2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,6-O-isopropylideneascorbic acid | 562043-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,6-O-isopropylideneascorbic acid
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-5-oxo-2H-furan-4-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 562043-85-0
• 化学式: C₂₃H₃₀O₁₅
• 分子量: 546.482
• InChiKey: SLOHTWOKKVOGDC-GZFLTJSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,6-O-isopropylideneascorbic acid 在 sodium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 β-D-glucopyranosyl-(1->2)-L-ascorbic acid
  参考文献：
  名称：

  2-O-β-d-吡喃葡萄糖基-l-抗坏血酸的简易和改进合成

  摘要：

  2- O -β- d -吡喃葡萄糖基- l -抗坏血酸 ( AA-2βG ) 是人体内α-葡萄糖苷酶活性持续释放抗坏血酸（维生素C）的来源，因此是化妆品的成分，食品，医药产品。该化合物的商业合成需求量很大，并且不时有人尝试，旨在改进和商业上可行的策略。我们从抗坏血酸开始分五步合成了AA-2βG ，总收率为 31.4%。合成步骤除一个外不需要柱纯化，最终产品纯度足以用于应用目的。

  DOI：

  10.1016/j.tetlet.2022.154314
• 作为产物：
  描述：

  维生素 C 在 盐酸 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 36.0h， 生成 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,6-O-isopropylideneascorbic acid
  参考文献：
  名称：

  2-O-β-d-吡喃葡萄糖基-l-抗坏血酸的简易和改进合成

  摘要：

  2- O -β- d -吡喃葡萄糖基- l -抗坏血酸 ( AA-2βG ) 是人体内α-葡萄糖苷酶活性持续释放抗坏血酸（维生素C）的来源，因此是化妆品的成分，食品，医药产品。该化合物的商业合成需求量很大，并且不时有人尝试，旨在改进和商业上可行的策略。我们从抗坏血酸开始分五步合成了AA-2βG ，总收率为 31.4%。合成步骤除一个外不需要柱纯化，最终产品纯度足以用于应用目的。

  DOI：

  10.1016/j.tetlet.2022.154314

文献信息

• 2-0-(-d-glucopyranosyl) ascorbic acid, process for its production, and foods and cosmetics containning compositions comprising it
  申请人：Maeda Mitsuru

  公开号：US20050113312A1

  公开（公告）日：2005-05-26

  The present invention provides a novel ascorbic acid derivative as a provitamin C with improved stability in the body and prolonged life in the body compared to conventionally known 2-O-(α-D-glucopyranosyl)ascorbic acid. The composition comprising the novel compound 2-β-(-D-glucopyranosyl)ascorbic acid has been extracted from plants such as from Ningxia Lycium barbarum L. and/or Lycium chinense Mill. The compositions comprising 2-O-(β-D-glucopyranosyl)ascorbic acid may be enzymatically synthesized using β-D-glucosyltransferase. Pure 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced from such compositions. Alternatively, 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced by chemical synthesis. The 2-O-(β-D-glucopyranosyl)ascorbic acid results in higher stability and a prolonged life of vitamin C when ingested in the body compared to the corresponding α-D-glucopyranosyl derivative, and is therefore highly suitable as a provitamin C to be used in cosmetics and foods.

  本发明提供了一种新型抗坏血酸衍生物作为一种前维生素C，与传统已知的2-O-(α-D-葡萄糖吡喃基)抗坏血酸相比，在体内具有更好的稳定性和更长的寿命。该新化合物2-β-(-D-葡萄糖吡喃基)抗坏血酸的组成物已从植物中提取，例如从宁夏枸杞和/或枸杞。含有2-O-(β-D-葡萄糖吡喃基)抗坏血酸的组成物可以使用β-D-葡萄糖基转移酶酶法合成。可以从这些组成物中制备纯的2-O-(β-D-葡萄糖吡喃基)抗坏血酸。另外，2-O-(β-D-葡萄糖吡喃基)抗坏血酸也可以通过化学合成制备。与相应的α-D-葡萄糖吡喃基衍生物相比，2-O-(β-D-葡萄糖吡喃基)抗坏血酸在体内摄入时具有更高的稳定性和更长的寿命，因此非常适合作为前维生素C用于化妆品和食品中。
• 2-O- (Beta-D-Glucopyranosyl) ascorbic acid, process for its production, and foods and cosmetics containing compositions comprising it
  申请人：Maeda Mitsuru

  公开号：US20080070983A1

  公开（公告）日：2008-03-20

  The present invention provides a novel ascorbic acid derivative as a provitamin C with improved stability in the body and prolonged life in the body compared to conventionally known 2-O-(α-D-glucopyranosyl)ascorbic acid. The composition comprising the novel compound 2-O-(β-D-glucopyranosyl)ascorbic acid has been extracted from plants such as from Ningxia Lycium barbarum L. and/or Lycium chinense Mill. The compositions comprising 2-O-(β-D-glucopyranosyl)ascorbic acid may be enzymatically synthesized using β-D-glucosyltransferase. Pure 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced from such compositions. Alternatively, 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced by chemical synthesis. The 2-O-(β-D-glucopyranosyl)ascorbic acid results in higher stability and a prolonged life of vitamin C when ingested in the body compared to the corresponding α-D-glucopyranosyl derivative, and is therefore highly suitable as a provitamin C to be used in cosmetics and foods.

