3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone | 87605-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone
• 英文别名: 1,8-dihydroxy-3-geranyloxy-6-methylanthraquinone；1,8-dihydroxy-6-geranyloxy-3-methylanthraquinone；3-geranyloxy-1,8-dihydroxy-6-methylanthraquinone；3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone；3'-geranyloxyemodin；3-O-geranyl-emodin；Geranyloxyemodin；3-[(2E)-3,7-dimethylocta-2,6-dienoxy]-1,8-dihydroxy-6-methylanthracene-9,10-dione
• CAS: 87605-71-8
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: JVTPNJZXKNTJEF-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以20 mg的产率得到大黄素
  参考文献：
  名称：

  来自 Psorospermum febrifugum 的 3-Geranyloxy-6-methyl-1,8-dihydroxyanthraquinone 和 vimmiones C、D 和 E

  摘要：

  摘要 从Psorospermum febrifugum 浆果中分离得到3 个新的vismiones 和3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone 以及已知的大黄酸、2-isoprenylemodin 和ferruginin B。通过化学和光谱方法确定了它们的结构。异戊二烯化蒽仅在 Vismieae 中出现表明它们可用作部落的系统标记。

  DOI：

  10.1016/0031-9422(83)83041-6
• 作为产物：
  描述：

  vismione D 在 吡啶 、 双氧水 作用下， 以 乙醚 为溶剂， 生成 3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone
  参考文献：
  名称：

  来自 Psorospermum febrifugum 的氧杂蒽酮和视黄酮

  摘要：

  摘要 两种新的氧杂蒽酮，psorofebrin 和 5'-hydroxyisopsorofebrin，包含稠合的四氢呋喃苯并呋喃环系统，二氢呋喃的两个新成员

  DOI：

  10.1016/0031-9422(91)80040-8

文献信息

• Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis
  作者：Salvatore Genovese、Francesco Epifano、Philippe de Medina、Nicolas Caron、Arnaud Rives、Marc Poirot、Sandrine Silvente-Poirot、Serena Fiorito

  DOI：10.1016/j.bioorg.2019.03.026

  日期：2019.6

  benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly

  最近已经表明，天然存在的氧戊烯化香豆素是有效的黑色素生成调节剂。在此简短的交流中，我们希望概括一下更广泛的天然和半合成芳族化合物（包括香豆素，肉桂酸和苯甲酸，肉桂醛，苯甲醛和蒽醌衍生物）作为皮肤美黑或增白剂的潜力。总共测试了43种化合物，分析了它们在培养的鼠Melan A细胞中抑制或刺激黑色素生物合成的能力。本文所研究的大量化学物质可描述出详细的结构与活性的关系，如下所示：（a）苯甲酸衍生物是轻微的色素形成剂，对于具有较长O的化合物，其作用更为明显。-侧链；（b）与取代类型无关，肉桂酸能够增加黑色素的生物合成，而苯甲醛能够减少黑色素的生物合成；（c）在7位具有3,3-二甲基烯丙基或更短骨架作为取代基的香豆素为鞣制剂，而具有法呢烷氧基的香豆素为增白剂；（d）在6和7位上的双氧基戊烯基化和3,3-二甲基烯丙基或香叶基骨架具有轻微的脱色能力，而法呢基骨架则倾向于略微提高鞣制效果；（e）在香豆素核
• [EN] SKIN PIGMENTATION MODIFIERS TO DARKEN OR LIGHTEN THE SKIN<br/>[FR] AGENTS DE MODIFICATION DE LA PIGMENTATION DE LA PEAU EN VUE DE L'ASSOMBRIR OU DE L'ÉCLAIRCIR
  申请人：AFFICHEM

  公开号：WO2016193220A1

  公开（公告）日：2016-12-08

  The present invention relates to a method for changing the pigmentation of a skin, a mucous membrane or hair with a compound of general formula (I), a cosmetic use of said compound of general formula (I), to cosmetic compositions comprising said compound of general formula (I), and to new depigmenting agents.

  本发明涉及一种改变皮肤、粘膜或头发色素的方法，使用一般式(I)的化合物，以及所述一般式(I)的化合物的化妆用途，包括所述一般式(I)的化合物的化妆组合物，以及新的脱色剂。
• DEPIGMENTING AGENTS TO LIGHTEN THE SKIN
  申请人：Affichem

  公开号：EP3097904A1

  公开（公告）日：2016-11-30

  The present invention relates to a method for lightening a skin or a mucous membrane with a depigmenting agent, a cosmetic use of said depigmenting agent, to cosmetic compositions comprising said agent, and to new depigmenting agents.

  本发明涉及一种使用脱色剂淡化皮肤或粘膜的方法、所述脱色剂的化妆品用途、包含所述脱色剂的化妆品组合物以及新型脱色剂。
• Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines
  作者：Céline Bruyère、Salvatore Genovese、Benjamin Lallemand、Alexandra Ionescu-Motatu、Massimo Curini、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.bmcl.2011.05.089

  日期：2011.7

  A series of 25 selected oxyprenylated natural phenylpropanoids were synthesized, and their growth inhibitory activities were evaluated in vitro together with 14 other commercially available non-alkylated compounds belonging to the same chemical series. The compounds were tested on six human cancer cell lines using MTT colorimetric assays. The data reveal that of the six chemical groups (G) studied, coumarins (G1), cinnamic and benzoic acids (G2), chalcones (G3), acetophenones (G4), anthraquinones (G5), and cinnamaldehydes and cinnamyl alcohols (G6), G2-related compounds displayed the weakest growth inhibitory activities in vitro, whereas G5-related compounds displayed the highest activities. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various levels of resistance to different pro-apoptotic stimuli. These analyses revealed that compounds 20 (4,2',4'-trihydroxychalcone), and 30 and 31 (two cinnamaldehydes) were cytostatic and able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli. (C) 2011 Elsevier Ltd. All rights reserved.
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.