(E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2H-chromen-2-one | 84825-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2H-chromen-2-one
• 英文别名: 4-geranyloxychromene-2-one；4-geranyloxycoumarin；4-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
• CAS: 84825-23-0
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: VFKKLGOFTSYJCN-RVDMUPIBSA-N

物化性质

• 沸点：
  470.3±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2H-chromen-2-one 在 高氯酸 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 16.0h， 生成 (+/-)-4-(6',7'-dihydroxy-3',7'-dimethyl-2'-octenyloxy)coumarin
  参考文献：
  名称：

  Yamada, Yasumasa; Nakatani, Nobuji; Fuwa, Hidetsugu, Agricultural and Biological Chemistry, 1987, vol. 51, # 6, p. 1711 - 1714

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基香豆素 、 香叶基溴 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以4.1 g的产率得到(E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2H-chromen-2-one
  参考文献：
  名称：

  Yamada, Yasumasa; Nakatani, Nobuji; Fuwa, Hidetsugu, Agricultural and Biological Chemistry, 1987, vol. 51, # 6, p. 1711 - 1714

  摘要：

  DOI：

文献信息

• Inhibitory Effects of Coumarin Derivatives on Tyrosinase
  作者：Eon-Joo Roh

  DOI：10.3390/molecules26082346

  日期：——

  In this study, a series of coumarin derivatives were synthesized and their inhibitory effects on the activity of mushroom tyrosinase were evaluated. As a result of measuring the inhibition of tyrosinase activity of these derivatives, the compounds 3e (1.05 μM), 3f (0.83 μM), 3h (0.85 μM), 3i (1.05 μM), and 3k (0.67 μM) of the geranyloxycoumarin derivatives were highly active at a concentration of 0.8%. The geranyloxycoumarin derivatives exhibited better activity than the hydroxycoumarin derivatives. Among the geranyloxycoumarin derivatives, compound 3k was two times more active than arbutin, a positive control, at a concentration of 0.4%. The above results suggest that geranyloxycoumarin derivatives have great potential for application as functional cosmetic ingredients with tyrosinase-inhibiting activity.

  在这项研究中，合成了一系列香豆素衍生物，并评估了它们对蘑菇酪氨酸酶活性的抑制效果。通过测量这些衍生物对酪氨酸酶活性的抑制作用，发现了在0.8%浓度下，3e（1.05μM）、3f（0.83μM）、3h（0.85μM）、3i（1.05μM）和3k（0.67μM）这些香豆素酯衍生物具有很高的活性。与羟基香豆素衍生物相比，香豆素酯衍生物表现出更好的活性。在香豆素酯衍生物中，化合物3k在0.4%浓度下比阳性对照熊果苷活性高出两倍。以上结果表明，香豆素酯衍生物具有很大的潜力作为具有酪氨酸酶抑制活性的功能性化妆品成分应用。
• Venturella, Pietro; Bellino, Aurora; Marino, Maria Luisa, Gazzetta Chimica Italiana, 1982, vol. 112, # 9/10, p. 433 - 434
  作者：Venturella, Pietro、Bellino, Aurora、Marino, Maria Luisa

  DOI：——

  日期：——
• JPS63104973A
  申请人：——

  公开号：JPS63104973A

  公开（公告）日：1988-05-10
• Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors
  作者：Mehrdad Iranshahi、Atena Jabbari、Ala Orafaie、Robabeh Mehri、Soudabeh Zeraatkar、Taraneh Ahmadi、Maliheh Alimardani、Hamid Sadeghian

  DOI：10.1016/j.ejmech.2012.09.006

  日期：2012.11

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Yamada, Yasumasa; Nakatani, Nobuji; Fuwa, Hidetsugu, Agricultural and Biological Chemistry, 1987, vol. 51, # 6, p. 1711 - 1714
  作者：Yamada, Yasumasa、Nakatani, Nobuji、Fuwa, Hidetsugu

  DOI：——

  日期：——