all-trans-5,6-Epoxyretinoic acid | 13100-69-1

• 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: all-trans-5,6-Epoxyretinoic acid
• 英文别名: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 13100-69-1
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: KEEHJLBAOLGBJZ-WEDZBJJJSA-N

物化性质

• 熔点：
  160-162°C
• 溶解度：
  可溶于氯仿（轻微）、甲醇（非常轻微）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

5,6-环氧视黄酸是维甲酸的已知人体代谢物。

5,6-Epoxy-retinoic acid is a known human metabolite of Tretinoin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 all-trans-5,6-Epoxyretinoic acid 以 乙醚 为溶剂， 生成 Methyl-5,6-epoxyretinoat
  参考文献：
  名称：

  Free Radical Oxidation of (E)-Retinoic Acid by Prostaglandin H Synthase

  摘要：

  Cooxidative metabolism of all-trans (E)-retinoic acid (RA) by prostaglandin H synthase was investigated employing ram seminal vesicle microsomes (RSVM) or purified, RSVM-derived enzyme. RA was shown to undergo hydroperoxide [H2O2 or 5-phenyl-4-penten-1-yl hydroperoxide (PPHP)]- or arachidonic acid-dependent cooxidation by microsomal prostaglandin H (PGH) synthase as evidenced by UV spectroscopic analysis of reaction mixtures. Cooxidation of RA by microsomal or purified PGH synthase, using PPHP as substrate, was characterized by uptake of dioxygen which was first order with respect to enzyme concentration. Dioxygen uptake was inhibited by the peroxidase reducing substrate 2-methoxyphenol. In addition, O-2 uptake was inhibited by the spin trap nitrosobenzene. ESR spin trapping studies, using alpha-phenyl-N-tert-butylnitrone (PBN) as the spin trap, demonstrated the formation of RA-PBN adducts, characterized by hyperfine coupling constants of a(H) = 3.2 G and a(N) = 15.8 G. Reverse phase HPLC analysis of reaction mixtures demonstrated the formation of 4-hydroxy-RA, 5,6-epoxy-RA, 4-oxo-RA, (13Z)-retinoic acid, and other geometric isomers which were identified on the basis of cochromatography with synthetic standards, UV spectroscopy, and/or mass spectrometry. Mechanisms are proposed for the hydroperoxide-dependent, PGH synthase-catalyzed oxidation of RA that are consistent with these results.

  DOI：

  10.1021/tx00047a022
• 作为产物：
  描述：

  维A酸 在 Γ-十八碳三烯酸 、 二乙烯三胺五醋酸 、 lipoxygenase-2 、 Na phosphate buffer 作用下， 生成 all-trans-5,6-Epoxyretinoic acid
  参考文献：
  名称：

  大豆脂氧合酶-2和-3的全反式视黄酸的5,6-Epoxidation。

  摘要：

  以全反式视黄酸为共底物，研究了高纯度大豆脂氧合酶-2和-3的共氧化活性。在亚油酸的存在下，两种同工酶都能迅速降解维甲酸，但脂氧合酶2的共氧化活性比脂氧合酶3的高。在共氧化过程中，形成了5，6-环氧维甲酸作为主要产物。手性相（Ceramospher Chiral RU-1）上的HPLC发现环氧化合物的外消旋混合物，表明它是由过氧自由基的氧化攻击形成的。

  DOI：

  10.1271/bbb.58.140

文献信息

• [EN] SYNTHETIC RETINOIDS FOR CONTROL OF CELL DIFFERENTIATION<br/>[FR] RÉTINOÏDES SYNTHÉTIQUES POUR LE CONTRÔLE DE LA DIFFÉRENCIATION DES CELLULES
  申请人：UNIV DURHAM

  公开号：WO2012076842A1

  公开（公告）日：2012-06-14

  The present invention relates to synthetic retinoid compounds of formula (I) and their use in the control of cell differentiation or apoptosis.

  本发明涉及式(I)的合成视黄酸化合物及其在控制细胞分化或凋亡方面的应用。
• Characterizationf of autoxidation products of retinoic acid
  作者：A.R. Oyler、M.G. Motto、R.E. Naldi、K.L. Facchine、P.F. Hamburg、D.J. Burinsky、R. Dunphy、M.L. Cotter

  DOI：10.1016/s0040-4020(01)85785-9

  日期：——

  Retinoic acid underwent autoxidation in 90% ethanol at 25–85.5 °C to give epoxides, dioxetanes, an endoperoxide, and double-bond cleavage products. The majority of these products appear to have resulted from the initial direct oxidation of the olefinic carbons rather than from the expected allylic α oxidation process.

