet been investigated. A survey of the reaction of adenine propenal with amino acids revealed that lysine

  碱基丙烯醛是 DNA 与过氧亚硝酸盐和博来霉素等氧化剂反应的产物。反应性最强的丙烯醛，腺嘌呤丙烯醛，在大肠杆菌中具有致突变性，并与 DNA 反应形成共价加合物；然而，腺嘌呤丙醛与蛋白质的反应尚未得到研究。对腺嘌呤丙烯醛与氨基酸反应的调查表明，赖氨酸和半胱氨酸形成加合物，而组氨酸和精氨酸则不然。N ε -氧代丙烯基赖氨酸、赖氨酸-赖氨酸交联和S-氧代丙烯基半胱氨酸是主要产品。腺嘌呤丙醛与人血清白蛋白和 DNA 修复蛋白 XPA 反应的综合分析表明，唯一稳定的加合物是N ε-氧代丙烯赖氨酸。人白蛋白中最活跃的修饰位点是 K190 和 K351。XPA 的三个修饰位点位于 DNA 结合域中，两个位点受到调节性乙酰化。腺嘌呤丙醛修饰显着降低了 XPA 与 DNA 底物结合的能力。
• Formation of Malonaldehyde−Acetaldehyde Conjugate Adducts in Calf Thymus DNA
  作者：Donata Pluskota-Karwatka、Agnieszka J. Pawłowicz、Leif Kronberg

  DOI：10.1021/tx060027h

  日期：2006.7.1

  It has previously been shown that malonaldehyde forms conjugates with acetaldehyde and that these conjugates react with nucleobases forming so-called conjugate adducts. In the current study, it is shown that conjugate adducts are also formed in calf thymus DNA when incubated simultaneously with malonaldehyde and acetaldehyde. The adducts were identified in the DNA hydrolysates by their positive ion electrospray MS/MS spectra and by coelution with the 2'-deoxynucleoside standards and, in the case of adducts exhibiting fluorescent properties, also by LC using a fluorescence detector. In the hydrolysates of double-stranded DNA (ds DNA), two deoxyguanosine and two deoxyadenosine conjugate adducts were detected, and in single-stranded DNA ( ss DNA) also, the deoxycytidine conjugate adduct was observed. The guanine base was the major target for the malonaldehyde-acetaldehyde conjugates, and 2'-deoxyguanosine adducts were produced in ds DNA at levels of 100-500 adducts/10(5) nucleotides (0.7-3 nmol/mg DNA). The 2'-deoxyadenosine adducts and the 2'-deoxycytidine adduct were generated in higher amounts when the incubation was performed at pH 6.0 than at pH 7.4, while the opposite formation profile was noted for the 2'-deoxyguanosine adducts, especially in the ss DNA reaction. This observation is exactly in accordance with our previously reported pH-dependent reactivity of the individual nucleosides with malonaldehyde-acetaldehyde conjugates. The findings of this work show that the genotoxic effects observed for malonaldehyde and acetaldehyde could be in part due to the formation of the conjugate adducts.