6-O-α-D-Glucopyranosyl-L-ascorbic acid | 126370-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-α-D-Glucopyranosyl-L-ascorbic acid
• 英文别名: 6-α-glucosyl ascorbic acid；6-o-alpha-Glucopyranosyl-l-ascorbic acid；(2R)-3,4-dihydroxy-2-[(1S)-1-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-2H-furan-5-one
• CAS: 126370-70-5
• 化学式: C₁₂H₁₈O₁₁
• 分子量: 338.268
• InChiKey: TZGJFGIVPNNUQI-DQXMJQANSA-N

物化性质

• 沸点：
  740.8±60.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  直链淀粉 、 维生素 C 在 Bacillus stearothermophilus maltogenic amylase 作用下， 以 水 为溶剂， 反应 48.0h， 生成 6-O-α-D-Glucopyranosyl-L-ascorbic acid 、 6-α-maltosyl ascorbic acid
  参考文献：
  名称：

  Modification of Ascorbic Acid Using Transglycosylation Activity of Bacillus stearothermophilus Maltogenic Amylase to Enhance Its Oxidative Stability

  摘要：

  Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an (alpha-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and C-13 NMR analyses revealed that the structures of the transfer products were 6-O-alpha-D-glucosyl- (2) and 6-O-alpha-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-alpha-acarviosine-D-glucosyl- (4) and 2-O-alpha-acarviosine-D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.

  DOI：

  10.1021/jf011550z

文献信息

• ASCORBIC ACID DERIVATIVES, THEIR PREPARATION METHODS, INTERMEDIATES AND USES IN COSMETICS
  申请人：Li Huashan

  公开号：US20100204464A1

  公开（公告）日：2010-08-12

  A kind of ascorbic acid derivates 3-O-glyco-L-ascorbic acid, their preparation methods, intermediates and uses in cosmetics. The derivates used as vitamin C precursors have better physiological effect than 2-O-α-D-glucopyranosyl ascorbic acid (AA-2G) and are more stable. Present compounds can be used in many fields, such as in cosmetics, pharmaceuticals, foodstuffs and livestock feed, and especially as whitening agents in cosmetics. The preparation method involves protecting the 5,6-dihydroxyl of ascorbic acid, then coupling with 1-haloacylglycosyl, obtaining the intermediate 3-O-(acylglycosyl)-(5,6-O-isopropylidine)-L-ascorbic acid, removing the isopropylidine and acyl from the intermediates, thereby obtaining the target substance.

  一种抗坏血酸衍生物3-O-糖基-L-抗坏血酸酸，其制备方法，中间体和在化妆品中的用途。这些衍生物作为维生素C前体比2-O-α-D-葡萄糖吡喃糖基抗坏血酸（AA-2G）具有更好的生理效果，并且更加稳定。目前的化合物可以用于许多领域，例如化妆品，药品，食品和饲料，特别是作为化妆品中的美白剂。制备方法涉及保护抗坏血酸的5,6-二羟基，然后与1-卤代酰基糖基偶联，得到中间体3-O-（酰基糖基）-（5,6-O-异丙基亚甲基）-L-抗坏血酸酸，从中间体中去除异丙基亚甲基和酰基，从而得到目标物质。
• [EN] NOVEL RETINOL DERIVATIVE AND COSMETIC COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAU DERIVE DE RETINOL ET COMPOSITION COSMETIQUE COMPRENANT LEDIT DERIVE
  申请人：COREANA COSMETICS CO LTD

  公开号：WO2004054992A1

  公开（公告）日：2004-07-01

  The present invention relates to a novel retinol derivative and a cosmetic composition comprising the same, in particular, to a novel retinol derivative represented by the formula (I) exhibiting the effects from both L-ascorbic acid and retinol as well as being free from the disadvantages of two compounds such as skin irritation and instability in cosmetic formulation, and a cosmetic composition comprising the retinol derivative. (I)

  本发明涉及一种新型视黄醇衍生物和包含该衍生物的化妆品组合物，具体来说，涉及一种由式(I)表示的新型视黄醇衍生物，展现出L-抗坏血酸和视黄醇的双重效果，并且不具有两种化合物的缺点，如皮肤刺激和在化妆品配方中的不稳定性，以及包含该视黄醇衍生物的化妆品组合物。 (I)
• Process for producing 2-0-alpha-d-glucopyranosyl-l-ascorbic acid
  申请人：Mukai Kazuhisa

