28787-36-2Relevant articles and documents
Synthesis of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one from maltol and its taste identification
Chen, Zhifei,Xi, Gaolei,Fu, Yufeng,Wang, Qingfu,Cai, Lili,Zhao, Zhiwei,Liu, Qiang,Bai, Bing,Ma, Yuping
, (2021/05/27)
2,3-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 by NMR and MS, and considered to be the same substance. The sensory analysis showed that DDMP derived from maltol was tasteless. Further studies indicated that some impurities in Maillard reaction made DDMP derived from glucose taste bitter.
Preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
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Paragraph 0031-0033, (2019/10/01)
The invention relates to a novel synthesis route of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. 3-hydroxy-2-methyl-4H-pyran-4-one used as a raw material undergoes acetyl protection, a brominationreaction, benzyl protection and oxidation reaction to synthesize a dolutegravir intermediate in four steps at a high yield. The above preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid has the advantages of high yield, low cost, environmental protection, easiness operation, and suitableness for realizing industrialization.
Evaluating prodrug strategies for esterase-triggered release of alcohols
Perez, Christian,Daniel, Kevin B.,Cohen, Seth M.
supporting information, p. 1662 - 1667 (2013/10/21)
Prodrugs are effective tools in overcoming drawbacks typically associated with drug formulation and delivery. Those employing esterase-triggered functional groups are frequently utilized to mask polar carboxylic acids and phenols, increasing drug-like properties such as lipophilicity. Herein we detail a comprehensive assessment for strategies that effectively release hydroxy and phenolic moieties in the presence of an esterase. Matrix metalloproteinases (MMPs) serve as our proof-of-concept target. Three distinct ester-responsive protecting groups are incorporated into MMP proinhibitors containing hydroxy moieties. Analytical evaluation of the proinhibitors demonstrates that the use of a benzyl ether group appended to the esterase trigger leads to considerably faster kinetics of conversion and enhanced aqueous stability when compared with more conventional approaches where the trigger is directly attached to the inhibitor. Biological assays confirm that all protecting groups effectively cleave in the presence of esterase to generate the active inhibitor. The superior reaction-based prodrug strategies presented here should serve as a platform for esterase-responsive prodrug design in the future.