2-羟基-3-(羟甲基)苯甲酸 | 93610-16-3

• 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-羟基-3-(羟甲基)苯甲酸
• 英文名称: 2-hydroxy-3-hydroxymethyl-benzoic acid
• 英文别名: 2-Hydroxy-3-hydroxymethyl-benzoesaeure；Saligenincarbonsaeure aus Salicylsaeure；2.3¹-Dioxy-3-methyl-benzol-carbonsaeure-(1)；3-(Oxy-methyl)-salicylsaeure；2.3¹-Dioxy-m-toluylsaeure；2-Hydroxy-3-(hydroxymethyl)benzoic acid
• CAS: 93610-16-3
• 化学式: C₈H₈O₄
• mdl: MFCD06202732
• 分子量: 168.149
• InChiKey: MCYJIWAVMOYBDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(羟甲基)苯甲酸 在 potassium permanganate 作用下， 生成 3-醛基水杨酸
  参考文献：
  名称：

  Postoperative pain management in patients undergoing major surgery after remifentanilvs fentanyl anesthesia

  摘要：

  Purpose: To determine ii morphine sulphate was an effective transition analgesic in patients receiving a remifentanil-based anesthetic regimen.Methods: Open-label remifentanil or fentanyl was administered to 210 randomized patients undergoing inpatient surgery Isoflurane and nitrous oxide was administered to all patients. Thirty minutes before the end of surgery, patients receiving remifentanil were randomized to receive morphine 0.15 mg.kg(-1) (R/M 15 group) or 0.20 mg.kg(-1) (R/M20 group). Following extubation and prior to patient-controlled analgesia (PCA) initiation, 2 mg boluses of morphine were administered for moderate/severe pain. Efficacy endpoints were total morphine used in the post anesthesia care unit (PACU) and 24 and 48 hr postoperatively; postoperative pain; time to first morphine bolus; time to first PCA administration; and time to recovery endpoints.Results: Mean total morphine used in PACU was not different among groups (15.5 mg, 16.5 mg and 13.3 mg in R/M 15, R/M20 and F groups, respectively). Mean total 24 hr morphine use (58.1 mg, 56.93 mg and 53.6 mg in R/M 15, R/M20 and F groups) and mean total morphine used at 48 hr were not different (69.8 mg, 64.7 mg and 62.1 mg in R/M 15, R/M20 and F/I groups). Groups were similar with respect to pain severity ratings at all postoperative times. Patients in the fentanyl arm experienced faster times to some recovery endpoints than patients receiving either remifentanil regimen.Conclusion: Morphine sulphate regimens of 0.15 or 0.20 mg.kg(-1) administered 30 min before the end of surgery are equally effective transition regimens for inpatient procedures.

  DOI：

  10.1007/bf03018943
• 作为产物：
  描述：

  3-醛基水杨酸 在 sodium amalgam 作用下， 生成 2-羟基-3-(羟甲基)苯甲酸
  参考文献：
  名称：

  Characterization and localization of cytochrome P450 mediated metabolism of MPTP to nor-MPTP in mouse brain: Relevance to Parkinson’s disease

  摘要：

  1-Methyl, 4-phenyl,l,2,5,6,tetrahydropyridine (MPTP) is a dopaminergic toxin which produces Parkinson's disease-like symptoms in primates and dopaminergic cell loss in mice. MPTP is bioactivated through monoamine oxidase to MPP+ and detoxified by cytochrome P450 to nor-MPTP. We have examined metabolisms of MPTP to nor-MPTP by mouse brain microsomes and compared it with corresponding activity in liver. In brain, but not in liver, this biotransformation was completely abolished by quinidine, an inhibitor of P4502D. Northern blotting experiments demonstrated constitutive expression of cytochrome P4502D in mouse brain. A fluorescencein situ hybridization study of mouse brain showed presence of P4502D mRNA predominantly in neuronal cells within the cortex, hippocampus, thalamus, Purkinje and granule cell layers of the cerebellum and in the reticular neurons of midbrain. Striatal neurons were sparsely stained indicating a relative paucity of expression. These studies demonstrate for the first time that detoxification of MPTP to nor-MPTP occurs in mouse brain through cytochrome P4502D which is primarily localized in neuronal cells. Cytochrome P4502D6 is known to exhibit genetic polymorphism in humans, and a defect in this isoform could potentially lead to decreased detoxification of neurotoxins in certain neuronal sub-population, which in turn may have implications in pathogenesis of Parkinson's disease.

