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A systematic study on the interactions between carnosic acid and ethylpyrrolidine methacrylate-methyl methacrylate copolymer in supercritical media

Rodríguez-Meizoso, Irene LU ; Cifuentes, Alejandro; Román, Julio San; Ibáñez, Elena and Elvira, Carlos (2007) In Journal of Supercritical Fluids 41(3). p.452-460
Abstract

In the present work, a systematic study on the interactions between carnosic acid (potent natural antioxidant from rosemary) and ethylpyrrolidine methacrylate-methyl methacrylate (EPyM/MMA) copolymer (synthesized in our laboratory) has been performed using different spectroscopic and thermogravimetric techniques. By comparing data obtained for the reference sample (carnosic acid + copolymer) with data of carnosic acid and copolymer alone, a polar interaction could be observed between the carboxylic acid group of carnosic acid with the tertiary amine of the EPyM/MMA copolymer, thus suggesting a charge-transfer complex of the carnosic acid molecules with the pyrrolidine nitrogen (conclusion supported by NMR, FT-IR and TGA data). In order... (More)

In the present work, a systematic study on the interactions between carnosic acid (potent natural antioxidant from rosemary) and ethylpyrrolidine methacrylate-methyl methacrylate (EPyM/MMA) copolymer (synthesized in our laboratory) has been performed using different spectroscopic and thermogravimetric techniques. By comparing data obtained for the reference sample (carnosic acid + copolymer) with data of carnosic acid and copolymer alone, a polar interaction could be observed between the carboxylic acid group of carnosic acid with the tertiary amine of the EPyM/MMA copolymer, thus suggesting a charge-transfer complex of the carnosic acid molecules with the pyrrolidine nitrogen (conclusion supported by NMR, FT-IR and TGA data). In order to evaluate the possibility of using, in the near future, the copolymer as a selective stationary phase for preparative-SFC (supercritical fluid chromatography), the work has been completed by studying the remaining interactions, in the reference sample, once treated under several supercritical conditions. After the supercritical treatment (using CO2 at different pressures and temperatures), depressurization takes place in the extraction cell and the samples remaining were characterized by 1H NMR, TGA and FT-IR. From the results obtained, it can be inferred that interactions remain after supercritical treatment, thus allowing the design of selective polymers to be used in the purification of carnosic acid.

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Please use this url to cite or link to this publication:
author
publishing date
type
Contribution to journal
publication status
published
keywords
Antioxidant, Carnosic acid, EPyM/MMA, Purification, Supercritical
in
Journal of Supercritical Fluids
volume
41
issue
3
pages
9 pages
publisher
Elsevier
external identifiers
  • scopus:34247464143
ISSN
0896-8446
DOI
10.1016/j.supflu.2006.12.018
language
English
LU publication?
no
id
6a2afd76-dd37-47be-a7f0-a58b6bdfc4fc
date added to LUP
2017-04-10 10:39:49
date last changed
2017-04-20 12:59:07
@article{6a2afd76-dd37-47be-a7f0-a58b6bdfc4fc,
  abstract     = {<p>In the present work, a systematic study on the interactions between carnosic acid (potent natural antioxidant from rosemary) and ethylpyrrolidine methacrylate-methyl methacrylate (EPyM/MMA) copolymer (synthesized in our laboratory) has been performed using different spectroscopic and thermogravimetric techniques. By comparing data obtained for the reference sample (carnosic acid + copolymer) with data of carnosic acid and copolymer alone, a polar interaction could be observed between the carboxylic acid group of carnosic acid with the tertiary amine of the EPyM/MMA copolymer, thus suggesting a charge-transfer complex of the carnosic acid molecules with the pyrrolidine nitrogen (conclusion supported by NMR, FT-IR and TGA data). In order to evaluate the possibility of using, in the near future, the copolymer as a selective stationary phase for preparative-SFC (supercritical fluid chromatography), the work has been completed by studying the remaining interactions, in the reference sample, once treated under several supercritical conditions. After the supercritical treatment (using CO<sub>2</sub> at different pressures and temperatures), depressurization takes place in the extraction cell and the samples remaining were characterized by <sup>1</sup>H NMR, TGA and FT-IR. From the results obtained, it can be inferred that interactions remain after supercritical treatment, thus allowing the design of selective polymers to be used in the purification of carnosic acid.</p>},
  author       = {Rodríguez-Meizoso, Irene and Cifuentes, Alejandro and Román, Julio San and Ibáñez, Elena and Elvira, Carlos},
  issn         = {0896-8446},
  keyword      = {Antioxidant,Carnosic acid,EPyM/MMA,Purification,Supercritical},
  language     = {eng},
  number       = {3},
  pages        = {452--460},
  publisher    = {Elsevier},
  series       = {Journal of Supercritical Fluids},
  title        = {A systematic study on the interactions between carnosic acid and ethylpyrrolidine methacrylate-methyl methacrylate copolymer in supercritical media},
  url          = {http://dx.doi.org/10.1016/j.supflu.2006.12.018},
  volume       = {41},
  year         = {2007},
}