瑞鲍迪甙 b | 58543-17-2

• 物质功能分类: 分析化学 - 标准品 - 食品和饮料标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 瑞鲍迪甙 b
• 中文别名: 瑞鲍迪甙b；瑞鲍迪甙B
• 英文名称: rebaudioside B
• 英文别名: (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 58543-17-2
• 化学式: C₃₈H₆₀O₁₈
• 分子量: 804.884
• InChiKey: DRSKVOAJKLUMCL-MMUIXFKXSA-N

物化性质

• 熔点：
  >190°C (dec.)
• 沸点：
  1000.6±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）
• 碰撞截面：
  261.19 Ų [M+H]+ [CCS Type: TW]

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

安全信息

• WGK Germany：
  3
• 海关编码：
  2938900000

制备方法与用途

生物活性方面，Rebaudioside B（ Reb B）是从甜叶菊（Stevia rebaudiana）中分离出的一种次要甜菊醇糖苷（SGs），其口感质量通常优于许多主要的SG。

反应信息

• 作为反应物：
  描述：

  瑞鲍迪甙 b 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 [²H₄]-16,17-dihydrorebaudioside B
  参考文献：
  名称：

  Quantitation of Sweet Steviol Glycosides by Means of a HILIC-MS/MS-SIDA Approach

  摘要：

  Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts.

  DOI：

  10.1021/jf404018g
• 作为产物：
  描述：

  瑞鲍迪甙 A 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 瑞鲍迪甙 b
  参考文献：
  名称：

  甜叶菊叶中含甜菊糖苷的鼠李糖或木糖的鉴定、化学合成及甜度评价

  摘要：

  从甜叶菊叶中获得的甜菊糖苷越来越多地作为天然低热量甜味剂用于食品工业。其中，由葡萄糖残基组成的主要苷类（如甜菊苷和莱鲍迪苷A）的甜味已被广泛研究。然而，含有鼠李糖或木糖残基的次要天然产物的性质研究很少。在这项研究中，从我们正在发育的甜菊叶中提取了五种未报道的含有鼠李糖或木糖的甜菊糖苷，并评估了它们的甜度。鉴定了高度糖基化的甜菊糖苷，并使用质谱法通过碎片分析检查了它们的结构。这些糖苷的化学合成证实了它们的结构，并允许对少量甜菊醇糖苷进行感官评价。我们的研究表明，一种含木糖的糖苷莱鲍迪甙 FX1 具有均衡的甜味，因此，它是食品工业中使用的天然甜味剂的有前途的候选者。

  DOI：

  10.1021/acs.jafc.3c01753

文献信息

• Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogs with improved organoleptic properties
  作者：Grant E. DuBois、Rebecca A. Stephenson

  DOI：10.1021/jm00379a017

  日期：1985.1

  (11) of stevioside, shown chromatographically to be of increased hydrophilicity, was prepared and found to exhibit no bitter-taste character. Similarly an analogue (13) of rebaudioside A, having increased polarity, was prepared and found not to exhibit any bitter taste. The rebaudioside A analogue 13 was determined to have higher potency than 11 is suggested as a potential non-nutritive sweetener for food

  已经制备了甜菊糖苷（1）和莱鲍迪苷A（3）类似物的同类系列。已经发现，天然化合物1和3中内源的苦味成分可以通过增加分子亲水性来消除。通过制备的一系列化合物，苦味特性与总亲水性的色谱指标k'相关。制备了在色谱上显示亲水性增加的甜菊糖苷类似物（11），发现其没有苦味。类似地，制备具有增加的极性的莱鲍迪甙A的类似物（13），发现没有表现出任何苦味。建议将莱鲍迪甙A类似物13的功效强于11，作为食品应用中潜在的非营养性甜味剂。
• [EN] NATURAL AND SYNTHETIC DITERPENE GLYCOSIDES, COMPOSITIONS AND METHODS<br/>[FR] GLYCOSIDES DITERPÉNIQUES NATURELS ET SYNTHÉTIQUES, COMPOSITIONS ET PROCÉDÉS
  申请人：COCA COLA CO

  公开号：WO2019147617A1

  公开（公告）日：2019-08-01

  Novel diterpene glycosides isolated from Stevia extract as well as diterpene glycosides that are synthetically prepared are provided herein. Compositions and consumables comprising the novel diterpene glycosides are also provided herein. Methods of enhancing the sweetness and/or flavor of consumables using the novel diterpene glycosides, methods of preparing compositions and consumables comprising the novel diterpene glycosides, methods of purifying the novel diterpene glycosides and methods of synthesizing the diterpene glycosides are also provided.

