2-乙酰氧基苯甲酸苄酯 | 52602-17-2

• 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-乙酰氧基苯甲酸苄酯
• 英文名称: 2-acetoxybenzoic acid benzyl ester
• 英文别名: benzyl 2-acetoxybenzoate；2-acetoxy-benzoic acid benzyl ester；2-Acetoxy-benzoesaeure-benzylester；Acetylsalicylsaeure-benzylester；benzyl 2-acetyloxybenzoate
• CAS: 52602-17-2
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: FTKJKXRSODPSDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2918229000

反应信息

• 作为反应物：
  描述：

  2-乙酰氧基苯甲酸苄酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 柳酸苄酯
  参考文献：
  名称：

  吸出α-氨基醇（Sarpogrelate M1）

  摘要：

  α-氨基醇（沙格雷酯 M1）的抽吸已在各种一般酯化条件下进行。在大多数情况下，所需的阿司匹林酯以低产率获得，并带有意想不到的副产物，其形成主要源自叔 α-氨基的化学性质。在对这些方法进行系统分析后，使用结合水杨酸酯形成和乙酰化的两步方法制备了抽吸沙格雷酯 M1。

  DOI：

  10.3390/molecules21091126
• 作为产物：
  描述：

  阿司匹林 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-乙酰氧基苯甲酸苄酯
  参考文献：
  名称：

  吸出α-氨基醇（Sarpogrelate M1）

  摘要：

  α-氨基醇（沙格雷酯 M1）的抽吸已在各种一般酯化条件下进行。在大多数情况下，所需的阿司匹林酯以低产率获得，并带有意想不到的副产物，其形成主要源自叔 α-氨基的化学性质。在对这些方法进行系统分析后，使用结合水杨酸酯形成和乙酰化的两步方法制备了抽吸沙格雷酯 M1。

  DOI：

  10.3390/molecules21091126

文献信息

• Process for preparing acylated esters of hydroxy carboxylates
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0002872A1

  公开（公告）日：1979-07-11

  A process for esterifying and acylating hydroxycarboxylate compounds in an organonitrile reaction medicine comprising the steps of contacting said compounds with an esterification agent-and thereafter acylating by adding an acylating agent to the reaction medium.

  一种在有机腈反应药剂中对羟基羧酸化合物进行酯化和酰化的工艺，包括以下步骤：将所述化合物与酯化剂接触，然后通过向反应介质中添加酰化剂进行酰化。
• Anti-ulcer composition
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0004686A2

  公开（公告）日：1979-10-17

  Zwitterionic surfactant compounds provide effective therapy for ulceration of the gastric mucosa. The tendency of . aspirin and other salicylate-based drugs to cause ulceration of the gastric mucosa is also reduced by administration of such drugs in conjunction with certain zwitterionic surfactants. The ammoniohexanoate zwitterionics are especially preferred in the management of both gastric and duodenal ulcers.

  表面活性剂是治疗胃粘膜溃疡的有效药物。将阿司匹林和其他水杨酸类药物与某些表面活性剂结合使用，也可减少此类药物导致胃黏膜溃疡的倾向。在治疗胃溃疡和十二指肠溃疡时，氨代己酸酯类表面活性剂尤其受到青睐。
• Positively charged water-soluble prodrugs of aspirin
  申请人：Techfields Biochem Co. Ltd

  公开号：EP2610242A1

  公开（公告）日：2013-07-03

  The novel positively charged prodrugs of acetylsalicylic acid and its analogues in the general formula(1) 'Structure 1' were designed and synthesized. The compounds of the general formula(1) 'Structure 1' indicated above can be prepared from functional derivatives of ASA or its analogues,(for example acid halides or mixed anhydrides), by reaction with suitable alcohols, thiols, or amines. The positively charged amino groups of these pro-drugs not only largely increases the solubility of the drugs, but also bonds to the negative charge on the phosphate head group of membranes and push the pro-drug into the cytosol. The experiment results suggest that the pro-drug, diethylaminoethyl acetylsalicylate. AcOH, diffuses through human skin -400 times faster than acetylsalicylic acid itself and ∼100 times faster than ethyl acetylsalicylate. In plasma, 80% of these pro-drugs can change back to the drug in a few minutes. The pro-drugs can be used medicinally in treating any aspirin-treatable conditions in humans or animals and be administered not only orally, but also transdermally for any kind of medical treatments and avoid most of the side effects of aspirin, most notably GI disturbances such as dyspepsia, gastroduodenal bleeding, gastric ulcerations, and gastritis. Controlled transdermal administration systems of the prodrug enables the aspirin to reach constantly optimal therapeutic blood levels to increase effectiveness and reduce the side effects of aspirin.

