(9Z,12Z)-9,12-十八碳二烯酸-过氧化氢(1:1) | 7722-17-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (9Z,12Z)-9,12-十八碳二烯酸-过氧化氢(1:1)
• 英文名称: linoleic acid hydroperoxide
• 英文别名: linoleic acid hydroperoxyde；Peroxylinoleic acid；(9Z,12Z)-octadeca-9,12-dieneperoxoic acid
• CAS: 7722-17-0；25657-09-4
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: DRKSTAFYCRUMEE-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  linoleoylperoxy radical 在 2-叔丁基苯酚 、 sodium dodecyl-sulfate 作用下， 生成 (9Z,12Z)-9,12-十八碳二烯酸-过氧化氢(1:1)
  参考文献：
  名称：

  Inhibition kinetics of chain-breaking phenolic antioxidants in SDS micelles. Evidence that intermicellar diffusion rates may be rate-limiting for hydrophobic inhibitors such as .alpha.-tocopherol

  摘要：

  DOI：

  10.1021/ja00280a041

文献信息

• Multi-faceted Reactivity of Alkyltellurophenols Towards Peroxyl Radicals: Catalytic Antioxidant Versus Thiol-Depletion Effect
  作者：Riccardo Amorati、Luca Valgimigli、Peter Dinér、Khadijeh Bakhtiari、Mina Saeedi、Lars Engman

  DOI：10.1002/chem.201300451

  日期：2013.6.3

  ortho arrangement. In the presence of thiols, hydroxyaryl alkyl tellurides act as catalytic antioxidants towards both hydroperoxides (mimicking the glutathione peroxidases) and peroxyl radicals. The high efficiency of the quenching of the peroxyl radicals and hydroperoxides could be advantageous under normal cellular conditions, but pro‐oxidative (thiol depletion) when thiol concentrations are low.

  羟芳基烷基碲化物在有机溶液和水性双相体系中都是有效的抗氧化剂。他们以非常规的方式与ROO做出反应。在303 K时速率常数高达10 7  M -1  s -1的自由基，性能优于普通酚。反应通过氧原子转移到碲，然后氢原子转移到生成的RO进行。酚羟基的自由基。反应速率不反映环取代基的电子性质，并且由于反应发生在溶剂笼中，因此当OH和TeR基团具有邻位时，淬灭更为有效安排。在硫醇的存在下，羟芳基烷基碲化物作为对氢过氧化物（模仿谷胱甘肽过氧化物酶）和过氧自由基的催化抗氧化剂。在正常的细胞条件下，过氧自由基和氢过氧化物的高效淬灭可能是有利的，但是当硫醇浓度低时，会促进氧化（巯基耗竭）。
• Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions
  申请人：Doyle Michael P.

  公开号：US20090093638A1

  公开（公告）日：2009-04-09

  The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.

  本发明涉及在水相条件下实现有机分子的高效烯丙基氧化的组合物和方法，特别是烯烃和类固醇。该发明涉及使用二铑（II,II）“桨轮”配合物，特别是二铑羧酸酯和叔丁基过氧化氢作为催化剂进行反应。在烯丙基氧化7-酮类固醇中使用水相条件特别有优势，无法使用无水方法有效氧化，以及将烯丙基氧化扩展到烯酰胺和烯醇醚。
• [EN] USE OF CONDENSED BENZO[B]THIAZINE DERIVATIVES AS CYTOPROTECTANTS<br/>[FR] UTILISATION DE DÉRIVÉS DE BENZO[B]THIAZINE EN TANT QU'AGENTS CYTOPROTECTEURS
  申请人：MEDEIA THERAPEUTICS LTD

  公开号：WO2014191632A1

  公开（公告）日：2014-12-04

  The present invention relates to arylthiazine compounds, metabolites, N-oxides, amides, esters,pharmaceutically acceptable salts, hydrates and solvates thereof and their use as cytoprotectants in the treatment or prophylaxis of diseases or states, either acute or chronic, involving aberrant cellular lipid peroxidation in the central nervous system or in the periphery of the body. The present invention also relates to a method for their preparation and to pharmaceutical composition comprising as an active ingredient one or more of the aforementioned compounds.

