3',4',7-trihydroxyflavylium chloride | 18393-49-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3',4',7-trihydroxyflavylium chloride
• 英文别名: 3',4',7-Trihydroxy-flavyliumchlorid；4-(7-hydroxychromenylium-2-yl)benzene-1,2-diol;chloride
• CAS: 18393-49-2
• 化学式: C₁₅H₁₁O₄*Cl
• 分子量: 290.703
• InChiKey: UXETVFBOMWILHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3',4',7-trihydroxyflavylium chloride 在 甲醇 、 铂 作用下， 生成 7-Acetoxy-2-(3,4-diacetoxy-phenyl)-chroman
  参考文献：
  名称：

  Freundenberg; Maitland, Justus Liebigs Annalen der Chemie, 1934, vol. 510, p. 193,201

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 120.0h， 生成 3',4',7-trihydroxyflavylium chloride
  参考文献：
  名称：

  3'，4'-二羟基取代的花色苷类似物：水溶液中酸碱，水合，金属结合和给氢性质的合成与研究

  摘要：

  有人提出羟基化黄酮离子的糖苷作为花色素苷的主要类似物，而花色素苷是一类主要的多酚类植物色素。在B环（儿茶酚核）上具有3'，4'-二羟基取代的花色苷因其金属螯合和供电子（抗氧化剂）能力而特别重要。在这项工作中，有效的化学合成3'，4'-dihydroxy-7- O - β - d报道了β-吡喃葡萄糖基氧合黄酮氯化物及其糖苷配基。然后，研究了两种颜料进行质子转移（形成有色醌类碱）和加水（形成无色查尔酮）的能力：在平衡状态下，有色醌类碱（运动产物）的浓度非常小（<相较于无色查尔酮（热力学产物），则为总颜料浓度的10％。吡喃葡萄糖基氧基黄酮离子的酸性似乎比糖苷配基低。总黄酮-查尔酮转化的整个序列的热力学不受β - d-葡萄糖基部分的影响，而动力学则慢了约一个因素。。8.尽管吡喃葡萄糖基氧基黄酮离子及其糖苷配基对Al 3+表现出相似的亲和力，但Al 3+-糖苷配体比Al 3+ -aglycone配体更稳定，因为后者对加水和转化为Al

  DOI：

  10.1016/j.dyepig.2012.07.006

文献信息

• 3?-(?-D-Glycopyranosyloxy)flavylium Ions: Synthesis and investigation of their properties in aqueous solution. Hydrogen bonding as a mean of colour variation
  作者：Hakima El Hajji、Olivier Dangles、Paulo Figueiredo、Raymond Brouillard

  DOI：10.1002/hlca.19970800206

  日期：1997.3.24

  interpreted in terms of possible intramolecular H-bonding between the glycosyl residue and the chromophore. The discussion is then extended to a series of malonylated anthocyanins recently reported for their unusual pigmentation properties. A possible role for the malonyl group (frequently encountered in the structure of naturally occurring anthocyanins) in plant colour expression is outlined for the

  这项工作描述了两个3'-（β-D-glycopyranosyloxy）黄酮离子的直接合成，被认为是天然花青素（色素）的良好模型。对于颜料和非糖基化黄酮离子，均在中等酸性水溶液中定量研究了H 2 O的加成和质子转移反应以及与绿原酸和咖啡因的分子复合物的形成（色素沉着）。证明了咖啡因对颜料的反查耳酮形式具有显着的亲和力。此外，黄酮p K a的差异值根据糖基残基和发色团之间可能的分子内H键来解释。然后，讨论范围扩展到了最近报道的一系列丙二酰化花色苷具有非常规的色素沉着特性。首次概述了丙二酰基（在天然花色苷的结构中经常遇到）在植物颜色表达中的可能作用。
• Anthocyanin–aluminium and –gallium complexes in aqueous solution
  作者：M. Elhabiri、P. Figueiredo、K. Toki、N, Saito、R. Brouillard

  DOI：10.1039/a603851d

  日期：——

  Complexation of aluminium and gallium ions with synthetic anthocyanin models and natural anthocyanins extracted from the blue flowers of Evolvulus pilosus cv ‘Blue Daze’ and the violet flowers of Matthiola incana has been thoroughly investigated in aqueous solution. From UV–VIS spectroscopic data collected at pH 2–5, the presence of complexes, involving not only the coloured forms but also the colourless forms of the pigments is demonstrated. A theoretical treatment is developed for the calculation of the corresponding stability constants. The pigments studied throughout this work can be divided into two series, one sharing a cyanidin chromophore and the other a delphinidin one. Within both series, individual pigments are distinguished according to the degree and type of glycosylation and/or acylation. Intramolecular effects such as copigmentation of anthocyanin–aluminium complexes and the effect of the presence of a malonyl group on the formation of those complexes are discussed. These results are important to plant pigmentation and, for instance, a narrow pH domain in which colour amplification due to complexation is at a maximum has been found.

