2,4-dimethoxy-6-heptadecylphenol | 144189-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-dimethoxy-6-heptadecylphenol
• 英文别名: Phaffiaol；2-heptadecyl-4,6-dimethoxyphenol
• CAS: 144189-26-4
• 化学式: C₂₅H₄₄O₃
• 分子量: 392.623
• InChiKey: PCBROMAIRGVTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2,4-dimethoxy-6-heptadecylphenol 在 吡啶 作用下， 反应 1.0h， 生成 phaffiaol acetate
  参考文献：
  名称：

  夫夫酚，一种从酵母夫夫酵母中分离出来的新型抗氧化剂。

  摘要：

  DOI：

  10.7164/antibiotics.51.508
• 作为产物：
  描述：

  (E/Z)-2,4-dibromo-6-(1-heptadecenyl)phenol 在 platinum(IV) oxide 2,4,6-三甲基吡啶 、 copper(l) iodide 、 氢气 、 sodium methylate 作用下， 以 乙酸乙酯 为溶剂， 反应 17.0h， 生成 2,4-dimethoxy-6-heptadecylphenol
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Phaffiaol and Related Antioxidants.

  摘要：

  通过从3,5-二溴水杨醛（2）开始的三个反应步骤，实现了从Phaffia rhodozyma中分离得到的强效抗氧化剂phaffiaol（1）这一新型长链烷基酚的完全合成。我们还制备了几种具有不同芳环或不同碳链长度的长链烷基酚，并通过兔红细胞膜系统评估了它们的抗氧化活性。在这些化合物中，具有十七烷基侧链且位于羟基邻位的甲氧基酚衍生物（6c、d、7）的活性约为α-生育酚的两倍。此外，侧链具有15个碳原子的4-甲氧基-2-十五烷基酚（10h）显示出最高的活性。

  DOI：

  10.1248/cpb.46.1688

文献信息

• Antimalarial agent, methods and uses thereof
  申请人：UNIVERSIDADE DO PORTO

  公开号：US10287228B2

  公开（公告）日：2019-05-14

  The present disclosure relates to compounds and compositions for the treatment of malarian diseases. The compounds comprise a class of halogenated alkyl-aromatic secondary metabolites, including hierridic C, or pharmaceutically acceptable salts, esters, solvates or prodrugs thereof. The compounds comprise a halogen; C1-C6 alkyl, H, COCH3, COH, CO-alkyl, or CO-aryl; and a C3-C30 alkyl. In at least one embodiment, the compound is 3-chloro-4,6-dimethoxy-2-pentadecylphenol. The present disclosure also relates to methods of obtain the compounds from a solution comprising a cyanobacterium.

  本公开涉及用于治疗恶性疾病的化合物和组合物。这些化合物包括一类卤代烷基芳香族次生代谢物，包括hierridic C，或其药学上可接受的盐、酯、溶液或原药。这些化合物包括卤素；C1-C6 烷基、H、COCH3、COH、CO-烷基或 CO-芳基；以及 C3-C30 烷基。在至少一个实施方案中，化合物是 3-氯-4,6-二甲氧基-2-十五烷基酚。本公开还涉及从包含蓝藻的溶液中获得上述化合物的方法。
• ANTIMALARIAL AGENT, METHODS AND USES THEREOF
  申请人：Universidade do Porto

  公开号：EP3313807B1

  公开（公告）日：2019-11-13
• [EN] ANTIMALARIAL AGENT, METHODS AND USES THEREOF<br/>[FR] AGENT ANTIPALUDIQUE, PROCÉDÉS ET UTILISATIONS CORRESPONDANTS
  申请人：UNIV DO PORTO

  公开号：WO2016207869A1

  公开（公告）日：2016-12-29

  The present disclosure relates to compound of the formula I wherein R1 is a halogen; R2, R4 are independently selected from a group consisting of C1–C6 alkyl, H, COCH3, COH, CO-alkyl, CO-aryl; R3 is a C3–C30 alkyl; or a pharmaceutically acceptable salt, ester, solvate or prodrug thereof, for use in medicine, in particular as antimalarial agent. The present solution relates to halogenated alkyl-aromatic secondary metabolites, in particular hierridin C from the cyanobacterium Cyanobium sp. LEGE 06113 - which was received on 29 May 2015 and accepted for deposit for patent purposes on 15th June 2015 at the Scottish Association for Marine Science Culture Collection of Algae and Protozoa (CCAP) - International Depositary Authority under the Budapest Treaty - under the CCAP number 1436/1- and its application as an antimalarial agent.
• Synthesis and Structure-Activity Relationships of Phaffiaol and Related Antioxidants.
  作者：Shuji JINNO、Takaaki OKITA

  DOI：10.1248/cpb.46.1688

  日期：——

  Total synthesis of a novel long chain alkyl phenol, phaffiaol (1), a potent antioxidant isolated from Phaffia rhodozyma, was achieved via three reaction steps starting from 3, 5-dibromosalicylaldehyde (2). We also prepared several types of long chain alkyl phenol having different aromatic rings or different carbon length, and evaluated their antioxidative activity using the rabbit erythrocyte membrane ghost system. Amongst these compounds, the novel methoxy phenol derivatives (6c, d, 7) having a heptadecyl moiety at the ortho-position to the hydroxy group, were approximately 2 times more active than α-tocopherol. In addition, 4-methoxy-2-pentadexylphenol (10h), which has a 15-carbon length in the side chain moiety, showed the maximum activity.

  通过从3,5-二溴水杨醛（2）开始的三个反应步骤，实现了从Phaffia rhodozyma中分离得到的强效抗氧化剂phaffiaol（1）这一新型长链烷基酚的完全合成。我们还制备了几种具有不同芳环或不同碳链长度的长链烷基酚，并通过兔红细胞膜系统评估了它们的抗氧化活性。在这些化合物中，具有十七烷基侧链且位于羟基邻位的甲氧基酚衍生物（6c、d、7）的活性约为α-生育酚的两倍。此外，侧链具有15个碳原子的4-甲氧基-2-十五烷基酚（10h）显示出最高的活性。
• Phaffiaol, a New Antioxidant Isolated from a Yeast Phaffia rhodozym.
  作者：SHUJI JINNO、KAZUHIKO HATA、NOBUYOSHI SHIMIDZU、TAKAAKI OKITA

  DOI：10.7164/antibiotics.51.508

  日期：——