  本发明涉及芳基噻嗪化合物、代谢物、N-氧化物、酰胺、酯、药用可接受盐、水合物和溶剂合物，以及它们在治疗或预防涉及中枢神经系统或身体周围存在异常细胞脂质过氧化的疾病或状态中作为细胞保护剂的用途。本发明还涉及它们的制备方法以及包含作为活性成分的上述化合物之一或多个的药物组合物。
• UVA irradiation of fatty acids and their oxidized products substantially increases their ability to generate singlet oxygen
  作者：Johannes Regensburger、Tim Maisch、Alena Knak、Anita Gollmer、Ariane Felgentraeger、Karin Lehner、Wolfgang Baeumler

  DOI：10.1039/c3cp51399h

  日期：——

  UVA radiation plays an important role for adverse reactions in human tissue. UVA penetrates epidermis and dermis of skin being absorbed by various biomolecules, especially endogenous photosensitizers. This may generate deleterious singlet oxygen (1O2) that oxidizes fatty acids in cell membranes, lipoproteins, and other lipid-containing structures such as the epidermal barrier. Indications exist that fatty acids are not only the target of 1O2 but also act as potential photosensitizers under UVA irradiation, if already oxidized. Five different fatty acids in ethanol solution (stearic, oleic, linoleic, linolenic and arachidonic acid) were exposed to UVA radiation (355 nm, 100 mW) for 30 seconds. 1O2 luminescence was detected time-resolved at 1270 nm and confirmed in spectrally-resolved experiments. The more double bonds fatty acids have the more 1O2 photons were detected. In addition, fatty acids were continuously exposed to broadband UVA for up to 240 min. During that time span, UVA absorption and 1O2 luminescence substantially increased with irradiation time, reached a maximum and decreased again. HPLC-MS analysis showed that the amount of peroxidized fatty acids and the 1O2 generation increased and decreased in parallel. This indicates the high potential of peroxidized fatty acids to produce 1O2 under UVA irradiation. In conclusion, fatty acids along with peroxidized products are weak endogenous photosensitizers but become strong photosensitizers under continuous UVA irradiation. Since fatty acids and their oxidized products are ubiquitous in living cells and in skin, which is frequently and long-lasting exposed to UVA radiation, this photosensitizing effect may contribute to initiation of deleterious photooxidative processes in tissue.

  UVA辐射在人类组织的不良反应中发挥着重要作用。UVA能够穿透皮肤的表皮和真皮，被各种生物分子吸收，特别是内源性光敏剂。这可能会产生有害的单重态氧（1O2），其会氧化细胞膜、脂蛋白和其他含脂结构（如表皮屏障）中的脂肪酸。有迹象表明，脂肪酸不仅是1O2的靶点，而且在已被氧化的情况下，还可以在UVA照射下充当潜在的光敏剂。在乙醇溶液中，五种不同的脂肪酸（硬脂酸、油酸、亚油酸、亚麻酸和花生酸）暴露于UVA辐射（355 nm，100 mW）下30秒。采用时间分辨法在1270 nm处检测到1O2的发光，并在光谱分辨实验中得到了确认。脂肪酸的双键数量越多，检测到的1O2光子就越多。此外，脂肪酸还在宽谱UVA下持续暴露长达240分钟。在此时间段内，UVA的吸收和1O2发光随着照射时间的增加显著上升，达到最大值后又下降。HPLC-MS分析显示，过氧化脂肪酸的量和1O2的生成在增加和减少的过程中是并行的。这表明过氧化脂肪酸在UVA照射下产生1O2的潜力很高。总之，脂肪酸及其过氧化产物作为弱的内源性光敏剂，但在持续的UVA照射下会成为强光敏剂。由于脂肪酸及其氧化产物在活细胞和皮肤中普遍存在，而皮肤往往会长时间暴露于UVA辐射中，这种光敏化效应可能会促成组织中有害光氧化过程的启动。
• [EN] COMPOUNDS COMPRISING A 3-PYRIDINOL OR 5-PYRIMIDINOL RING HAVING AN ORGANOSELENO OR ORGANOTELLURO SUBSTITUENT FOR USE AS ANTIOXIDANTS<br/>[FR] COMPOSÉS COMPRENANT UN NOYAU 3-PYRIDINOL OU 5-PYRIMIDINOL À SUBSTITUANT ORGANOSÉLÉNO OU ORGANOTELLURO UTILISÉS COMME ANTI-OXYDANTS
  申请人：KAROLINSKA INST INNOVATIONS AB

  公开号：WO2009144253A1

  公开（公告）日：2009-12-03

  Compounds comprising a 3-pyridinol or 5-pyrimidinol ring carrying an organoseleno- or organotelluro- substituent on the pyridine or pyrimidine ring, exhibit useful antioxidant properties. The compounds may for example be in accordance with the following formula (I) as defined herein. Catalytic chain-breaking and hydroperoxide decomposing antioxidant properties are also disclosed. Furthermore the compounds may be used in combination with a reducing agent. The compounds are useful for the stabilization of man-made and natural materials, or for the prevention or treatment of disorders caused by or involving free radical-mediated or oxidative tissue damage.

  含有3-吡啶醇或5-嘧啶醇环，在吡啶或嘧啶环上带有有机硒或有机碲取代基团的化合物，表现出有用的抗氧化性能。这些化合物可能符合以下定义的化学式(I)。还披露了催化链断裂和过氧化物分解抗氧化性能。此外，这些化合物可以与还原剂结合使用。这些化合物可用于稳定人造和天然材料，或用于预防或治疗由自由基介导或氧化组织损伤引起的疾病。