pentamethyl rosmarinic acid | 54814-43-6

• 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
• 英文名称: pentamethyl rosmarinic acid
• 英文别名: rosmarinic acid permethylate；pentamethyl rosmarinate
• CAS: 54814-43-6
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: JAGTWZJJNXEFGC-OGECGYFKSA-N

物化性质

• 沸点：
  576.4±50.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  pentamethyl rosmarinic acid 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以62%的产率得到3-(3,4-dimethoxy-phenyl)-2-hydroxy-propionic acid methyl ester
  参考文献：
  名称：

  二氢苯并[ b ]呋喃的简便方法：（+）-紫精酸的正式全合成

  摘要：

  Sonogashira偶联，Pd（II）催化的羰基环化和苯并呋喃还原（Mg，MeOH，NH 4 Cl）的序列为反式-2-芳基-2,3-二氢苯并[ b ]呋喃提供了一种收敛的模块化合成途径。-3-羧酸盐，是许多具有生物活性的天然产物的结构特征。这种多用途的策略适用于抗HIV天然产物（+）-紫精酸的正式全合成。

  DOI：

  10.1021/ol201130h
• 作为产物：
  描述：

  迷迭香酸 在 potassium carbonate 、 硫酸二甲酯 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以97%的产率得到pentamethyl rosmarinic acid
  参考文献：
  名称：

  Highly Convergent Total Synthesis of (+)-Lithospermic Acid via a Late-Stage Intermolecular C−H Olefination

  摘要：

  The total synthesis of (+)-lithospermic acid is reported, which exploits two successive C-H activation reactions as key steps. Rh-catalyzed carbene C-H insertion reaction utilizing Davies's catalyst was used to forge dihydrobenzofuran core, and a late-stage intermolecular C-H olefination coupled the olefin unit with the dihydrobenzofuran core to construct the molecule in a highly convergent manner.

  DOI：

  10.1021/ja2010225

文献信息

• Antimicrobial Activity of Rosmarinus officinalis against Oral Pathogens: Relevance of Carnosic Acid and Carnosol
  作者：Wagner A. Bernardes、Rodrigo Lucarini、Marcos G. Tozatti、Maria G. M. Souza、Márcio L. Andrade Silva、Ademar A. da Silva Filho、Carlos H. Gomes Martins、Antonio E. Miller Crotti、Patricia M. Pauletti、Milton Groppo、Wilson R. Cunha

  DOI：10.1002/cbdv.200900301

  日期：——

  antibacterial activity than the stem extract, led to the identification of carnosic acid (2) and carnosol (3) as the major compounds in the fraction displaying the highest activity, as identified by HPLC analysis. Rosmarinic acid (1), detected in another fraction, did not display any activity against the selected microorganisms. HPLC Analysis revealed the presence of low amounts of ursolic acid (4) and oleanolic

  评估了迷迭香的叶和茎中粗制EtOH / H2O提取物对下列引起龋齿的微生物的体外抑制活性：变形链球菌，唾液链球菌，so。sobrinus链球菌，S. mitis，S.血红蛋白和粪肠球菌。最低抑菌浓度（MIC）用肉汤微量稀释法测定。叶提取物的生物测定指导分馏显示出比茎提取物更高的抗菌活性，导致鉴定出鼠尾草酸（2）和鼠尾草酚（3）是该馏分中显示出最高活性的主要化合物，已被鉴定通过HPLC分析。在另一部分中检测到的迷迭香酸（1）对所选的微生物没有任何活性。HPLC分析表明，所得级分中存在少量的熊果酸（4）和齐墩果酸（5）。结果表明，厚朴叶中提取物的抗菌活性可能主要归因于2和3的作用。
• C₂₈ Terpenoids from Lamiaceous Plant <i>Perovskia scrophulariifolia</i>: Their Structures and Anti-neuroinflammatory Activity
  作者：Naonobu Tanaka、Kanji Niwa、Seita Kajihara、Daisuke Tsuji、Kohji Itoh、Nilufar Z. Mamadalieva、Yoshiki Kashiwada

  DOI：10.1021/acs.orglett.0c02855

  日期：2020.10.2

  Structurally unique C28 terpenoids, perovsfolins A (1) and B (2), were isolated from the aerial parts of an Uzbek medicinal plant, Perovskia scrophulariifolia (Lamiaceae). Their chemical structures including an unprecedented 6/8/6/6/6 pentacyclic carbon skeleton with a C6–C3 ester moiety were elucidated on the basis of spectroscopic analyses aided by density functional theory calculations as well as

  从乌兹别克药用植物Perovskia scrophulariifolia（唇形科）的地上部分分离出结构独特的 C 28萜类化合物，即 perovsfolins A ( 1 ) 和 B ( 2 )。基于密度泛函理论计算和化学证据辅助的光谱分析，阐明了它们的化学结构，包括前所未有的具有 C 6 -C 3酯部分的6/8/6/6/6 五环碳骨架。Perovsfolin B ( 2 ) 表现出抗神经炎症活性。
• Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation
  作者：Steven J. O'Malley、Kian L. Tan、Anja Watzke、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja052680h

  日期：2005.10.1

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.
• Improving the NQO1-Inducing Activities of Phenolic Acids from Radix Salvia miltiorrhiza: a Methylation Strategy
  作者：Xiaoyu Zhang、Zhihang Song、Jinzhong Xu、Zhongjun Ma

  DOI：10.1111/j.1747-0285.2011.01171.x

  日期：2011.10

  NAD(P)H: quinone oxidoreductase1 (NQO1) is an important detoxification enzyme that can protect mammalian cells against toxic quinones and reduce the risk of tumorigenesis. In this study, it was found that salvianolic acid B (SaB), lithospermic acid (LA), and rosmarinic acid (RA), three main hydrophilic constituents in Danshen, conjugated with glutathione (GSH) easily in vitro but exhibited no NQO1‐inducing activities in Hepa 1c1c7 cells, which might attribute to their poor absorptions. After a simple methylation strategy that aimed at improving the liposolubility, both the NQO1‐inducing activities and the absorptions in cells of the phenolic acids improved obviously, without losing the GSH‐conjugating abilities. The concentration to double the specific activity of NQ01 values of methylated products of lithospermic acid and rosmarinic acid were 17.86 ± 2.34 μg/mL and 11.97 ± 0.60 μg/mL, respectively. The findings indicated that methylation is an effective strategy to improve the NQO1‐inducing activities of phenolic acids in Danshen.
• Isolation, modification, and aldose reductase inhibitory activity of rosmarinic acid derivatives from the roots of Salvia grandifolia
  作者：Jie Kang、Yanbo Tang、Quan Liu、Nan Guo、Jian Zhang、Zhiyan Xiao、Ruoyun Chen、Zhufang Shen

  DOI：10.1016/j.fitote.2016.05.011

  日期：2016.7

  To find aldose reductase inhibitors, two previously unreported compounds, grandifolias H and I, and five known compounds, including rosmarinic acid and rosmarinic acid derivatives, were isolated from the roots of Salvia grandifolia. A series of rosmarinic acid derivatives was obtained from rosmarinic acid using simple synthetic methods. The aldose reductase inhibitory activity of the isolated and synthesized compounds was assessed. Seven of the tested compounds showed moderate aldose reductase inhibition (IC50 = 0.06-0.30 M). The structure-activity relationship of aldose reductase inhibitory activity of rosmarinic acid derivatives was discussed for the first time. This study provided useful information that will facilitate the development of aldose reductase inhibitors. (C) 2016 Published by Elsevier B.V.