methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate | 34874-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate
• 英文别名: methyl isorhizinonate；2-methoxy-atraric acid；4-hydroxy-2-methoxy-3,6-dimethyl-benzoic acid methyl ester；4-Hydroxy-2-methoxy-3,6-dimethyl-benzoesaeure-methylester；Methyl-4-hydroxy-2-methoxy-3,6-dimethylbenzoat；Benzoic acid, 4-hydroxy-2-methoxy-3,6-dimethyl-, methyl ester
• CAS: 34874-75-4
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: LPHVUYDIEIQKTA-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  344.9±37.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)
• 保留指数：
  1585.9

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate 在 盐酸 、 氢氧化钾 、 三氯化铝 、 potassium carbonate 、 mercury dichloride 、 锌 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-hydroxy-4-methoxy-3,5,6-trimethylbenzoic acid
  参考文献：
  名称：

  Bruun,T., Acta Chemica Scandinavica (1947), 1971, vol. 25, p. 2837 - 2851

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4,6-Dimethoxy-5-formyl-2-methyl-benzoyloxy)-6-methoxy-2,5-dimethyl-benzoesaeure-methylester; Trimethoxy-atranorin 在 氢氧化钾 作用下， 生成 methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Chromium-Induced Glucose Uptake, Superoxide Anion Production, and Phagocytosis in Cultured Pulmonary Alveolar Macrophages of Weanling Pigs

  摘要：

  The dose-dependent effects of chromium chloride(CrCl3) and chromium picolinate (CrPic) were evaluated for their glucose uptake, superoxide anion (O-2(-)) production, activity of glucose-6-phosphate dehydrogenase, and phagocytosis of incubated pulmonary alveolar macrophages in medium containing no or 5 x 10(-8)M insulin. Glucose uptake was found to increase in cells treated with 20 mug/L CrCl3. Incubation with 20 mug/L of CrPic enhanced glucose uptake and O-2(-) production in an insulin-dependent manner. However, the inclusion of CrPic to 100 mug/L in the medium absent of insulin also increased O-2(-) production. The activity of glucose-6-phosphate dehydrogenase was not affected by either the addition of Cr or insulin. The phagocytosis of Escherichia coli by macrophages was enhanced significantly (p < 0.05) in medium containing 10-100 g/L CrCl3 or 20-100 mug/L CrPic in the presence of insulin. These results suggest that the addition of 10-20 mug/L CrCl3 enhances directly the cellular activity of macrophages, whereas the effect of CrPic requires the cooperative action of insulin in enhancing their glucose uptake and phagocytosis.

  DOI：

  10.1385/bter:77:1:53

文献信息

• Depsidone synthesis. Part 19. Some β-orcinol depsidones
  作者：Tony Sala、Melvyn V. Sargent

  DOI：10.1039/p19810000877

  日期：——

  The synthesis of the lichen depsidones 3,8-dihydroxy-1,4,6,9-tetramethyl-11-oxo-11H-dibenzo[b,e][1,4]-dioxepin-7-carboxylic acid (hypoprotocetraric acid)(4), 8-hydroxy-3-methoxy-1,4,6,9-tetramethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid (O-methylhyprprotocetraric acid)(5), 4-formyl-3,8-dihydroxy-1,6,9-trimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid (virensic acid)(6)

  地衣二萜3,8-dihydroxy-1,4,6,9-tetramethyl-11-oxo-11 H -dibenzo [ b，e ] [1,4] -dioxepin-7-羧酸（次戊四酸）的合成）（4），8-羟基-3-甲氧基- 1,4,6,9四甲基-11-氧代-11- ħ -二苯并[ b，ë ] [1,4]二氧杂环庚烯-7-羧酸（ø - （5），4-甲酰基-3,8-二羟基-1,6,9-三甲基-11-氧代-11 H-二苯并[ b，e ] [1,4]二氧己环-7-羧酸（ （6）和4-甲酰基-3,8-二羟基-9-羟甲基-1,6-二甲基-11-氧代-11 H-二苯并[ b，e描述了] [1,4]二氧杂庚酮-7-羧酸（原对苯二甲酸）（7）。
• Phytochemical Composition of Lichen Parmotrema hypoleucinum (J. Steiner) Hale from Algeria
  作者：Marwa Kerboua、Ali Ahmed Monia、Nsevolo Samba、Lúcia Silva、Cesar Raposo、David Díez、Jesus Miguel Rodilla

