2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine
• 英文别名: 2-Methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine；2-methyl-5-[(2-methylfuran-3-yl)sulfanylmethyl]pyrimidin-4-amine
• 化学式: C₁₁H₁₃N₃OS
• 分子量: 235.31
• InChiKey: FFUFDVBXWWSORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸硫胺 以 phosphate buffer 为溶剂， 反应 2.0h， 以20 mg的产率得到2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine
  参考文献：
  名称：

  Characterization of 2-Methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from Thermal Degradation of Thiamin

  摘要：

  Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 degreesC for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques ((1)H NMR, (13)C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.

  DOI：

  10.1021/jf011591v

文献信息

• [EN] SAVOURY AND MOUTHFULNESS TASTE ENHANCERS<br/>[FR] EXHAUSTEURS DE SAVEUR ET DE CONSISTANCE DE GOÛT
  申请人：LUCTA S A

  公开号：WO2020074561A1

  公开（公告）日：2020-04-16

  The present invention relates to a compound of formula (I1); to a mixture comprising an amount from 86% to 99% by weight measured by quantitative proton-NMR of a compound of formula (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH) and (IJ); and an edible composition and an edible article comprising them. The invention also relates to processes for their preparation and their use as a savoury and mouthfulness taste enhancer; particularly kokumi and/or umami taste enhancer. Formulae (I') (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH), (IJ).

  本发明涉及一种化合物，其化学式为（I1）；一种混合物，包括按量的质子核磁共振法测得的化合物（IA）、（IB）、（IC）、（ID）、（IE）、（IF）、（IG）、（IH）和（IJ）的86%至99%的量；以及包含它们的食用组合物和食用品。该发明还涉及它们的制备过程及其用作风味和口感增强剂的用途；特别是可口味和/或鲜味增强剂。化学式（I'）（IA）、（IB）、（IC）、（ID）、（IE）、（IF）、（IG）、（IH）、（IJ）。
• Novel Taste-Enhancing 4-Amino-2-methyl-5-heteroalkypyrimidines Formed from Thiamine by Maillard-Type Reactions
  作者：Laura Brehm、Oliver Frank、Manon Jünger、Miriam Wimmer、Josef Ranner、Thomas Hofmann

  DOI：10.1021/acs.jafc.9b05896

  日期：2019.12.18

  demonstrated thiamine as the only precursor and an intermolecular formation pathway for the compounds (S)-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. On the basis of the knowledge that several thiamine derivatives showed taste-modulating activity, selected thiamine-based binary model reactions and synthesis

  增加相应加工香料中的硫胺素浓度可得到具有显着较高的浓厚活性的产品。硫胺素本身，4-甲基-5-噻唑乙醇，（S）-（（（4-氨基-2-甲基嘧啶-5-基）甲基）-1-半胱氨酸，N-（ （4-氨基-2-甲基嘧啶-5-基）甲基）甲酰胺，3-（（（4-氨基-2-甲基嘧啶-5-基）甲基）硫基）-5-羟基戊烷-2-和2-甲基-5-（（（（2-2-甲基呋喃-3-基）硫基）甲基）嘧啶-4-胺作为标记分子的硫胺素浓度较高的加工香料。基于感官的目标隔离显示（S）-（（（4-氨基-2-甲基嘧啶-5-基）甲基）-1-半胱氨酸，3-（（（（4-氨基-2-甲基嘧啶-5-基）甲基）thio）-5-羟基戊烷-2-一 和2-甲基-5-（（（（2-甲基呋喃-3-基）硫基）甲基）嘧啶-4-胺显示出对苦味味活性的影响，其味觉阈浓度在35至120μmol/ L之间。改编的基于质谱的碳模块标记实验以及定量研究清楚地证明了硫胺素是化合物（
• SAVOURY AND MOUTHFULNESS TASTE ENHANCERS
  申请人：Lucta, S.A.

  公开号：EP3864012A1

  公开（公告）日：2021-08-18
• Characterization of 2-Methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from Thermal Degradation of Thiamin
  作者：Jin-Woo Jhoo、Ming-Chi Lin、Shengmin Sang、Xiaofang Cheng、Nanqun Zhu、Ruth E. Stark、Chi-Tang Ho

  DOI：10.1021/jf011591v

  日期：2002.7.1

  Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 degreesC for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques ((1)H NMR, (13)C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.