2-[(4Z,7Z,10E)-十五碳-4,7,10-三烯-2-基]苯-1,3-二醇 | 79473-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-[(4Z,7Z,10E)-十五碳-4,7,10-三烯-2-基]苯-1,3-二醇
• 英文名称: 5[8′(Z),11′(Z),14′-pentadecatrienyl]resorcinol
• 英文别名: [5-(8Z,11Z)-8,11,14-pentadecatrien-1-yl-1,3-benzenediol]；5-[(8Z,11Z)-pentadeca-8,11,14-trien-1-yl]resorcinol；cardol (C15:3)；cardol triene；5-(Pentadeca-8,11,14-trien-1-yl)resorcinol；5-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzene-1,3-diol
• CAS: 79473-24-8
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: OOXBEOHCOCMKAC-UTOQUPLUSA-N

物化性质

• 沸点：
  470.0±40.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：15mg/mL；乙醇：22mg/mL；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4Z,7Z,10E)-十五碳-4,7,10-三烯-2-基]苯-1,3-二醇 、 硫酸二甲酯 在 potassium carbonate 作用下， 反应 30.0h， 生成 1,3-Dimethoxy-5-((8Z,11Z)-pentadeca-8,11,14-trienyl)-benzene
  参考文献：
  名称：

  长链酚。第17部分。5-[（Z）-十五烷基-8-烯基]间苯二酚，'cardol monoene'和5-[（ZZ）-十五烷基-8,11-二烯基]-间苯二酚二甲醚，'cardol'的合成二烯二甲醚

  摘要：

  合成了两种“ cardol”系列中的不饱和化合物，这是一种来自西洋参（Anacardium occidentale）的重要成分酚。3,5-二甲氧基苯甲醛在锂的存在下与OH保护的6-氯己-1-醇相互作用，经过酸处理后生成1-（3,5-二甲氧基苯基）庚烷-1,7-二醇，将其选择性地氢解为7-（3,5-二甲氧基苯基）庚-1-醇。转化为溴化物并进行硫代辛基-1-炔的烷基化，得到5-（十五烷基-8-炔基）间苯二酚二甲醚，其被选择性地转化为8-（Z）-烯烃。用碘化锂脱甲基得到5-[（Z）-十五烷-8-烯基间苯二酚，与“心单烯”相同。7-（3,5-二甲氧基苯基）庚基溴化物与OH保护的炔丙醇的锂衍生物反应，经酸处理后得到10-（3,5-二甲氧基苯基）dec-2-yn-1-ol。用戊-1-炔基溴化镁制得5-戊基-8，11-二炔基间苯二酚二甲醚。选择性氢化得到5-[（ZZ）-pentadeca-8,11-二烯基]间苯二酚二甲醚，与“

  DOI：

  10.1039/p19810000132

文献信息

• Two Novel Alkylresorcinol Synthase Genes from Sorghum; Cloning, Expression, Transformation and Characterization
  申请人：Baerson Scott R.

  公开号：US20110225676A1

  公开（公告）日：2011-09-15

  Sorghum is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8′,11′,14′-pentadecatriene]-p-benzoquinone) which likely accounts for much of its allelopathic properties. Prior investigations into the biosynthesis of sorgoleone have suggested the participation of one or more alkylresorcinol synthases (ARS), which are type III polyketide synthases (PKS) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells, involving the synthesis of a 5-pentadecatrienyl resorcinol intermediate derived from an unusual 16:3 fatty acyl-CoA starter unit. To characterize the enzymes responsible for the biosynthesis of this alkylresorcinol intermediate, a previously-described expressed sequence tag (EST) database prepared from isolated root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that two of these sequences were preferentially expressed in root hairs, and recombinant enzyme studies demonstrated that both sequences (designated ARS1 and ARS2) encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units. Furthermore, RNA interference (RNAi) experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols.

