葡萄糖基丁香酸 | 33228-65-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 葡萄糖基丁香酸
• 中文别名: 丁香酸葡萄糖苷
• 英文名称: glucosyringic acid
• 英文别名: syringic acid β-D-glucopyranoside；3,5-dimethoxybenzoic acid 4-O-β-D-glucopyranoside；syringic acid-4-O-β-D-glucopyranoside；syringic acid glucoside；syringic acid 4-O-glucoside；3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• CAS: 33228-65-8
• 化学式: C₁₅H₂₀O₁₀
• 分子量: 360.318
• InChiKey: BLKMDORKRDACEI-OVKLUEDNSA-N

物化性质

• 熔点：
  212 °C (decomp)
• 沸点：
  611.1±55.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-Β-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 水 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 葡萄糖基丁香酸
  参考文献：
  名称：

  GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS

  摘要：

  本公开提供了包含具有如下式I的结构的化合物的新型甜味剂组合物： 其中R1、R2、R3和R4如本文所述。还提供了通过向产品添加式I的化合物来调节产品的甜味特性的方法，例如饮料产品或食品产品。例如，本文描述的化合物可添加以增加富含甜味剂的饮料的整体甜度；减少高效甜味剂（如甜菊糖A）的甜味起始时间；减少高效甜味剂的苦味、金属味和甘草味等异味；并改善甜味产品的甜味质量。

  公开号：

  US20180020708A1

文献信息

• New syntheses of plant aryl glycosides as potential gene inducers
  作者：Didier Delay、Francis Delmotte

  DOI：10.1016/0008-6215(90)84294-5

  日期：1990.5

  Abstract Aryl β- d -glycopyranosides have been synthesized by coupling acetovanillone (4-hydroxy-3-methoxyacetophenone) with d -glucose, d -galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with d -glucose and d -galactose; syringaldehyde (3-methoxyvanillin) with d -glucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with d -glucose. The Mauthner's procedure

  摘要通过将乙酰香草醛（4-羟基-3-甲氧基苯乙酮）与d-葡萄糖，d-半乳糖和麦芽糖偶联，合成了芳基β-d-吡喃葡萄糖苷。具有d-葡萄糖和d-半乳糖的乙酰丁香酮（4-羟基-3,5-二甲氧基苯乙酮）；带有D-葡萄糖的丁香醛（3-甲氧基香兰素）; 和具有d-葡萄糖的丁香酸（4-羟基-3,5-二甲氧基苯甲酸）。使用在丙酮水溶液中的过乙酰化的糖基溴化物和酚盐的Mauthner方法，得到了乙酰化的β-d-糖苷，将其脱乙酰化。
• Glucosyringic acid analogs as sweetness profile modifiers
  申请人：PepsiCo, Inc.

  公开号：US10966447B2

  公开（公告）日：2021-04-06

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R1, R2, R3, and R4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了新型甜味剂组合物，该组合物包含具有根据式 I 所述结构的化合物：其中 R1、R2、R3 和 R4 已在本文中描述。 还提供了通过向饮料产品或食品等产品中添加式 I 化合物来调节产品甜度曲线的方法。 例如，添加本文所述的化合物可增加营养型甜味剂甜饮料的总体甜度；减少高活性甜味剂（如雷公藤甙 A）的甜味起效时间；减少高活性甜味剂的苦味、金属味和甘草味；以及改善甜味产品的甜味质量。
• DELAY, DIDIER;DELMOTTE, FRANCIS, CARBOHYDR. RES., 198,(1990) N, C. 223-234
  作者：DELAY, DIDIER、DELMOTTE, FRANCIS

  DOI：——

  日期：——
• [EN] GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS<br/>[FR] ANALOGUES DE L'ACIDE GLUCOSYRINGIQUE EN TANT QUE MODIFICATEURS DU PROFIL ÉDULCORANT
  申请人：PEPSICO INC

  公开号：WO2018017574A1

  公开（公告）日：2018-01-25

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula (I): wherein R1, R2, R3, and R4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula (I) to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-ofonset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.
• GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS
  申请人：PepsiCo, Inc.

  公开号：US20180020708A1

  公开（公告）日：2018-01-25

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R 1 , R 2 , R 3 , and R 4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了包含具有如下式I的结构的化合物的新型甜味剂组合物： 其中R1、R2、R3和R4如本文所述。还提供了通过向产品添加式I的化合物来调节产品的甜味特性的方法，例如饮料产品或食品产品。例如，本文描述的化合物可添加以增加富含甜味剂的饮料的整体甜度；减少高效甜味剂（如甜菊糖A）的甜味起始时间；减少高效甜味剂的苦味、金属味和甘草味等异味；并改善甜味产品的甜味质量。