1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one | 149732-52-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
• 英文别名: (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one；(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 149732-52-5
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: PALMCMYYFAHUGA-BPTNNVFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-丙烯醛,3-[4-[(四氢-2H-吡喃-2-基)氧代]苯基]-,(E)- 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
  参考文献：
  名称：

  Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids

  摘要：

  A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.105

文献信息

• METHOD TO PREPARE PURE CURCUMIN
  申请人：Kim Darrick S.H.L.

  公开号：US20100048957A1

  公开（公告）日：2010-02-25

  This invention describes a preparation of at least 99% by weight pure curcumin from less pure grades of curcumin utilizing phenol protecting groups to favor a selective recrystallization of curcumin in the presence of demethoxycurcumin and bis-demethoxycurcumin and other curcuminoids of minor composition.

  这项发明描述了利用酚保护基从较不纯的姜黄素中制备至少99%重量纯度的姜黄素，利用酚保护基有利于在去甲氧基姜黄素、双去甲氧基姜黄素和其他少量成分的姜黄素存在下选择性地重新结晶姜黄素。
• MALODOR COUNTERACTING COMPOSITIONS
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3101171A1

  公开（公告）日：2016-12-07

  A malodor counteracting composition contains a malodor counteractant that is capable of neutralizing a malodor and a stabilizer that is capable of decreasing or preventing self-polymerization of the malodor counteractant. The malodor counteractant has a backbone and one or more reactive end groups that are covalently attached to the backbone, the backbone has a molecular weight of 100 to 50,000 Daltons, and the one or more reactive end groups each have an α,β-unsaturated carbonyl group. Also disclosed are consumer, industrial or textile products containing the malodor counteracting composition and methods of neutralizing malodor using the composition.

  一种恶臭抑制组合物含有一种能够中和恶臭的恶臭抑制剂和一种能够减少或防止恶臭抑制剂自聚合的稳定剂。恶臭抑制剂具有骨架和一个或多个共价连接到骨架上的活性末端基团，骨架的分子量为 100 至 50,000 道尔顿，一个或多个活性末端基团各自具有一个 α、β-不饱和羰基。此外，还公开了含有恶臭抑制组合物的消费品、工业品或纺织品，以及使用该组合物中和恶臭的方法。
• Malodor counteracting compositions
  申请人：Sasaki Takashi

  公开号：US10226544B2

  公开（公告）日：2019-03-12

  A malodor counteracting composition contains a malodor counteractant that is capable of neutralizing a malodor and a stabilizer that is capable of decreasing or preventing self-polymerization of the malodor counteractant. The malodor counteractant has a backbone and one or more reactive end groups that are covalently attached to the backbone, the backbone has a molecular weight of 100 to 50,000 Daltons, and the one or more reactive end groups each have an α,β-unsaturated carbonyl group. Also disclosed are consumer, industrial or textile products containing the malodor counteracting composition and methods of neutralizing malodor using the composition.

  一种恶臭抑制组合物含有一种能够中和恶臭的恶臭抑制剂和一种能够减少或防止恶臭抑制剂自聚合的稳定剂。恶臭抑制剂具有骨架和一个或多个共价连接到骨架上的活性末端基团，骨架的分子量为 100 至 50,000 道尔顿，一个或多个活性末端基团各自具有一个 α、β-不饱和羰基。此外，还公开了含有恶臭抑制组合物的消费品、工业品或纺织品，以及使用该组合物中和恶臭的方法。
• Probiotic and polyphenol against neurodegeneration
  申请人：NESTEC S.A.

  公开号：US10912803B2

  公开（公告）日：2021-02-09

  A composition containing the probiotic strain Lactobacillus johnsonii CNCM 1-1225 in combination with a polyphenol for use in the treatment or prevention of a cognitive and/or neurodegenerative disorder, in particular Alzheimer's disease. The polyphenol can be one or more of rosmarinic acid, chicoric acid, or caftaric acid, and can be provided in the form of a plant extract.

  一种含有益生菌株约翰逊乳杆菌 CNCM 1-1225 和一种多酚的组合物，用于治疗或预防认知和/或神经退行性疾病，特别是阿尔茨海默氏症。多酚可以是迷迭香酸、菊苣酸或茶檀酸中的一种或多种，可以植物提取物的形式提供。
• Methods for treatment of beta-amyloid protein-induced ocular disease
  申请人：Kim S. H. L. Darrick

  公开号：US20060148905A1

  公开（公告）日：2006-07-06

  The invention provides methods for treating beta-amyloid protein-involved ocular disease including age-related macular degeneration and glaucoma, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., and Rosmarinus sp. and synthetic chemical analogues thereof, for the treatment of a beta-amyloid protein-involved ocular disease.

  本发明提供了治疗β-淀粉样蛋白参与的眼部疾病（包括老年性黄斑变性和青光眼）的方法、药物组合物和对其有用的化合物，以及使用这些化合物制造治疗上述疾病的药物。更具体地说，本发明涉及从以下植物中分离出的天然产物化合物的用途 莪术 sp、 薑 sp、 银杏叶、丹参 和 蔷薇 及其合成化学类似物，用于治疗受β-淀粉样蛋白影响的眼部疾病。