  高粱被认为是一种化感作物，产生植物毒素，如脂肪苯醌sorgoleone（2-羟基-5-甲氧基-3-[(Z，Z)-8'，11'，14'-十五碳烯三烯基]-p-苯醌），这很可能解释了其大部分化感特性。对sorgoleone生物合成的先前研究表明，参与其中的是一种或多种烷基间苯酚合酶（ARS），它们是III型聚酮合酶（PKS），使用中到长链脂肪酰辅酶A起始单元通过与丙酰辅酶A的迭代缩合产生5-烷基间苯酚。目前的证据表明，sorgoleone生物合成仅发生在根毛细胞中，涉及从不寻常的16：3脂肪酰辅酶A起始单元衍生的5-十五碳烯三烯基间苯酚中间体的合成。为了表征负责合成这种烷基间苯酚中间体的酶，首先从分离的根毛制备的已描述表达序列标签（EST）数据库中挖掘所有类似于PKS的序列。定量实时RT-PCR分析表明，其中两个序列在根毛中优先表达，重组酶研究表明这两个序列（称为ARS1和ARS2）编码的ARS酶能够接受各种脂肪酰辅酶A起始单元。此外，针对ARS1和ARS2的RNA干扰（RNAi）实验导致产生多个独立的转化事件，其sorgoleone水平显著降低。因此，ARS1和ARS2都可能参与植物中sorgoleone的生物合成。ARS1和ARS2的序列还用于鉴定编码ARS的几个水稻基因，这些基因可能参与产生与防御相关的烷基间苯酚。
• A Functional Genomics Investigation of Allelochemical Biosynthesis in Sorghum bicolor Root Hairs
  作者：Scott R. Baerson、Franck E. Dayan、Agnes M. Rimando、N. P. Dhammika Nanayakkara、Chang-Jun Liu、Joachim Schröder、Mark Fishbein、Zhiqiang Pan、Isabelle A. Kagan、Lee H. Pratt、Marie-Michèle Cordonnier-Pratt、Stephen O. Duke

  DOI：10.1074/jbc.m706587200

  日期：2008.2

  Sorghum is considered to be one of the more allelopathic crop species, producing phytotoxins such as the potent benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8',11',14'-pentadecatriene]-p-benzoquinone) and its analogs. Sorgoleone likely accounts for much of the allelopathy of Sorghum spp., typically representing the predominant constituent of Sorghum bicolor root exudates. Previous and ongoing

  高粱被认为是变感作用较强的农作物之一，可产生植物毒素，例如强效的苯醌高粱酮（2-羟基-5-甲氧基-3-[（Z，Z）-8'，11'，14'-十五碳三烯]。 -对-苯醌）及其类似物。高粱油酸可能是高粱属植物化感作用的大部分，通常代表高粱双色根系分泌物的主要成分。先前和正在进行的研究表明，这种植物生长抑制剂的生物合成途径发生在根毛细胞中，涉及利用非典型的16：3脂肪酰基辅酶A起始单元的聚酮化合物合酶活性，从而导致戊三烯间苯二酚中间体的形成。该间苯二酚中间体的后续修饰可能由S-腺苷甲硫氨酸依赖性O-甲基转移酶和细胞色素P450单加氧酶的二羟基化介导，尽管之前尚未确定确切的反应顺序。通过气相色谱-质谱法对高粱根提取物进行的分析确定了可能的十五碳三烯基间苯二酚中间体的3-甲基醚衍生物，表明间苯二酚环的二羟基化作用是在3'-位进行O-甲基化，然后是新的5-利用正烷基（烯）基间苯二酚的O-甲基转移酶活性。
• Dioxygenation of Long-Chain Alkadien(trien)ylphenols by Soybean Lipoxygenase
  作者：Monika Roth、Birgit Gutsche、Markus Herderich、Hans-Ulrich Humpf、Peter Schreier

  DOI：10.1021/jf980196a

  日期：1998.8.17

  Long-chain alkadien(trien)ylphenols, i.e., cardanols, cardols, and anacardic acids, as well as their acetylated and methylated derivatives were used in enzymatic dioxygenation catalyzed by soybean lipoxygenase-1 (LOX-1). Kinetic studies revealed the influence of functional groups, chain length, number of double bonds, and the distance of the double bonds from the terminal end. Free functional groups were found to be a structural prerequisite for high affinity and turnover number; exceptional kinetic parameters were obtained for omega-6 compounds possessing the same chain length as linoleic acid. The regioselectivity and enantioselectivity of LOX-1 catalysis were investigated with 3-[(Z,Z)-8',11'-pentadecadienyl]phenol as the representative substrate, yielding 3-[12'-(S)-hydroperoxy-(Z,E)-8',10'-pentadecadienyl]phenol as the main product, Our extensive chromatographic and spectroscopic studies comprised HPLC-MS/MS for differentiation of the regioisomers, H-1 NMR spectroscopy for determination of the double-bond configuration, GC-MS to evaluate the enantiomeric excess, and exciton-coupled circular dichroism for determination of the absolute configuration.
• EP0897400A4
  申请人：——

  公开号：EP0897400A4

  公开（公告）日：1999-03-17
• WOOD-PRODUCT LAMINATED COMPOSITES
  申请人：Borden Chemical, Inc.

  公开号：EP0897400A1

  公开（公告）日：1999-02-24