  公开号：US20060216792A1

  公开（公告）日：2006-09-28

  The object of the present invention is to provide a method and a process for producing 2-O-α-glucopyranosyl-L-ascorbic acid where 5-O-α-glucopyranosyl-L-ascorbic acid and 6-O-α-glucopyranosyl-L-ascorbic acid are not formed or formed in such a small amount that the formation of these can nor be detected. The present invention solves the above object by providing a process for producing 2-O-α-glucopyranosyl-L-ascorbic acid comprising the steps of allowing α-isomaltosyl glucosaccharide-forming enzyme together with or without cyclomaltodextrin glucanotransferase (EC 2.4.1.19) to act on a solution comprising L-ascorbic acid and, an α-glucosyl saccharide to form 2-O-α-glucopyranosyl-L-ascorbic acid and collecting the formed 2-O-α-glucopyranosyl-L-ascorbic acid.

  本发明的目的是提供一种生产2-O-α-葡萄糖吡喃糖基-L-抗坏血酸的方法和过程，其中不形成或形成的5-O-α-葡萄糖吡喃糖基-L-抗坏血酸和6-O-α-葡萄糖吡喃糖基-L-抗坏血酸数量很少，以至于无法检测到这些物质的形成。本发明通过提供一种方法来解决上述问题，该方法包括以下步骤：让α-异麦芽糖基葡萄糖酶形成酶与或不带环糊精葡聚糖转移酶（EC 2.4.1.19）作用于包含L-抗坏血酸和α-葡萄糖基糖的溶液中，形成2-O-α-葡萄糖吡喃糖基-L-抗坏血酸并收集所形成的2-O-α-葡萄糖吡喃糖基-L-抗坏血酸。
• Alpha-glycosyl-L-ascorbic acid, and its preparation and uses
  申请人：KABUSHIKI KAISHA HAYASHIBARA SEIBUTSU KAGAKU KENKYUJO

  公开号：EP0398484A2

  公开（公告）日：1990-11-22

  α-Glycosyl-L-ascorbic acid exhibiting no direct reducing activity is formed in a solution containing L-ascorbic acid and an α-glucosyl saccharide when subjected to the action of a saccharide-transferring enzyme. α-Glycosyl-L-ascorbic acid is superiorly stable, and readily hydrolyzable in vivo to exhibit the activities inherent to L-ascorbic acid. Thus, α-glycosyl-L-ascorbic acid is favorably useful as a stabilizer, quality-improving agent, antioxidant, physiologically active agent and uv-absorbent in food pharmaceutical and cosmetic industries.

  在含有 L-抗坏血酸和 α-葡萄糖基糖的溶液中，在糖转移酶的作用下会形成不具有直接还原活性的 α-糖基-L-抗坏血酸。因此，α-糖基-L-抗坏血酸可用作食品、药品和化妆品行业的稳定剂、质量改进剂、抗氧化剂、生理活性剂和紫外线吸收剂。
• Crystalline 2-0-alpha-D-glucopyranosyl-L-ascorbic acid, and its preparation and uses
  申请人：KABUSHIKI KAISHA HAYASHIBARA SEIBUTSU KAGAKU KENKYUJO

  公开号：EP0425066A1

  公开（公告）日：1991-05-02

  2-O-α-D-Glucopyranosyl-L-ascrobic acid is crystal­lizable in its supersaturated solution. Crystalline 2-O-α-D-­glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, crystalline 2-O-α-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-α-D-gluco­pyranosy-L-acorbic acid is favorably useful in vitamin C-­enriching agents, foodstuffs, pharmaceuticals and cosmetics.

  2-O-α-D-Glucopyranosyl-L-ascrobic acid 可在过饱和溶液中结晶。结晶的 2-O-α-D-吡喃葡萄糖基-L-抗坏血酸基本上不吸湿、可自由流动、不潮解、不固结、不具有直接还原活性，但很容易溶于水。正因为如此，结晶的 2-O-α-D-Glucopyranosyl-L-ascorbic acid 容易处理，而且稳定性和生理活性极高。因此，结晶的 2-O-α-D-吡喃葡萄糖基-L-抗坏血酸可用于富含维生素 C 的制剂、食品、药品和化妆品。