β-D-glucopyranosyl-(1->2)-L-ascorbic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: β-D-glucopyranosyl-(1->2)-L-ascorbic acid
• 英文别名: 2-O-β-D-glucopyranosyl L-ascorbic acid；2-O-β-D-glucopyranosyl-L-ascorbic acid；2-O-(β-D-glucopyranosyl)ascorbic acid；2-O-glucosyl-L-ascorbic acid；L-ascorbic acid 2-O-β-glucoside；L-ascorbyl 2-glucoside；2-o-beta-d-Glucopyranosyl-l-ascorbic acid；(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-furan-5-one
• 化学式: C₁₂H₁₈O₁₁
• 分子量: 338.268
• InChiKey: MLSJBGYKDYSOAE-DNYNHWTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 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

• 作为反应物：
  描述：

  乙酸酐 、 β-D-glucopyranosyl-(1->2)-L-ascorbic acid 在 高氯酸 作用下， 反应 1.0h， 以71%的产率得到hepta-O-acetyl-2-O-β-D-glucopyranosyl L-ascorbic acid
  参考文献：
  名称：

  Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris)

  摘要：

  Non-targeted LC-MS metabolomics on fruit of three wild and domesticated apple species (Malus sylvestris, M. sieversii and M. domestica) showed that two crab apple (M. sylvestris) accessions were distinguished by high concentrations of an ascorbic acid glycoside (AAG). This was partly purified, but key NMR signals were masked by inseparable sucrose. Reference samples of 2-O-beta-D-glucopyranosyl L-ascorbic acid and 2-O-beta-D-galactopyranosyl L-ascorbic acid were synthesised, but both coincided with the crab apple AAG on LC-MS. Peracetylation of the crab apple extract allowed both purification and characterisation, and the AAG was proven to be 2-O-beta-D-glucopyranosyl L-ascorbic acid by comparison of 1H NMR, HRMS and HPLC data with synthesised peracetylated scorbyl glycoside standards. The stability of the natural AA 2-beta-glycoside was similar to synthetic 2-O-alpha-D-glucopyranosyl L-ascorbic acid, used widely in cosmetic and pharmaceutical products. This discovery in crab apples (Rosaceae) is only the fourth reported occurrence of any ascorbyl glycoside from plants, the others being from Cucurbitaceae, Solanaceae and Brassicaceae. It is hypothesised that AAGs may be more widespread in plants than currently realised.

  DOI：

  10.1016/j.phytochem.2020.112297
• 作为产物：
  描述：

  维生素 C 在 盐酸 、 4-二甲氨基吡啶 、 sodium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 56.5h， 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
• 作为试剂：
  描述：

  、 维生素 C 、 Cellobiose 、 6-o-(beta-d-Glucopyranosyl)ascorbic acid 、 β-D-glucopyranosyl-(1->2)-L-ascorbic acid 在 水 、 溶剂黄146 、 β-D-glucopyranosyl-(1->2)-L-ascorbic acid 作用下， 以 乙酸盐 为溶剂， 反应 48.0h， 生成 beta-d-Glucopyranosylascorbic acid
  参考文献：
  名称：

  2-O-(β-D-glucopyranosyl) ascorbic acid, process for its production, and foods and cosmetics containing compositions comprising it

  摘要：

  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，在人体中具有更好的稳定性和延长寿命。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生产。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)抗坏血酸在人体内摄入时会导致维生素C的更高稳定性和延长寿命，因此非常适合用作化妆品和食品中的前维生素C。

  公开号：

  US07566698B2

文献信息

• COMPOUNDS FOR PREVENTING, REDUCING AND/OR ALLEVIATING ITCHY SKIN CONDITION(S)
  申请人：SCHMAUS Gerhard

  公开号：US20160008297A1

  公开（公告）日：2016-01-14

  The present invention primarily relates to the use of one or more specific compounds and/or one or more respective salt(s) thereof for preventing, reducing or alleviating itchy skin condition(s), and/or as PAR-2 antagonist. Furthermore, the present invention relates to compositions (products or, respectively, formulations), in particular for topical administration, preferably cosmetic or pharmaceutical compositions, in particular for preventing, reducing or alleviating one or more itchy skin conditions and/or for providing a PAR-2 antagonistic effect, comprising or consisting of an effect amount of such compound(s) and/or salt(s) and one or more cosmetically and/or pharmaceutically acceptable carriers.

