(+)-脱落醛 | 41944-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (+)-脱落醛
• 中文别名: (+)-脱落酸中间体
• 英文名称: (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal
• 英文别名: methyl (1'S,2Z,4E,)-5-(1-hydroxy-4-oxo-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methyl-2,4-pentadienal；(+)-abscisyl aldehyde；abscisic aldehyde；(2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienal
• CAS: 41944-86-9
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: RIKWDZWVHUIUAM-KICRZJJPSA-N

物化性质

• 熔点：
  >117oC (dec.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-脱落醛 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 生成 (+)-脱落酸
  参考文献：
  名称：

  合成von（+）-Abscisinsäure

  摘要：

  （+）-脱落酸的合成。

  DOI：

  10.1002/hlca.19890720222
• 作为产物：
  描述：

  (+)-脱落酸 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 草酰氯 作用下， 以 乙酸乙酯 、 Petroleum ether 为溶剂， 反应 4.0h， 生成 (+)-脱落醛
  参考文献：
  名称：

  从 (S)-(+)-ABA 制备对映体纯脱落酸 (ABA) 类似物的简单方法

  摘要：

  摘要 (1'S, 2Z, 4E)-3-Methyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexenyl)-2,4-pentadienoic acid (abscisic acid, ABA ) 使用现成的试剂（草酰氯、NaBH4、MnO2）和简单的反应条件有效地转化为相应的醛、伯醇和三醇衍生物。

  DOI：

  10.1080/00397919708006821

文献信息

• Synthesis of chiral acetylenic analogs of the plant hormone abscisic acid
  作者：Patricia A. Rose、Suzanne R. Abrams、Angela C. Shaw

  DOI：10.1016/s0957-4166(00)80288-8

  日期：1992.1

  Syntheses of optically active acetylenic analogs of abscisic acid are described. The key step involves the diastereoselective alkylation of the (2S,3S)-butanediol ketal of oxoisophorone, which produces a 3:1 mixture of separable diastereoisomers. The absolute stereochemistry of the analogs was established by conversion to a known derivative and by correlation of ORD data.

  描述了脱落酸的光学活性炔属类似物的合成。关键步骤涉及氧代异佛尔酮的（2S，3S）-丁二醇缩酮的非对映选择性烷基化，生成可分离的非对映异构体的3：1混合物。类似物的绝对立体化学是通过转化为已知的衍生物并通过ORD数据的相关性建立的。
• Synthese von optisch aktiven, nat�rlichen Carotinoiden und strukturell verwandten Verbindungen. III. Synthese von (+)-Abscisins�ure, (?)-Xanthoxin, (?)-Loliolid, (?)-Actinidiolid und (?)-Dihydroactinidiolid
  作者：Frnak Kienzle、Hans Mayer、Rudolf E. Minder、Hans Thommen

  DOI：10.1002/hlca.19780610733

  日期：1978.11.1

  Synthesis of optically active natural carotenoids and structurally related compounds. III. Synthesis of (+)-abscisic acid, (−)-xanthoxin, (−)-loliolide, (−)-actinidiolide, and (−)-dihydroactinidiolide

  光学活性天然类胡萝卜素和结构相关化合物的合成。三，（+）-脱落酸，（-）-黄嘌呤毒素，（-）-卤代内酯，（-）-肌diol糖酐和（-）-二氢肌ini糖酐的合成
• MATERIALS AND METHODS FOR IMMUNOASSAY OF PTERINS
  申请人：Adamczyk Maciej

