4-(6-hydroxyhexyl)benzoic acid | 137757-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(6-hydroxyhexyl)benzoic acid
• CAS: 137757-24-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: VVOAPFUTUIVKHE-UHFFFAOYSA-N

物化性质

• 沸点：
  402.4±38.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4-(6-hydroxyhexyl)benzoic acid 在 potassium dihydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.59h， 生成 4-[6-(2-Cyano-2-hydroxy-4-methoxy-4-oxobutyl)sulfanylhexyl]benzoic acid
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 platinum(IV) oxide 氢气 、 二异丁基氢化铝 、 dimsyl sodium 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 2.0h， 生成 4-(6-hydroxyhexyl)benzoic acid
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• TW2021/4161
  申请人：——

  公开号：——

  公开（公告）日：——
• REACTIVE MESOGENS
  申请人：Merck Patent GmbH

  公开号：EP3963026A1

  公开（公告）日：2022-03-09
• US5641846A
  申请人：——

  公开号：US5641846A

  公开（公告）日：1997-06-24
• [EN] REACTIVE MESOGENS<br/>[FR] MÉSOGÈNES RÉACTIFS
  申请人：MERCK PATENT GMBH

  公开号：WO2020221677A1

  公开（公告）日：2020-11-05

  The invention relates to novel reactive mesogens (RMs), to mixtures and formulations comprising them, to polymers obtained from such RMs and RM mixtures, and the use of the RMs, RM mixtures and polymers in optical or electrooptical components or devices, like optical films for liquid crystal displays (LCDs).
• ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme
  作者：Andrew D. Gribble、Roland E. Dolle、Antony Shaw、David McNair、Riccardo Novelli、Christine E. Novelli、Brian P. Slingsby、Virendra P. Shah、David Tew、Barbara A. Saxty、Mark Allen、Pieter H. Groot、Nigel Pearce、John Yates

  DOI：10.1021/jm960167w

  日期：1996.1.1

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.