  本文提供了从甜菊提取物中分离出的新型二萜苷和合成制备的二萜苷。本文还提供了包含这些新型二萜苷的组合物和消费品。还提供了使用这些新型二萜苷增强消费品的甜味和/或风味的方法，制备包含这些新型二萜苷的组合物和消费品的方法，纯化这些新型二萜苷的方法以及合成二萜苷的方法。
• Rebaudioside Analogs
  申请人：PepsiCo, Inc.

  公开号：US20180016291A1

  公开（公告）日：2018-01-18

  The present disclosure provides novel compounds that are steviol derivatives. The compounds generally can be characterized by a structure according to Formula I: wherein A 1 , L 1 , and G 1 are described herein. Also provided are sweetener compositions comprising the compound described herein either as a sweetener or a sweetener enhancer. Additionally, the compound or the sweetener composition can be included in a product such as a beverage product or a food product, which can reduce the amount of sweetener in the product required to achieve the same sweetness level in an otherwise identical product not including the compound or the sweetener composition.

  本公开提供了一些新颖的化合物，这些化合物是史蒂维醇衍生物。这些化合物通常可通过以下式I所示的结构来表征：其中A1、L1和G1如本文所述。还提供了包含所述化合物的甜味剂组合物，可以作为甜味剂或增甜剂。此外，该化合物或甜味剂组合物可以包含在产品中，例如饮料产品或食品产品中，可以减少产品中所需的甜味剂量，以达到在另一种不包含该化合物或甜味剂组合物的相同产品中所需的甜度水平。
• Method of converting RB to RD by using cutinase under stepwise changing temperatures
  申请人：Xia Yongmei

  公开号：US20180073049A1

  公开（公告）日：2018-03-15

  The present invention provides a method to produce RD by using a cutinase to catalyze the esterification of RB under stepwise cooling temperatures, which is related to the field of biosynthesis of organic compounds. The method uses a cutinase from Thermobifida fusca to catalyze the esterification of RB and sophorose to produce RD. The stepwise cooling temperatures are used to reduce the heat inactivation of the enzyme as well as to improve the mass transfer. The method catalyzes the esterification of RB to produce RD in a solvent such as methanol, DMSO and DMF. The reaction is safe, efficient and highly selective. In addition, the method uses stepwise additions of substrate RB and cooling temperatures for the esterification reaction. In this way, it speeds up the initial reaction rate, increases the amount of solved RB as it is converted to RD, and improves the mass transfer to further increase the reaction speed. In summary, the method uses moderate reaction conditions, and has a high yield and a simple purification procedure.

  本发明提供了一种利用切酶催化RB的酯化反应来生产RD的方法，该方法涉及有机化合物生物合成领域。该方法利用Thermobifida fuscato中的切酶来催化RB和辅酶葡萄糖苷的酯化反应以产生RD。逐步降温温度用于减少酶的热失活并改善质量传递。该方法利用溶剂如甲醇、二甲基亚砜和二甲基甲酰胺催化RB的酯化反应以产生RD。该反应安全、高效且高度选择性。此外，该方法利用逐步添加底物RB和降温温度进行酯化反应。这样可以加快初始反应速率，增加转化为RD的溶解RB量，并改善质量传递以进一步提高反应速度。总而言之，该方法使用适度的反应条件，产率高且具有简单的纯化程序。
• Novel Process for the Preparation of Rebaudioside D and Other Related Naturally Occurring Sweetners
  申请人：SU ZHOU JING HONG BIOTECH CO., LTD.

  公开号：US20140296499A1

  公开（公告）日：2014-10-02

  A novel process for preparation of Rebaudioside D (RD), and other related naturally occurring sweeteners is provided. RD is a natural sweetening agent which can decrease the bitter aftertaste of steviol glycosides. The said process is suitable for commercial manufacturing by using readily available natural products and nontoxic reagents.

  提供了一种制备雷巴甙D（RD）和其他相关天然甜味剂的新工艺。RD是一种天然甜味剂，可以减少史蒂维奥甙的苦涩余味。该工艺适用于商业生产，使用易获得的天然产品和无毒试剂。