(9Z,12Z,15Z)-十八碳-9,12,15-三烯过氧酸 | 19356-22-0

• 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,15Z)-十八碳-9,12,15-三烯过氧酸
• 英文名称: linolenic acid hydroperoxide
• 英文别名: peroxylinolenic acid；13-Hydroperoxylinolenic acid；(9Z,12Z,15Z)-octadeca-9,12,15-trieneperoxoic acid
• CAS: 19356-22-0
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: OEYKGJFTEBHJCL-PDBXOOCHSA-N

物化性质

• 沸点：
  376.19°C (rough estimate)
• 密度：
  1.0726 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9Z,12Z,15Z)-十八碳-9,12,15-三烯过氧酸 在 sodium hydroxide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 4-carbamoyl-2-[(9Z,12Z)-(15,16-epoxy)octadeca-9,12-dienoylamino]butyric acid
  参考文献：
  名称：

  N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15,16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae

  摘要：

  N-(15,16-Dihydroxylinoleoyl)-glutamine (1) and N-(15,16-epoxylinoleoyl)-glutamine (2) and were identified in the regurgitant of lepidopteran larvae (Spodoptera exigua and Spodoptera frugiperda) by LC-MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1 were identified by GC-MS. The structures of both conjugates were confirmed by synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01489-8
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 air 、 没食子酸乙酯 作用下， 以 乙醇 为溶剂， 生成 (9Z,12Z,15Z)-十八碳-9,12,15-三烯过氧酸
  参考文献：
  名称：

  A simple and convenient method to determine the activities of antioxidants using .ALPHA.-methylindole reagent and high-performance thin-layer chromatography.

  摘要：

  本文介绍了一种利用α-甲基吲哚（MI）试剂结合高效薄层色谱法（HPTLC）测定化学物质抗氧化活性的简便方法。将 1 μl 含有 2% 亚麻酸和测试样品的乙醇溶液混合物涂抹在薄层色谱（TLC）板上，在 80°C 下过氧化 20 分钟。喷洒 MI 试剂后，TLC 上亚麻酸产生的脂质过氧化物被检测为粉红色斑点，用 TLC 密度计在 557 纳米波长下进行测量。测试样品的抗氧化活性用抑制亚麻酸过氧化 50%所需的量来表示。这种方法非常简单、快速，在测试样品数量很少的情况下非常有用。

  DOI：

  10.1248/cpb.34.174

文献信息

• 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。
• Methods and compositions for production of lipo-chito oligosaccharides by rhizobacteria
  申请人：——

  公开号：US20030096375A1

  公开（公告）日：2003-05-22

  Lipo-chito oligosaccharides (LCOs) are produced by culturing rhizobacteria cells in or on a culture medium comprising at least one of: jasmonic acid or a derivative thereof; linoleic acid or a derivative thereof; or linolenic acid or a derivative thereof. Preferably, the rhizobacteria cells are Bradyrhizobium japonicum cells having the identifying characteristics of B. japonicum strain USDA 3. Preferably, the derivative of jasmonic acid is an ester thereof, preferably methyl jasmonate. Also provided are methods for improving LCO production at low temperatures, particularly temperatures below 25° C.

  Lipo-chito寡糖（LCO）是通过在培养基中或在培养基上培养根瘤菌细胞时，至少包含以下物质之一：茉莉酸或其衍生物；亚油酸或其衍生物；或亚麻酸或其衍生物而产生的。最好使用具有B. japonicum USDA 3菌株的鉴定特征的Bradyrhizobium japonicum细胞。最好，茉莉酸衍生物是其酯，最好是甲基茉莉酸酯。还提供了在低温下，特别是25°C以下的条件下提高LCO产量的方法。
• Glutathione peroxidase, process for production thereof, method and composition for the quantitative determination of lipid peroxide
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0049078A2

  公开（公告）日：1982-04-07

  Glutathione peroxidase is produced by fermentation of a microorganism of the genus Mucor. The peroxidase is selenium free and may be used for the determination of lipid peroxide by oxidation of a reduced glutathione in the presence of the glutathione peroxidase, blocking the unreacted reduced glutathione, and determining the oxidised glutathione. Also disclosed is a reagent for the determination of lipid peroxide comprising the glutathione peroxidase, reduced glutathione, an SH blocking agent, alkali and a fluorescent agent.

  谷胱甘肽过氧化物酶是通过粘菌属微生物发酵产生的。该过氧化物酶不含硒，可用于在谷胱甘肽过氧化物酶存在下通过氧化还原型谷胱甘肽来测定过氧化脂质，阻断未反应的还原型谷胱甘肽，并测定氧化型谷胱甘肽。还公开了一种用于测定过氧化脂质的试剂，该试剂由谷胱甘肽过氧化物酶、还原型谷胱甘肽、SH 阻断剂、碱和荧光剂组成。
• Hydroperoxide lyases
  申请人：GIVAUDAN-ROURE (INTERNATIONAL) S.A.

  公开号：EP0801133A2

  公开（公告）日：1997-10-15

  The present invention relates to the production of HPO lyase proteins in hosts via recombinant expression of said proteins. Recombinant HPO lyase proteins, DNA sequences encoding these proteins, vectors containing these DNA sequences and hosts containing these vectors are provided, along with methods for recombinantly producing such proteins, DNA sequences, vectors and hosts. Also provided are processes for producing green note compounds.

  本发明涉及通过重组表达宿主中的HPO裂解酶蛋白。本发明提供了重组 HPO 裂解酶蛋白、编码这些蛋白的 DNA 序列、含有这些 DNA 序列的载体和含有这些载体的宿主，以及重组生产这些蛋白、DNA 序列、载体和宿主的方法。还提供了生产绿色音符化合物的工艺。
• PROCESS FOR PRODUCING KODA USING LEMNA PAUCICOSTATA
  申请人：Shiseido Company, Ltd.

  公开号：EP2546350A1

  公开（公告）日：2013-01-16

  The genes of a novel lipoxygenase and a novel allene oxide synthase derived from Lemna paucicostata strain SH are identified, and a plant growth regulator (KODA) is produced with high yield by using a Lemna paucicostata strain that expresses said lipoxygenase and said allene oxide synthase.

  确定了源自白柠檬（Lemna paucicostata）菌株 SH 的新型脂氧合酶和新型氧化烯合成酶的基因，并利用表达所述脂氧合酶和所述氧化烯合成酶的白柠檬菌株高产生产出植物生长调节剂（KODA）。