dimeric dehydroascorbic acid | 1100265-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimeric dehydroascorbic acid
• 英文别名: Dehydroascorbic acid；Dehydroascorbinsaeure；3,7,12,16-Tetrahydroxy-2,5,9,11,14,18-hexaoxapentacyclo[10.6.0.01,15.03,10.06,10]octadecane-4,13-dione
• CAS: 1100265-05-1
• 化学式: C₁₂H₁₂O₁₂
• 分子量: 348.22
• InChiKey: DBAUAPYTRMIWBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  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

• Application of dehydroascorbic acid or derivatives/isomers thereof for artificially coloring the skin
  申请人：Pruche Francis

  公开号：US20090016974A1

  公开（公告）日：2009-01-15

  Dehydroascorbic acid and polymeric/monomeric derivatives and isomers thereof are useful for artificially coloring the skin and more particularly as a skin self-tanning agent; the dehydroascorbic acid may be formed “in situ” from ascorbic acid or a derivative or salt thereof via chemical oxidation and/or via enzymatic oxidation, and a two-component agent thereof includes a) a first component (B) containing, in a physiologically acceptable medium, at least ascorbic acid or a derivative or salt thereof; b) a second component (C) containing, in a physiologically acceptable medium, at least one chemical oxidizing agent and/or one enzymatic oxidizing agent; components (B) and (C) being stored separately.

  脱氢抗坏血酸及其聚合物/单体衍生物和异构体可用于人工着色皮肤，特别是作为皮肤自我晒黑剂；脱氢抗坏血酸可以通过化学氧化和/或酶促氧化从抗坏血酸或其衍生物或盐“原位”形成，并且其两组分剂包括a）第一组分（B）在生理上可接受的介质中，至少含有抗坏血酸或其衍生物或盐；b）第二组分（C）在生理上可接受的介质中，至少含有一种化学氧化剂和/或一种酶促氧化剂；组分（B）和（C）分别存储。
• Colouring composition for the skin comprising a self-tanning agent and a dye obtained by reacting an amine with dehydroascorbic acid or a monomeric polymeric or isomeric derivative thereof
  申请人：Cassin Guillaume

  公开号：US20090035241A1

  公开（公告）日：2009-02-05

  The present invention relates to a composition for artificially colouring the skin, comprising, in a physiologically acceptable medium: a) at least one self-tanning agent, and b) at least one dye that can be obtained by reacting dehydroascorbic acid and/or a monomeric derivative thereof of formula (I) and/or an isomer thereof of formula (I′) and/or a polymeric derivative thereof, especially dimers of formula (II), with an amine compound. The present invention also relates to a process for artificially colouring the skin, comprising the application of a composition comprising, in a physiologically acceptable medium: a) at least one self-tanning agent, and b) at least one dye that can be obtained by reacting dehydroascorbic acid and/or a monomeric derivative thereof of formula (I) and/or an isomer thereof of formula (I′) and/or a polymeric derivative thereof, especially dimers of formula (II), with an amine compound.

  本发明涉及一种用于人工着色皮肤的组合物，包括在生理学上可接受的介质中：a）至少一种自黑剂，和b）至少一种染料，该染料可通过将去氢抗坏血酸和/或式(I)的单体衍生物和/或其异构体式(I')和/或其聚合物衍生物，特别是二聚体式(II)与胺化合物反应而获得。本发明还涉及一种用于人工着色皮肤的方法，包括应用包括在生理学上可接受的介质中：a）至少一种自黑剂，和b）至少一种染料，该染料可通过将去氢抗坏血酸和/或式(I)的单体衍生物和/或其异构体式(I')和/或其聚合物衍生物，特别是二聚体式(II)与胺化合物反应而获得的组合物。
• SELF-TANNING AGENTS AND DEHYDROASCORBIC ACID OR A MONOMERIC, POLYMERIC OR ISOMERIC DERIVATIVE THEREOF FOR ARTIFICALLY COLORING THE SKIN
  申请人：BAZELAIRE Eve

  公开号：US20100215597A1

  公开（公告）日：2010-08-26

  Cosmetic compositions for artificially coloring the skin contain, formulated into a physiologically acceptable medium, a) at least dehydroascorbic acid and/or a monomeric derivative and/or isomeric form and/or polymeric derivative thereof, and b) at least one preferably monocarbonyl or polycarbonyl self-tanning agent; the dehydroascorbic acid may be formed “in situ” from ascorbic acid or a derivative thereof or a salt thereof via chemical oxidation and/or via enzymatic oxidation.

