teferin | 54526-95-3

• 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: teferin
• 英文别名: jaeschkeanadiol vanillate；[(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxy-3-methoxybenzoate
• CAS: 54526-95-3
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: YEQVRBJRNFLOQJ-PABCKOPISA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  514.5±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  teferin 生成 [(1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-2a,7a-dimethyl-5-propan-2-yl-2,3,4,5a,6,7-hexahydro-1aH-azuleno[6,7-b]oxiren-6-yl] 4-hydroxy-3-methoxybenzoate
  参考文献：
  名称：

  MISKI, MAHMUT;MABRY, TOM J.;SAYA, OMER, J. NATUR. PROD., 50,(1987) N 5, 829-834

  摘要：

  DOI：
• 作为产物：
  描述：

  3-methoxy-4-(pivaloyloxy)benzoic acid 在 4-二甲氨基吡啶 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.17h， 生成 teferin
  参考文献：
  名称：

  Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues

  摘要：

  The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by esterification of jaeschkenadiol with different acids. These compounds were assayed for their in vitro antiproliferative activity against estrogen‐dependent (MCF‐7) and estrogen‐independent (MDA‐MB‐231) breast cancer cell lines. Among the compounds, 3c’ exhibited a potent inhibitory selective activity against MCF‐7 with IC50 value of 1 μm. Docking simulation of 3c’ in the ligand binding domain of the ERs indicated a potential antagonism interaction with both ER subtypes. Functional assay showed that 3c’ binds as an antagonist to ERα protein while ferutinin acts as an agonist.

  DOI：

  10.1111/cbdd.12670

文献信息

• Small molecule inhibitors of TRPA1
  申请人：B.R.A.I.N. Biotechnology Research and Information Network AG

  公开号：US10000438B2

  公开（公告）日：2018-06-19

  The present invention relates to the use of compounds which are capable of attenuating skin irritation when they are applied to the skin. Skin irritation can be caused, inter alia, by ingredients of cosmetic or pharmaceutical compositions and/or environmental irritants. In particular, the present invention relates to compounds having the property of antagonizing the activation of the transient receptor potential (TRP) ankyrin 1 (TRPA1) ion channel and the use of said compounds as soothing agents. Such compounds can be used in many fields, particularly in personal-care products, cosmetics, textile and packaging products, pharmaceutical compositions, medical devices, and foodstuffs. The present invention further relates to products and/or pharmaceutical compositions containing said compounds. The present invention also relates to the use of the compounds described herein for the modulation of the taste of a food product.

  本发明涉及化合物的使用，当这些化合物用于皮肤时，能够减轻对皮肤的刺激。皮肤刺激可由化妆品或药物组合物的成分和/或环境刺激物等引起。本发明尤其涉及具有拮抗瞬时受体电位（TRP）ankin 1（TRPA1）离子通道活化特性的化合物，以及将上述化合物用作舒缓剂。此类化合物可用于许多领域，特别是个人护理产品、化妆品、纺织品和包装产品、药物组合物、医疗器械和食品。本发明还涉及含有上述化合物的产品和/或药物组合物。本发明还涉及本文所述化合物在调节食品口味方面的用途。
• Daucane Phytoestrogens:  A Structure−Activity Study
  作者：Giovanni Appendino、Paola Spagliardi、Giancarlo Cravotto、Victoria Pocock、Stuart Milligan

  DOI：10.1021/np0201671

  日期：2002.11.1

  The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor a. Rather strict structure-activity relationships were observed. Thus, while the parent polvol (jaeschkeanadiol, 2a) was inactive, the presence of a p-hydroxybenzoyl moiety was necessary for activity in the yeast screen. Homologation and vinylation were both detrimental for activity, as were methylation of the p-hydroxyl substituent and the introduction of oxygen functions on the adjacent carbons.
• SMALL MOLECULE INHIBITORS OF TRPA1
  申请人：B.R.A.I.N. Biotechnology Research and Information Network AG

  公开号：EP2706995B1

  公开（公告）日：2016-11-30
• US9440993B2
  申请人：——

  公开号：US9440993B2

  公开（公告）日：2016-09-13
• [EN] SMALL MOLECULE INHIBITORS OF TRPA1<br/>[FR] INHIBITEURS DE TRPA1 À PETITE MOLÉCULE
  申请人：BRAIN BIOTECHNOLOGY RES & INFORMATION NETWORK AG

  公开号：WO2012152940A2

  公开（公告）日：2012-11-15

  The present invention relates to the use of compounds which are capable of attenuating skin irritation when they are applied to the skin. Skin irritation can be caused, inter alia, by ingredients of cosmetic or pharmaceutical compositions and/or environmental irritants. In particular, the present invention relates to compounds having the property of antagonizing the activation of the transient receptor potential (TRP) ankyrin 1 (TRPA1) ion channel and the use of said compounds as soothing agents. Such compounds can be used in many fields, particularly in personal-care products, cosmetics, textile and packaging products, pharmaceutical compositions, medical devices,and foodstuffs. The present invention further relates to products and/or pharmaceutical compositions containing said compounds. The present invention also relates to the use of the compounds described herein for the modulation of the taste of a food product.