N-octyl-N'-vanillyl thiourea | 86052-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-octyl-N'-vanillyl thiourea
• 英文别名: 1-[(4-Hydroxy-3-methoxyphenyl)methyl]-3-octylthiourea
• CAS: 86052-20-2
• 化学式: C₁₇H₂₈N₂O₂S
• 分子量: 324.488
• InChiKey: UFLQVWSMZGRRAU-UHFFFAOYSA-N

物化性质

• 沸点：
  461.6±55.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  85.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-硫代异氰酸辛酯 、 香兰素胺盐酸盐 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-octyl-N'-vanillyl thiourea
  参考文献：
  名称：

  The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin

  摘要：

  Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane. These sensory neurons are involved in nociception, and so, these agents are targets for the design of a novel class of analgesics. Although synthetic agonists at the capsaicin receptor have been described previously, competitive antagonists at this receptor would be interesting and novel pharmacological agents. Structure-activity relationships for capsaicin agonists have previously been rationalized, by ourselves and others, by dividing the capsaicin molecule into three regions-the A (aromatic ring)-, B (amide bond)-, and C (hydrophobic side chain)-regions. In this study, the effects on biological activity of conformational constraint of the A-region with respect to the B-region are discussed. Conformational constraint was achieved by the introduction of saturated ring systems of different sizes. The resulting compounds provided agonists of comparable potency to unconstrained analogues as well as a moderately potent antagonist, capsazepine. This compound is the first competitive antagonist of capsaicin and resiniferatoxin to be described and is active in various systems, in vitro and in vivo. It has recently attracted considerable interest as a tool for dissecting the mechanisms by which capsaicin analogues evoke their effects. NMR spectroscopy and X-ray crystallography experiments, as well as molecular modeling techniques, were used to study the conformational behavior of a representative constrained agonist and antagonist. The conformation of the saturated ring contraint in the two cases was found to differ markedly, dramatically affecting the relative disposition of the A-ring and B-region pharmacophores. In agonist structures, the A- and B-regions were virtually coplanar in contrast to those in the antagonist, in which they were approximately orthogonal. A rationale for agonist and antagonist activity at the capsaicin receptor is proposed, based on the consideration of these conformational differences.

  DOI：

  10.1021/jm00039a006

文献信息

• FLAVOUR MODULATING SUBSTANCES
  申请人：Winkel Chris

  公开号：US20100129515A1

  公开（公告）日：2010-05-27

  The present invention in a first aspect relates to flavour modulation in foodstuffs, beverages, tobacco products and oral care products, using a flavour modulating substance selected from the group represented by formula (I), edible salts thereof and edible esters thereof. It has been found that these substances are capable imparting highly desirable taste attributes in the products they are incorporated in. In addition said flavour modulating substances are capable of modulating and complementing, the sensory impact of other, taste imparting, substances. Thus, the present substances are advantageously applied in flavour compositions, foodstuffs, tobacco products and oral care products. Typical examples of flavour modulating substances according to the present invention include N-vanillyl urea, N-vanillyl thiourea, N-vanillyl guanidine, N-isovanillyl urea, N-(3-ethoxy-4-hydroxybenzyl) urea, N-(3,4 dimethoxybenzyl) urea, N,N′-divanillyl urea, N,N′-divanillyl thiourea, N-octyl-N′-vanillyl urea, N-octyl-N′-vanillyl thiourea, N-hexyl-N′-vanillyl urea, N-hexyl-N′-vanillyl thiourea, N-decyl-N′-vanillyl urea, N-decyl-N′-vanillyl thiourea, N-benzyl-N′-vanillyl urea, N-benzyl-N′-vanillyl thiourea, edible salts thereof and edible esters thereof.

  本发明在第一方面涉及使用从式(I)所代表的化合物组中选择的调味调节物质、其可食用盐和可食用酯，对食品、饮料、烟草制品和口腔护理产品中的味道进行调节。已经发现这些物质能够在它们被加入的产品中赋予高度可取的口感特性。此外，所述调味调节物质能够调节和补充其他具有口感影响的物质的感官影响。因此，本发明的物质优点地应用于调味组合物、食品、烟草制品和口腔护理产品中。根据本发明的典型的调味调节物质包括N-香草基尿素，N-香草基硫脲，N-香草基胍，N-异香草基尿素，N-(3-乙氧基-4-羟基苯基)尿素，N-(3,4-二甲氧基苯基)尿素，N,N'-二香草基尿素，N,N'-二香草基硫脲，N-辛基-N'-香草基尿素，N-辛基-N'-香草基硫脲，N-己基-N'-香草基尿素，N-己基-N'-香草基硫脲，N-癸基-N'-香草基尿素，N-癸基-N'-香草基硫脲，N-苄基-N'-香草基尿素，N-苄基-N'-香草基硫脲，其可食用盐和可食用酯。
• SALTY TASTE ENHANCER
  申请人：AJINOMOTO CO., INC.

