dehydrodiisoeugenol | 2680-81-1

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: dehydrodiisoeugenol
• 英文别名: cis-Dehydrodiisoeugenol；2-methoxy-4-[7-methoxy-3-methyl-5-[(Z)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
• CAS: 2680-81-1
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: ITDOFWOJEDZPCF-WAYWQWQTSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  452.0±45.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥250mg/mL（765.95mM）
• LogP：
  4.188 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29329990
• WGK Germany：
  3
• 储存条件：
  室温

制备方法与用途

概述

去氢二异丁香酚是肉豆蔻中的一种特征性化学成分，其英文名为Dehydrodiisoeugenol，分子式为C₂₀H₂₂O₄⁺，分子量为326.39，属于木脂素类化合物。虽然2010年版中国药典以去氢二异丁香酚作为鉴别肉豆蔻药材标准的唯一依据，但查阅大量文献发现，目前仅有对常规结晶状态下的去氢二异丁香酚的研究报道，高纯度分离技术尚未成熟。

生物活性

从Myristica fragrans Houtt中分离得到的去氢二异丁香酚具有显著的抗炎和抗菌作用。它能够抑制LPS刺激的小鼠巨噬细胞中NF-κB的活化及环氧合酶(COX)-2基因的表达。

靶点

• NF-κB; COX-2

化学性质

去氢二异丁香酚为白色针状结晶，能溶于甲醇，几乎不溶于乙醚。它来源于肉豆蔻。

用途

• 去氢二异丁香酚具有抗肿瘤的作用。
• 主要用于含量测定、鉴定及药理实验等。
• 具有温中行气、涩肠止泻的药效。

反应信息

• 作为产物：
  描述：

  异丁香酚 在 双氧水 、 horseradish peroxidase 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran 、 dehydrodiisoeugenol
  参考文献：
  名称：

  Formation of dehydrodiisoeugenol and dehydrodieugenol from the reaction of isoeugenol and eugenol with DPPH radical and their role in the radical scavenging activity

  摘要：

  The aim of this work was to investigate the products of the reactions between isoeugenol and eugenol with the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and their role in the radical scavenging mechanism. The reaction of isoeugenol and eugenol with the DPPH radical produced, as evidenced by GC-MS and HPLC-MS, a complex mixture of dimeric species in which dehydrodiisoeugenol and its adducts with methanol (reaction solvent) and dehydrodieugenol were the main reaction products, respectively. The antioxidant activity of dehydrodiisoeugenol, determined by the DPPH method, resulted lower than that of isoeugenol considering both the parameters Effective Concentration (EC50) and Anti-radical Efficiency (AE). In particular. due to its very slow kinetic behaviour (T-EC50 = 201 min), the possible contribution of dehydrodiisoeugenol to the DPPH radical scavenging activity of isoeugenol (T-EC50 = 3.1 min) was practically negligible. On the contrary, dehydrodieugenol had an antioxidant activity higher than that of eugenol and its lower T-EC50. (85 min with respect to 126 min) made it possible to contribute to the DPPH radical scavenging activity of eugenol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2009.04.115

文献信息

• USE OF DIHYDRODEHYDRODIISOEUGENOL AND PREPARATIONS COMPRISING DIHYDRODEHYDRODIISOEUGENOL
  申请人：Meyer Imke

  公开号：US20130101650A1

  公开（公告）日：2013-04-25

  This invention relates to cosmetic and pharmaceutical preparations comprising (i) a diastereomer or a mixture of two or more diastereomers of the compound of formula (I) or (ii) a salt of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I) or (iii) a mixture of two or more salts of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I), a diastereomer, salt or a mixture as defined above as a drug for topical application and/or for the treatment of lipoatrophy; the non-therapeutic use of a diastereomer, salt or a mixture as defined above for the prevention, treatment or reduction of skin aging, especially skin wrinkles; the use of a diastereomer, salt or a mixture as defined above for the production of an orally administered non-pharmaceutical preparation.

  本发明涉及包含(i)化合物的对映异构体或两个或两个以上对映异构体的混合物或(ii)化合物的对映异构体或两个或两个以上对映异构体的混合物的盐或(iii)化合物的对映异构体或两个或两个以上对映异构体的混合物的两个或两个以上盐的混合物的化妆品和药用制剂，上述对映异构体、盐或混合物被定义为用于局部应用的药物和/或治疗脂肪萎缩；上述对映异构体、盐或混合物的非治疗用途被定义为用于预防、治疗或减少皮肤老化，特别是皱纹；上述对映异构体、盐或混合物被定义为用于制造口服非药用制剂。
• Neue dilignolähnliche Verbindungen, dilignolähnliche Verbindungen zur Verwendung bei der Behandlung von Lebererkrankungen sowie diese enthaltende pharmazeutische Präparate
  申请人：PHARMACEUTICAL LICENCES COMPANY LTD.

  公开号：EP0004522A2

  公开（公告）日：1979-10-03

  Dilignole und dilignolähnliche Verbindungen sind wirksam gegen Erkrankungen der Leber. Man steltt die Verbindungen her, indem man Styrolderivate der Formel oxydativ oder säurekatalysiert dimerisiert.

  二木酚和二木酚类化合物对肝脏疾病有效。这些化合物是由式如下的苯乙烯衍生物通过氧化或酸催化二聚反应生成的 通过氧化或酸催化二聚反应。
• US9066880B2
  申请人：——

  公开号：US9066880B2

  公开（公告）日：2015-06-30
• Formation of dehydrodiisoeugenol and dehydrodieugenol from the reaction of isoeugenol and eugenol with DPPH radical and their role in the radical scavenging activity
  作者：Renzo Bortolomeazzi、Giancarlo Verardo、Anna Liessi、Alessandro Callea

  DOI：10.1016/j.foodchem.2009.04.115

  日期：2010.1

  The aim of this work was to investigate the products of the reactions between isoeugenol and eugenol with the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and their role in the radical scavenging mechanism. The reaction of isoeugenol and eugenol with the DPPH radical produced, as evidenced by GC-MS and HPLC-MS, a complex mixture of dimeric species in which dehydrodiisoeugenol and its adducts with methanol (reaction solvent) and dehydrodieugenol were the main reaction products, respectively. The antioxidant activity of dehydrodiisoeugenol, determined by the DPPH method, resulted lower than that of isoeugenol considering both the parameters Effective Concentration (EC50) and Anti-radical Efficiency (AE). In particular. due to its very slow kinetic behaviour (T-EC50 = 201 min), the possible contribution of dehydrodiisoeugenol to the DPPH radical scavenging activity of isoeugenol (T-EC50 = 3.1 min) was practically negligible. On the contrary, dehydrodieugenol had an antioxidant activity higher than that of eugenol and its lower T-EC50. (85 min with respect to 126 min) made it possible to contribute to the DPPH radical scavenging activity of eugenol. (C) 2009 Elsevier Ltd. All rights reserved.