  公开号：US20120115244A1

  公开（公告）日：2012-05-10

  Methods of assaying for (i) a pterin by immunoassay employing a pterin as capture agent, (ii) neopterin by chemiluminescent microparticle immunoassay (CMIA) employing an anti-neopterin antibody (Ab) as capture agent, (iii) neopterin by an immunoassay (IA) employing an acridinium (Acr)-labeled anti-neopterin Ab as conjugate, and (iv) neopterin by an IA employing Acr-labeled neopterin as tracer; an Acr-labeled anti-neopterin Ab; a conjugate/complex comprising anti-neopterin Ab and a carrier scaffold; a conjugated pterin; a conjugate comprising an Acr-labeled pterin and a carrier scaffold; an immunogen comprising neopterin and a carrier protein; a conjugate comprising such an immunogen and an Acr compound; an immunogen comprising a carrier protein and a neopterin hapten; a conjugate comprising such an immunogen and an Acr compound; a kit for assaying a pterin comprising a pterin as a capture agent and instructions for IA; and a kit for assaying neopterin comprising an anti-neopterin Ab as a capture agent and instructions for CMIA, neopterin comprising an Acr-labeled anti-neopterin Ab as a conjugate and instructions for IA, or Acr-labeled neopterin as a tracer and instructions for IA.

  测定(i)一种黄素的免疫测定方法，采用一种黄素作为捕获试剂，(ii)一种新生黄素的化学发光微粒免疫测定(CMIA)方法，采用一种抗新生黄素抗体(Ab)作为捕获试剂，(iii)一种新生黄素的免疫测定(IA)方法，采用一种荧光素(Acr)标记的抗新生黄素抗体作为结合物，以及(iv)一种新生黄素的免疫测定方法，采用Acr标记的新生黄素作为追踪物；一种Acr标记的抗新生黄素抗体；一种包含抗新生黄素抗体和载体支架的结合物/复合物；一种共轭的黄素；一种包含Acr标记的黄素和载体支架的结合物；一种含有新生黄素和载体蛋白的免疫原；一种包含这种免疫原和Acr化合物的结合物；一种含有载体蛋白和新生黄素半抗原的免疫原；一种包含这种免疫原和Acr化合物的结合物；一种黄素测定试剂盒，包括一种黄素作为捕获试剂和IA的说明书；以及一种新生黄素测定试剂盒，包括一种抗新生黄素抗体作为捕获试剂和CMIA的说明书，或者包括一种Acr标记的抗新生黄素抗体作为结合物和IA的说明书，或者包括一种Acr标记的新生黄素作为追踪物和IA的说明书。
• Aldehyde Oxidase and Xanthine Dehydrogenase in a<i>flacca</i> Tomato Mutant with Deficient Abscisic Acid and Wilty Phenotype1
  作者：Moshe Sagi、Robert Fluhr、S. Herman Lips

  DOI：10.1104/pp.120.2.571

  日期：1999.6.1

  The flacca tomato (Lycopersicon esculentum) mutant displays a wilty phenotype as a result of abscisic acid (ABA) deficiency. The Mo cofactor (MoCo)-containing aldehyde oxidases (AO; EC 1.2.3.1) are thought to play a role in the final oxidation step required for ABA biosynthesis. AO and related MoCo-containing enzymes xanthine dehydrogenase (XDH; EC 1.2.1.37) and nitrate reductase (EC 1.6.6.1) were examined in extracts of the flacca tomato genotype and of wild-type (WT) roots and shoots. The levels of MoCo were found to be similar in both genotypes. No significant XDH or AO (MoCo-containing hydroxylases) activities were detected inflacca leaves; however, the mutant exhibited considerable MoCo-containing hydroxylase activity in the roots, which contained notable amounts of ABA. Native western blots probed with an antibody to MoCo-containing hydroxylases revealed substantial, albeit reduced, levels of cross-reactive protein in the flaccamutant shoots and roots. The ABA xylem-loading rate was significantly lower than that in the WT, indicating that the flacca is also defective in ABA transport to the shoot. Significantly, in vitro sulfurylation with Na2S reactivated preexisting XDH and AO proteins in extracts from flacca, particularly from the shoots, and superinduced the basal-level activity in the WT extracts. The results indicate that in flacca,MoCo-sulfurylase activity is impaired in a tissue-dependent manner.