  用于人工着色皮肤的化妆品组合物包含以下物质，配制成生理可接受的介质：a）至少一种脱氢抗坏血酸和/或单体衍生物和/或同分异构体和/或其聚合物衍生物，和b）至少一种优选的单酰基或多酰基自身晒黑剂。脱氢抗坏血酸可以通过化学氧化和/或通过酶促氧化从抗坏血酸或其衍生物或其盐中“原位”形成。
• DEHYDROASCORBIC ACID OR MONOMERIC, POLYMERIC OR ISOMERIC DERIVATIVE THEREOF AND AN AMINE FOR ARTIFICIALLY COLORING THE SKIN
  申请人：CHOISY Patrick

  公开号：US20100221203A1

  公开（公告）日：2010-09-02

  A regime or regimen for artificially coloring the skin entails topically applying thereon at least a) dehydroascorbic acid and/or a monomeric derivative thereof of formula (I) below and/or an isomeric form thereof of formula (I′) below and/or a polymeric derivative thereof: in which: OR 1 and OR 2 , which may be identical or different, are each OH; a saturated or unsaturated, linear or branched C 1 -C 30 and more preferentially C 1 -C 18 alkoxy radical; a glycoside and more preferentially glucose; an ester of a saturated or unsaturated, linear or branched C 1 -C 30 (preferably C 1 -C 18 ) aliphatic carboxylic acid, which may be substituted with an aryl radical or a heterocycle; an aryl or heterocyclic carboxylic acid ester, which may be substituted with at least one saturated or unsaturated, linear or branched C 1 -C 30 (more preferentially C 1 -C 18 ) alkyl radical; a phosphate group; a sulfate group, and b) at least one amine compound.

  一种人工着色皮肤的方案或方案包括在其上局部应用至少a) 下列式(I)的脱氢抗坏血酸和/或其单体衍生物和/或其式(I')的同分异构体和/或其聚合物衍生物：其中：OR1和OR2，可以相同也可以不同，分别为OH；饱和或不饱和，线性或支链C1-C30并更倾向于C1-C18的烷氧基团；一种糖苷，更倾向于葡萄糖；饱和或不饱和，线性或支链C1-C30（优选C1-C18）脂肪族羧酸的酯，它可以用芳基基团或杂环取代；一种芳基或杂环羧酸酯，它可以用至少一个饱和或不饱和，线性或支链C1-C30（更倾向于C1-C18）烷基基团取代；一种磷酸基；一种硫酸酯基，和b) 至少一种胺化合物。
• On the stability of symmetric dimers of dehydroascorbic acid: A study of the esters in the crystalline and the solute state
  作者：Jan Hvoslef、H»kon Hope、Brendan D. Murray

  DOI：10.1016/0008-6215(86)85002-9

  日期：1986.3

  Abstract Acetylated and benzoylated dimeric dehydroascorbic acid have the same molecular structure as the crystalline parent compound. X-Ray analysis of the tetra-acetate reveals only moderate deviation from two-fold symmetry, caused, presumably, by the packing requirements of the acetate groups. The central dioxane ring is stabilised by the conversion of OH into OAc or OBz. In methyl sulfoxide or

  摘要乙酰化和苯甲酰化的二聚脱氢抗坏血酸具有与结晶母体化合物相同的分子结构。四乙酸酯的X射线分析显示，与对称性的两倍对称仅适度偏差，这大概是由乙酸酯基团的填充要求引起的。中心二恶烷环可通过OH转化为OAc或OBz来稳定。在甲基亚砜或N，N-二甲基甲酰胺溶液中，不会发生脱氢抗坏血酸的异构化反应。