pyrrolidino-hexose-reductone | 91999-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyrrolidino-hexose-reductone
• 英文别名: Piperidinohexose reductone；2,5-Dihydroxy-5-methyl-3-(pyrrolidin-1-yl)cyclopent-2-en-1-one；2,5-dihydroxy-5-methyl-3-pyrrolidin-1-ylcyclopent-2-en-1-one
• CAS: 91999-35-8
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: LUDYBTNWCIXIMM-UHFFFAOYSA-N

物化性质

• 沸点：
  356.4±42.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyrrolidino-hexose-reductone 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.08h， 生成 3-hydroxy-4-<(E)-(2-furyl)methylidene>methyl-3-cyclopentene-1,2-dione
  参考文献：
  名称：

  AcetylformoinA Chemical Switch in the Formation of Colored Maillard Reaction Products from Hexoses and Primary and Secondary Amino Acids

  摘要：

  Thermal treatment of a methanolic solution of N-(1-deoxy-D-fructos-1-yl)-L-proline and furan-2-carboxaldehyde led to the rapid formation of colored compounds, among which 4-hydroxy-2-methoxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (1) could be identified as one of the main colored compounds by NMR, LC/MS, and UV-vis spectroscopy. Studies on its formation revealed that condensation of the hexose dehydration product acetylformoin (2a/2b) with furan-2-carboxaldehyde formed the labile 2,4-hydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (3a/3b), which then reacts with methanol to the more stable colorant 1. Reacting furan-2-carboxaldehyde with N-(1-deoxy-D-fructos-1-yl)-L-alanine, however, completely stalled the formation of acetylformoin and, consequently, also of colorant 1. Further model studies revealed acetylformoin as a chemical snitch in the Maillard reaction determining different reaction pathways in the presence of primary and secondary amino acids; for example, the reaction with glycine methyl ester and glycine revealed 2,4-dihydroxy-2,5-dimethyl-1-methoxycarbonylmethyl- (4) and 2,4-dihydroxy-2,5-dimethyl-1-carboxymethyl -3-oxo-2H-pyrrole (5), respectively, whereas the reaction with L-proline resulted in the formation of pyrrolidino- (6) and bispyrrolidino-hexose-reductone (7). Dry heating of these amino reductones in the presence of furan-2-carboxaldehyde produced the colorants 2,4-dihydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-1-methoxycarbonylmethyl-3-oxo-2H-pyrrole (8) from 4 and 3-hydroxy-4-[(E)-(2-furyl)methylidene] methyl-3-cyclopentene-1,2-dione (9) from 6 and 7. Quantitative studies revealed 3-hydroxy-4-methyl-3-cyclopentene-1,2-dione (10) and methylene-reductinic acid (11) as the key intermediates in the formation of colorant 9.

  DOI：

  10.1021/jf980512l
• 作为产物：
  描述：

  D-葡萄糖 、 L-脯氨酸 反应 0.25h， 生成 pyrrolidino-hexose-reductone 、 bispyrrolidino-hexose-reductone
  参考文献：
  名称：

  L-半胱氨酸对葡萄糖和L-脯氨酸形成苦味氨基己糖还原酮的影响：新型呋喃[2,3-b]噻嗪的鉴定。

  摘要：

  葡萄糖和L-脯氨酸的1 + 1混合物的热处理导致形成强烈的苦味，这在大量形成的苦味双吡咯烷醇（1）和吡咯烷己糖还原酮（2）中得到反映。在L-半胱氨酸存在下加热反应混合物大大减少了这些氨基己糖还原酮的量，从而降低了苦味的强度。对半胱氨酸引起的苦味减少的机理的研究表明，氨基己糖还原酮的前体，即己糖衍生的乙酰基福明（3），更容易与L-半胱氨酸反应形成7-羟基-4a，6-二甲基-2H，3H，4aH-呋喃[2,3-b]噻嗪（4），一种以前未知的美拉德反应产物，比用L-脯氨酸生成氨基己糖还原酮1和2，从而阻止了苦味化合物的形成。

  DOI：

  10.1021/jf9903152

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• Compounds useful as modulators of TRPM8
  申请人：Senomyx, Inc.

  公开号：US10392371B2

  公开（公告）日：2019-08-27

  Provided herein are compounds which are useful as cooling sensation compounds.

  本文提供的化合物可用作冷感化合物。
• Chemosensory receptor ligand-based therapies
  申请人：Anji Pharma (US) LLC

  公开号：US10610500B2

  公开（公告）日：2020-04-07

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administrating a composition comprising a chemosensory receptor ligand, such as a bitter receptor ligand. Also provided herein are chemosensory receptor ligand compositions, including bitter receptor ligand compositions, and methods for the preparation thereof for use in the methods of the present invention. Also provided herein are compositions comprising metformin and salts thereof and methods of use.

  本文提供了通过施用包含化感受体配体（如苦味受体配体）的组合物来治疗与化感受体相关的病症（包括糖尿病、肥胖症和其他代谢性疾病、失调或病症）的方法。本文还提供了化学感觉受体配体组合物，包括苦味受体配体组合物，及其用于本发明方法的制备方法。本文还提供了包含二甲双胍及其盐类的组合物和使用方法。
• High intensity sweeteners
  申请人：Firmenich Incorporated

  公开号：US11357246B2

  公开（公告）日：2022-06-14

  Disclosed herein are compounds having structural Formula (I), or salts thereof. These compounds are useful as sweet tasting agents and/or sweetness enhancers. Also disclosed are compositions comprising the present compounds and methods of increasing the sweet taste of ingestible compositions. Furthermore, methods for preparing the compounds are also disclosed.

  本文公开了具有结构式（I）的化合物或其盐类。这些化合物可用作甜味剂和/或甜味增强剂。还公开了包含本化合物的组合物以及增加可食用组合物甜味的方法。此外，还公开了制备这些化合物的方法。