红粉苔酸 | 480-56-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 红粉苔酸
• 中文别名: 紅粉苔酸
• 英文名称: lecanoric acid
• 英文别名: 4-[(2,4-dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoic acid；lecanolic acid；lecanoric aicd；Lecanorsaeure；4-(2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-6-methyl-benzoic acid；4-(2,4-Dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-6-methyl-benzoesaeure；4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid
• CAS: 480-56-8
• 化学式: C₁₆H₁₄O₇
• 分子量: 318.283
• InChiKey: HEMSJKZDHNSSEW-UHFFFAOYSA-N

物化性质

• 熔点：
  175～176℃
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶
• LogP：
  4.390 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭

制备方法与用途

蜡醛酸是从真菌中提取的一种组氨酸脱羧酶抑制剂，其抑制作用通过与组氨酸竞争实现，并不与磷酸吡哆醛竞争。此外，蜡醛酸并不抑制芳香族氨基酸脱羧酶。

反应信息

• 作为反应物：
  描述：

  红粉苔酸 在 calcium hydroxide 作用下， 生成 2,4-二羟基-6-甲基苯甲酸
  参考文献：
  名称：

  Stenhouse, Justus Liebigs Annalen der Chemie, 1848, vol. 68, p. 61,68

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟基-6-甲基苯甲酸 在 sodium hydroxide 、 丙酮 作用下， 生成 红粉苔酸
  参考文献：
  名称：

  Patients’ views on out-of-hours care in general practice in Dublin

  摘要：

  Background Little is known regarding patients' views and levels of satisfaction with out-of-hours care in Irish general practice despite significant recent changes in service delivery.Aims This study aimed to record patients' experience of out-of-hours care on a specific occasion and elicit their satisfaction with out-of-hours care in general.Methods Patients requesting out-of-hours care in three south inner city Dublin practices in June and July 2000 were identified and sent an anonymous postal questionnaire.Results Two hundred and forty patients were identified and 58% responded to the questionnaire, The approximate call rate was 195 calls per 1,000 patients per year. Sixty-one per cent of patients used the co-operative service, 28% received a house call and 3% received telephone advice only; 86% are currently satisfied with out-of-hours care.Conclusions The majority of patients are satisfied with the current out-of-hours service. Telephone consultation rates are significantly lower than other countries. These findings need to be considered before the widespread introduction of systems involving increased telephone consultations.

  DOI：

  10.1007/bf03173889

文献信息

• Aromatic ethers and process for producing aromatic ethers
  申请人：——

  公开号：US20040181099A1

  公开（公告）日：2004-09-16

  According to a production process, aromatic ethers are producible by reacting phenols with an oxirane compound with use of an anion exchange resin as a catalyst. According to another production process, aromatic ethers having an alcoholic hydroxyl group are producible by a crystallization-purification step of using a solvent having a solubility parameter ranging from 7.5 to 12.5 for purification by crystallization. Further, according to still another production process, producible are aromatic ethers having an alcoholic hydroxyl group, wherein the content of a metal in the aromatic ethers is less than 100 ppm by mass, and the content of a halogen element in the aromatic ethers is less than 100 ppm by mass.

  根据一个生产过程，芳香醚可通过将酚与环氧化合物反应，并使用阴离子交换树脂作为催化剂来生产。根据另一个生产过程，具有醇羟基的芳香醚可通过结晶纯化步骤，使用溶剂进行结晶纯化，其溶解度参数范围为7.5至12.5进行生产。此外，根据另一个生产过程，可生产具有醇羟基的芳香醚，其中芳香醚中金属的含量小于100ppm，卤素元素的含量小于100ppm。
• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Inhibition of Mushroom Tyrosinase Activity by Orsellinates
  作者：Thiago Inácio Barros Lopes、Roberta Gomes Coelho、Neli Kika Honda

  DOI：10.1248/cpb.c17-00502

  日期：——

  This study evaluated the tyrosinase-related activity of resorcinol (1), orcinol (2) lecanoric acid (3), and derivatives of this acid (4-15). Subjected to alcoholysis, lecanoric acid (3), a depside isolated from the lichen Parmotrema tinctorum, produces orsellinic acid (2,4-dihydroxy-6-methylbenzoic acid) (4) and orsellinates (2,4-dihydroxy-6-methyl benzoates) (5-15). At 0.50 mM, methyl (5), ethyl (6)

