(5E)-6-(4-羟基-3-甲氧基苯基)-5-己烯-2,4-二酮 | 189181-53-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (5E)-6-(4-羟基-3-甲氧基苯基)-5-己烯-2,4-二酮
• 英文名称: (E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione
• 英文别名: feruloylacetone
• CAS: 189181-53-1
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: SQDOMQCCCHMXBP-HWKANZROSA-N

物化性质

• 熔点：
  125-141oC (dec.)
• 沸点：
  403.9±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (5E)-6-(4-羟基-3-甲氧基苯基)-5-己烯-2,4-二酮 在 boron trioxide 、 sodium hydroxide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 1.5h， 生成 1-(3-methoxy-4-hydroxyphenyl)-7-(4-oxoacetoxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Pharmacological protection of mitochondrial function mitigates acute limb ischemia/reperfusion injury

  摘要：

  We describe several novel curcumin analogues that possess both anti-inflammatory antioxidant properties and thrombolytic activities. The therapeutic efficacy of these curcumin analogues was verified in a mouse ear edema model, a rat arterial thrombosis assay, a free radical scavenging assay performed in PC12 cells, and in both in vitro and in vivo ischemia/reperfusion models. Our findings suggest that their protective effects partially reside in maintenance of optimal mitochondrial function. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.06.079
• 作为产物：
  描述：

  姜黄素 以 aq. phosphate buffer 为溶剂， 反应 2.0h， 生成 (5E)-6-(4-羟基-3-甲氧基苯基)-5-己烯-2,4-二酮
  参考文献：
  名称：

  阿魏酸丙酮可能是姜黄素的主要转化产物

  摘要：

  姜黄素是一些植物产生的酚类化合物，其中姜黄是该主要姜黄素中的一种。在升高的温度下，姜黄素降解为反式-6-（4'-羟基-3'-甲氧基苯基）-2,4-二氧代-5-己烯醛，香兰素，阿魏酸和阿魏酰甲烷，但是形成阿魏酰丙酮（（5E）-姜黄素降解过程中的6-（4-羟基-3-甲氧基苯基）己-5-烯-2,4-二酮）尚未见报道。作为实验结果，分别在碱性或酸性姜黄素溶液加热2小时后，甚至有28.8％或20.6％的降解姜黄素也转化为阿魏酰丙酮。MS n确认了鉴定出的阿魏酰丙酮的结构，HRMS和NMR数据。所提出的结果对于食品加工非常重要，因为在食品制备过程中会形成阿魏酰丙酮，而且其生物学活性尚未得到充分认识。

  DOI：

  10.1016/j.foodchem.2019.01.194

文献信息

• Synthesis and complexation properties of two new curcuminoid molecules bearing a diphenylmethane linkage
  作者：Agus Sundaryono、Aziz Nourmamode、Christian Gardrat、Alain Fritsch、Alain Castellan

  DOI：10.1016/s0022-2860(03)00050-4

  日期：2003.4

  and 4 , bearing a diphenylmethane bridge for both compounds and a crown ether chain adapted to complex Li + for compound 4 , were synthesized and characterized by mass and NMR spectroscopies. By their preorganized geometry, they represent a new class of curcuminoids able to complex transition metal cations. Their absorption spectra in DMF by comparison with those of curcumin 1 and dimethylcurcumin

  摘要 双姜黄素类化合物 3 和 4 被合成并通过质谱和核磁共振光谱表征，这两个化合物都带有一个二苯甲烷桥和一个适合化合物 4 络合 Li + 的冠醚链。通过其预先组织的几何形状，它们代表了一类能够络合过渡金属阳离子的新型姜黄素。与姜黄素 1 和二甲基姜黄素 2 的吸收光谱相比，它们在 DMF 中的吸收光谱表明，两半中的酚盐形式在化合物 3 中相互作用，而在化合物 4 中是独立的。络合研究表明类姜黄素对过渡金属的选择性较差。然而，通过紫外可见吸收光谱研究的 Cu (II) 络合显示出姜黄素 1 和双类姜黄素 3 之间的细微差异。
• Discovery of novel anti-tumor curcumin analogues from the optimization of curcumin scaffold
  作者：Laiyin Zhang、Haiyang Zong、Huiping Lu、Jingru Gong、Fenfen Ma

