S-(+)-2-ethylhexyl-para-methoxycinnamate

• 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: S-(+)-2-ethylhexyl-para-methoxycinnamate
• 英文别名: (S)-octinoxate；[(2S)-2-ethylhexyl] (E)-3-(4-methoxyphenyl)prop-2-enoate
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: YBGZDTIWKVFICR-VOMSXAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-ethylhexan-1-ol 、 vinyl-para-methoxycinnamate 以 正己烷 为溶剂， 反应 20.0h， 生成 S-(+)-2-ethylhexyl-para-methoxycinnamate
  参考文献：
  名称：

  Preparation of S-2-Ethylhexyl-para-methoxycinnamate by lipase catalyzed sequential kinetic resolution

  摘要：

  S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4,5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00078-x

文献信息

• PHOTOPROTECTIVE EYE CREAM AND METHODS
  申请人：THAGGARD Holly E.

  公开号：US20140170089A1

  公开（公告）日：2014-06-19

  Photoprotectant cosmetic compositions adapted to application on a user's skin that include a sunscreen component comprising at least two sun-blocking components, each present in an amount sufficient to collectively provide ultraviolet A and B protection with an SPF of at least about 10; a mica component including mica in an amount sufficient to reduce or eliminate at least the appearance of dark skin adjacent an eye; and an oat peptide component in an amount sufficient to reduce or eliminate at least the appearance of fine lines and wrinkles on the user's skin. Methods of improving the aesthetic appearance of skin with such compositions are also included.
• Preparation of S-2-Ethylhexyl-para-methoxycinnamate by lipase catalyzed sequential kinetic resolution
  作者：Maja Majerié、Vitomir Šunjié

  DOI：10.1016/0957-4166(96)00078-x

  日期：1996.3

  S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4,5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate. (C) 1996 Elsevier Science Ltd