Diketo–ketoenol tautomers in curcuminoids: synthesis, separation of tautomers, and kinetic and structural studies
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00559677" target="_blank" >RIV/61388963:_____/22:00559677 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/22:10445412
Result on the web
<a href="https://doi.org/10.1021/acs.joc.2c01357" target="_blank" >https://doi.org/10.1021/acs.joc.2c01357</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c01357" target="_blank" >10.1021/acs.joc.2c01357</a>
Alternative languages
Result language
angličtina
Original language name
Diketo–ketoenol tautomers in curcuminoids: synthesis, separation of tautomers, and kinetic and structural studies
Original language description
Curcumin and its congeners exist in an equilibrium between diketo and ketoenol tautomers, which have different potencies to bind biomolecules. This work describes procedures for the preparation of 4-alkylated curcumin derivatives and the separation of their two tautomeric forms. Comprehensive NMR studies of the tautomer equilibria in various solvents have been accomplished. Additionally, a pure ketoenol tautomeric form of the active pharmaceutical ingredient (API) ASC-JM17 has been unequivocally determined by X-ray crystallography. Two different polymorphs of this API have been microscopically identified in the X-ray sample and manually separated, and a solid-state NMR study of the two polymorphs has also been performed. This work reports on the slow kinetics of diketo-ketoenol tautomerization in particular solvents that allow the separation and full characterization of both curcuminoids' tautomers.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
87
Issue of the periodical within the volume
15
Country of publishing house
US - UNITED STATES
Number of pages
10
Pages from-to
10309-10318
UT code for WoS article
000837975900001
EID of the result in the Scopus database
2-s2.0-85136141481