6-O-glucosyl-L-ascorbic acid | 910646-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-glucosyl-L-ascorbic acid
• 英文别名: ascorbic acid 6-glucoside；6-O-d-glucopyranosyl-l-ascorbic acid；(2R)-3,4-dihydroxy-2-[(1S)-1-hydroxy-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-2H-furan-5-one
• CAS: 910646-87-6
• 化学式: C₁₂H₁₈O₁₁
• 分子量: 338.268
• InChiKey: TZGJFGIVPNNUQI-YTZPJNFPSA-N

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：

  维生素 C 、 Cellobiose 在 cellulase 作用下， 以 acetate buffer 为溶剂， 反应 24.0h， 生成 6-O-glucosyl-L-ascorbic acid
  参考文献：
  名称：

  Ascorbic acid conjugates isolated from the phloem of Cucurbitaceae

  摘要：

  Analysis of phloem exudates from the fruit of Cucurbitaceae revealed the presence of several compounds with UV-visible absorption spectra identical to that of L-ascorbic acid. In Cucurbita pepo L. (zucchini), the compounds could be isolated from phloem exudates collected from aerial parts of the plant but were not detected in whole tissue homogenates. The compounds isolated from the phloem exudates of C. pepo fruit were eluted from strong anion exchange resin in the same fraction as L-ascorbic acid and were oxidised by ascorbate oxidase (E.C. 1.10.3.3). The major compound purified from C. pepo fruit exudates demonstrated similar redox properties to L-ascorbic acid and synthetic 6-O-glucosyl-L-ascorbic acid (6-GlcAsA) but differed from those of 2-O-glucosyl-L-ascorbic acid (2-GlcAsA) isolated from the fruit of Lycium barbarum L. Parent and fragment ion masses of the compound were consistent with hexosyl-ascorbate in which the hexose moiety was attached to C5 or C6 of AsA. Acid hydrolysis of the major C. pepo compound resulted in the formation of L-ascorbic acid and glucose. The purified compound yielded a proton NMR spectrum that was almost identical to that of synthetic 6-GlcAsA. A series of L-ascorbic acid conjugates have, therefore, been identified in the phloem of Cucurbitaceae and the most abundant conjugate has been identified as 6-GlcAsA. The potential role of such conjugates in the long-distance transport of L-ascorbic acid is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.03.022

文献信息

• FORMULATIONS OF LIPOPHILIC BIOACTIVE MOLECULES
  申请人：Zumes, LLC

  公开号：US20140039052A1

  公开（公告）日：2014-02-06

  This invention provides aqueous and non-aqueous clear formulations including at least one lipophilic bioactive molecules and an amphiphilic solubilizing agent. Exemplary aqueous formulations include a water-soluble reducing agent, which diminishes or prevents chemical degradation of the lipophilic bioactive molecule. The invention also provides methods of using the formulations of the invention. For example, the invention provides beverages including the formulations of the invention. The invention further provides methods of making the formulations and beverages.

  本发明提供了包括至少一种亲脂性生物活性分子和一种两性溶解剂的水性和非水性透明配方。其中，水性配方包括水溶性还原剂，可减少或防止亲脂性生物活性分子的化学降解。本发明还提供了使用该配方的方法。例如，本发明提供了包括该配方的饮料。本发明还提供了制备该配方和饮料的方法。
• 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。
• Magnolia extract containing compositions
  申请人：Mary Kay, Inc.

  公开号：EP2455134A2

  公开（公告）日：2012-05-23

  Disclosed is a cosmetic method of treating a skin condition, comprising topically applying a composition comprising magnolia extract to skin, wherein topical application of the composition treats the skin condition and wherein the skin condition is eye circles or puffy eyes. Also disclosed is a composition for use in said method, wherein the composition comprises magnolia extract and citrus grandis extract.

  本发明公开了一种治疗皮肤状况的化妆品方法，该方法包括在皮肤上局部施用包含玉兰提取物的组合物，其中局部施用该组合物可治疗皮肤状况，而皮肤状况是眼圈或眼袋。还公开了一种用于所述方法的组合物，其中所述组合物包含玉兰提取物和柑橘提取物。
• AGENT FOR PREVENTION OF DECOMPOSITION OF BIOPYRRIN
  申请人：Resvo Inc.

  公开号：EP3998325A1

  公开（公告）日：2022-05-18

  The inventors discovered that antioxidant substances having enediol structure can prevent the decomposition of biopyrrin. Therefore, the invention provides agents for preventing decomposition of biopyrrin, comprising an antioxidant substance having enediol structure, or a salt, an ester or a glycoside thereof, or a solvate, a stereoisomer or a tautomer thereof. In a biological sample to which the agent for preventing decomposition of the invention is added, the decomposition of biopyrrin can be prevented at ambient temperature or lower for a long term.

  发明者发现，具有烯二醇结构的抗氧化物质可以防止生物菊酯的分解。因此，本发明提供了防止生物炔诺酮分解的制剂，包括具有烯二醇结构的抗氧化物质，或其盐、酯或糖苷，或其溶解物、立体异构体或同系物。在添加了本发明防止分解剂的生物样品中，可在环境温度或更低温度下长期防止生物yrrin的分解。
• Skin lightening compositions
  申请人：Majmudar Gopa

  公开号：US20060216254A1

  公开（公告）日：2006-09-28

  The present invention concerns methods and compositions that can be used, for example, in skin whitening or hyperpigmentation applications. The composition, in non-limiting aspects, can include a vitamin C derivative, niacinamide, an extract formulation comprising cucumber and lemon extract or compounds that include the following formulas: where R 1 , R 2 , R 3 , R 4 , and R 5 are independently an H, an alkyl group, a hydroxyalkyl group, or a carboxyalkyl group where R 1 , R 2 , R 3 , R 4 , and R 5 are independently an H, an alkyl group, a hydroxyalkyl group, or a carboxyalkyl group and where x is an integer from 1 to 30.

  本发明涉及可用于皮肤美白或色素沉着等应用的方法和组合物。在非限制性方面，组合物可以包括维生素 C 衍生物、烟酰胺、由黄瓜和柠檬提取物组成的提取物配方或包括以下配方的化合物： 其中 R 1 , R 2 , R 3 , R 4 和 R 5 独立地为 H、烷基、羟基烷基或羧基烷基 其中 R 1 , R 2 , R 3 , R 4 和 R 5 独立地为 H、烷基、羟基烷基或羧基烷基，其中 x 为 1 至 30 的整数。