  设计并合成了带正电荷的新型乙酰水杨酸原药及其通式（1）"结构 1 "中的类似物。上述通式（1）"结构 1 "化合物可由 ASA 或其类似物的功能性衍生物（如酸卤化物或混合酸酐）与适当的醇、硫醇或胺反应制备而成。这些原药带正电荷的氨基不仅能大大增加药物的溶解度，还能与膜上磷酸头基的负电荷结合，将原药推入细胞质中。实验结果表明，原药乙酰水杨酸二乙氨基乙酯（Diethylaminoethyl acetylsalicylate.AcOH 在人体皮肤中的扩散速度比乙酰水杨酸本身快 400 倍，比乙酰水杨酸乙酯快 100 倍。在血浆中，80% 的原药可在几分钟内变回药物。这些原药可用于治疗人类或动物的任何阿司匹林可治疗的疾病，不仅可以口服，还可以透皮给药，用于任何类型的医疗，并可避免阿司匹林的大部分副作用，尤其是消化道紊乱，如消化不良、胃十二指肠出血、胃溃疡和胃炎。原药的可控透皮给药系统可使阿司匹林不断达到最佳治疗血药浓度，从而提高疗效并减少阿司匹林的副作用。
• Methods for improving size and appearance of a wound
  申请人：Avocet Polymer Technologies, Inc.

  公开号：US20020013300A1

  公开（公告）日：2002-01-31

  The present invention relates to compositions, methods and kits for improving the size and appearance of a healed wound or scar. The composition includes a therapeutically effective amount of at least one cyclooxygenase inhibitor, NF-kB inhibitor, or an antiirritant. For topical, transdermal administration, the cyclooxygenase inhibitor or NF-kB inhibitor may be present in a thermal insulating material such as a hydrogel. The thermal insulating material may also include a deodorant agent to reduce surface bacteria and odor formation.

  本发明涉及用于改善愈合伤口或疤痕的大小和外观的组合物、方法和试剂盒。该组合物包括治疗有效量的至少一种环氧化酶抑制剂、NF-kB 抑制剂或抗刺激剂。对于局部透皮给药，环氧化酶抑制剂或 NF-kB 抑制剂可存在于隔热材料（如水凝胶）中。隔热材料还可包括除臭剂，以减少表面细菌和气味的形成。
• Chemical Feasibility Studies Concerning Potential Prodrugs of Acetylsalicylic Acid.
  作者：Asger B. Hansen、Alexander Senning、Xu Jie-Cheng、Ulla Björkroth、Lu Yi-An、Liu Yin-Zeng

  DOI：10.3891/acta.chem.scand.37b-0351

  日期：——

  A rationale is developed for aspirin prodrugs based on non-acidic latentiated derivatives. Knowledge of the gastro-intestinal liabilities and pharmacological profile is required for this approach whereby aspirin is built into a common ortho ester function of the type 2-substituted 2-methyl-4H-1,3-benzodioxin-4-one with latentiated carboxyl and acetoxy groups. Twelve compounds of this type, ten substituted with various alkoxy and aryloxy groups and two with arylthio groups, have been isolated and characterized. A new synthetic route, comprising the reaction of 2-acetoxybenzoyl chloride with TMS derivatives of the corresponding alcohols and phenols, has been devised for the preparation of some of the compounds while others were prepared according to known methods. Subsequently, the prodrug candidates have been subjected to non-enzymatic hydrolysis for a first rapid screening in vitro. Only 2-tert-butoxy-2-methyl-4H-1,3-benzodioxin-4-one is observed to act as a true proaspirin, releasing aspirin, under these conditions, but analogous compounds with tertiary substituents may display the same behavior, and this chemical approach to aspirin modification may offer a viable rationale for aspirin prodrugs with reduced gastric irritancy or for making "superaspirins".