  本发明主要涉及使用一种或多种特定化合物和/或其一个或多个相应盐来预防、减少或缓解瘙痒皮肤状况，和/或作为PAR-2拮抗剂。此外，本发明涉及组合物（产品或相应的配方），特别是用于局部给药，优选为化妆品或药用组合物，特别是用于预防、减少或缓解一种或多种瘙痒皮肤状况和/或产生PAR-2拮抗作用的组合物，包括或由效果量的这种化合物和/或盐以及一个或多个化妆品和/或药用可接受载体组成。
• 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and its use in cosmetic and pharmaceutical preparations
  申请人：Schmaus Gerhard

  公开号：US20090208434A1

  公开（公告）日：2009-08-20

  The present invention concerns applications of the compound of formula 1 in cosmetic or pharmaceutical preparations.

  本发明涉及化合物1的在化妆品或药物制剂中的应用。
• FORMULATION WITH IRRITATION REDUCING ACTION COMPRISING BISABOLOL AND [6]-PARADOL
  申请人：Herrmann Martina

  公开号：US20120258058A1

  公开（公告）日：2012-10-11

  The present invention relates to formulations having an irritation-reducing action, corresponding cosmetic and pharmaceutical products as well as associated methods and uses thereof.

  本发明涉及具有减少刺激作用的配方，相应的化妆品和药用产品，以及相关的方法和用途。
• The Vitamin C Analogue 2-O-?-D-Glucopyranosyl-L-ascorbic Acid in Rhizomes, Stems and Leaves of Lycium barbarum
  作者：Carole Bubloz、Isabelle Udrisard、Fabrice Micaux、Umberto Piantini、Lara Amini-Rentsch、Roger Marti、Wilfried Andlauer

  DOI：10.2533/chimia.2020.828

  日期：——

  The aim of this study was to evaluate the contents of 2-O-?-D-glucopyranosyl-L-ascorbic acid in rhizomes, stems and leaves from Lycium barbarum. Rhizomes, stems and leaveswere extracted and the content of 2-O-?-D-glucopyranosyl-L-ascorbic acid and non glucosylated, free ascorbic acid was determined by HPLC-DAD. 2-O-?-D-glucopyranosyl-L-ascorbic acid was found in all goji plant tissues investigated. Based

  人们越来越意识到枸杞子的生物活性化合物（主要是抗坏血酸等抗氧化剂）对健康的益处。最近，报道了一种来自枸杞的抗坏血酸类似物，2-O-α-D-吡喃葡萄糖基-L-抗坏血酸。在大鼠中，该类似物以游离维生素 C 的形式被完整吸收，因此被提议作为维生素 C 原。该类似物的合成要求较高且费力，因此需要寻找可靠的天然来源。关于枸杞植物其他部分中类似物存在的知识尚缺乏。本研究的目的是评价枸杞根茎、茎和叶中2-O-β-D-吡喃葡萄糖基-L-抗坏血酸的含量。提取根茎、茎和叶，用HPLC-DAD测定2-O-β-D-吡喃葡萄糖基-L-抗坏血酸和非糖基化游离抗坏血酸的含量。在所有研究的枸杞植物组织中都发现了2-O-β-D-吡喃葡萄糖基-L-抗坏血酸。以干重计，叶中含有 3.34 毫克/100 克，茎中含有 4.05 毫克/100 克，根茎中高达 12.6 毫克/100 克。然而，枸杞中的类似物含量要高得多（40 至 280
• 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。