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MICINN [CTQ2009-13699, CTQ2010-14882]; Generalitat Valenciana [GV/2009/104]; Carlos III Institute of Health [RIRAAF]; COST [CM603]

Analysis of institutional authors

Andreu, IAuthorRico, EAuthor

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October 31, 2024
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Probing Lipid Peroxidation by Using Linoleic Acid and Benzophenone

Publicated to:Chemistry-A European Journal. 17 (36): 10089-10096 - 2011-08-01 17(36), DOI: 10.1002/chem.201100983

Authors: Andreu, Inmaculada; Neshchadin, Dmytro; Rico, Enrique; Griesser, Markus; Samadi, Abdelouahid; Morera, Isabel M; Gescheidt, Georg; Miranda, Miguel A

Affiliations

Graz Univ Technol, Inst Phys & Theoret Chem - Author
Univ Politecn Valencia, Dept Quim, Inst Tecnol Quim UPV, CSIC - Author

Abstract

A thorough mechanistic study has been performed on the reaction between benzophenone (BZP) and a series of 1,4-dienes, including 1,4-cyclohexadiene (CHD), 1,4-dihydro-2-methylbenzoic acid (MBA), 1,4-dihydro-1,2-dimethylbenzoic acid (DMBA) and linoleic acid (LA). A combination of steady-state photolysis, laser flash photolysis (LFP), and photochemically induced dynamic nuclear polarization (photo-CIDNP) have been used. Irradiation of BZP and CHD led to a cross-coupled sensitizer-diene product, together with 6, 7, and 8. With MBA and DMBA as hydrogen donors, photoproducts arising from cross-coupling of sensitizer and diene radicals were found; compound 7 was also obtained, but 6 and o-toluic acid were only isolated in the irradiation of BZP with MBA. Triplet lifetimes were determined in the absence and in the presence of several diene concentrations. All three model compounds showed similar reactivity (k(q) approximate to 10(8) M-1 s(-1)) towards triplet excited BZP. Partly reversible hydrogen abstraction of the allylic hydrogen atoms of CHD, MBA, and DMBA was also detected by photo-CIDNP on different timescales. Polarizations of the diamagnetic products were in full agreement with the results derived from LFP. Finally, LA also underwent partly reversible hydrogen abstraction during photoreaction with BZP. Subsequent hydrogen transfer between primary radicals led to conjugated derivatives of LA. The unpaired electron spin population in linoleyl radical (LA(center dot)) was predominantly found on H(1-5) protons. To date, LA-related radicals were only reported upon hydrogen transfer from highly substituted model compounds by steady-state EPR spectroscopy. Herein, we have experimentally established the formation of LA(center dot) and shown that it converts into two dominating conjugated isomers on the millisecond timescale. Such processes are at the basis of alterations of membrane structures caused by oxidative stress.

Keywords

1 ,4-cyclohexadienes1 ,4-dienesAbsorption spectroscopyAbstractingAllylic hydrogen atomAllylic hydrogensArticleBenzophenoneBenzophenone derivativeBenzophenonesChemical reactionsChemistryCidnpCross-coupledCross-couplingsDienesElectron spin resonance spectroscopyEpr spectroscopyFlexible structuresHydrogenHydrogen abstractionHydrogen donorHydrogen transferIrradiationIsomersLaser flash photolysisLightLinoleic acidLipid peroxidationMechanismsMechanistic studiesModel compoundOlefinsOrganic polymersOxidative stressPhoto-cidnpPhotochemically induced dynamic nuclear polarization (photo-cidnp)PhotochemistryPhotolysisPhotoproductsPhotoreactionsPolarizationPrimary radicalsSteady-state photolysisThree modelsTime-scalesTransient absorption spectroscopyUnpaired electronsUnsaturated fatty acids

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Chemistry-A European Journal due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2011, it was in position 20/154, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Multidisciplinary.

From a relative perspective, and based on the normalized impact indicator calculated from the Field Citation Ratio (FCR) of the Dimensions source, it yields a value of: 1.46, which indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: Dimensions Jul 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-07-04, the following number of citations:

  • WoS: 12
  • Scopus: 12

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-07-04:

  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 24 (PlumX).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: Austria.

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (Andreu Ros, María Inmaculada) and Last Author (Miranda, MA).