2,3,5-三羧酸吡咯 | 945-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,3,5-三羧酸吡咯
• 中文别名: 1H-吡咯-2,3,5-三羧酸
• 英文名称: 1H-pyrrole-2,3,5-tricarboxylic acid
• 英文别名: pyrrole 2,3,5-tricarboxylic acid；pyrrole-2,3,5-tricarboxylic acid；Pyrrol-2,3,5-tricarbonsaeure
• CAS: 945-32-4
• 化学式: C₇H₅NO₆
• mdl: MFCD09991933
• 分子量: 199.12
• InChiKey: UGSAVTSXHXRENH-UHFFFAOYSA-N

物化性质

• 熔点：
  >220°C (dec.)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,3,5-三羧酸吡咯 在 盐酸 作用下， 生成 pyrrole-2,3,5-tricarboxylic acid trimethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Nicolaus, Gazzetta Chimica Italiana, 1953, vol. 83, p. 239,242 Anm. 10, 251

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二羟基-2-吲哚甲酸 在 双氧水 、 氧气 、 potassium carbonate 、 tyrosinase 作用下， 生成 2,3,5-三羧酸吡咯
  参考文献：
  名称：

  Oxidative degradation of melanins to pyrrole acids: A model study

  摘要：

  The origin of pyrrole-2,3,5-tricarboxylic acid (PTCA), the most characteristic degradation product of melanins, was investigated by use of synthetic pigments prepared from the major biosynthetic precursors, 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA). Under the reported conditions, i.e. acidic permanganate, oxidative degradation of DHI- and DHICA-melanins afforded PTCA in 0.15 and 3.0% w/w yield, respectively. A significant improvement of PTCA yields up to 7% was obtained using alkaline hydrogen peroxide as the oxidising agent. Under these conditions pyrrole-2,3-dicarboxylic acid (PDCA) was also obtained in significant yields. Investigation of the oxidative degradation of some model indole oligomers (1-4) provided unambiguous evidence that PTCA may originate from 2-linked DHI-units in the pigment polymer as well as from DHICA-derived units, whereas PDCA arises from DHI-units not substituted at 2-position. Monitoring of the oxidation of dimer 1 to PTCA showed the intermediate formation of DHICA. Accordingly, a mechanistic route is proposed for the degradation of 2-substituted DHI-units in melanin polymer to PTCA which also accounts for the observed yields of formation of the pyrrole acid from the model oligomers.

  DOI：

  10.1016/0040-4020(95)00259-b

文献信息

• New pyrrole acids by oxidative degradation of eumelanins with hydrogen peroxide. Further hints to the mechanism of pigment breakdown
  作者：Alessandra Napolitano、Alessandro Pezzella、Marco d'Ischia、Giuseppe Prota

  DOI：10.1016/0040-4020(96)00418-8

  日期：1996.6

  Oxidative degradation of natural and synthetic eumelanins with alkaline H2O2 afforded a complex mixture of low molecular weight products which comprised, besides 1 and 2, three novel pyrrole acids. These were isolated and identified as 2-carboxyhydroxymethylpyrrole-3,5-dicarboxylic acid (3), 2-carboxymethylpyrrole-3,5-dicarboxylic acid (4) and 2-hydroxymethylpyrrole-3,5-dicarboxylic acid (5). Investigation

  用碱性H 2 O 2对天然和合成油棕素进行氧化降解，得到了低分子量产物的复杂混合物，该产物除1和2外还包含三种新型吡咯酸。将它们分离并鉴定为2-羧基羟甲基吡咯-3，5-二羧酸（3），2-羧甲基吡咯-3，5-二羧酸（4）和2-羟甲基吡咯-3，5-二羧酸（5）。对木聚糖素前体5,6-二羟基吲哚和5,6-二羟基吲哚-2-羧酸以及低聚物6-10的氧化降解研究表明，吡咯酸3-5由羧基和非羧基吲哚单元的过氧化破坏引起的吡咯4主要由未在7位取代的吲哚单元产生。通过用碱性H 2 O 2处理，没有任何新的吡咯转化为1，表明它们是由不同的降解途径形成的。可将这些结果纳入改进的机制方案中，以通过Eumelanins的H 2 O 2降解使吡咯酸的来源合理化。
• METHOD AND SYSTEM FOR EFFECTING CHANGES IN PIGMENTED TISSUE
  申请人：Moazed Kambiz Thomas

  公开号：US20110280909A1

  公开（公告）日：2011-11-17

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are nanoparticle compositions for lightening the pigmented tissues or treating a pigmented tissue related disease.

  描述了一种快速和可持续改变虹膜基质黑色素含量的黑色素细胞的方法和系统，从而改变眼睛的颜色。还描述了用于淡化有色组织或治疗有色组织相关疾病的纳米颗粒组合物。
• Novel synthesis of [¹³C₄,¹⁵N]1H-pyrrole-2,3,5-tricarboxylic acid: an important biomarker for melatonin metabolism
  作者：Marc B. Skaddan

  DOI：10.1002/jlcr.1704

  日期：——

  1H-pyrrole-2,3,5-tricarboxylic acid is a breakdown product of melatonin. A labeled version of this compound would serve as a key biomarker for drug candidates which track this substance to monitor their effectiveness (e.g. hyperpigmentation drugs). A Hantzsch synthesis using readily available starting materials was used to generate [13C4,15N]1H-pyrrole-2,3,5-tricarboxylic acid in six steps (12% overall yield). Copyright © 2009 John Wiley & Sons, Ltd.

  1H-吡咯-2,3,5-三羧酸是褪黑激素的分解产物。该化合物的标记版本将作为候选药物的关键生物标志物，跟踪该物质以监测其有效性（例如色素沉着过度药物）。使用易于获得的起始原料进行 Hantzsch 合成，分六步生成 [13C4,15N]1H-吡咯-2,3,5-三羧酸（总产率 12%）。版权所有 © 2009 约翰·威利父子有限公司
• Method and system for effecting changes in pigmented tissue
  申请人：Moazed Kambiz Thomas

  公开号：US20120207809A1

  公开（公告）日：2012-08-16

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are compositions for lightening or darkening the pigmented tissues or treating a pigmented tissue disease.

  本文描述了一种快速和可持续改变虹膜基质黑素细胞中黑色素含量的方法和系统，从而改变眼睛的颜色。还描述了用于使色素组织变浅或变深或治疗色素组织疾病的组合物。
• Use of an edelweiss extract in hair care for the prevention of hair graying
  申请人：DSM IP Assets B.V.

  公开号：EP2873414A1

  公开（公告）日：2015-05-20

  The present invention relates to a new use of an edelweiss extract for application to skin having hair, scalp, or hair of a human for the prevention of the graying of hair and/or for restoration and/or maintenance of the natural hair color. Furthermore, the invention relates to a method for preventing the graying of hair and/or restoring and/or maintaining the natural hair color which comprises the step of applying to skin having hair of a human a topical composition comprising an effective amount of an edelweiss extract.

  本发明涉及一种酢浆草提取物的新用途，该提取物可用于有头发的皮肤、头皮或人的头发，以防止头发变白和/或恢复和/或保持自然发色。此外，本发明还涉及一种防止头发变白和/或恢复和/或保持自然发色的方法，该方法包括以下步骤：将含有有效量酢浆草提取物的外用组合物涂抹在人的有头发的皮肤上。