Δ8'-4-hydroxy-3,3',5',7-tetramethoxy-8-O-4'-neolignan | 72253-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Δ8'-4-hydroxy-3,3',5',7-tetramethoxy-8-O-4'-neolignan
• 英文别名: 4-[2-(2,6-Dimethoxy-4-prop-2-enylphenoxy)-1-methoxypropyl]-2-methoxyphenol
• CAS: 72253-41-9
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: YRXTUYZHIHAYPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Δ8'-4-hydroxy-3,3',5',7-tetramethoxy-8-O-4'-neolignan 生成 Acetic acid 4-[2-(4-allyl-2,6-dimethoxy-phenoxy)-1-methoxy-propyl]-2-methoxy-phenyl ester
  参考文献：
  名称：

  Studies on dental caries prevention by traditional medicines. X Antibacterial action of phenolic components from mace against Streptococcus mutans.

  摘要：

  The methanolic extract of the aril of Myristica fragrans HOUTT. (mace) had anti-plaque action against a cariogenic becterium, Streptococcus mutans. Through fractionation of the extract followed by microbial assay by using the tube dilution technique, dehydrodiisoeugenol (1) and 5'-methoxydehydrodiisoeugenol (2) were identified as the major antibacterial principles. Both compounds completely inhibited the bacterial growth at a concentration of 12.5 μg/ml. During this experiment, threo-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propan-1-ol methyl ether (6) and guaiacin (8) were isolated for the first time from mace.

  DOI：

  10.1248/cpb.34.3885
• 作为产物：
  描述：

  (Z)-2-甲氧基-4-(丙-1-烯基)苯酚 、 4-烯丙基-2,6-二甲氧基苯酚 生成 Δ8'-4-hydroxy-3,3',5',7-tetramethoxy-8-O-4'-neolignan
  参考文献：
  名称：

  ANODIC OXIDATION OFE- ANDZ-ISOEUGENOL

  摘要：

  使用未分割电池，在 +800 mV vs SCE 的受控电位下，在 MeOH 中对 E- 和 Z- 异丁香酚（1 和 2）进行阳极氧化，得到氧化产物（1 中的 3、4、5、6、7、8 和 9；2 中的 3、4、5、6、10、11 和 12）。对 Z-异丁香酚（2）和 2,6-二甲氧基-4-烯丙基苯酚（13）的混合物进行类似处理，可得到芳基丙酮（14）。

  DOI：

  10.1246/cl.1978.1015

文献信息

• Cooling Agent and TRPM8 Activator
  申请人：Kao Corporation

  公开号：US20140329910A1

  公开（公告）日：2014-11-06

  Provided are a cooling agent having an excellent TRPM8 activating action, a TRPM8 activator, a method for imparting cooling sensation, and a novel compound useful for imparting cooling sensation. Disclosed is a cooling agent comprising, as an active ingredient, a compound represented by the following formula (1): wherein R 1 represents a hydrogen atom; R 2 represents a hydrogen atom, a hydroxyl group, or an alkoxy group having from 1 to 3 carbon atoms; R 3 represents a hydrogen atom or a hydroxyl group; R 4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, or an alkoxy group having from 1 to 3 carbon atoms; R 5 represents a hydrogen atom or an alkoxy group having from 1 to 3 carbon atoms; and R 6 represents a hydrogen atom, a hydroxyl group, an alkoxy group having from 1 to 14 carbon atoms, an alkoxyalkoxy group having from 2 to 12 carbon atoms in total, a cycloalkoxy group having from 3 to 12 carbon atoms, an aryloxy group having from 6 to 12 carbon atoms, an aralkyloxy group having from 7 to 14 carbon atoms in total, or an alkanoyloxy group having from 2 to 12 carbon atoms in total.

  提供了一种具有出色的TRPM8激活作用的冷却剂、一种TRPM8激活剂、一种赋予冷感的方法，以及一种用于赋予冷感的新化合物。公开了一种冷却剂，其包括以下式（1）所代表的化合物作为活性成分： 其中R1代表氢原子；R2代表氢原子、羟基或具有1至3个碳原子的烷氧基；R3代表氢原子或羟基；R4代表氢原子、具有1至6个碳原子的烷基、具有2至6个碳原子的烯基，或具有1至3个碳原子的烷氧基；R5代表氢原子或具有1至3个碳原子的烷氧基；R6代表氢原子、羟基、具有1至14个碳原子的烷氧基、总共具有2至12个碳原子的烷氧烷氧基、具有3至12个碳原子的环烷氧基、具有6至12个碳原子的芳基氧基、总共具有7至14个碳原子的芳基烷氧基，或总共具有2至12个碳原子的烷酰氧基。
• Identification of a Novel TRPM8 Agonist from Nutmeg: A Promising Cooling Compound
  作者：Tomohiro Shirai、Kentaro Kumihashi、Mitsuyoshi Sakasai、Hiroshi Kusuoku、Yusuke Shibuya、Atsushi Ohuchi

  DOI：10.1021/acsmedchemlett.7b00104

  日期：2017.7.13

  The transient receptor potential melastatin 8 (TRPM8) ion channel is the primary receptor for innocuous cold stimuli (<28 °C) in humans. TRPM8 agonists such as l-(−)-menthol are widely used as flavors and additives to impart briskness, in addition to medicinal uses for inflammation and pain. Though various natural and synthetic agonists have been explored, only few natural compounds are known. We report

  瞬时受体电位褪黑素8（TRPM8）离子通道是人类无害冷刺激（<28°C）的主要受体。除用于炎症和疼痛的医学用途外，TRPM8激动剂（例如1 -（-）-薄荷醇）还广泛用作调味剂和添加剂，以赋予轻快感。尽管已经研究了各种天然和合成的激动剂，但是仅知道很少的天然化合物。我们在此报告的新的新木脂素激动剂的鉴定和表征赤-和苏式-Δ 8' -7-乙氧基-4-羟基- 3,3'，5'-三甲氧基-8- ö -4'-新木脂素（1） EC 50为0.332μM，是从著名的香料肉豆蔻（肉豆蔻（Myristica fragrans Houtt。）。还公开了结构活性关系，表明7- d-薄荷氧基衍生物是最有效的激动剂（EC 50＝ 11nM）。的组合1和升（ - - ） -薄荷醇具有累加效应，这表明新木脂素化合物与TRPM8相互作用在不同位点的那些的升- （ - ） -薄荷醇。
• Anodic oxidation of some propenylphenols: Synthesis of physiologically active neolignans.
  作者：ATSUKO NISHIYAMA、HIDEO ETO、YUKIMASA TERADA、MASANOBU IGUCHI、SHOSUKE YAMAMURA

  DOI：10.1248/cpb.31.2834

  日期：——

  Some propenylphenols have been subjected to anodic oxidation to afford a number of oxidation products including arylpropanoid-, asatone-, austrobailignan-, carpanone- and licarin-type neolignans. The formation process of these compounds involves both radical and cationic reactions controlled by the applied potentials, solvent media and substituents on the aromatic rings.

  一些丙烯基苯酚在阳极氧化过程中会产生一系列氧化产物，包括芳基丙酮、asatone、austrobailignan、carpanone 和 licarin 型新木质素。这些化合物的形成过程涉及自由基反应和阳离子反应，受应用电位、溶剂介质和芳香环上取代基的控制。
• US9340478B2
  申请人：——

  公开号：US9340478B2

  公开（公告）日：2016-05-17