2-(3',4'-二甲氧基苯氧基)苯甲酸 | 101094-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3',4'-二甲氧基苯氧基)苯甲酸
• 英文名称: 2-(3,4-dimethoxyphenoxy)benzoic acid
• 英文别名: 2-(3,4-Dimethoxyphenoxy)benzoic acid
• CAS: 101094-13-7
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: MQNRPMPFTLJOGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  402.4±40.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3',4'-二甲氧基苯氧基)苯甲酸 生成 2,3-Dihydroxyxanthone
  参考文献：
  名称：

  Xanthones as inhibitors of growth of human cancer cell lines and Their effects on the proliferation of human lymphocytes In Vitro

  摘要：

  Twenty-seven oxygenated xanthones have been assessed for their capacity to inhibit in vitro the growth of three human cancer cell lines, MCF-7 (breast cancer). TK-10 (renal cancer) and UACC-62 (melanoma). The effect of these xanthones on the proliferation of human T-lymphocytes was also evaluated. Differences on their potency towards the effect on the growth of the human cancer cell lines as well as on the proliferation of human T-lymphocytes can be ascribed to the nature and positions of the substituents on the xanthonic nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00379-6
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 sodium hydroxide 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 反应 122.0h， 生成 2-(3',4'-二甲氧基苯氧基)苯甲酸
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r

文献信息

• Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging
  作者：Diana I. S. P. Resende、Mariana C. Almeida、Bruna Maciel、Helena Carmo、José Sousa Lobo、Carlotta Dal Pozzo、Sara M. Cravo、Gonçalo P. Rosa、Aida Kane-Pagès、Maria do Carmo Barreto、Isabel F Almeida、Maria Emília de Sousa、Madalena M. M. Pinto

  DOI：10.3390/molecules25122782

  日期：——

  stress, making the search for new antioxidant compounds highly desirable in this field. Naturally occurring xanthones are polyphenolic compounds that can be found in microorganisms, fungi, lichens, and some higher plants. This class of polyphenols has a privileged scaffold that grants them several biological activities. We have previously identified simple oxygenated xanthones as promising antioxidants

  抗氧化剂长期以来一直用于化妆品行业，以防止由氧化应激介导的皮肤光老化，这使得该领域非常需要寻找新的抗氧化剂化合物。天然存在的氧杂蒽酮是多酚化合物，可以在微生物、真菌、地衣和一些高等植物中找到。这类多酚具有特殊的支架，赋予它们多种生物活性。我们之前已将简单的含氧氧杂蒽酮确定为有前途的抗氧化剂，并披露为命中的 1,2-二羟基氧杂蒽酮 (1)。在此，我们合成并研究了具有不同多氧化模式的氧杂蒽酮作为皮肤抗光老化成分的潜力。在 DPPH 抗氧化试验中，两种新合成的衍生物的 IC50 值与抗坏血酸的范围相同。合成的呫吨酮被发现是极好的酪氨酸酶抑制剂和弱至中度的胶原酶和弹性蛋白酶抑制剂，但没有显示针对透明质酸酶的活性。表征了它们的金属螯合效应（FeCl3 和 CuCl2）以及它们在不同 pH 值下的稳定性，以了解它们作为未来化妆品活性剂的潜力。在合成的聚氧化氧杂蒽酮中，1,2-二羟基氧杂蒽酮 (1) 被
• 447. The biosynthesis of phenols. Part III. Oxidative coupling leading to geodoxin and related compounds
  作者：C. H. Hassall、J. R. Lewis

  DOI：10.1039/jr9610002312

  日期：——
• 335. The chemistry of fungi. Part VIII. The oxidation of methylene groups in compounds analogous to O-dimethylcitromycin
  作者：G. W. K. Cavill、Alexander Robertson、W. B. Whalley

  DOI：10.1039/jr9490001567

  日期：——
• Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone
  作者：Luis Gales、Maria Emilia de Sousa、Madalena M. M. Pinto、Anake Kijjoa、Ana M. Damas

  DOI：10.1107/s010827010101349x

  日期：2001.11.15

  In order to study structure-activity relationships, a series of mono-, di- and trioxygenated xanthones has been synthesized and the structures of methyl 2-(3,4-dimethoxyphenoxy)benzoate, C16H16O5, 2-(3,4-dimethoxyphenoxy)benzoic acid, C15H14O5, 1,2-dimethoxy-9H-xanthen-9-one, C15H12O4, and 1,2,8-trimethoxy-9H-xanthen-9-one, C16H14O5, have been determined. The first two compounds both assume skew conformations, the dihedral angles between the two phenyl rings being 80.04 (8) and 83.0 (1)degrees, respectively. The latter two compounds are essentially planar and their methoxy substituents assume orientations consistent with minimum steric interactions.
• ——
  作者：Emília P. Sousa、Artur M. S. Silva、Madalena M. M. Pinto、Madalena M. Pedro、Fátima A. M. Cerqueira、Maria S. J. Nascimento

  DOI：10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r

  日期：2002.9

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.