  DOI：10.1007/s00044-017-1946-2

  日期：2017.10

  A series of novel curcumin analogues were synthesized by optimization of its aromatic ring. The antiproliferative activities of these analogues were screened against four human cancer cell lines by MTT assay and some displayed significant improvement in antiproliferative activity compared with curcumin. The most potent compound 10 exhibited antiproliferative activity against Caco-2, Bel-7402, MDA-MB-231

  通过优化其芳香环合成了一系列新型姜黄素类似物。通过MTT测定法筛选了这些类似物对四种人类癌细胞系的抗增殖活性，并且与姜黄素相比，有些具有抗增殖活性。最有效的化合物10对Caco-2，Bel-7402，MDA-MB-231和DU145癌细胞表现出抗增殖活性，IC 50值分别为2.04、1.54、4.99和3.22μM。Annexin V /碘化丙啶双重染色和流式细胞仪细胞周期分析，使用碘化丙啶DNA染色显示化合物10诱导Bel-7402细胞的G1期凋亡和细胞周期停滞，呈剂量依赖性。此外，在肝癌异种移植的体内小鼠模型中，化合物10以20mg / kg /天的剂量基本上抑制肝肿瘤生长，而没有可观察到的毒性作用。
• The annular tautomerism of the curcuminoid NH-pyrazoles
  作者：Pilar Cornago、Pilar Cabildo、Rosa M. Claramunt、Latifa Bouissane、Elena Pinilla、M. Rosario Torres、José Elguero

  DOI：10.1039/b812018h

  日期：——

  The structures of four NH-pyrazoles, (E)-3,5-bis[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-1H-pyrazole (3), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-5(3)-methyl-1H-pyrazole (4), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) and (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8), have been determined by X-ray crystallography. Compounds that have a phenol residue crystallize forming sheets that are stabilized by a complex pattern of hydrogen bonds between a unique tautomer (4), or by a 2 : 1 mixture of both tautomers (5) (these tautomers being identical in the case of 3). Pyrazole 8, which lacks OH groups, crystallizes in cyclic dimers that are stabilized by N–H⋯N hydrogen bonds. The tautomerism in solution and in the solid state was determined by 13C and 15N CPMAS NMR spectroscopy. For compounds 4, 5 and 8, the solid state results agree with those observed by crystallography; the most abundant tautomer in solution coincides with the tautomer present in the solid state (4 and 8) or with the most abundant tautomer in the crystal (5).

  四种 NH 吡唑的结构：(E)-3,5-双[β-(4-羟基-3-甲氧基苯基)-乙烯基]-1H-吡唑 (3)、(E)-3(5)-[β-(4-羟基-3-甲氧基苯基)-乙烯基]-5(3)-甲基-1H-吡唑 (4)、(E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) 和 (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8) 已通过 X 射线晶体学测定。含有苯酚残基的化合物在结晶时会形成薄片，这些薄片通过独特的同分异构体（4）或两种同分异构体（5）的 2:1 混合物（3 的同分异构体完全相同）之间复杂的氢键模式来稳定。缺乏羟基的吡唑 8 结晶为环状二聚体，通过 N-H⋯N 氢键稳定。13C 和 15N CPMAS NMR 光谱测定了溶液和固态中的同分异构现象。对于化合物 4、5 和 8，固态结果与晶体学观察到的结果一致；溶液中含量最高的同分异构体与固态中的同分异构体（4 和 8）或晶体中含量最高的同分异构体（5）一致。
• Detoxification of amyloid β fibrils by curcumin derivatives and their verification in a <i>Drosophila</i> Alzheimer's model
  作者：Rohmad Yudi Utomo、Atsushi Sugie、Satoshi Okada、Kazuki Miura、Hiroyuki Nakamura

