betanidin

• 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
• 英文名称: betanidin
• 英文别名: (2S,4E)-4-[2-[(2S)-2-carboxy-5,6-dihydroxy-2,3-dihydroindol-1-ium-1-ylidene]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid
• 化学式: C₁₈H₁₇N₂O₈
• 分子量: 389.342
• InChiKey: XHJKHSXHWJCBLX-AAEUAGOBSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  167
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  betanidin 在 酪氨酸酶 作用下， 生成 (2S)-4-[2-[(2S)-2-carboxy-5,6-dioxo-2,3-dihydroindol-1-ium-1-ylidene]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid
  参考文献：
  名称：

  Characterization of the Activity of Tyrosinase on Betanidin

  摘要：

  Betalains are an important class of water-soluble pigments, with radical scavenging capacity, which is characteristic of the order Caryophyllales. The structural unit of the violet betacyanins, betanidin is reported as a substrate for the enzyme tyrosinase (EC 1.14.18.1), which plays a key role in the betalains biosynthetic scheme. The compound was identified in Lampranthus productus violet flowers, from which it was extracted and purified. The tyrosinase-mediated oxidation of betanidin was characterized in depth and followed by high-performance liquid chromatography and spectrophotometry. The addition of ascorbic acid reversed the reaction product, betanidin-quinone, to the original pigment. Kinetic analysis revealed a K-m = 0.66 mM. Betanidin degradation kinetics was also studied in the absence of the enzyme and demonstrated that pH values over 6.0 and high ionic strength reduce the pigment stability.

  DOI：

  10.1021/jf062858z
• 作为产物：
  描述：

  betanin 在 β-D-glucoside glucohydrolase 作用下， 生成 betanidin
  参考文献：
  名称：

  Characterization of the Activity of Tyrosinase on Betanidin

  摘要：

  Betalains are an important class of water-soluble pigments, with radical scavenging capacity, which is characteristic of the order Caryophyllales. The structural unit of the violet betacyanins, betanidin is reported as a substrate for the enzyme tyrosinase (EC 1.14.18.1), which plays a key role in the betalains biosynthetic scheme. The compound was identified in Lampranthus productus violet flowers, from which it was extracted and purified. The tyrosinase-mediated oxidation of betanidin was characterized in depth and followed by high-performance liquid chromatography and spectrophotometry. The addition of ascorbic acid reversed the reaction product, betanidin-quinone, to the original pigment. Kinetic analysis revealed a K-m = 0.66 mM. Betanidin degradation kinetics was also studied in the absence of the enzyme and demonstrated that pH values over 6.0 and high ionic strength reduce the pigment stability.

  DOI：

  10.1021/jf062858z

文献信息

• Oxidative Färbemittel
  申请人：Henkel AG & Co. KGaA

  公开号：EP2301520A2

  公开（公告）日：2011-03-30

  Gegenstand der vorliegenden Anmeldung sind Mittel zur oxidativen Färbung keratinischer Fasern, insbesondere menschlicher Haare, enthaltend in einem kosmetisch akzeptablen Träger mindestens ein Oxidaionsfarbstoffvorprodukt sowie eine Wirkstoffkombination aus (a) mindestens einer basischen Aminosäure, (b) Pyrrolidoncarbonsäure oder einer ihrer physiologisch verträglichen Salze, wobei die Mittel im Wesentlichen frei von sauren Aminosäuren sind.

  本申请涉及用于角质纤维（尤其是人类头发）氧化染色的组合物，该组合物在 美容上可接受的载体中包含至少一种氧化染色前体和以下活性成分组合 (a) 至少一种碱性氨基酸、 (b) 吡咯烷酮羧酸或其生理上可接受的盐、 其中的制剂基本上不含酸性氨基酸。
• Betanidin formation from dihydroxyphenylalanine in a model assay system
  作者：Willibald Schliemann、Ulrike Steiner、Dieter Strack

  DOI：10.1016/s0031-9422(98)00276-3

  日期：1998.11

  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.
• Photoelectrochemical Solar Cell Comprising Sensitizing Anthocyanin And Betalain Dyes Of Vegetal Or Synthetic Origin, Or Mixtures Thereof
  申请人：Calogero Giuseppe

  公开号：US20120125439A1

  公开（公告）日：2012-05-24

  The present invention relates to the use of sensitizing dyes of natural origin in the photoelectrochemical solar cells and to the process for obtaining such vegetal extracts from fruits and vegetables.
• [DE] FÄRBEMITTEL MIT NATURFARBSTOFFEN UND 1,3-DIHYDROXYACETON<br/>[EN] COLORING AGENT HAVING NATURAL DYES AND 1,3-DIHYDROXYACETONE<br/>[FR] PRODUIT DE COLORATION À BASE DE COLORANTS NATURELS ET DE 1,3-DIHYDROXYACÉTONE
  申请人：HENKEL AG & CO KGAA

  公开号：WO2009033833A2

  公开（公告）日：2009-03-19

  Mit einem Mittel, enthaltend eine Kombination von 1,3-Dihydroxyaceton und mindestens einem Naturfarbstoff, insbesondere aus der Gruppe der Diaryloylmethanfarbstoffe, Naphthochinonfarbstoffe, Flavonoidfarbstoffe, Anthrachinonfarbstoffe, Betalainfarbstoffe, Gallotanninfarbstoffe und indigoiden Farbstoffe, lassen sich keratinhaltige Fasern, insbesondere menschliche Haare, natürlich, intensiv und waschecht färben.
• [DE] HAARBEHANDLUNGSMITTEL MIT TILIROSID UND VITAMIN B<br/>[EN] HAIR TREATMENT AGENT COMPRISING TILIROSIDE AND VITAMIN B<br/>[FR] PRODUIT DE TRAITEMENT CAPILLAIRE AVEC TILIROSIDE ET VITAMINE B
  申请人：HENKEL AG & CO KGAA

  公开号：WO2009060017A1

  公开（公告）日：2009-05-14

  Eine kosmetische Zusammensetzung, enthaltend ein Flavonoid gemäß Formel (I) und mindestens einen weiteren Wirkstoff aus dem Vitamin B Komplex, eignet sich hervorragend im Rahmen einer Behandlung von keratinischer Fasern, insbesondere menschlichem Haar, zur Verbesserung des Feuchtigkeit in der Faser, zur Reparatur und Restrukturierung der Fasern und zum Schutz der Fasern vor Oxidationsmitteln und UV-Strahlung, sowie zur Verbesserung des Farberhalts und der Farbintensität, sofern es sich bei den Fasern um gefärbte Haare handelt.