dehydroascorbic acid | 59173-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: dehydroascorbic acid
• 英文别名: Dehydroascorbate (bicyclic form)；3,6,6,6a-tetrahydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one
• CAS: 59173-60-3
• 化学式: C₆H₈O₇
• 分子量: 192.125
• InChiKey: QPPOKIPSRPKDEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  dimeric dehydroascorbic acid 在 水 作用下， 生成 dehydroascorbic acid
  参考文献：
  名称：

  Hyperpolarized [1-¹³C]-Ascorbic and Dehydroascorbic Acid: Vitamin C as a Probe for Imaging Redox Status in Vivo

  摘要：

  Dynamic nuclear polarization (DNP) of C-13-labeled metabolic substrates in vitro and their subsequent intravenous administration allow both the location of the hyperpolarized substrate and the dynamics of its subsequent conversion into other metabolic products to be detected in vivo. We report here the hyperpolarization of [1-C-13]-ascorbic acid (AA) and [1-C-13]-dehydroascorbic acid (DMA), the reduced and oxidized forms of vitamin C, respectively, and evaluate their performance as probes of tumor redox state. Solution-state polarization of 10.5 +/- 1.3% was achieved for both forms at pH 3.2, whereas at pH 7.0, [1-C-13]-AA retained polarization of 5.1 +/- 0.6% and {1-C-13]-DHA retained 8.2 +/- 1.1%. The spin-lattice relaxation times (T-1's) for these labeled nuclei are long at 9.4 T: 15.9 +/- 0.7 s for AA and 20.5 +/- 0.9 s for DMA. Extracellular oxidation of [1-C-13]-AA and intracellular reduction of [1-C-13]-DHA were observed in suspensions of murine lymphoma cells. The spontaneous reaction of DHA with the cellular antioxidant glutathione was monitored in vitro and was approximately 100-fold lower than the rate observed in cell suspensions, indicating enzymatic involvement in the intracellular reduction. [1-C-13]-DHA reduction was also detected in lymphoma tumors in vivo. In contrast, no detectable oxidation of [1-C-13]-AA was measured in the same tumors, consistent with the notion that tumors maintain a reduced micro environment. This study demonstrates that hyperpolarized C-13-labeled vitamin C could be used as a noninvasive biomarker of redox status in vivo, which has the potential to translate to the clinic.

  DOI：

  10.1021/ja2045925

文献信息

• New aspects of the oxidation–reduction mechanism of the ascorbic–dehydroascorbic acid system on the dropping mercury electrode
  作者：Juan J. Ruiz、José M. Rodríguez-Mellado、Manuel Domínguez、Antonio Aldaz

  DOI：10.1039/f19898501567

  日期：——

  and tri-carbonyl compounds on a mercury electrode have made it advisable to review the oxidation–reduction mechanism of the ascorbic–dehydroascorbic acid system on the dropping mercury electrode. On the basis of the variation of E½ with log t, the Tomes and Tafel slopes and the reaction orders with respect to both the reactant and the H+ ion we propose reaction mechanisms for both processes. In both,

  对汞电极上烯二醇化合物的氧化以及二羰基化合物和三羰基化合物的还原的最新研究已使人们有必要对滴下汞电极上的抗坏血酸-脱氢抗坏血酸体系的氧化还原机理进行研究。上的变化的基础上Ë ½与日志吨，所述托姆斯和塔菲尔斜率和反应级数相对于反应物和H都+离子，我们提出了两种方法中的反应机制。在这两种情况下，转移之前的化学步骤都是在与波底相对应的电势下的速率确定步骤。还讨论了氧化还原过程的可逆性。容量与 获得的电势曲线表明，在我们的实验条件下，抗坏血酸未吸附在汞表面上。
• COMPOSITION AND METHODS FOR OBTAINING NUCLEIC ACIDS FROM SPUTUM
  申请人：DNA Genotek Inc.

  公开号：EP1513952B1

  公开（公告）日：2010-12-29
• Hyperpolarized [1-¹³C]-Ascorbic and Dehydroascorbic Acid: Vitamin C as a Probe for Imaging Redox Status in Vivo
  作者：Sarah E. Bohndiek、Mikko I. Kettunen、De-en Hu、Brett W. C. Kennedy、Joan Boren、Ferdia A. Gallagher、Kevin M. Brindle

  DOI：10.1021/ja2045925

  日期：2011.8.3

  Dynamic nuclear polarization (DNP) of C-13-labeled metabolic substrates in vitro and their subsequent intravenous administration allow both the location of the hyperpolarized substrate and the dynamics of its subsequent conversion into other metabolic products to be detected in vivo. We report here the hyperpolarization of [1-C-13]-ascorbic acid (AA) and [1-C-13]-dehydroascorbic acid (DMA), the reduced and oxidized forms of vitamin C, respectively, and evaluate their performance as probes of tumor redox state. Solution-state polarization of 10.5 +/- 1.3% was achieved for both forms at pH 3.2, whereas at pH 7.0, [1-C-13]-AA retained polarization of 5.1 +/- 0.6% and 1-C-13]-DHA retained 8.2 +/- 1.1%. The spin-lattice relaxation times (T-1's) for these labeled nuclei are long at 9.4 T: 15.9 +/- 0.7 s for AA and 20.5 +/- 0.9 s for DMA. Extracellular oxidation of [1-C-13]-AA and intracellular reduction of [1-C-13]-DHA were observed in suspensions of murine lymphoma cells. The spontaneous reaction of DHA with the cellular antioxidant glutathione was monitored in vitro and was approximately 100-fold lower than the rate observed in cell suspensions, indicating enzymatic involvement in the intracellular reduction. [1-C-13]-DHA reduction was also detected in lymphoma tumors in vivo. In contrast, no detectable oxidation of [1-C-13]-AA was measured in the same tumors, consistent with the notion that tumors maintain a reduced micro environment. This study demonstrates that hyperpolarized C-13-labeled vitamin C could be used as a noninvasive biomarker of redox status in vivo, which has the potential to translate to the clinic.