monodecyl malonate

• 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: monodecyl malonate
• 英文别名: 2-(Decyloxycarbonyl)acetic acid；3-decoxy-3-oxopropanoic acid
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: NFJLFLMILACWJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  monodecyl malonate 在 硫酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Abdel Salam; El-Sadek; Kandeel, Egyptian Journal of Chemistry, 2009, vol. 52, # 5, p. 597 - 609

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 癸醇 以 甲苯 为溶剂， 反应 4.0h， 以55%的产率得到monodecyl malonate
  参考文献：
  名称：

  咖啡酸疏水性的微调：对金黄色葡萄球菌和大肠杆菌的抗菌活性研究

  摘要：

  由于不适当使用和过度使用抗菌素引起的细菌对多种药物的耐药性增加是全球关注的问题。为了避免这个问题，人们广泛认可了对开发新的活性剂的追求。植物产生的一些植物化学产品是其化学防御策略的一部分，被认为是开发新型抗微生物剂的新刺激，这些抗微生物剂不像目前的药物那样容易受到细菌耐药性机制的影响。在这项研究中，评估了咖啡酸（CAF）和一系列CAF烷基酯的抗微生物活性和作用方式对大肠杆菌和金黄色葡萄球菌的作用，目的是分析烷基酯侧链长度对活性的影响。最小抑菌浓度（MIC），最小杀菌浓度（MBC），理化表面性质的变化和细胞内钾泄漏被用作抗菌作用方式的生理指标。发现CAF烷基酯是对两种细菌有效的抗微生物剂。它们的活性直接取决于它们的亲脂性，亲脂性影响细菌的敏感性，细菌的理化性质和膜的完整性。大肠杆菌不如金黄色葡萄球菌易感对化合物的作用。较长的烷基侧链对革兰氏阳性细菌更有效，而中等长度的烷基侧链化合物对革兰氏阴

  DOI：

  10.1039/c5ra05840f

文献信息

• Selective Monoesterification of Malonic Acid Catalyzed by Boric Acid
  作者：Stephan M. Levonis、Laurent F. Bornaghi、Todd A. Houston

  DOI：10.1071/ch07231

  日期：——

  Boric acid catalyzes the monoesterification of malonic acid, likely through a chelation mechanism that is not available to the monoester product. Under more forcing conditions, diesters form to some extent, but conditions can be optimized to favour the monoester product (56–80%). With the easily handled solid acid catalyst, these reactions can be run with excess alcohol as solvent or with stoichiometric

  硼酸催化丙二酸的单酯化，可能是通过单酯产品不可用的螯合机制。在更强制的条件下，会在一定程度上形成二酯，但可以优化条件以有利于单酯产品（56-80%）。使用易于处理的固体酸催化剂，这些反应可以用过量的酒精作为溶剂或用化学计量的酒精在乙腈中进行适度加热。
• Optimizing the efficiency of antioxidants in emulsions by lipophilization: tuning interfacial concentrations
  作者：Marlene Costa、Sonia Losada-Barreiro、Fátima Paiva-Martins、Carlos Bravo-Díaz

  DOI：10.1039/c6ra18282h

  日期：——

  hydrophobicity (alkyl chain lengths of 1 to 16 carbon atoms) to investigate the effects of hydrophobicity on the oxidative stability of stripped corn oil-in-water emulsions. AO efficiency was determined by monitoring the production of primary oxidation products (conjugated dienes) with time and a non-linear, parabolic-like, variation of their efficiency with the number of C atoms in their alkyl chain

  抗氧化剂，政务主任的效率优化，基于脂质乳剂通过由于固有的实验困难以及由于AO的调节状态，它们的反应性部分的化学修饰并非总是可能的。亲水性AO的酯化可能是一种实用，方便的替代方法。在这里，我们采用了一系列带有相同反应性部分但疏水性不同（1至16个碳原子的烷基链长度）的咖啡酸衍生物，以研究疏水性对汽提玉米水包油乳液氧化稳定性的影响。AO效率是通过监测随时间变化的初级氧化产物（共轭二烯）的产生以及非线性，类似于抛物线的效率来确定的，该效率随烷基链中C原子数的变化而变化，最大C 8发现。为了使结果合理化，我们还使用最新开发的动力学方法确定了相同乳液的油，界面和水区域之间的AO分布，该方法提供了AO在油-界面之间的分配常数P I O，完整乳液的水界面P I W区域。两者的值P我ö和P我W¯¯范围180-2000之间，这表明在AOS转移到界面区域是自发的。结果表明，界面区域中AO的百分比百分比AO I
• Evaluation of the antimicrobial and antioxidant properties of synthetic phenolipids
  作者：Horiya Nassiba Ham、Matthieu M. Mention、Blandine Godon、Fanny Brunissen、Manon Thomas、Florent Allais、Michel Lopez、Nabila Imatoukene

