2,5-二羟基-5-甲基-3-哌啶-1-基环戊-2-烯-1-酮 | 34421-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2,5-二羟基-5-甲基-3-哌啶-1-基环戊-2-烯-1-酮
• 中文别名: 2,5-二羟基-5-甲基-3-(1-哌啶基)-2-环戊烯酮
• 英文名称: piperidino-hexose-reductone
• 英文别名: 2-Cyclopenten-1-one, 2,5-dihydroxy-5-methyl-3-(1-piperidinyl)-；2,5-dihydroxy-5-methyl-3-piperidin-1-ylcyclopent-2-en-1-one
• CAS: 34421-11-9
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: HICPSQHUQBAFIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2,5-二羟基-5-甲基-3-哌啶-1-基环戊-2-烯-1-酮 在 盐酸 作用下， 生成 1,4',5'-Trihydroxy-3,1'-dimethyl-bicyclopentyl-3,4'-diene-2,5,3'-trione
  参考文献：
  名称：

  Condensed methyl reductic acid from hydrolysis of aminohexose-reductones

  摘要：

  DOI：

  10.1021/jo00954a019
• 作为产物：
  描述：

  N-(1-脱氧-D-果糖-1-基)哌啶 生成 2,5-二羟基-5-甲基-3-哌啶-1-基环戊-2-烯-1-酮
  参考文献：
  名称：

  The Amadori Rearrangement under New Conditions and its Significance for Non-enzymatic Browning Reactions²

  摘要：

  DOI：

  10.1021/ja01098a019

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。
• Synthesis of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one from maltol and its taste identification
  作者：Zhifei Chen、Gaolei Xi、Yufeng Fu、Qingfu Wang、Lili Cai、Zhiwei Zhao、Qiang Liu、Bing Bai、Yuping Ma

  DOI：10.1016/j.foodchem.2021.130052

  日期：2021.11

  3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) exists in many foods, and its effect on taste is controversial. The aim of this study was to clarify whether DDMP has bitter taste or not. For this purpose, DDMP was synthesized from maltol instead of from glucose for the first time. In contrast, DDMP derived from glucose was also prepared and further purified. Their structures were identified

  2,3-二氢-3,5-二羟基-6-甲基-4 H-吡喃-4-酮（DDMP）存在于许多食品中，其对味道的影响是有争议的。这项研究的目的是澄清DDMP是否具有苦味。为此目的，DDMP首次由麦芽酚而不是葡萄糖合成。相反，还制备了源自葡萄糖的DDMP，并进一步纯化。它们的结构通过NMR和MS鉴定，并且被认为是相同的物质。感官分析表明，源自麦芽酚的DDMP无味。进一步的研究表明，美拉德反应中的一些杂质使DDMP产生了葡萄糖味苦味。
• 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。
• Synthesis of a derivative of 1-deoxy-d-erythro-2,3-hexodiulose and its conversion into nonenzymic browning products
  作者：Benjamin E. Fisher、Henry B. Sinclair、James C. Goodwin

  DOI：10.1016/0008-6215(83)88110-5

  日期：1983.6

  hydrolysis of 5 produced 6 , which without isolation was treated with piperidine acetate to yield piperidino-hexose-reductone ( 7 ) and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one ( 8 ). A third component in the reaction mixture has been tentatively assigned from mass-spectroscopic data the structure 4-hydroxy-2-hydroxymethyl-5-methyl-3(2 H )-furanone ( 9 ).

  摘要一种新型的1-脱氧-4,5-O-异亚丙基-d-赤藓-2,3-己二糖（5）的合成方法，是一种难以捉摸的1-脱氧-赤藓-2,3-己二糖的稳定衍生物（在图6中，描述了从3，6-脱水-4，5-O-异亚丙基-d-甘露糖醇（1）开始。5的酸水解产生6，将其未经分离地用乙酸哌啶处理，得到哌啶子基-己糖-还原酮（7）和2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮（7） 8）。已从质谱数据中初步确定了反应混合物中的第三种成分为结构4-羟基-2-羟基甲基-5-甲基-3（2 H）-呋喃酮（9）。
• Structure of piperidino-hexose-reductone
  作者：F. Weygand、H. Simon、W. Bitterlich、J.E. Hodge、B.E. Fisher

  DOI：10.1016/0040-4020(59)85004-3

  日期：1959.1

  The structure of piperidino-hexose-reductone, first described by Hodge and co-workers, was clarified by degradation reactions. Dihydro-anhydro-piperidino-hexose-reductone, obtained from piperidino-hexose-reductone in a clear way, was synthesized by reacting 1-methyl-4-chloro-cyclopenten(1)-ol(2)-one(3) with piperidine.

  Hodge及其同事首先描述的哌啶子基己糖还原酮的结构通过降解反应得以阐明。二氢脱水哌啶子基己糖还原酮，以清楚的方式从哌啶子基己糖还原酮得到，通过反应1-甲基-4-氯合成环戊烯（1） -醇（2） -酮（3）与哌啶。