  DOI：10.3390/molecules27165229

  日期：——

  methyl esters of the predominant fatty acids in the lichen were identified: palmitic acid, linoleic acid, oleic acid and stearic acid; a hydrocarbon was also identified: 13-methyl-17-norkaur-15-ene and several derivatives of orsellinic acid. In the 1-Cires and 2-Cires fractions, the previous fatty acids were no longer observed, and only the derivatives of orsellinic acid were found. The analysis of the 1-Hexane

  在这项工作中，我们对在阿尔及利亚采集的两份 Parmotrema hypoleucinum地衣样品的己烷、氯仿和乙醇提取物的化学成分进行了研究。地衣P. hypoleucinum的每个样品都收集在两个不同的支持物上：Olea europaea和Quercus coccifera. 在 Soxhlet 中制备己烷提取物；每种己烷提取物根据其在甲醇中的溶解度进行分级；分离（冷）溶于甲醇的产物：1-己烷、2-己烷；不溶于甲醇的产品（冷）：1-Cires、2-Cires。用 GC-MS 分析了 1-Hexane、2-Hexane、1-Cires 和 2-Cires 的重氮甲烷酯化样品，其成分被鉴定为甲酯。在 1-己烷和 2-己烷馏分中，确定了地衣中主要脂肪酸的甲酯：棕榈酸、亚油酸、油酸和硬脂酸；还发现了一种碳氢化合物：13-methyl-17-norkaur-15-ene 和几种 orsellinic
• In the arms of morpheus: the development of morphine for postoperative pain relief
  作者：Gillian R. Hamilton、Thomas F. BAskett

  DOI：10.1007/bf03020955

  日期：2000.4

  Purpose: To analyse the historical development of morphine for postoperative analgesia and how this development was shaped by the evolution of anesthetic techniques.Methods: After a systematic review of the literature, information was gathered from primary sources.Principal Findings: in ancient medicine, some plant derivatives were used to alleviate pain including: alcohol, cannabis, mandrake, and opium. Over the past two centuries, opium and its derivatives have become the most widely used analgesics for severe pain. Before the development of general anesthesia, surgery was only performed out of extreme necessity. It is probable that an analgesic such as opium would have been given following surgery although its use may not have been recorded. The first description of postoperative opium was by James Moore in 1784, Morphine was isolated from opium by Friedrich Serturner in 1805. However, it was not until the development of the hypodermic needle and syringe nearly 50 yr later that the use of morphine became widespread. Over the last century, various delivery systems for morphine have been developed including sub-arachanoid and epidural injection, and more recently patient-controlled intravenous, epidural and intranasal analgesia. In addition, many new opioids have been synthesized.Conclusion: Since its isolation from opium almost 200 yr ago, morphine remains the most widely used analgesic and the standard against which all new opioids for postoperative pain relief are compared.
• 222. Lichen acids. Part III. The constitution of barbatic acid and the syntheses of isorhizonic acid and methyl barbatate
  作者：Alexander Robertson、Richard John Stephenson

  DOI：10.1039/jr9320001675

  日期：——
• Elix, John A.; Chester, Douglas O.; Gaul, Kim L., Australian Journal of Chemistry, 1989, vol. 42, # 7, p. 1191 - 1200
  作者：Elix, John A.、Chester, Douglas O.、Gaul, Kim L.、Parker, John L.、Wardlaw, Judith H.

  DOI：——

  日期：——