butyryl ester of capsaicin

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: butyryl ester of capsaicin
• 英文别名: 4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate；4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenyl butanoate；[2-methoxy-4-[[[(E)-8-methylnon-6-enoyl]amino]methyl]phenyl] butanoate
• 化学式: C₂₂H₃₃NO₄
• 分子量: 375.508
• InChiKey: PAOWARHHFSBHQL-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  辣椒碱 、 丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到butyryl ester of capsaicin
  参考文献：
  名称：

  Esters of capsaicinoids as dietary supplements

  摘要：

  提供的是含酯化辣椒素的营养保健品或膳食补充剂组合物。酯化辣椒素可以在酶解或化学水解后转化为活性母辣椒素化合物。在各种实施方式中，这些酯化辣椒素具有较高的亲脂性、脂溶性，对胃部的刺激较小，因此可以包含在某些膳食补充剂配方中，包括胶囊、药丸和片剂膳食补充剂配方。这些膳食补充剂组合物可用于体内哺乳动物的疼痛管理和/或用于治疗人类的各种病理状况。

  公开号：

  US20100120912A1

文献信息

• TRPV1 agonist compounds and methods for making and using the same
  申请人：Jamieson Curtis Gene

  公开号：US20060240097A1

  公开（公告）日：2006-10-26

  Described here are TRPV1 agonist compounds and their methods of synthesis and use. In addition to specifically identified compounds, capsaicin prodrugs, gemini dimers, and mutual prodrugs are also described. Formulations of the TRPV1 agonist compounds may be in the form of a liquid, tablets, capsules, gel, cream, emulsion, a patch, or the like. Methods for treating medical conditions using the compounds, compositions, or prodrugs described, are also provided.

  这里描述了TRPV1激动剂化合物及其合成和使用方法。除了具体识别的化合物外，还描述了辣椒素前药、双子星二聚体和相互前药。TRPV1激动剂化合物的配方可以是液体、片剂、胶囊、凝胶、乳霜、乳状液、贴片等形式。还提供了使用所述化合物、组合物或前药治疗医疗状况的方法。
• Novel pharmaceutical compositions for treating chronic pain and pain associated with neuropathy
  申请人：Singh Ulagaraj Chandra

  公开号：US20080058362A1

  公开（公告）日：2008-03-06

  Chronic pain is alleviated in a mammal suffering there from by administering to the mammal a chronic pain alleviating amount of a nontoxic N-methyl-D-aspartate receptor antagonist such as dextromethorphan, dextrorphan, ketamine or pharmaceutically acceptable salt thereof, in combination with a μ-opiate analgesic such as tramadol or an analogously acting molecular entity, and a capsaicin or an ester of capsaicin, and optionally in sustained release dosage form.

  通过向哺乳动物投予一定量的无毒N-甲基-D-天冬氨酸受体拮抗剂，如右美沙芬、右美沙芬酮、氯胺酮或其药用盐，结合μ-阿片类镇痛药，如曲马多或类似作用的分子实体，以及辣椒素或辣椒素酯，可缓解患有慢性疼痛的哺乳动物的疼痛，也可以采用持续释放剂量形式。
• Esters of capsaicin for treating pain
  申请人：Singh Chandra Ulagaraj

  公开号：US20080020996A1

  公开（公告）日：2008-01-24

  The present invention relates to the formulations of ester derivatives of capsaicin and ester derivatives of myristoleic acid. These derivatives are capable of reverting to the active parent compound following enzymatic or chemical hydrolysis. These derivatives have a higher lipophilicity, lipid solubility and less irritation to the skin than the parent compound, and hence are better able to be incorporated into certain pharmaceutical formulations, including cream and ointment pharmaceutical formulations. The pharmaceutical compositions of the present invention contain a compound of following formula (Ia): R—CO-CAP   (Ia) wherein CAP refers to collectively the capsaicins represented in FIG. 1 and a compound of formula (Ib): MCO-O—R   (Ib) wherein MCO refers to myristoleic acid. In formulae Ia and Ib, R is selected from alkyl groups of up to about 18 carbon atoms and aryl groups of up to about 18 carbon atoms and alkylene group of up to about 18 carbon atoms and an arylene group of up to about 18 carbon atoms. The alkyl, aryl and alkylene groups may be substituted or un-substituted, branched or straight chains. In addition, R may contain heteroatoms and may be straight chained or branched. The pharmaceutical compositions containing compounds of formulae Ia and Ib are useful for pain management in mammals in vivo and have been contemplated to be used in the treatment of various pains in humans.

  本发明涉及辣椒素酯衍生物和肉豆蔻油酸酯衍生物的配方。这些衍生物能够在酶解或化学水解后恢复为活性母化合物。这些衍生物具有更高的亲脂性、脂溶性，对皮肤的刺激性较小，因此更容易被纳入某些药物配方中，包括膏剂和药膏配方。本发明的药物组合物含有下式（Ia）的化合物：R—CO-CAP（Ia），其中CAP指的是在图1中表示的辣椒素，和下式（Ib）的化合物：MCO-O—R（Ib），其中MCO指的是肉豆蔻油酸。在式Ia和Ib中，R选自碳原子数最多约为18的烷基基团和碳原子数最多约为18的芳基基团以及碳原子数最多约为18的烷基基团和碳原子数最多约为18的芳基基团。烷基、芳基和烷基基团可以是取代或未取代的，支链或直链。此外，R可能含有杂原子，可能是直链或支链的。含有式Ia和Ib的药物组合物对于体内哺乳动物的疼痛管理是有用的，并已考虑用于治疗人类的各种疼痛。
• Esters of Capsaicin for Treating Pain
  申请人：Singh Chandra Ulagaraj

  公开号：US20110218180A1

  公开（公告）日：2011-09-08

  The present invention relates to the formulations of ester derivatives of capsaicin and ester derivatives of myristoleic acid. These derivatives are capable of reverting to the active parent compound following enzymatic or chemical hydrolysis. These derivatives have a higher lipophilicity, lipid solubility and less irritation to the skin than the parent compound, and hence are better able to be incorporated into certain pharmaceutical formulations, including cream and ointment pharmaceutical formulations. The pharmaceutical compositions of the present invention contain a compound of following formula (Ia): R—CO—CAP  (Ia) wherein CAP refers to collectively the capsaicins represented in FIG. 1 and a compound of formula (Ib): MCO—O—R  (Ib) wherein MCO refers to myristoleic acid. In formulae Ia and Ib, R is selected from alkyl groups of up to about 18 carbon atoms and aryl groups of up to about 18 carbon atoms and alkylene group of up to about 18 carbon atoms and an arylene group of up to about 18 carbon atoms. The alkyl, aryl and alkylene groups may be substituted or un-substituted, branched or straight chains. In addition, R may contain heteroatoms and may be straight chained or branched. The pharmaceutical compositions containing compounds of formulae Ia and Ib are useful for pain management in mammals in vivo and have been contemplated to be used in the treatment of various pains in humans.
• PRODRUGS OF PHENOLIC TRPV1 AGONISTS
  申请人：Concentric Analgesics, Inc.

  公开号：US20190284132A1

  公开（公告）日：2019-09-19

  Described herein are compounds, pharmaceutical compositions and medicaments that include such compounds, and methods of using such compounds to modulate transient receptor potential vanilloid 1 receptor (TRPV1) activity.