  我们深入研究了铝和镓离子在水溶液中与合成花青素模型以及从蓝花楹（Evolvulus pilosus cv âBlue Daze）和紫花地丁（Matthiola incana）中提取的天然花青素的络合情况。根据在 pH 值为 2â5 时采集的紫外可见光谱数据，证明了存在络合物，其中不仅包括有色形式的颜料，还包括无色形式的颜料。为计算相应的稳定性常数，还开发了一种理论处理方法。本研究中研究的颜料可分为两个系列，一个系列中的颜料具有青花苷发色团，另一个系列中的颜料具有翠绿苷发色团。在这两个系列中，根据糖基化和/或酰化的程度和类型来区分不同的色素，并讨论了分子内效应，如花青素铝络合物的共着色以及丙二酰基团的存在对形成这些络合物的影响。这些结果对植物色素沉着非常重要，例如，研究人员发现了一个狭窄的 pH 值域，在该值域中，络合作用导致的颜色放大达到最大值。
• Use of flavylium type compounds non-substituted in position 3 for dyeing keratinous fibres and compositions containing them
  申请人：L'Oreal

  公开号：US06241785B1

  公开（公告）日：2001-06-05

  The invention concerns the use of flavylium type compounds, non-substituted in position 3, and substituted by at least a hydroxyl or alcoxy radical, in particular Apigenidin, in pure form or in the form of plant extracts containing them, as coloring agent in or for making compositions for dyeing keratinous fibers, particularly human keratinous fibers such as hair. The invention also concerns the dyeing compositions containing them, particularly cosmetic compositions for direct hair dyeing, and the corresponding dyeing method. The hair dyes resulting from the use of these coloring agents are particularly stable to light and washing.

  本发明涉及使用黄烷酮类化合物，其中第3位未被取代，并且被至少一个羟基或烷氧基取代，特别是Apigenidin，以纯形式或含有它们的植物提取物的形式，作为染色剂用于制作染色角蛋白纤维的组合物，特别是人类角蛋白纤维如头发。本发明还涉及含有它们的染料组合物，特别是用于直接染发的化妆品组合物，以及相应的染色方法。使用这些染料剂染发后的头发具有特别的耐光和耐洗性。
• Artificial tanning compositions comprising flavylium salts
  申请人：——

  公开号：US20020048555A1

  公开（公告）日：2002-04-25

  Topically applicable cosmetic/dermatological compositions for artificially tanning/darkening human skin to such extent as to resemble a natural tan, comprise a thus effective amount of at least one flavylium salt compound formulated into a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor, the at least one flavylium salt compound being unsubstituted at position-3 thereof, but otherwise substituted with at least one hydroxyl group or alkoxy radical; characteristically the amount of the at least one flavylium salt compound is such as to impart a skin coloration, within about 30 minutes after application onto a fair skin, at a rate of 2 mg/cm 2 , having a &Dgr;L* ranging from −0.5 to −20 in the L*a*b* colorimetric measuring system.

  局部适用的化妆品/皮肤学组合物用于人工鞣制/变黑人体皮肤，使其达到类似天然棕褐色的程度，该组合物包括配制到局部适用的、化妆品/皮肤学上可接受的载体、稀释剂或载体中的有效量的至少一种黄烷基鎓盐化合物，至少一种黄烷基鎓盐化合物在其位置-3处未被取代，但在其他位置被至少一个羟基或烷氧基取代；至少一种黄烷基鎓盐化合物的用量应能在涂抹于白皙皮肤后约 30 分钟内使皮肤着色，其用量为 2 mg/cm2 2 在 L*a*b* 比色测量系统中，&Dgr;L*的范围为-0.5至-20。
• Compositions for coloring the skin comprising at least one flavylium salt which is unsubstituted in position 3 and at least one organomodified silicone
  申请人：——

  公开号：US20020048556A1

  公开（公告）日：2002-04-25

  Methods for manufacturing cosmetic and dermatological compositions for coloring the skin; and composition, for example, an emulsion, comprising (1) at least one aqueous phase, (2) at least one fatty phase, (3) at least one flavylium salt which is unsubstituted in position 3; which is substituted with at least one radical chosen from hydroxyl and alkoxy radicals; and which is, for example, obtained at least one of synthetically, from a plant extract, and from an enriched plant extract, in an amount which is effective for artificially coloring the skin, for example, effective for obtaining, 30 minutes after application of the emulsion to a fair skin in an amount of 2 mg/cm 2 , a darkening of the skin color characterized in the L*a*b* colorimetric measuring system by a &Dgr;L* ranging from −0.5 to −20, and (4) at least one organomodified silicone, where the emulsion is configured as at least one of a cosmetic and a dermatological emulsion.

  制造用于给皮肤着色的化妆品和皮肤病组合物的方法；以及组合物，例如乳液，包括：(1) 至少一种水相；(2) 至少一种脂肪相；(3) 至少一种黄基盐，其第 3 位未被取代；其被至少一种选自羟基和烷氧基的基取代；例如，至少从人工合成、植物萃取物和富集植物萃取物中的一种获得，其用量对人工着色皮肤有效，例如，在白皙皮肤上涂抹乳液 30 分钟后，可获得 2 mg/cm2 的用量。 2 (4) 至少一种有机改性硅氧烷，其中乳液被配置为化妆品乳液和皮肤病乳液中的至少一种。