  DOI：

  10.1007/bf03033198

文献信息

• Photobromination of Substituted Toluenes as a Route to Substituted Benzyl Alcohols and Benzaldehydes
  作者：Ernest L. Eliel、Donald E. Rivard

  DOI：10.1021/jo50009a010

  日期：1952.9
• Postoperative pain management in patients undergoing major surgery after remifentanilvs fentanyl anesthesia
  作者：Harold S. Minkowitz

  DOI：10.1007/bf03018943

  日期：2000.6

  Purpose: To determine ii morphine sulphate was an effective transition analgesic in patients receiving a remifentanil-based anesthetic regimen.Methods: Open-label remifentanil or fentanyl was administered to 210 randomized patients undergoing inpatient surgery Isoflurane and nitrous oxide was administered to all patients. Thirty minutes before the end of surgery, patients receiving remifentanil were randomized to receive morphine 0.15 mg.kg(-1) (R/M 15 group) or 0.20 mg.kg(-1) (R/M20 group). Following extubation and prior to patient-controlled analgesia (PCA) initiation, 2 mg boluses of morphine were administered for moderate/severe pain. Efficacy endpoints were total morphine used in the post anesthesia care unit (PACU) and 24 and 48 hr postoperatively; postoperative pain; time to first morphine bolus; time to first PCA administration; and time to recovery endpoints.Results: Mean total morphine used in PACU was not different among groups (15.5 mg, 16.5 mg and 13.3 mg in R/M 15, R/M20 and F groups, respectively). Mean total 24 hr morphine use (58.1 mg, 56.93 mg and 53.6 mg in R/M 15, R/M20 and F groups) and mean total morphine used at 48 hr were not different (69.8 mg, 64.7 mg and 62.1 mg in R/M 15, R/M20 and F/I groups). Groups were similar with respect to pain severity ratings at all postoperative times. Patients in the fentanyl arm experienced faster times to some recovery endpoints than patients receiving either remifentanil regimen.Conclusion: Morphine sulphate regimens of 0.15 or 0.20 mg.kg(-1) administered 30 min before the end of surgery are equally effective transition regimens for inpatient procedures.
• Characterization and localization of cytochrome P450 mediated metabolism of MPTP to nor-MPTP in mouse brain: Relevance to Parkinson’s disease
  作者：Sudarshan C. Upadhya、Michael R. Boyd、Vijayalakshmi Ravindranath

  DOI：10.1007/bf03033198

  日期：2001.7

  1-Methyl, 4-phenyl,l,2,5,6,tetrahydropyridine (MPTP) is a dopaminergic toxin which produces Parkinson's disease-like symptoms in primates and dopaminergic cell loss in mice. MPTP is bioactivated through monoamine oxidase to MPP+ and detoxified by cytochrome P450 to nor-MPTP. We have examined metabolisms of MPTP to nor-MPTP by mouse brain microsomes and compared it with corresponding activity in liver. In brain, but not in liver, this biotransformation was completely abolished by quinidine, an inhibitor of P4502D. Northern blotting experiments demonstrated constitutive expression of cytochrome P4502D in mouse brain. A fluorescencein situ hybridization study of mouse brain showed presence of P4502D mRNA predominantly in neuronal cells within the cortex, hippocampus, thalamus, Purkinje and granule cell layers of the cerebellum and in the reticular neurons of midbrain. Striatal neurons were sparsely stained indicating a relative paucity of expression. These studies demonstrate for the first time that detoxification of MPTP to nor-MPTP occurs in mouse brain through cytochrome P4502D which is primarily localized in neuronal cells. Cytochrome P4502D6 is known to exhibit genetic polymorphism in humans, and a defect in this isoform could potentially lead to decreased detoxification of neurotoxins in certain neuronal sub-population, which in turn may have implications in pathogenesis of Parkinson's disease.