5,8-Monoepoxy-vitamin-A-saeure | 3012-76-8

• 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: 5,8-Monoepoxy-vitamin-A-saeure
• 英文别名: 5,8-Monoepoxyretinoic acid；(2E,4E,6E)-7-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid
• CAS: 3012-76-8
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: QDOSIDVGVRAXSE-JUPVTLSTSA-N

物化性质

• 熔点：
  154-156°C
• 沸点：
  466.1±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)
• 溶解度：
  DCM、乙酸乙酯、乙醚

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  维A酸 在 air 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 all-trans-5,6-Epoxyretinoic acid 、 5,8-Monoepoxy-vitamin-A-saeure 、 5,8-epidioxy-5,8-dihydroretinoic acid 、 5-hydroxy-8-oxo-6,7-dihydroretinoic acid
  参考文献：
  名称：

  Superoxidation of Retinoic Acid†

  摘要：

  Atmospheric pressure chemical ionization mass spectroscopy (APCI-MS) was used to examine the light-induced oxidation products of retinoic acid under conditions that favor and preclude its aggregation. We observed that in conditions that favor aggregation, i.e. in aqueous solutions, retinoic acid undergoes superoxidation to yield highly oxidized species. Oxidation is limited, however, in the absence of such communication, i.e. when the polyene is fully solvated. From a comparison of the measured MS with that obtained from chemical oxidation of retinoic acid under conditions that promote radical oxidation and singlet oxygen-mediated oxidation, we conclude that superoxidation is mediated by reactive oxygen species other than singlet oxygen.

  DOI：

  10.1562/2006-02-28-ra-828

文献信息

• [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。
• METHOD FOR PRODUCING N-RETINOYLAMINOALKANE SULFONIC ACID
  申请人：Oasmia Pharmaceutical AB

  公开号：EP3386947B1

  公开（公告）日：2021-05-19
• METHOD FOR PRODUCING N-RETINOYLCYSTEIC ACID ALKYL ESTER
  申请人：ARDENIA INVESTMENTS, LTD.

  公开号：US20190127322A1

  公开（公告）日：2019-05-02

  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 acid and 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 compounds thereby forming a reaction mixture comprising a liquid phase, wherein the liquid phase is one phase and the derivatives of N-retinoylaminoalkane sulfonic acid are formed in said liquid phase.
• Superoxidation of Retinoic Acid†
  作者：Ilyas Washington、Nicholas J. Turro、Koji Nakanishi

  DOI：10.1562/2006-02-28-ra-828

  日期：——

  Atmospheric pressure chemical ionization mass spectroscopy (APCI-MS) was used to examine the light-induced oxidation products of retinoic acid under conditions that favor and preclude its aggregation. We observed that in conditions that favor aggregation, i.e. in aqueous solutions, retinoic acid undergoes superoxidation to yield highly oxidized species. Oxidation is limited, however, in the absence of such communication, i.e. when the polyene is fully solvated. From a comparison of the measured MS with that obtained from chemical oxidation of retinoic acid under conditions that promote radical oxidation and singlet oxygen-mediated oxidation, we conclude that superoxidation is mediated by reactive oxygen species other than singlet oxygen.