3-(10-hydroxydecyl)-2-methyl-2-cyclohexen-1-one

• 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: 3-(10-hydroxydecyl)-2-methyl-2-cyclohexen-1-one
• 英文别名: 3-(10-hydroxydecyl)-2-methylcyclohex-2-en-1-one
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: CCUJBDDWDSXJQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,10-癸二醇 在 正丁基锂 、 氢溴酸 、 对甲苯磺酸 作用下， 以 氯仿 、 环己烷 、 丙酮 为溶剂， 反应 33.0h， 生成 3-(10-hydroxydecyl)-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Effect of cyclohexenonic long chain fatty alcohols on neurite outgrowth. Study on structure-activity relationship

  摘要：

  Four series of long chain fatty alcohols bearing a cyclohexenone moiety in addition to a omega-alkanol side chain were synthesized using "Umpolung" reactivity strategy. Their effect on neurite outgrowth was evaluated by means of fetal rat neurons in culture. The length of the omega-hydroxy side chain is a crucial factor for biological activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00406-2

文献信息

• Cyclohexenonic Long-Chain Fatty Alcohols as Neuronal Growth Stimulators
  作者：Bang Luu、José-Luis De Aguilar、Céline Girlanda-Junges

  DOI：10.3390/51201439

  日期：——

  Neurotrophic factors play an important role in the development and maintenance of neurons, thus providing a suitable therapeutic approach for the treatment of neurodegenerative diseases. However, their clinical use has revealed problematic because of a number of technical and biological disadvantages. Among the different strategies proposed to overcome such difficulties, the search for non-peptide substances with neurotrophic potential is giving promising results. Here we will expose major findings in this field, drawing special attention to cyclohexenonic long-chain fatty alcohols, a novel family of compounds that promote neuronal survival and neurite outgrowth.

  神经营养因子在神经元的发育和维持中起着重要作用，因此为治疗神经退行性疾病提供了合适的疗法。然而，由于存在一系列技术和生物学上的缺点，它们在临床应用中遇到了问题。在提出的不同克服这些困难的策略中，寻找具有神经营养潜力的非肽类物质正取得令人鼓舞的成果。本文将展示该领域的主要发现，特别关注环己烯型长链脂肪醇，这是一个促进神经元存活和神经突延伸的新型化合物家族。
• Preventive and/or Therapeutic Agent for Diabetic Vascular Disorder and Respiratory Disorder
  申请人：Satoh Keisuke

  公开号：US20080312336A1

  公开（公告）日：2008-12-18

  The present invention provides preventive and/or therapeutic agents for either one, or both, of a diabetic vascular disorder and a diabetic respiratory disorder comprising, as an active ingredient, a cyclohexenone long chain alcohol compound represented by the following formula (1): [wherein R 1 , R 2 , and R 3 each represent a hydrogen atom or a methyl group, and X represents a linear or branched C10-C28 alkylene or alkenylene group]. Since the cyclohexenone long chain alcohol of formula (1) improves diabetic vascular smooth muscle contraction and bronchial smooth muscle contraction, it is useful as a preventive and/or therapeutic agent for a diabetic vascular disorder or a respiratory disorder.

  本发明提供了预防和/或治疗糖尿病血管疾病和糖尿病呼吸道疾病的预防和/或治疗剂，其活性成分为以下式（1）所表示的环己烯酮长链醇化合物： [其中R1、R2和R3分别表示氢原子或甲基基团，X表示线性或支链C10-C28烷基或烯基基团]。 由于式（1）中的环己烯酮长链醇改善了糖尿病血管平滑肌收缩和支气管平滑肌收缩，因此它可用作糖尿病血管疾病或呼吸道疾病的预防和/或治疗剂。
• [EN] CYCLOHEXENONE LONG-CHAIN ALCOHOL AND MEDICAMENT CONTAINING SAME<br/>[FR] ALCOOL A CHAINE LONGUE CYCLOHEXENONE ET MEDICAMENT LE CONTENANT
  申请人：MEIJI MILK PRODUCTS CO., LTD.

  公开号：WO1999008987A1

  公开（公告）日：1999-02-25

  (EN) Described is a cyclohexenone long-chain alcohol represented by formula (1), wherein R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and X represents a C10-18 alkylene or alkenylene group. The cyclohexenone long-chain alcohol according to the present invention has excellent neurite growth stimulating effects and is therefore useful as a preventive and/or therapeutic agent for Alzheimer's disease.(FR) L'invention concerne un alcool à chaîne longue cyclohexénone représenté par la formule (1) dans laquelle R1, R2 et R3 représentent chacun indépendamment un atome d'hydrogène ou un groupe méthyle et X représente un groupe alkylène ou alcénylène C10-18. L'alcool à chaîne longue cyclohexénone selon la présente invention présente d'excellents effets stimulant la croissance de neurites et il est par conséquent utile en tant qu'agent préventif et/ou thérapeutique contre la maladie d'Alzheimer.

  (中) 描述了一种由式（1）表示的环己烯酮长链醇，其中R1、R2和R3各自独立地表示氢原子或甲基基团，而X表示一个C10-18烷基或烯基烷基团。根据本发明，该环己烯酮长链醇具有优异的神经元生长刺激作用，因此可作为预防和/或治疗阿尔茨海默病的药物。
• Cyclohexenone long-chain alcohol and medicament containing same
  申请人：Meiji Milk Products Co., Ltd.

  公开号：US06228893B1

  公开（公告）日：2001-05-08

  Described is a cyclohexenone long-chain alcohol represented by the formula (1): wherein R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and X represents a C10-18 alkylene or alkenylene group. The cyclohexanone long-chain alcohol according to the present invention has excellent neurite growth stimulating effects and is therefore useful as a preventive and/or therapeutic agent for Alzheimer's disease.

  本发明涉及一种环己烯酮长链醇，其化学式表示为（1）：其中R1、R2和R3各自独立地表示氢原子或甲基基团，X表示C10-18烷基或烯基基团。本发明中的环己酮长链醇具有优异的神经元生长刺激效果，因此可作为预防和/或治疗阿尔茨海默病的药物。
• Use of cyclohexenone long-chain alcohol for treating neurodegenerative diseases
  申请人：Meiji Dairies Corporation

  公开号：US07166642B1

  公开（公告）日：2007-01-23

  A preventive and therapeutic drug for a neurodegenerative disease containing, as an active ingredient, a cyclohexenone long-chain alcohol compound represented by formula (1) wherein each of R1, R2, and R3 represents a hydrogen atom or a methyl group; and X represents a C10–C28 alkylene group or alkenylene group. Since the compound of the present invention exhibits excellent neurite-extension ability and an inhibition effect on disorders caused by mutation in an SOD gene, it is useful as the active ingredient of a preventive and therapeutic drug for neurodegenerative diseases, inter alia, amyotrophic lateral sclerosis, and as the active ingredient of an inhibitory drug for disorders caused by mutation in an SOD gene.

  一种预防和治疗神经退行性疾病的药物，其含有一个环己烯酮长链醇化合物作为活性成分，该化合物由式（1）表示，其中R1、R2和R3中的每一个表示氢原子或甲基基团；X表示C10-C28烷基或烯基烷基。由于本发明的化合物具有出色的神经元生长延伸能力和对由SOD基因突变引起的疾病的抑制作用，因此它可用作预防和治疗神经退行性疾病，尤其是肌萎缩侧索硬化症的活性成分，以及用作对由SOD基因突变引起的疾病的抑制药物的活性成分。