  视黄酸在25％至85.5°C的90％乙醇中进行自氧化，得到环氧化物，二氧环乙烷，内过氧化物和双键裂解产物。这些产物中的大多数似乎是由于烯烃碳的直接直接氧化而不是预期的烯丙基α氧化过程而产生的。
• [EN] METHOD FOR PRODUCING N-RETINOYLCYSTEIC ACID ALKYL ESTER<br/>[FR] PROCÉDÉ DE PRODUCTION D'ESTER ALKYLIQUE DE L'ACIDE N-RÉTINOYLCYSTÉIQUE
  申请人：ARDENIA INVESTMENTS LTD

  公开号：WO2017099662A1

  公开（公告）日：2017-06-15

  A method for producing derivatives of N-retinoylaminoalkane sulfonic acid, the method comprising providing retinoic acid, chloroformate, aminoalkanesulfonic acid selected from the group consisting of cysteic acidand alkyl ester thereof, cysteinesulfinic acid and alkyl ester thereof, homocysteic acid and alkyl ester thereof, homocysteinesulfinic acid and alkyl esters thereof, taurine and derivatives thereof, and an organic solvent,and a base, mixing said components under substantial absence of oxidizing compoundsthereby forming a reaction mixture comprising a liquid phase, wherein the liquid phase is one phaseand the derivatives of N-retinoylaminoalkane sulfonic acid are formed in said liquid phase.

  一种生产N-视黄酰氨基烷磺酸衍生物的方法，所述方法包括提供视黄酸、氯甲酸酯、来自半胱氨酸和其烷基酯组成的氨基烷磺酸、半胱氨酸亚磺酸及其烷基酯、同型半胱氨酸及其烷基酯、同型半胱氨酸亚磺酸及其烷基酯、牛磺酸及其衍生物、有机溶剂和一种碱，将所述组分在实质上缺乏氧化物的情况下混合，从而形成包含液相的反应混合物，其中所述液相是一相，且N-视黄酰氨基烷磺酸衍生物在所述液相中形成。
• Retinoid receptor compositions and methods
  申请人：THE SALK INSTITUTE FOR BIOLOGICAL STUDIES

  公开号：EP0999271A2

  公开（公告）日：2000-05-10

  The present invention relates to novel receptor polypeptides, which, upon interaction with certain ligands, or activation by certain compounds, modulate transcription of certain genes by binding to cognate response elements associated with promoters of such genes. The novel receptors of the invention modulate transcription in the presence of retinoid compounds. The receptors of the present invention differ significantly from known retinoid acid receptors, in protein primar yseqence and in responsiveness to exposure to various retinoids. The invention provides DNAs encoding the novel receptors, expression vectors for expression of the receptors, cells transformed with such expression vectors, cells co-transformed with such expression vectors and with reporter vectors to monitor modulation of transcription by the receptors, and methods of using such co-transformed cells in screening for compounds which are capable, directly or indirectly, of activating the receptors. The invention also provides nucleic acid probes for identifying DNAs which encode additional retinoid receptors of the same class as the novel receptors disclosed herein.

  本发明涉及新型受体多肽，它们在与某些配体相互作用或被某些化合物激活后，通过与与这些基因启动子相关的同源反应元件结合，调节某些基因的转录。本发明的新型受体可在视黄醇化合物存在的情况下调节转录。本发明的受体与已知的视黄酸受体在蛋白质序列和对各种视黄酸的反应性方面有很大不同。本发明提供了编码新型受体的 DNA、表达受体的表达载体、用这种表达载体转化的细胞、用这种表达载体和报告载体共同转化的细胞以监测受体对转录的调节，以及用这种共同转化的细胞筛选能直接或间接激活受体的化合物的方法。本发明还提供了用于鉴定 DNA 的核酸探针，这些 DNA 编码与本发明公开的新型受体属于同一类的其他视黄醇受体。
• Factor for regulation of neurite growth
  申请人：Oxford Biomedica (UK) Ltd

  公开号：EP1762243A1

  公开（公告）日：2007-03-14

  The present invention relates to the use of RARβ2 and/or an agonist thereof in the preparation of a medicament to cause neurite development.

  本发明涉及将 RARβ2 和/或其激动剂用于制备可促进神经元发育的药物。