  flacca番茄（Lycopersicon esculentum）突变体因缺乏脱落酸（ABA）而表现出萎缩表型。钼辅因子（MoCo）含有的醛氧化酶（AO; EC 1.2.3.1）被认为在ABA生物合成所需的最终氧化步骤中发挥作用。AO和相关的MoCo含有的酶黄嘌呤脱氢酶（XDH; EC 1.2.1.37）和硝酸还原酶（EC 1.6.6.1）在flacca番茄基因型和野生型（WT）根和茎的提取物中进行了检查。发现两种基因型中MoCo的水平相似。在flacca的叶片中没有检测到显著的XDH或AO（MoCo含有的羟化酶）活性; 然而，突变体的根部表现出相当数量的MoCo含有的羟化酶活性，其中含有显著的ABA。原生西方印迹用MoCo含有的羟化酶抗体探测显示出flacca突变体的茎和根中存在大量的交叉反应蛋白，尽管水平有所降低。ABA木质部装载速率显著低于WT，表明flacca在ABA运输到茎中也存在缺陷。值得注意的是，在体外用Na2S进行硫酸化可重新激活flacca提取物中预先存在的XDH和AO蛋白质，特别是来自茎的提取物，并超诱导WT提取物中的基础水平活性。结果表明，在flacca中，MoCo-硫酸化酶活性受到组织依赖性的损害。

• The <i>Arabidopsis</i> aldehyde oxidase 3 ( <i>AAO3</i> ) gene product catalyzes the final step in abscisic acid biosynthesis in leaves
  作者：Mitsunori Seo、Anton J. M. Peeters、Hanae Koiwai、Takayuki Oritani、Annie Marion-Poll、Jan A. D. Zeevaart、Maarten Koornneef、Yuji Kamiya、Tomokazu Koshiba

  DOI：10.1073/pnas.220426197

  日期：2000.11.7

  Abscisic acid (ABA) is a plant hormone involved in seed development and germination and in responses to various environmental stresses. The last step of ABA biosynthesis involves oxidation of abscisic aldehyde, and aldehyde oxidase (EC 1.2.3.1 ) is thought to catalyze this reaction. An aldehyde oxidase isoform, AOδ, encoded by AAO3 , one of four Arabidopsis aldehyde oxidase genes ( AAO1 , AAO2 , AAO3 , and AAO4 ), is the most likely candidate for the enzyme, because it can efficiently catalyze the oxidation of abscisic aldehyde to ABA. Here, we report the isolation and characterization of an ABA-deficient Arabidopsis mutant that maps at the AAO3 locus. The mutant exhibits a wilty phenotype in rosette leaves, but seed dormancy is not affected. ABA levels were significantly reduced in the mutant leaves, explaining the wilty phenotype in rosettes, whereas the level in the mutant seeds was less reduced. No AOδ activity could be detected in the rosette leaves of the mutant. Sequence data showed that the mutant contains a G to A substitution in the AAO3 gene. The mutation causes incorrect splicing of the ninth intron of AAO3 mRNA. We thus conclude that the ABA-deficient mutant is impaired in the AAO3 gene and that the gene product, AOδ, is an aldehyde oxidase that catalyzes the last step of ABA biosynthesis in Arabidopsis , specifically in rosette leaves. Other aldehyde oxidases may be involved in ABA biosynthesis in other organs.

  脱落酸（ABA）是一种植物激素，参与种子的发育和萌发以及对各种环境压力的响应。ABA生物合成的最后一步涉及脱落醛的氧化，醛氧化酶（EC 1.2.3.1）被认为催化这个反应。一种醛氧化酶亚型AOδ，由四个阿拉伯芥醛氧化酶基因（AAO1，AAO2，AAO3和AAO4）之一编码的AOδ，是该酶的最可能候选者，因为它可以有效催化脱落醛的氧化为ABA。在这里，我们报道了一个ABA缺陷的阿拉伯芥突变体，在AAO3位点上映射。突变体在莲座叶上表现出枯萎的表型，但种子休眠不受影响。突变体叶片中ABA水平显著降低，解释了莲座叶中枯萎表型，而突变体种子中的水平较少降低。在突变体的莲座叶中无法检测到AOδ活性。序列数据显示，突变体在AAO3基因中含有G到A的突变。该突变导致AAO3 mRNA的第九个内含子的错误剪接。因此，我们得出结论，ABA缺陷突变体在AAO3基因中受损，基因产物AOδ是一种醛氧化酶，催化阿拉伯芥中ABA生物合成的最后一步，特别是在莲座叶中。其他醛氧化酶可能参与其他器官的ABA生物合成。