<13C6>ascorbic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: <13C6>ascorbic acid
• 英文别名: [U-¹³C]-L-ascorbic acid；L-Ascorbic Acid-13C6；(2R)-2-[(1S)-1,2-dihydroxy(1,2-13C2)ethyl]-3,4-dihydroxy-(2,3,4,5-13C4)2H-furan-5-one
• 化学式: C₆H₈O₆
• 分子量: 182.06
• InChiKey: CIWBSHSKHKDKBQ-RQFYRPEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <13C6>ascorbic acid 、 丙烯醛 以 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  丙烯醛的维生素 C 缀合物的形成及其对氧磷酶介导的转化为 5,6,7,8-四羟基-4-氧代辛醛

  摘要：

  据报道，维生素 C（抗坏血酸）参与体外迈克尔加成反应，与 α,β-不饱和醛（如丙烯醛）形成维生素 C 缀合物。该研究显示了丙烯醛维生素 C 结合物 (AscACR) 在暴露于丙烯醛二乙酸酯的培养的人类单核细胞 THP-1 细胞中形成和代谢的证据。通过使用18 O 和13C 标记与液相色谱-串联质谱法相结合，显示 AscACR 将抗坏血酸内酯水解转化为中间体羧酸。随后羧酸的脱羧产生 5,6,7,8-四羟基-4-氧代辛醛 (THO)。当 THP-1 细胞用抗坏血酸 (1 mM, 18 h) 预处理，然后暴露于二乙酸丙烯醛时，在细胞裂解物和培养基中检测到 THO 作为其五氟苄基肟衍生物。THO形成需要用抗坏血酸和丙烯醛二乙酸酯处理THP-1细胞。内酯酶、人重组对氧磷酶 1 和 2 促进了 AscACR 形成 THO。THP-1 细胞表现出 PON 活性，这解释了 AscACR 在这些细胞中催化转化为

  DOI：

  10.1021/tx900452j

文献信息

• Variation in ascorbic acid oxidation routes in hydrogen peroxide and cupric ion solution as determined by GC/MS
  作者：John C. Deutsch、C. R. Santhosh-Kumar、Kathryn L. Hassell、J. Fred. Kolhouse

  DOI：10.1021/ac00075a006

  日期：1994.2.1

  Recent reports have suggested that ascorbic acid protects low-density lipoprotein from peroxide-induced oxidation, but does not protect and may actually function as a prooxidant in the presence of cupric ions. However, dehydroascorbic acid, (the first oxidation product of ascorbic acid) has been shown to protect low-density lipoprotein from cupric ion oxidation but not peroxide-induced oxidation. We have examined the degradation of ascorbic acid, uniformly labeled [C-13(6)]ascorbic acid, and [6,6-H-2(2)]ascorbic acid in hydrogen peroxide and cupric ion solutions using gas chromatography/mass spectrometry to determine products and routes of oxidation using different oxidant sources. We have found that hydrogen peroxide leads to the formation of a six-carbon product with a mass increment of 32 (a double oxygen addition) relative to ascorbic acid, consistent with the oxidation sequence of ascorbic acid(mass 176) going to dehydroascorbic acid (mass 174) to 2,3-diketogulonic acid (mass 192) to 2,3-diketo-4,5,5,6-tetrahydroxyhexanoic acid (mass 208). Cupric ion solutions, on the other hand, do not appear to induce significant amounts of 2,3-diketo-4,5,5,6-tetrahydroxyhexanoic acid but rather lead to the formation of a threo-hexa-2,4-dienoic acid lactone (mass 174) as the major six-carbon species. These data suggest that different oxidation stresses lead to solutions containing different ascorbic acid oxidation products. These ascorbic acid-derived species could, in turn, interact differently with other substances in the aqueous environment, including free metal ions and low-density lipoprotein. This may help explain previous reports showing divergent protective effects of ascorbic acid and dehydroascorbic acid on low-density lipoprotein when different oxidation methods are used.