7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin | 5673-37-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin
• 英文别名: meranzin hydrate；8-(2,3-dihydroxy-3-methylbutyl)-7-methoxychromen-2-one
• CAS: 5673-37-0
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: KGGUASRIGLRPAX-UHFFFAOYSA-N

物化性质

• 保留指数：
  2445.9;2432

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 cnidimonin A
  参考文献：
  名称：

  Cnidimonins A–C, Three Types of Hybrid Dimer from Cnidium monnieri: Structural Elucidation and Semisynthesis

  摘要：

  Three pairs of racemic dimers, (+/-)-cnidimonins A-C (1-3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an unprecedented terminal chiral carbon of prenyl. The absolute configurations of the enantiomers were determined by electronic circular dichroism (ECD). To investigate their bioactivities in depth, (+/-)-cnidimonins A-C (1-3) were synthesized. The racemic mixture (+/-)-1 exhibited stronger antiviral activity against HSV-1 (IC50: 1.23 mu M) than its corresponding optically pure enantiorriers.

  DOI：

  10.1021/acs.orglett.7b02290
• 作为产物：
  描述：

  蛇床子提取物 在 甲基磺酰胺 、 AD-mix β 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.5h， 以90%的产率得到7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin
  参考文献：
  名称：

  Cnidimonins A–C, Three Types of Hybrid Dimer from Cnidium monnieri: Structural Elucidation and Semisynthesis

  摘要：

  Three pairs of racemic dimers, (+/-)-cnidimonins A-C (1-3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an unprecedented terminal chiral carbon of prenyl. The absolute configurations of the enantiomers were determined by electronic circular dichroism (ECD). To investigate their bioactivities in depth, (+/-)-cnidimonins A-C (1-3) were synthesized. The racemic mixture (+/-)-1 exhibited stronger antiviral activity against HSV-1 (IC50: 1.23 mu M) than its corresponding optically pure enantiorriers.

  DOI：

  10.1021/acs.orglett.7b02290

文献信息

• Murrayatin, a coumarin from murraya exotica
  作者：Bikash Ranjan Barik、Ashesh Kumar Dey、Asima Chatterjee

  DOI：10.1016/s0031-9422(00)80160-0

  日期：1983.1

  Abstract The structure of murrayatin isolated from the leaves of Murraya exotica was established as 7-methoxy-8-(2′-isovaleryloxy-3′-hydroxy-3′-methylbutyl) coumarin from spectral analysis, chemical transformation and synthesis.

  摘要 通过光谱分析、化学转化和合成，确定了从异国木兰叶中分离出的木兰素的结构为7-甲氧基-8-(2'-异戊酰氧基-3'-羟基-3'-甲基丁基)香豆素。
• Microbial transformation of osthole by human intestinal fungi and anti-osteoporosis activities of its metabolites
  作者：Xin He、Min Nie、Mengyuan Wang、Shifei Wu、Xuemei Wei、Jiayuan Li、Changliang Yao、Chao Wang、Xiaochi Ma、De-an Guo

  DOI：10.1016/j.fitote.2023.105510

  日期：2023.6

  the biotransformation of osthole was performed based on the human intestinal fungi Mucor circinelloides. Six metabolites including three new metabolites (S2, S3, S4) were obtained, and their chemical structures were elucidated by spectroscopic data analysis. The major biotransformation reactions involved hydroxylation and glycosylation. In addition, all metabolites were evaluated for their anti-osteoporosis

  蛇床子素是蛇床子( L.) Cuss中的主要成分之一。并具有抗骨质疏松活性。在这项工作中，蛇床子素的生物转化是基于人类肠道真菌Mucor circinelloides进行的。获得了六种代谢物，包括三种新代谢物（S2、S3、S4），并通过光谱数据分析阐明了它们的化学结构。主要的生物转化反应涉及羟基化和糖基化。此外，使用 MC3T3-E1 细胞评估所有代谢物的抗骨质疏松症活性。结果表明S4、S5和S6与蛇床子素相比，可显着促进 MC3T3-E1 细胞生长。
• Compositions and methods for treating female sexual response
  申请人：——

  公开号：US20020034557A1

  公开（公告）日：2002-03-21

  The present invention relates to compositions, articles of manufacture, methods of preparation thereof, methods of use thereof, etc., for enhancement of sexual pleasure, conditions, disorders, and diseases related to reproductive physiology and systems, especially of mammalian females. For instance, the present invention relates to all aspects of modulating the female sexual response, including female sexual dysfunction, such as female sexual arousal disorders (FSAD), orgasmic disorders, and sexual pain disorders, and enhancing female sexual pleasure and satisfaction of the female sexual experience. Accordingly, the present invention relates to compositions comprising botanical extracts, active agents, etc., which are useful to treat or affect any of the aforementioned conditions. For example, the present invention relates to a composition, preferably for topical or local use, which comprises one or more of the following ingredients, including, but not limited to, borage seed oil, Angelica pubescens root and other angelica species, Coleus forskohlii extract, vinpocetine, ferulic acid, magnesium, ascorbyl palmitate, capric/caprylic triglyceride, silica, and equivalents thereof.

  本发明涉及组合物、制造品、其制备方法、其使用方法等，用于提高性快感，改善与生殖生理和系统有关的状况、失调和疾病，特别是哺乳动物雌性的性快感。例如，本发明涉及调节女性性反应的各个方面，包括女性性功能障碍，如女性性唤起障碍（FSAD）、性高潮障碍和性疼痛障碍，以及提高女性性快感和女性性体验的满意度。因此，本发明涉及由植物提取物、活性剂等组成的组合物，这些组合物可用于治疗或影响上述任何病症。例如，本发明涉及一种组合物，优选用于局部或局部使用，其中包含一种或多种以下成分，包括但不限于琉璃苣籽油、 当归 根和其他当归品种、 鞘氨醇 提取物、长春花碱、阿魏酸、镁、抗坏血酸棕榈酸酯、癸/癸酸甘油三酯、二氧化硅及其等同物。
• Identification and structure-activity relationship studies of osthol, a cytotoxic principle from Cnidium monnieri
  作者：Yukio Hitotsuyanagi、Hiroshi Kojima、Hiroshi Ikuta、Koichi Takeya、Hideji Itokawa

  DOI：10.1016/0960-894x(96)00315-0

  日期：1996.8

  Osthol (1) was isolated from the fruit of Cnidium monnieri as a cytotoxic principle. Its structure-activity relationship study reveals that the 3,4-olefinic bond is essential for its cytotoxic activity, and the prenyl (C-5) unit attached at the 8 position enhances the cytotoxicity. Analogues 7 and 8 that have a longer alkoxy unit at the 7 position showed ten times higher cytotoxicity than 1. Copyright (C) 1996 Elsevier Science Ltd
• Barik, Bikash R.; Dey, Ashesh K.; Das, Probhash C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 3, p. 223 - 226
  作者：Barik, Bikash R.、Dey, Ashesh K.、Das, Probhash C.、Kundu, Amit B.、Chatterjee, Asima

  DOI：——

  日期：——