m-geranyl-p-hydroxybenzoic acid | 68631-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: m-geranyl-p-hydroxybenzoic acid
• 英文别名: 3-Geranyl-4-hydroxybenzoic acid；3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-hydroxybenzoic acid
• CAS: 68631-48-1
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: HKIMBCGCVPYUTJ-NTUHNPAUSA-N

物化性质

• 沸点：
  459.4±45.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-geranyl-p-hydroxybenzoic acid 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 m-geranyl-p-methoxybenzoic acid methyl ester
  参考文献：
  名称：

  Enzyme activities in cell-free extracts of shikonin-producing Lithospermum erythrorhizon cell suspension cultures

  摘要：

  DOI：

  10.1016/s0031-9422(00)82262-1
• 作为产物：
  描述：

  香叶基溴 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 m-geranyl-p-hydroxybenzoic acid
  参考文献：
  名称：

  紫草愈伤组织培养物中紫草素的生物合成

  摘要：

  摘要 对在补充有 IAA 和激动素的 Linsmaier-Skoog 培养基上生长的 Lithospermum erythrorhizon 愈伤组织培养物施用各种假定的前体，确定成分紫草素是通过莽草酸、对羟基苯甲酸、间香叶基对羟基苯甲酸和香叶基氢醌。在缺乏合成紫草素能力的愈伤组织培养物中，在具有这种能力但由于在补充有 2,4-D 的培养基上培养而失去这种能力的愈伤组织培养物中，高达间香叶基-对羟基苯甲酸的物质生物合成序列已被检测到。尽管用白光照射也阻止了紫草素的产生，但可能仍形成了色素痕迹，原因可能是光线没有到达愈伤组织培养物的最内部。

  DOI：

  10.1016/0031-9422(79)83012-5

文献信息

• Identification of a bacteria-produced benzisoxazole with antibiotic activity against multi-drug resistant Acinetobacter baumannii
  作者：Robert W. Deering、Kristen E. Whalen、Ivan Alvarez、Kathryn Daffinee、Maya Beganovic、Kerry L. LaPlante、Shreya Kishore、Sijing Zhao、Brent Cezairliyan、Shen Yu、Margaret Rosario、Tracy J. Mincer、David C. Rowley

  DOI：10.1038/s41429-021-00412-7

  日期：2021.6

  The emergence of multi-drug resistant pathogenic bacteria represents a serious and growing threat to national healthcare systems. Most pressing is an immediate need for the development of novel antibacterial agents to treat Gram-negative multi-drug resistant infections, including the opportunistic, hospital-derived pathogen, Acinetobacter baumannii. Herein we report a naturally occurring 1,2-benzisoxazole with minimum inhibitory concentrations as low as 6.25 μg ml⁻¹ against clinical strains of multi-drug resistant A. baumannii and investigate its possible mechanisms of action. This molecule represents a new chemotype for antibacterial agents against A. baumannii and is easily accessed in two steps via de novo synthesis. In vitro testing of structural analogs suggest that the natural compound may already be optimized for activity against this pathogen. Our results demonstrate that supplementation of 4-hydroxybenzoate in minimal media was able to reverse 1,2-benzisoxazole’s antibacterial effects in A. baumannii. A search of metabolic pathways involving 4-hydroxybenzoate coupled with molecular modeling studies implicates two enzymes, chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyltransferase, as promising leads for the target of 3,6-dihydroxy-1,2-benzisoxazole.

