3,4-二羟基-3-己烯-2,5-二酮 | 10153-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-二羟基-3-己烯-2,5-二酮
• 英文名称: 3,4-dihydroxy-3-hexene-2,5-dione
• 英文别名: (E)-3,4-dihydroxyhex-3-ene-2,5-dione
• CAS: 10153-61-4
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: QDILFPZEGWZMON-AATRIKPKSA-N

物化性质

• 沸点：
  334.8±42.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二羟基-3-己烯-2,5-二酮 在 盐酸 作用下， 以 水 为溶剂， 反应 0.34h， 生成 3-hydroxy-4-methyl-3-cyclopentene-1,2-dione
  参考文献：
  名称：

  Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product

  摘要：

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0278-6915(01)00093-x
• 作为产物：
  描述：

  丙酮醛 在 potassium cyanide 、 磷酸 、 碳酸氢钠 作用下， 反应 1.0h， 以16%的产率得到3,4-二羟基-3-己烯-2,5-二酮
  参考文献：
  名称：

  AcetylformoinA Chemical Switch in the Formation of Colored Maillard Reaction Products from Hexoses and Primary and Secondary Amino Acids

  摘要：

  Thermal treatment of a methanolic solution of N-(1-deoxy-D-fructos-1-yl)-L-proline and furan-2-carboxaldehyde led to the rapid formation of colored compounds, among which 4-hydroxy-2-methoxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (1) could be identified as one of the main colored compounds by NMR, LC/MS, and UV-vis spectroscopy. Studies on its formation revealed that condensation of the hexose dehydration product acetylformoin (2a/2b) with furan-2-carboxaldehyde formed the labile 2,4-hydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (3a/3b), which then reacts with methanol to the more stable colorant 1. Reacting furan-2-carboxaldehyde with N-(1-deoxy-D-fructos-1-yl)-L-alanine, however, completely stalled the formation of acetylformoin and, consequently, also of colorant 1. Further model studies revealed acetylformoin as a chemical snitch in the Maillard reaction determining different reaction pathways in the presence of primary and secondary amino acids; for example, the reaction with glycine methyl ester and glycine revealed 2,4-dihydroxy-2,5-dimethyl-1-methoxycarbonylmethyl- (4) and 2,4-dihydroxy-2,5-dimethyl-1-carboxymethyl -3-oxo-2H-pyrrole (5), respectively, whereas the reaction with L-proline resulted in the formation of pyrrolidino- (6) and bispyrrolidino-hexose-reductone (7). Dry heating of these amino reductones in the presence of furan-2-carboxaldehyde produced the colorants 2,4-dihydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-1-methoxycarbonylmethyl-3-oxo-2H-pyrrole (8) from 4 and 3-hydroxy-4-[(E)-(2-furyl)methylidene] methyl-3-cyclopentene-1,2-dione (9) from 6 and 7. Quantitative studies revealed 3-hydroxy-4-methyl-3-cyclopentene-1,2-dione (10) and methylene-reductinic acid (11) as the key intermediates in the formation of colorant 9.

  DOI：

  10.1021/jf980512l

文献信息

• Medical bathing device
  申请人：BSN Medical GmbH

  公开号：US10813831B2

  公开（公告）日：2020-10-27

  The present invention relates to a medical bathing equipment for the manufacture and use of a bathing solution containing an active substance and in particular a bathing solution containing NO. The invention also relates to a bathing equipment based on a multi-stage method for generating NO and the bathing equipment in its use for the treatment of diseases, in particular of diabetically caused circulatory disorders and wounds of the lower extremities.

  本发明涉及一种医用沐浴设备，用于制造和使用含有活性物质的沐浴液，特别是含有 NO 的沐浴液。本发明还涉及一种基于多级生成 NO 方法的沐浴设备，以及该沐浴设备在治疗疾病，特别是糖尿病引起的循环障碍和下肢伤口方面的用途。
• DAIRY PRODUCT AND PROCESS
  申请人：Fonterra Co-Operative Group Limited

  公开号：EP2175738A1

  公开（公告）日：2010-04-21
• MEDIZINISCHE BADEVORRICHTUNG
  申请人：BSN Medical GmbH

  公开号：EP3288517A1

  公开（公告）日：2018-03-07
• MEHRSTUFIGES VERFAHREN ZUR NO-HERSTELLUNG
  申请人：BSN Medical Holding GmbH

  公开号：EP3288893A1

  公开（公告）日：2018-03-07
• MEDICAL BATHING DEVICE
  申请人：BSN Medical GmbH

  公开号：US20180153768A1

  公开（公告）日：2018-06-07

  The present invention relates to a medical bathing equipment for the manufacture and use of a bathing solution containing an active substance and in particular a bathing solution containing NO. The invention also relates to a bathing equipment based on a multi-stage method for generating NO and the bathing equipment in its use for the treatment of diseases, in particular of diabetically caused circulatory disorders and wounds of the lower extremities.