  已经提出了酪氨酸酶抑制剂在制药，食品生物加工和环境工业中的几种应用。但是，已知只有少数化合物可作为有效的酪氨酸酶抑制剂。这项研究评估了间苯二酚（1），蓖麻酚（2）柠檬酸（3）和该酸的衍生物（4-15）的酪氨酸酶相关活性。从酒精中分离出来的lecanoric acid（3）是从地衣Parmotrema tinctorum中分离得到的一种生成物，生成奥来酸（2,4-dihydroxy-6-methylbenzoic acid）（4）和奥山酸酯（2,4-dihydroxy-6-methyl benzoates） ）（5-15）。在0.50 mM时，甲基（5），乙基（6），正丙基（7），叔丁基（11）和正十六烷基山梨酸酯（15）充当酪氨酸酶激活剂，而正丁基（8）则是酪氨酸酶激活剂。丙基（9），仲丁基（10），正戊基（12），正己基（13）和山梨酸正辛酯（14）充当抑制剂。
• Process for arylamine production
  申请人：Goodbrand Bruce H.

  公开号：US20060111582A1

  公开（公告）日：2006-05-25

  4-aminobiphenyl derivative arylamine compounds are formed by providing an iodinated organic compound; substituting the iodinated organic compound at carboxylic acid groups thereof to provide ester protecting groups; conducting an Ullman condensation reaction to convert the product of step (ii) into an arylamine compound; and conducting a Suzuki coupling reaction to add an additional phenyl group to the arylamine compound in the 4-position relative to the nitrogen.

  通过提供碘代有机化合物来形成4-氨基联苯衍生物芳胺化合物；用羧酸基取代碘代有机化合物以提供酯保护基；进行乌尔曼缩合反应将步骤（ii）的产物转化为芳胺化合物；并进行铃木偶联反应，在与氮相对的4位上向芳胺化合物中添加额外的苯基。
• Radical-Scavenging Activity of Orsellinates
  作者：Thiago Inácio Barros Lopes、Roberta Gomes Coelho、Nídia Cristiane Yoshida、Neli Kika Honda

  DOI：10.1248/cpb.56.1551

  日期：——

  Lichens are an important source of phenolic compounds and have been intensively investigated for their biological and pharmacological activities. Lecanoric acid (1), a lichen depside, was isolated from a Parmotrema tinctorum specimen and treated with alcohols to produce orsellinic acid (2) and orsellinates (3) to (9) (2,4-dihydroxy-6-n-methyl benzoates). Free radical scavenging activity of methyl (3), ethyl (4), n-propyl (5), n-butyl (6), iso-propyl (7), sec-butyl (8), tert-butyl (9) orsellinates was evaluated using 2,2′-diphenyl-1-picrylhydrazyl (DPPH) method. Results showed that chain elongation of methyl (3) to n-butyl (6) causes a rise in the antioxidant activity. However, iso-propyl (7) and tert-butyl (9) were more active than the correspondent linear compounds, although sec-butyl (8) was less active among the chain ramified compounds. All the orsellinates were less active than lecanoric acid (1) and orsellinic acid (2). Orcinol (10) and resorcinol (11) were also determined for comparison with activities of orsellinates. Gallic acid (12) was used as control.

  地衣是酚类化合物的重要来源，人们对其生物和药理活性进行了深入研究。从 Parmotrema tinctorum 标本中分离出地衣苷酸 Lecanoric acid (1)，并用醇处理生成 orsellinic acid (2) 和 orsellinates (3) 至 (9)（2,4-二羟基-6-正甲基苯甲酸酯）。采用 2,2′-二苯基-1-苦基肼（DPPH）法评估了橙皮苷酸甲酯（3）、乙酯（4）、正丙酯（5）、正丁酯（6）、异丙酯（7）、仲丁酯（8）和叔丁酯（9）的自由基清除活性。结果表明，甲基（3）链延长为正丁基（6）会导致抗氧化活性上升。不过，异丙基（7）和叔丁基（9）的活性高于相应的线性化合物，但仲丁基（8）的活性在链延伸化合物中较低。所有橙皮苷酸的活性都低于柠檬酸（1）和橙皮苷酸（2）。此外，还测定了 Orcinol (10) 和 resorcinol (11)，以便与 orsellinates 的活性进行比较。没食子酸（12）用作对照。