  本发明提供了一种新型的抗坏血酸衍生物作为一种前维生素C，与传统已知的2-O-(α-D-葡萄糖吡喃基)抗坏血酸相比，在体内具有更好的稳定性和更长的寿命。包含新化合物2-O-(β-D-葡萄糖吡喃基)抗坏血酸的组合物已从植物中提取，例如从宁夏枸杞和/或枸杞子中提取。包含2-O-(β-D-葡萄糖吡喃基)抗坏血酸的组合物可以使用β-D-葡萄糖基转移酶进行酶促合成。可以从这些组合物中生产纯的2-O-(β-D-葡萄糖吡喃基)抗坏血酸。或者，2-O-(β-D-葡萄糖吡喃基)抗坏血酸可以通过化学合成来制备。与相应的α-D-葡萄糖吡喃基衍生物相比，2-O-(β-D-葡萄糖吡喃基)抗坏血酸在体内摄入时可以导致更高的稳定性和更长的维生素C寿命，因此非常适合用作化妆品和食品中的前维生素C。
• Composition for External Use
  申请人：Maeda Mitsuru

  公开号：US20070269454A1

  公开（公告）日：2007-11-22

  A composition for external use, comprising 2-O-(β-D-glucopyranosyl)ascorbic acid represented by the formula (I): or a salt or ester thereof which is safe to the human body, and a koji mold or a processed koji. The composition for external use is excellent in skin permeability, containing an ascorbic acid derivative which is excellent in stability, utilized persistently in the living body, and strong in antioxidant activity, and has little skin irritation.

  一种外用组合物，包括由式(I)表示的2-O-(β-D-葡萄糖吡喃糖基)抗坏血酸，或者其对人体安全的盐或酯，以及麴菌或经过处理的麴菌。该外用组合物具有出色的皮肤渗透性，含有抗坏血酸衍生物，其稳定性优异，在人体内持续利用，并具有强大的抗氧化活性，且对皮肤刺激较小。
• 2-O-(beta-D-glucopyranosyl) ascorbic acid, process for its production, and foods cosmetics containing compositions comprising it
  申请人：Maeda Mitsuru

  公开号：US20070065380A1

  公开（公告）日：2007-03-22

  The present invention provides a novel ascorbic acid derivative as a provitamin C with improved stability in the body and prolonged life in the body compared to conventionally known 2-O-(α-D-glucopyranosyl)ascorbic acid. The composition comprising the novel compound 2-O-(β-D-glucopyranosyl)ascorbic acid has been extracted from plants such as from Ningxia Lycium barbarum L. and/or Lycium chinense Mill. The compositions comprising 2-O-(β-D-glucopyranosyl)ascorbic acid may be enzymatically synthesized using β-D-glucosyltransferase. Pure 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced from such compositions. Alternatively, 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced by chemical synthesis. The 2-O-(β-D-glucopyranosyl)ascorbic acid results in higher stability and a prolonged life of vitamin C when ingested in the body compared to the corresponding α-D-glucopyranosyl derivative, and is therefore highly suitable as a provitamin C to be used in cosmetics and foods.

  本发明提供了一种新的抗坏血酸衍生物，作为一种前维生素C，与传统已知的2-O-(α-D-葡萄糖吡喃基)抗坏血酸相比，在体内具有改善稳定性和延长寿命的特点。包含新化合物2-O-(β-D-葡萄糖吡喃基)抗坏血酸的组合物已从植物中提取，例如从宁夏枸杞和/或枸杞中提取。含有2-O-(β-D-葡萄糖吡喃基)抗坏血酸的组合物可以使用β-D-葡萄糖基转移酶进行酶法合成。纯2-O-(β-D-葡萄糖吡喃基)抗坏血酸可以从这些组合物中制备。或者，2-O-(β-D-葡萄糖吡喃基)抗坏血酸可以通过化学合成得到。与相应的α-D-葡萄糖吡喃基衍生物相比，2-O-(β-D-葡萄糖吡喃基)抗坏血酸在体内摄入时具有更高的稳定性和延长寿命，因此非常适合作为用于化妆品和食品中的前维生素C。
• 2-O-(β-<scp>d</scp>-Glucopyranosyl)ascorbic Acid, a Novel Ascorbic Acid Analogue Isolated from <i>Lycium</i> Fruit
  作者：Yoshiko Toyoda-Ono、Mitsuru Maeda、Masahiro Nakao、Makiko Yoshimura、Namino Sugiura-Tomimori、Harukazu Fukami

  DOI：10.1021/jf035445w

  日期：2004.4.1

  A novel stable precursor of ascorbic acid (vitamin C), 2-O-(beta-D-glucopyranosyl)ascorbic acid, was isolated from both the ripe fresh fruit and dried fruit of Lycium barbarum L., a plant of the Solanaceae family. The chemical structure was inferred by instrumental analyses and confirmed by chemical synthesis. The dried fruit of Lycium barbarum L. contained ca. 0.5% of it, which is comparable to the ascorbic acid content of fresh lemons. It increased the blood ascorbic acid by oral administration to rats, and it was also detected in blood from the portal vein.