3,4-(disulphooxy) caffeic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,4-(disulphooxy) caffeic acid
• 英文别名: (E)-3-(3,4-disulfooxyphenyl)prop-2-enoic acid
• 化学式: C₉H₈O₁₀S₂
• 分子量: 340.289
• InChiKey: CUJWQICOLIMNQR-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯磺酸 作用下， 以 吡啶 为溶剂， 生成 3,4-(disulphooxy) caffeic acid
  参考文献：
  名称：

  The antifouling activity of natural and synthetic phenol acid sulphate esters

  摘要：

  p-(sulphooxy) Cinnamic acid was isolated as a natural product for the first time from the seagrass Zostera marina (eelgrass) and was found to prevent attachment of marine bacteria and barnacles to artificial surfaces at non-toxic concentrations. Analogous synthetic sulphate esters had similar antifouling properties, while the non-sulphated phenolic acid precursors were ineffective. The antifouling properties of phenolic acid sulphates are consistent with an emerging pattern of biological activity exhibited by other sulphate esters isolated from a variety of marine organisms, and their low toxicity offers promise for the development of environmentally benign antifouling agents to protect structures in aquatic environments.

  DOI：

  10.1016/0031-9422(93)80017-m

文献信息

• PHENOLIC ACID SULFATE ESTERS FOR PREVENTION OF MARINE BIOFOULING
  申请人：ARCH DEVELOPMENT CORPORATION

  公开号：EP0675801A1

  公开（公告）日：1995-10-11
• EP0675801A4
  申请人：——

  公开号：EP0675801A4

  公开（公告）日：1997-12-17
• US5384176A
  申请人：——

  公开号：US5384176A

  公开（公告）日：1995-01-24
• US5607741A
  申请人：——

  公开号：US5607741A

  公开（公告）日：1997-03-04
• [EN] PHENOLIC ACID SULFATE ESTERS FOR PREVENTION OF MARINE BIOFOULING<br/>[FR] ESTERS DE SULFATE D'ACIDE PHENOLIQUE UTILES DANS LA PREVENTION DE LA BIOSALISSURE MARINE
  申请人：ARCH DEVELOPMENT CORPORATION

  公开号：WO1994013462A1

  公开（公告）日：1994-06-23

  (EN) p-sulfoxy cinnamic acid isolated from methanolic extracts of the eelgrass $i(Zostera marina) having significant antifouling aquatic properties. p-sulfoxy cinnamic acid was synthesized in the laboratory from p-coumaric acid, and antifouling activity was identical to the natural compound in laboratory bioassays. In addition, sulfate esters of other phenolic acids showed similar antifouling activity, suggesting that the sulfate ester was responsible for the antifouling effect.(FR) L'acide cinnamique p-sulfoxy isolé des extraits méthanoliques de la zostère $i(Zostera marina) possède d'importantes propriétés aquatiques anti-salissure. L'acide cinnamique p-sulfoxy a été synthétisé en laboratoire à partir de l'acide p-coumarique, et l'activité anti-salissure s'est avérée identique au composé naturel des titrages biologiques de laboratoire. De plus, des esters de sulfate d'autres acides phénoliques présentaient une activité anti-salissure similaire, laissant supposer que l'ester de sulfate était responsable de l'effet anti-salissure.