  DOI：10.1039/d1cc07000b

  日期：——

  Curcumin derivatives B and N were developed as disaggregation agents of amyloid β (Aβ) fibrils. The detoxification provided by each compound at a concentration of 1 μM was observed in neuroblastoma cells. Furthermore, both compounds significantly rescued locomotion dysfunction in an Aβ-expressing Drosophila model of Alzheimer's disease.

  姜黄素衍生物B和N被开发为淀粉样蛋白 β (Aβ) 原纤维的解聚剂。在神经母细胞瘤细胞中观察到浓度为 1 μM 的每种化合物提供的解毒作用。此外，这两种化合物都显着挽救了阿尔茨海默病Aβ 表达果蝇模型中的运动功能障碍。
• Hydroxyphenylalkadiones and Their Use for Masking Bitter Taste and/or for Intensifying Sweet Taste
  申请人：Ley Jakob

  公开号：US20080227866A1

  公开（公告）日：2008-09-18

  The use of a hydroxyphenylalkadione derivative of the formula (I) wherein, for X, a and Y: X is a —CH 2 —, —NH— or —O— group, Y is a —CH 2 — group and a is a single bond or X and Y are in each case a —CH— group and a is a double bond in the Z or E configuration, wherein, for R 1 , R 2 and R 3 R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group and R 2 and R 3 independently of one another denote hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 1 and R 2 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 1 and R 2 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 3 denotes hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 2 and R 3 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 2 and R 3 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group, wherein, for R 4 and R: R 4 and R independently of one another denote hydrogen, methyl or ethyl and wherein, for R 5 , R 6 and R 7 : R 5 , R 6 and R 7 independently of one another denote hydrogen or an aliphatic radical having 1 to 4 C atoms, a salt of such a hydroxyphenylalkadione of the formula (I), a mixture comprising or consisting of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, a mixture comprising or consisting of salts of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, or a mixture comprising or consisting of a hydroxyphenylalkadione of the formula (I) or two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, and a salt of a hydroxyphenylalkadione of the formula (I) or two or more salts of different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, for modifying, masking or reducing the unpleasant flavour impression of an unpleasantly tasting substance and/or for intensifying the sweet taste of a sweet-tasting substance and/or the sweet odour impression of an aroma substance which causes a sweet odour impression, as well as formulations and processes including a hydroxyphenylalkadione of the formula (I), are described.

  本文描述了使用公式（I）的羟基苯基丙酮衍生物的用途，其中，对于X、a和Y： X是一个-CH2-，-NH-或-O-基团， Y是一个-CH2-基团， a是一个单键； 或者X和Y在每种情况下都是一个-CH-基团，并且在Z或E构型中有一个双键； 对于R1、R2和R3，它们分别表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； R2和R3独立地表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R1和R2共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R1和R2表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代，而R3表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R2和R3共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R2和R3表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代； R1表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； 对于R4和R： R4和R分别独立地表示氢、甲基或乙基； 对于R5、R6和R7： R5、R6和R7分别独立地表示氢或具有1至4个C原子的脂肪基； 本文还描述了使用公式（I）的羟基苯基丙酮衍生物的盐，包括或仅包括两种或两种以上不同的公式（I）的羟基苯基丙酮衍生物的混合物，其中X、a、Y、R、R1、R2、R3、R4、R5、R6和R7在每种情况下具有上述给定的含义，以及包括公式（I）的羟基苯基丙酮衍生物的制剂和过程，用于修改、掩盖或减少令人不愉快的味道物质的不愉快的口感印象，以及用于增强甜味物质的甜味和/或引起甜味印象的香气物质的甜味气味印象。