  公开号：US20140004243A1

  公开（公告）日：2014-01-02

  The present invention provides a compound having a salty taste enhance activity, and a salty taste enhancer containing the compound, and the like. The present invention relates to a salty taste enhancer for a food or drink, which contains a compound represented by the following formula: wherein each symbol is as defined in the specification, or an edible salt thereof.

  本发明提供了一种具有增强咸味活性的化合物，以及含有该化合物的增强咸味剂等。本发明涉及一种用于食品或饮料的增强咸味剂，其包含下式所示的化合物：其中每个符号如规范中所定义，或其可食用盐。
• METHOD FOR USING SOLUBLE CURCUMIN TO INHIBIT PHOSPHORYLASE KINASE IN INFLAMMATORY DISEASES
  申请人：——

  公开号：US20010051184A1

  公开（公告）日：2001-12-13

  The compound curcumin, derived from turmeric, inhibits phosphorylase kinase and, by doing so, exhibits a number of physiological effects related to the control of inflammation and cellular proliferation. However, curcumin is effective only when in solution. Curcumin is almost completely insoluble in water or in oils, but is soluble in alcohols. Accordingly, a method for treating inflammation in a mammal comprising administering curcumin in a solution containing at least one alcohol to a mammal to detectably inhibit the activity of phosphorylase kinase in the blood of the mammal or in a tissue of the mammal. The alcohol is preferably ethanol, 1-propanol, or 2-propanol; most preferably, it is ethanol. Instead of curcumin, a curcumin derivative or curcuminoid can be administered. The method can further comprise the administration of at least one additional compound that can be (1) vitamin D 3 and vitamin D 3 analogues; (2) vitamin A, vitamin A derivatives, and vitamin A analogues (3) a calmodulin inhibitor; (4) an anti-inflammatory drug; (5) a calcium channel blocker; (6) a H1 or H2 histamine blocker; (7) an antioxidant; (8) a polyphenolic compound; (9) a monoterpene; (10) genistein; (11) a soybean derived lectin; and (12) dehydrozingerone. Another aspect of the present invention is a pharmaceutical composition comprising curcumin, a curcuminoid, or a curcumin derivative in a solution containing at least one alcohol, at least one additional compound as described above, and a pharmaceutically acceptable carrier.

  姜黄素是从姜黄中提取的化合物，它能抑制磷酸化酶激酶，并由此产生一系列与控制炎症和细胞增殖有关的生理效应。不过，姜黄素只有在溶液中才有效。姜黄素几乎完全不溶于水或油，但可溶于醇。因此，一种治疗哺乳动物炎症的方法，包括给哺乳动物服用含有至少一种醇的姜黄素溶液，以检测抑制哺乳动物血液或组织中磷酸激酶的活性。醇最好是乙醇、1-丙醇或 2-丙醇；最优选的是乙醇。可以施用姜黄素衍生物或姜黄类化合物来代替姜黄素。该方法可进一步包括施用至少一种额外的化合物，可以是 (1) 维生素 D 3 和维生素 D 3 钙调蛋白抑制剂；(4) 抗炎药物；(5) 钙通道阻滞剂；(6) H1 或 H2 组胺阻滞剂；(7) 抗氧化剂；(8) 多酚化合物；(9) 单萜；(10) 遗传素；(11) 大豆衍生凝集素；(12) 去氢姜酮。本发明的另一方面是一种药物组合物，该组合物包含姜黄素、姜黄类化合物或姜黄素衍生物，其溶液含有至少一种醇、至少一种上述附加化合物和药学上可接受的载体。
• Novel urea derivatives
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0068590B1

  公开（公告）日：1985-01-02
• N-VANILLYL UREA DERIVATIVES AS FLAVOUR MODULATING SUBSTANCES
  申请人：Quest International Services B.V.

  公开号：EP1915063A2

  公开（公告）日：2008-04-30