(2S)-5,6-二羟基-2,3-二氢-1H-吲哚-2-羧酸 | 18766-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: (2S)-5,6-二羟基-2,3-二氢-1H-吲哚-2-羧酸
• 英文名称: leucodopachromene
• 英文别名: leucodopachrome；(S)-Cyclodopa, Leukodopachrom；(2S)-5,6-dihydroxy-2,3-dihydro-1H-indole-2-carboxylic acid
• CAS: 18766-67-1
• 化学式: C₉H₉NO₄
• 分子量: 195.175
• InChiKey: JDWYRSDDJVCWPB-LURJTMIESA-N

物化性质

• 沸点：
  534.2±50.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4E)-1,2,3,4-四氢-4-(2-氧代乙亚基)吡啶-2,6-二甲酸 、 (2S)-5,6-二羟基-2,3-二氢-1H-吲哚-2-羧酸 反应 0.17h， 生成 betanidin
  参考文献：
  名称：

  Betanidin formation from dihydroxyphenylalanine in a model assay system

  摘要：

  Formation of betanidin, the aglycone of the red-violet betacyanins, has been demonstrated by a two-step model assay system. In the first step, dihydroxyphenylalanine (Dopa) was:incubated with a Dopa dioxygenase preparation from Amanita muscaria, resulting in the formation of 4,5-seco-Dopa that spontaneously recyclized to betalamic acid. In the second step, a tyrosinase preparation from Portulaca grandiflora a was added to the Dopa dioxygenase assay, resulting in Dopa oxidation followed by a spontaneous formation of cyclo-Dopa that, in turn, reacted spontaneously with betalamic acid to form betanidin. Thus, two enzymatic reactions, Dopa extradiol ring cleavage by the fungal enzyme and Dopa oxidation by the plant enzyme, initiate three spontaneous steps: the formation of cyclo-Dopa and betalamic acid and finally the condensation of these compounds to betanidin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00276-3
• 作为产物：
  描述：

  左旋多巴 反应 0.17h， 生成 (2S)-5,6-二羟基-2,3-二氢-1H-吲哚-2-羧酸
  参考文献：
  名称：

  Betanidin formation from dihydroxyphenylalanine in a model assay system

  摘要：

  Formation of betanidin, the aglycone of the red-violet betacyanins, has been demonstrated by a two-step model assay system. In the first step, dihydroxyphenylalanine (Dopa) was:incubated with a Dopa dioxygenase preparation from Amanita muscaria, resulting in the formation of 4,5-seco-Dopa that spontaneously recyclized to betalamic acid. In the second step, a tyrosinase preparation from Portulaca grandiflora a was added to the Dopa dioxygenase assay, resulting in Dopa oxidation followed by a spontaneous formation of cyclo-Dopa that, in turn, reacted spontaneously with betalamic acid to form betanidin. Thus, two enzymatic reactions, Dopa extradiol ring cleavage by the fungal enzyme and Dopa oxidation by the plant enzyme, initiate three spontaneous steps: the formation of cyclo-Dopa and betalamic acid and finally the condensation of these compounds to betanidin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00276-3

文献信息

• Early steps in the free radical polymerisation of 3,4-dihydroxyphenylalanine (dopa) into malanin
  作者：Miles R. Chedekel、Edward J. Land、Ambler Thompson、T. George Truscott

  DOI：10.1039/c39840001170

  日期：——

  Pulse radiolysis and flash photolysis-initiated one-electron oxidation of 3,4-dihydroxyphenylalanine (dopa) and other catecholamines have allowed the direct measurement of the kinetics of semiquinone disproportionation leading successively to the corresponding melanin precursors dopaquinones and dopachromes.

  脉冲放射分解和快速光解引发的3,4-二羟基苯丙氨酸（dopa）和其他儿茶酚胺的单电子氧化已允许直接测量半醌歧化动力学，从而导致相应的黑色素前体多巴醌和多巴色素。
• Radioassay for oxidation of tyrosine by tyrosinase using L-(ring-3H)tyrosine and L-(carboxyl-14C)tyrosine.
  作者：NORIKO MOTOHASHI、HARUMI EGUCHI、ITSUHIKO MORI

  DOI：10.1248/cpb.30.2094

  日期：——

  Two intermediates involved in the synthesis of melanin from L-tyrosine by mushroom tyrosinase (EC 1.14.18.1) were assayed simultaneously by using L-[ring-3H] tyrosine and L-[carboxyl-14C] tyrosine. Tritium ions released from the 3-position of L-[3, 5-3H] tyrosine or the 6-position of L-[2, 6-3H] tyrosine were isolated as 3H2O and employed to determine the quantity of L-dopa or leucodopachrome, respectively (3H2O method). 5, 6-Dihydroxyindole formed at the decarboxylation step was estimated from the radioactivity remaining after the evolution of 14CO2 from L-[carboxyl-14C] tyrosine (14CO2-release method). The lower limits of determination in the 3H2O and the 14CO2-release methods were 0.1 pmol and nmol of the intermediates, respectively. The formations of L-dopa, leucodopachrome, and 0.1 5, 6-dihydroxyindole were measured at various concentrations of L-tyrosine by both methods, and dopachrome was determined colorimetrically by measuring the absorbance changes at 475nm. The maximum velocities were estimated from Lineweaver-Burk plots.

  通过使用 L-[环-3H]酪氨酸和 L-[羧基-14C]酪氨酸，同时测定了蘑菇酪氨酸酶（EC 1.14.18.1）从 L-酪氨酸合成黑色素的两个中间产物。从 L-[3，5-3H]酪氨酸的 3 位或 L-[2，6-3H]酪氨酸的 6 位释放出的氚离子以 3H2O 的形式分离出来，并分别用于测定左旋多巴或亮氨酸的数量（3H2O 法）。根据 L-[羧基-14C]酪氨酸释放出 14CO2 后剩余的放射性来估算脱羧步骤中形成的 5，6-二羟基吲哚（14CO2 释放法）。3H2O 和 14CO2 释放法的测定下限分别为中间产物的 0.1 pmol 和 nmol。在不同浓度的 L-酪氨酸条件下，这两种方法都能测定 L-多巴、亮多巴醌和 0.1 5，6-二羟基吲哚的形成，多巴醌则通过测量 475nm 处的吸光度变化进行比色测定。最大速度由 Lineweaver-Burk 图估算得出。
• COSMETIC COMPOSITION INCLUDING LEUCODOPACHROME DERIVATIVE
  申请人：Desmurs Jean-Roger

  公开号：US20120177588A1

  公开（公告）日：2012-07-12

  A cosmetic or dermatological composition contains, in a physiologically acceptable medium, at least one compound from Formula (I). A method of using the composition, for reducing or preventing pigmenting, and/or whitening and/or lightening of the skin is described, as well as novel compounds from Formula (I′) that are included in Formula (I).
• UV-OVERPROTECTING IRIDESCENT COLORED CONTACT LENSES
  申请人：The University of Akron

  公开号：US20210373358A1

  公开（公告）日：2021-12-02

  In various embodiments, the present invention is directed to contact lenses that utilize a multilayer coating of alternating high RI materials, such as melanin or polydopamine (PDA) and other low RI materials to create tunable iridescent colors and contain melanin or similar materials that impart photoprotection due to their broadband UV-vis absorption spectrum and ability to quench radicals.
• US8703107B2
  申请人：——

  公开号：US8703107B2

  公开（公告）日：2014-04-22