(-)-bornyl p-coumarate | 77942-66-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (-)-bornyl p-coumarate
• 英文别名: (−)-pressafonin-A；Biondinin C；[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 77942-66-6
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: QDCGSCBAIQIGDY-NPEXALCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-bornyl p-coumarate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以9 mg的产率得到冰片
  参考文献：
  名称：

  Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots

  摘要：

  This work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment. This system has important advantages over traditional plant production techniques because it provides opportunities to optimize the yield of metabolite production under well-controlled conditions, thereby facilitating commercial-scale production of bioactive compounds. Thus, for the first time a study of this type has permitted the isolation from the roots of seven undescribed dextrorotatory lactones: the alkane-gamma-lactones ( + )-majoranolide and ( + )-dihydromajorenolide, the alkene-gamma-lactones ( + )-majorenolide and (+ )-majorenolide acetate, and the alkyne-gamma-lactones, ( + )-majorynolide, ( + )-majorynolide acetate and ( + )-isomajorynolide. In addition, thirteen known compounds were also isolated including two possible avocadofurane precursors, avocadynone acetate and avocadenone acetate, the monoterpene esters cis- and trans-p-coumarate of ( - )-borneol, and the ryanoid diterpenes cinnzeylanone, anhidrocinnzeylanine, cinnzeylanine, cinnzeylanol, epiryanodol, perseanol, cinncassiol E, perseaindicol and secoperseanol. The configuration at C-14 de two ryanodane diterpenes has also been revised in this work. Furthermore, ( - )-borneol cis-p-coumarate has showed to be insecticidal to S. littoralis and cytotoxic to insect (Sf9) cells, ( + )-majorenolide antifeedant to aphids and cytotoxic to Sf9, cinnceylanol antifeedant and insecticidal to S. littoralis, and ( + )-majorynolide (2), insecticidal against S. littoralis, cytotoxic to Sf9 and nematicidal, suggesting a defensive role for these compounds.

  DOI：

  10.1016/j.phytochem.2020.112398

文献信息

• Use of guaiol for treating the skin
  申请人：Baschong Werner

  公开号：US20050058610A1

  公开（公告）日：2005-03-17

  The use is described of compositions comprising (a) (−)-guaiol, (b) further skin-lightening active substance(s) and, optionally, (c) one or more UV-A and/or UV-B absorbers as melanogenesis inhibitors and for skin-lightening.

  所述组合物的用途包括：(a) (-)- 愈创木酚；(b) 其他皮肤美白活性物质；(c) 一种或多种 UV-A 和/或 UV-B 吸收剂，作为黑色素生成抑制剂和皮肤美白剂。
• USE OF GUAIOL FOR TREATING THE SKIN
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1432400A1

  公开（公告）日：2004-06-30
• US7425320B2
  申请人：——

  公开号：US7425320B2

  公开（公告）日：2008-09-16
• [EN] USE OF GUAIOL FOR TREATING THE SKIN<br/>[FR] UTILISATION DE GUAIOL POUR LE TRAITEMENT DE LA PEAU
  申请人：CIBA SC HOLDING AG

  公开号：WO2003024417A1

  公开（公告）日：2003-03-27

  The use is described of compositions comprising (a) (-)-guaiol, (b) further skin-lightening active substance(s) and, optionally, (c) one or more UV-A and/or UV-B absorbers as melanogenesis inhibitors and for skin-lightening.
• Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots
  作者：Braulio M. Fraga、Carmen E. Díaz、Patricia Bolaños、María Bailén、María Fe Andrés、Azucena González-Coloma

  DOI：10.1016/j.phytochem.2020.112398

  日期：2020.8

  This work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment. This system has important advantages over traditional plant production techniques because it provides opportunities to optimize the yield of metabolite production under well-controlled conditions, thereby facilitating commercial-scale production of bioactive compounds. Thus, for the first time a study of this type has permitted the isolation from the roots of seven undescribed dextrorotatory lactones: the alkane-gamma-lactones ( + )-majoranolide and ( + )-dihydromajorenolide, the alkene-gamma-lactones ( + )-majorenolide and (+ )-majorenolide acetate, and the alkyne-gamma-lactones, ( + )-majorynolide, ( + )-majorynolide acetate and ( + )-isomajorynolide. In addition, thirteen known compounds were also isolated including two possible avocadofurane precursors, avocadynone acetate and avocadenone acetate, the monoterpene esters cis- and trans-p-coumarate of ( - )-borneol, and the ryanoid diterpenes cinnzeylanone, anhidrocinnzeylanine, cinnzeylanine, cinnzeylanol, epiryanodol, perseanol, cinncassiol E, perseaindicol and secoperseanol. The configuration at C-14 de two ryanodane diterpenes has also been revised in this work. Furthermore, ( - )-borneol cis-p-coumarate has showed to be insecticidal to S. littoralis and cytotoxic to insect (Sf9) cells, ( + )-majorenolide antifeedant to aphids and cytotoxic to Sf9, cinnceylanol antifeedant and insecticidal to S. littoralis, and ( + )-majorynolide (2), insecticidal against S. littoralis, cytotoxic to Sf9 and nematicidal, suggesting a defensive role for these compounds.