  《摘要》 多药耐药致病菌的出现对国家医疗保健系统构成了严重且日益增长的威胁。最紧迫的是迫切需要开发新型抗菌剂来治疗革兰氏阴性多药耐药感染，包括机会性、来源于医院的病原体鲍曼不动杆菌。在这里，我们报告了一种天然存在的1,2-苯并异噁唑，对多药耐药鲍曼不动杆菌的临床菌株具有最低的最小抑制浓度，低至6.25μg ml⁻¹，并研究了其可能的作用机制。这种分子代表了一种新的化学类型，用于对抗鲍曼不动杆菌的抗菌剂，并可通过新合成的两个步骤轻松获得。对结构类似物的体外测试表明，这种天然化合物可能已经针对这种病原体的活性进行了优化。我们的结果表明，在最小培养基中补充4-羟基苯甲酸能够逆转1,2-苯并异噁唑对鲍曼不动杆菌的抗菌效果。搜索涉及4-羟基苯甲酸的代谢途径，并结合分子建模研究，暗示了两种酶，分别是赤霉酸丙酮酸裂解酶和4-羟基苯甲酸辛烯基转移酶，作为3,6-二羟基-1,2-苯并异噁唑的靶点的有希望的线索。
• [EN] PHENYL-PRENYL DERIVATIVES, OF MARINE AND SYNTHETIC ORIGIN, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS<br/>[FR] DÉRIVÉS DE PHÉNYLE-PRÉNYLE D'ORIGINE MARINE ET SYNTHÉTIQUE, DESTINÉS AU TRAITEMENT DE MALADIES OU TROUBLES COGNITIFS, NEURODÉGÉNÉRATIFS OU NEURONAUX
  申请人：NOSCIRA SA

  公开号：WO2009098287A1

  公开（公告）日：2009-08-13

  The present invention is related to a family of phenyl-prenyl derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the compounds of formula (I) for medical use, particularly for the use for the treatment and/or prevention of a cognitive, neurodegenerative or neuronal disease or disorder, and to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a cognitive, neurodegenerative or neuronal disease or disorder.

  本发明涉及一类具有式（I）的苯基-烯丙基衍生物，以及它们在治疗认知、神经退行性或神经疾病或障碍，如阿尔茨海默病或帕金森病中的用途。本发明还涉及包含相同化合物的药物组合物。此外，本发明针对式（I）的化合物用于医疗用途，特别是用于治疗和/或预防认知、神经退行性或神经疾病或障碍，并且用于制造用于治疗和/或预防认知、神经退行性或神经疾病或障碍的药物的化合物。
• PHENYL-PRENYL DERIVATIVES, OF MARINE AND SYNTHETIC ORIGIN, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS
  申请人：Lopez Ogalla Javier

  公开号：US20110092591A1

  公开（公告）日：2011-04-21

  The present invention is related to a family of phenyl-prenyl derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the compounds of formula (I) for medical use, particularly for the use for the treatment and/or prevention of a cognitive, neurodegenerative or neuronal disease or disorder, and to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a cognitive, neurodegenerative or neuronal disease or disorder.

  本发明涉及一类公式（I）的苯基-异戊烯基衍生物家族，以及它们在治疗认知、神经退行性或神经性疾病或疾病方面的用途，例如阿尔茨海默病或帕金森病。本发明还涉及包含这些化合物的制药组合物。此外，本发明针对公式（I）的化合物用于医疗用途，特别是用于治疗和/或预防认知、神经退行性或神经性疾病或疾病的用途，以及将这些化合物用于制造治疗和/或预防认知、神经退行性或神经性疾病或疾病的药物。
• IMPROVED MUCONIC ACID PRODUCTION FROM GENETICALLY ENGINEERED MICROORGANISMS
  申请人：Myriant Corporation

  公开号：EP3423563A1

  公开（公告）日：2019-01-09
• MUCONIC ACID PRODUCTION FROM GENETICALLY ENGINEERED MICROORGANISMS
  申请人：PTT GLOBAL CHEMICAL PUBLIC COMPANY LIMITED

  公开号：US20210277429A1

  公开（公告）日：2021-09-09

  The subject of this invention is improvements in the yield and titer of biological production of muconic acid by fermentation. Increased activity of one or more enzymes involved in the muconic acid pathway leads to increased production of muconic acid.