甲基十五碳-14-炔酸酯 | 56909-04-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基十五碳-14-炔酸酯
• 英文名称: pentadecane-14-ynoic acid methyl ester
• 英文别名: pentadecan-14-ynoic acid methyl ester；14-pentadecynoic acid, methyl ester；pentadec-14-ynoic acid methyl ester；methyl pentadec-14-ynoate；Methyl pentadec-14-ynoate
• CAS: 56909-04-7
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: YGNRYNIJWVNKSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基十五碳-14-炔酸酯 在 lithium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 triisopropylsilyl (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-pentakis(benzyloxy)-26-(((R)-1-(tert-butoxy)-3-methyl-1-oxobutan-2-yl)amino)-17-hydroxy-26-oxohexacos-14-ynoate
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d
• 作为产物：
  描述：

  12‐(benzyloxy)dodecanal 在 palladium on activated charcoal pyridine-SO3 complex 、 氢气 、 potassium carbonate 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 26.5h， 生成 甲基十五碳-14-炔酸酯
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d

文献信息

• [EN] VERY-LONG-CHAIN POLYUNSATURATED FATTY ACIDS, ELOVANOID HYDROXYLATED DERIVATIVES, AND METHODS OF USE<br/>[FR] ACIDES GRAS POLYINSATURÉS À TRÈS LONGUE CHAÎNE, DÉRIVÉS HYDROXYLÉS D'ÉLOVANOÏDE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV LOUISIANA STATE

  公开号：WO2021046448A1

  公开（公告）日：2021-03-11

  This disclosure relates to methods of use related to omega-3 very-long-chain polyunsaturated fatty acids (n-3 VLC-PUFA) and their hydroxylated derivatives known as elovanoids to alleviate a symptom of, treat, or prevent disease. Furthermore, this invention is directed to compositions and methods for modulating VLC-PUFA bioactivity and availability.

  本公开涉及使用方法与ω-3非常长链多不饱和脂肪酸（n-3 VLC-PUFA）及其羟基化衍生物（称为elovanoids）缓解症状、治疗或预防疾病。此外，本发明还涉及调节VLC-PUFA生物活性和可用性的组合物和方法。
• [EN] VERY-LONG-CHAIN POLYUNSATURATED FATTY ACIDS, ELOVANOID HYDROXYLATED DERIVATIVES, AND METHODS OF USE<br/>[FR] ACIDES GRAS POLYINSATURÉS À CHAÎNE TRÈS LONGUE, DÉRIVÉS HYDROXYLÉS D'ELOVANOID, ET PROCÉDÉS D'UTILISATION
  申请人：UNIV LOUISIANA STATE

  公开号：WO2018175288A1

  公开（公告）日：2018-09-27

  Provided are compounds, pharmaceutical compositions, cosmetic and dermatological compositions or nutritional supplement compositions, comprising omega-3 very-long-chain polyunsaturated fatty acids (n-3 VLC-PUFAs) and/or their endogenous hydroxylated derivatives thereof, known as elovanoids. This disclosure provides methods for neuroprotection, organ and tissue protection or restoration, prevention or slowing down of aging-related diseases and conditions, and sustainment of function during the aging process.

  提供了化合物、药物组成、化妆品和皮肤科组成或营养补充剂组成，包括ω-3超长链多不饱和脂肪酸（n-3 VLC-PUFAs）和/或其内源性羟基化衍生物，被称为elovanoids。本公开提供了神经保护、器官和组织保护或修复、预防或减缓与衰老相关的疾病和状况以及在衰老过程中维持功能的方法。
• [EN] VERY-LONG-CHAIN POLYUNSATURATED FATTY ACIDS, ELOVANOID HYDROXYLATED DERIVATIVES, AND METHODS OF USE<br/>[FR] ACIDES GRAS POLYINSATURÉS À TRÈS LONGUE CHAÎNE, DÉRIVÉS HYDROXYLÉS D'ÉLOVANOÏDE ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV LOUISIANA STATE

  公开号：WO2022056311A1

  公开（公告）日：2022-03-17

  This disclosure is directed is directed to compositions and methods for preventing, treating, or ameliorating the symptoms of a viral infection.

  本披露涉及用于预防、治疗或缓解病毒感染症状的组合物和方法。
• Compounds, compositions, and methods for the treatment of inflammatory, degenerative, and neurodegenerative diseases
  申请人：Board of Supervisors of Louisiana State University and Agricultural and Mechanical College

  公开号：US10633324B2

  公开（公告）日：2020-04-28

  This disclosure provides compounds, pharmaceutical compositions, and methods of use for the prevention and treatment of inflammatory diseases or degenerative diseases including neurodegenerative diseases. Embodiments of the present disclosure provide compounds related to very long chain polyunsaturated fatty acids, pharmaceutical compositions containing the provided compounds, and methods of treating a subject with a condition or disease using provided compounds or pharmaceutical compositions.

  本公开提供了用于预防和治疗炎症性疾病或退行性疾病（包括神经退行性疾病）的化合物、药物组合物和使用方法。本公开的实施方案提供了与超长链多不饱和脂肪酸有关的化合物、含有所提供的化合物的药物组合物，以及使用所提供的化合物或药物组合物治疗患有某种病症或疾病的受试者的方法。
• COMPOUNDS, COMPOSITIONS, AND METHODS FOR THE TREATMENT OF INFLAMMATORY, DEGENERATIVE, AND NEURODEGENERATIVE DISEASES
  申请人：The Board of Supervisors of Louisiana State University and Agricultural and Mechanical College

  公开号：EP3256438A1

  公开（公告）日：2017-12-20