2-甲氧基-6-戊基苯-1,4-二醇 | 34272-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-甲氧基-6-戊基苯-1,4-二醇
• 英文名称: miconidin
• 英文别名: 2-methoxy-6-pentylbenzene-1,4-diol
• CAS: 34272-58-7
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: QYDCWUURASKCKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  2-甲氧基-6-戊基苯-1,4-二醇 在 硫酸 、 三氯化铁 作用下， 以 苯 为溶剂， 生成 acetic acid,5-methoxy-3-pentylbenzene-1,2,4-triol
  参考文献：
  名称：

  Marini-Bettolo,G.B. et al., Gazzetta Chimica Italiana, 1971, vol. 101, p. 41 - 46

  摘要：

  DOI：
• 作为产物：
  描述：

  橄榄醇二甲基醚 在 chromium(VI) oxide 、 sodium dithionite 、 溶剂黄146 作用下， 以 乙醚 、 水 为溶剂， 生成 2-甲氧基-6-戊基苯-1,4-二醇
  参考文献：
  名称：

  轻松获得primin，miconidin和相关的天然间苯二酚

  摘要：

  报道了一种有效且短时间的合成方法，该方法以高收率提供了具有生物活性的天然产物primin，miconidin，Olivetol，grevillol和Cardol（adipostatin A）。这两种策略涉及Sonogashira和Suzuki交叉偶联，这是安装烷基侧链的关键步骤。合成从便宜的，可商购的1-溴-3,5-二甲氧基苯开始，得到1,3-二甲氧基-5-（alk-1-yn-1-yl）苯作为关键中间体。该中间体可以容易且经济地氧化以提供优异的总收率的primin，同时由于其对称性而避免了不希望的副产物。关键中间体的脱甲基作用分别提供了天然间苯二酚橄榄酚，格雷维洛尔和腰果酚。primin的还原提供了其氢醌衍生物miconidin。

  DOI：

  10.1016/j.tet.2017.07.029

文献信息

• Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core
  作者：Miroslav Sisa、Marcela Dvorakova、Veronika Temml、Veronika Jarosova、Tomas Vanek、Premysl Landa

  DOI：10.1016/j.ejmech.2020.112620

  日期：2020.10

  Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1

  基于天然醌primin（5a）的显着抗炎活性，设计，合成，表征和测试了一系列1,4-苯醌，对苯二酚和相关间苯二酚抑制环氧化酶（COX-1）的能力。和COX-2）和5-脂氧合酶（5-LOX）酶。结构修饰导致鉴定出两种化合物5b（2-甲氧基-6-十一烷基-1,4-苯醌）和6b（2-甲氧基-6-十一烷基-1,4-氢醌）作为有效的双重COX / 5-LOX抑制剂。使用酶促测定在体外评估的IC 50值对于化合物5b为IC 50 = 1.07、0.57和0.34μM，对于化合物6b对于COX-1，COX-2和5-LOX酶，IC 50分别为1.07、0.55和0.28μM。此外，化合物6d被鉴定为测试化合物中最有效的5-LOX抑制剂（IC 50 = 0.14μM；参考抑制剂齐留通IC 50 = 0.66μM），而其对COX酶的抑制潜力（IC 50 = 2.65和2.71μM对于COX-1和COX-2的浓度分别与参考抑制剂布洛芬（IC
• Arogba, Sunday S., Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 639 - 644
  作者：Arogba, Sunday S.

  DOI：——

  日期：——
• Skin whitening compositions based on hydroxyaryl alkyl ketones and their isosteric derivatives
  申请人：Gupta K. Shyam

  公开号：US20050271608A1

  公开（公告）日：2005-12-08

  I have discovered that certain hydroxyaryl or polyhydroxyaryl compounds that contain an alkyl carbon side chain with a hetero-atom group attached by a double bond at the first carbon atom of the alkyl side chain that is directly attached to the aromatic ring, as illustrated in FIG. 1 , provide a surprising and unexpected skin whitening effect. The addition of metal ions, such as copper, zinc, selenium, or vanadium and certain antioxidant compositions additionally increases the skin whitening effect.
• Skin Antiaging & Brightening via Multi-function Treatment of Enzyme Dysfunction
  申请人：GUPTA SHYAM K.

  公开号：US20080254130A1

  公开（公告）日：2008-10-16

  The present invention relates to a topical method of treatment for dysfunction of certain dermal enzymes, and the treatment of skin condition or disorder caused by said dysfunction. The said method of treatment consists of (i) an extra-cellular, matrix metalloprotease regulating agent, and (ii) an intra-cellular ubiquitin—proteasome regulating agent, and (iii) an epidermal melanocyte-regulating agent; and, wherein, said extra-cellular agent, said intracellular agent, and said epidermal agent can, surprisingly and unexpectedly, be a single multi-function compound having chemical formula (I). Additionally, the method of the present invention provides treatment of skin condition or disorder caused by dysfunction of said dermal enzymes; wherein said skin disorder is skin aging, skin wrinkles, dark skin, age spots, acne, skin inflammation, loss of cellular antioxidants, loss of collagen, loss of skin pliability, loss of skin suppleness, oily skin, or a combination thereof:
• Concise access to primin, miconidin and related natural resorcinols
  作者：Miroslav Sisa、Marcela Dvorakova、Tomas Vanek

  DOI：10.1016/j.tet.2017.07.029

  日期：2017.8

  intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin.

  报道了一种有效且短时间的合成方法，该方法以高收率提供了具有生物活性的天然产物primin，miconidin，Olivetol，grevillol和Cardol（adipostatin A）。这两种策略涉及Sonogashira和Suzuki交叉偶联，这是安装烷基侧链的关键步骤。合成从便宜的，可商购的1-溴-3,5-二甲氧基苯开始，得到1,3-二甲氧基-5-（alk-1-yn-1-yl）苯作为关键中间体。该中间体可以容易且经济地氧化以提供优异的总收率的primin，同时由于其对称性而避免了不希望的副产物。关键中间体的脱甲基作用分别提供了天然间苯二酚橄榄酚，格雷维洛尔和腰果酚。primin的还原提供了其氢醌衍生物miconidin。