  DOI：10.1016/j.procbio.2024.03.015

  日期：2024.6

  of phenolic compounds by lipophilization allowing the synthesis of new compounds with improved biological properties. This study aims to investigate the antimicrobial effects of eight synthesized phenolipids, derived from bioactive coumaric and ferulic acid esters, against , , and . Antioxidant activity, as well as antimicrobial capacity were evaluated through DPPH assays and classical disc agar diffusion

  通过亲脂化对酚类化合物进行官能化，从而可以合成具有改善的生物特性的新化合物。本研究旨在研究源自生物活性香豆酸酯和阿魏酸酯的八种合成酚脂对 、 、 和 的抗菌作用。分别通过 DPPH 测定和经典圆盘琼脂扩散评估抗氧化活性以及抗菌能力，同时使用流式细胞术测定评估细胞活力。抗氧化活性结果表明阿魏酸酯比香豆酸酯表现出更高的抗自由基活性。琼脂扩散测定结果表明，1-甲基丙基香豆酸酯和 1-甲基丙基阿魏酸酯 (1-MPF) 对所有测试的微生物均具有有效的抗菌活性，最低抑制浓度 (MIC) 值在 0.9 至 3.5 mM 之间。此外，流式细胞术显示 1-MPF 和香豆酸癸酯表现出显着的杀菌活性 (p < 0.05)，几乎有 63% 的细胞死亡。与常用的琼脂方法相比，流式细胞术被证明是一种快速、直接的分析工具，可以评估抗菌活性，同时提供抑制类型的信息。这些结果表明酚脂作为有效的亲脂性生物活性分子可用于保护食
• Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
  作者：Razieh Hosseini、Fatemeh Moosavi、Hamid Rajaian、Tiago Silva、Diogo Magalhães e Silva、Pedro Soares、Luciano Saso、Najmeh Edraki、Ramin Miri、Fernanda Borges、Omidreza Firuzi

  DOI：10.1111/cbdd.12829

  日期：2016.12

  The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum‐deprived conditions and enhancement of nerve growth factor (NGF)‐induced neurite outgrowth in PC12 neuronal cells. p‐Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25 μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF‐induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5 μm led to 25‐ and 22‐fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3‐kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.
• Inhibitory effects of hydroxylated cinnamoyl esters on lipid absorption and accumulation
  作者：Masahiko Imai、Takaya Kumaoka、Makiko Hosaka、Yui Sato、Chuan Li、Masashi Sudoh、Yoshiko Tamada、Hiromasa Yokoe、Setsu Saito、Masayoshi Tsubuki、Noriko Takahashi

  DOI：10.1016/j.bmc.2015.03.086

  日期：2015.7

  Obesity is a risk factor associated with several lifestyle-related diseases, for example, diabetes, high blood pressure, hyperlipidemia and cancer. Caffeic acid 2-phenylethyl ester (CAPE, 1), a naturally-occurring compound found in various plants and propolis, which exhibits anti-inflammatory, immunomodulatory and cytotoxic activities and inhibits 3T3-L1 differentiation to adipocytes. As part of our efforts to moderate lifestyle-related diseases, we synthesized analogs of 1 and studied their effects on pancreatic lipase activities, lipid absorption, and 3T3-L1 differentiation. We found that catechols 1-4 show inhibitory activities against pancreatic lipase in a dose-dependent manner in vitro. Compounds 1-3 proved to be more potent inhibitors of pancreatic lipase than 5, 6, 8, and 9, which have one hydroxyl group, respectively. Compound 7 has three aromatic hydroxyl groups and restrains greater lipase inhibitory activity than the other compounds. In addition, 7 and 3 significantly suppress a rise in blood triglyceride (TG) levels in mice given corn oil orally. Furthermore, 2 and 3 are more potent at preventing 3T3-L1 differentiation (lipid accumulation) than 1, while 7 is more potent than 3, 8, and 9 in these assays. Compounds 2, 3, and 7 inhibit lipid absorption and accumulation, with new compound 7 being the most potent. These results indicate that 7 may have potential benefits as a health agent with anti-obesity properties. (C) 2015 Elsevier Ltd. All rights reserved.