N-[(4-羟基-3-甲氧基苯基)甲基]十六烷酰胺 | 69693-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: N-[(4-羟基-3-甲氧基苯基)甲基]十六烷酰胺
• 英文名称: Palvanil
• 英文别名: N-[(4-hydroxy-3-methoxyphenyl)methyl]-hexadecanamide；N-(4-hydroxy-3-methoxybenzyl)hexadecanamide；N-vanillyl-hexadecanamide；N-vanillyl-palmitamide；N-Vanillyl-palmitinamid；Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-；N-[(4-hydroxy-3-methoxyphenyl)methyl]hexadecanamide
• CAS: 69693-13-6
• 化学式: C₂₄H₄₁NO₃
• 分子量: 391.594
• InChiKey: SGEUEXJZQFSBNX-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  565.4±40.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

帕凡尼是一种辣椒素类似物，对TRPV1受体具有较强的脱敏能力。它还具有抗伤害和抗炎作用。

反应信息

• 作为产物：
  描述：

  香兰素胺盐酸盐 在 borate buffer 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 反应 96.0h， 生成 N-[(4-羟基-3-甲氧基苯基)甲基]十六烷酰胺
  参考文献：
  名称：

  肝丙酮粉酶促合成辣椒素类似物

  摘要：

  通过使用肝丙酮粉末作为催化剂已经实现了具有饱和或不饱和酰基部分的辣椒素类似物的酶促合成。

  DOI：

  10.1016/0040-4039(96)00429-7

文献信息

• Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids
  作者：Gerardo F. Barbero、José M. G. Molinillo、Rosa M. Varela、Miguel Palma、Francisco A. Macías、Carmelo G. Barroso

  DOI：10.1021/jf9035029

  日期：2010.3.24

  been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of

  作为结构和活性之间定量关系研究的一部分，我们描述了两种类化合物的合成方法：辣椒素和辣椒素。总共合成了14个增加的侧链长度（从2到16个碳原子）的辣椒素。另外，已经合成了14个具有相同侧链的辣椒素以及衣壳和二氢衣壳，并且已经开发了用于合成这些化合物的新方法。产率为48.35至98.98％。已经发现，合成的辣椒素类和辣椒素类具有与天然化合物相似的亲脂性，并具有相似的生物学活性。与天然化合物相比，合成辣椒素和辣椒素的生物活性与亲脂性差异程度（较高或较低）成比例地降低。使用黄化的小麦测定生物活性（小麦胚芽鞘生物测定法，并通过将合成结果与其对应的天然化合物呈现的结果进行比较。发现的生物活性与合成化合物的亲脂性直接相关。
• PHARMACOLOGICAL PREPARATION FOR TOPICAL USE CONTAINING N-PALMITOYL-VANILLAMIDE
  申请人：DELLA VALLE Francesco

  公开号：US20120115808A1

  公开（公告）日：2012-05-10

  The present invention relates to topical preparations containing N-palmitoyl-vanillamide having hyperalgesic activity. In particular, the invention relates to N-palmitoyl-vanillamide for use in the treatment of pathologies selected from: post-herpetic neuralgia, neuralgia of trigeminus, occipital neuralgia, dental neuralgia, glottopharyngeal neuralgia, uremic neuralgia, diabetic neuralgia, headache of different origin, neuropathic itch, neurogenic itch, uremic itch, vulvodinia, vulvar vestibulitis, ano-rectal pain and itch, balano-preputial pain and itch, painful urogenital disorders of dogs and cats, psoriasis-associated pruritus and pain, itching skin diseases (e.g. atopic dermatitis) in the human and veterinary field, muscular pain, pain of the tendon, osteoarthritis associated pain in humans, dogs and cats; painful eye diseases in the human and veterinary field, inflammatory pathologies of the oral cavity in the human and veterinary field.

  本发明涉及含有具有高痛觉敏感活性的N-棕榈酰基香草酰胺的局部制剂。具体而言，本发明涉及将N-棕榈酰基香草酰胺用于治疗以下病理选择：带状疱疹后神经痛，三叉神经痛，枕神经痛，牙痛神经痛，咽喉返神经痛，尿毒症神经痛，糖尿病神经痛，不同起源的头痛，神经病性瘙痒，神经源性瘙痒，尿毒症瘙痒，外阴疼痛，外阴前庭炎，肛门疼痛和瘙痒，包皮龟头疼痛和瘙痒，犬和猫的疼痛性泌尿生殖系统疾病，牛皮癣相关的瘙痒和疼痛，人类和兽医领域的瘙痒性皮肤病（例如特应性皮炎），肌肉疼痛，肌腱疼痛，人类、犬和猫的骨关节炎相关疼痛，人类和兽医领域的眼部疾病疼痛，人类和兽医领域的口腔炎症病理学。
• A pharmaceutical composition for the treatment of pathologies caused by the general response of the immune system
  申请人：Epitech Group S.r.l.

  公开号：EP1844784A1

  公开（公告）日：2007-10-17

  The present invention relates to a pharmaceutical composition consisting of amides of mono- and dicarboxylic acids and hydroxystilbenes, and may be used for the treatment of pathologies caused, sustained and/or characterised by an abnormal general response of the immune system, in both humans and animals.

  本发明涉及一种由单羧酸和二羧酸酰胺以及羟基二苯乙烯组成的药物组合物，可用于治疗人和动物因免疫系统总体反应异常而引起、持续和/或特征性的病症。
• Pharmacological preparation for topical use containing n-palmitoyl-vanillamide
  申请人：Epitech Group S.r.l.

  公开号：EP2455066A1

  公开（公告）日：2012-05-23

  The present invention relates to a topical preparation containing N-palmitoyl-vanillamide with antihyperalgic activity. In particular, the invention relates to N-palmitoyl-vanillamide for use in the treatment of a pathology selected from: post-herpetic neuralgia, neuralgia of trigeminus, occipital neuralgia, dental neuralgia, glottofaryngeal neuralgia, uremic neuralgia, diabetic neuralgia, headache of different origin, neuropathic itch, neurogenic itch, uremic itch, vulvodinia, vulvar vestibulitis, ano-rettal pain and itch, balano-preputial pain and itch, painful urogenital disorders of dogs and cats, psoriasis-associated pruritus and pain, itching skin diseases (e.g. atopic dermatitis) in the human and veterinary field, muscular pain, pain of the tendon, osteoarthritis associated pain in humans, dogs and cats; painful eye diseases in the human and veterinary field, inflammatory pathologies of the oral cavity in the human and veterinary field.

  本发明涉及一种含有具有抗过敏活性的 N-棕榈酰香草酰胺的外用制剂。 特别是，本发明涉及用于治疗以下病症的 N-棕榈酰香草酰胺：带状疱疹后遗神经痛、三叉神经痛、枕叶神经痛、牙神经痛、咽喉神经痛、尿毒症神经痛、糖尿病神经痛、不同原因的头痛、神经性痒、神经源性痒、尿毒症痒、外阴瘙痒、尿毒症性瘙痒、外阴阴道炎、外阴前庭炎、肛门阴道疼痛和瘙痒、肛门阴道疼痛和瘙痒、猫狗泌尿生殖系统疼痛、牛皮癣相关性瘙痒和疼痛、瘙痒性皮肤病（如特应性皮炎）。人和兽医领域的肌肉疼痛、肌腱疼痛、人、狗和猫的骨关节炎相关疼痛；人和兽医领域的疼痛性眼病；人和兽医领域的口腔炎症性病变。
• Ford-Moore; Phillips, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 855
  作者：Ford-Moore、Phillips

  DOI：——

  日期：——