Acid-Promoted Reactions of Ethyl Linoleate with Nitrite Ions: Formation and Structural Characterization of Isomeric Nitroalkene, Nitrohydroxy, and Novel 3-Nitro-1,5-hexadiene and 1,5-Dinitro-1,3-pentadiene Products
Abstract
The reaction of ethyl linoleate (1) with NO(2)(-) in different air-equilibrated acidic media resulted in the formation of complex patterns of products, some of which could be isolated by repeated TLC fractionation and were formulated as the nitroalkenes 2-5, the novel (1E, 5Z)-3-nitro-1,5-hexadienes 6/7, the novel (E,E)-1, 5-dinitro-1,3-pentadiene derivatives 8 and 9, and the nitro alcohols 10/11 and 12/13 by extensive GC-MS and 2D NMR analysis, as aided by 1D Hartmann-Hahn proton mapping experiments. Similar reaction of methyl oleate gave mainly nitroalkene (14/15) and allylic nitro derivatives (16/17). Formation of 2-13 may be envisaged in terms of HNO(2)-mediated nitration pathways in which regioisomeric beta-nitroalkyl radical intermediates derived from attack of NO(2) to the 1,4-pentadiene moiety of 1 evolve through competitive H-atom abstraction and free radical combination routes.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Nitrito functional groups undergo rapid hydrolysis to yield the corresponding alcohol, with further elimination of water, resulting in a vinyl nitro product.
“Nitrito functional groups would undergo rapid hydrolysis to yield the corresponding alcohol, with further elimination of water, resulting in a vinyl nitro product (43).”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [43]
Cites
Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids
Green, L. C., Wagner, D. A., Glogowski, J. A., Skipper, P. L., Wishnok, J. S., & Tannenbaum, S. R. (1982) · Analytical Biochemistry · doi:10.1016/0003-2697(82)90118-x · Cited by 12,089 · see citing works
Rapid colorimetric assay for cell growth and survival
Denizot, F., & Lang, R. (1986) · Journal of Immunological Methods · doi:10.1016/0022-1759(86)90368-6 · Cited by 4,907 · see citing works
Rubbo, H., Radí, R., Trujillo, M., Telleri, R., Kalyanaraman, B., Barnes, S., KIRK, M. C., & Freeman, B. Α. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)47160-8 · Cited by 1,350 · see citing works
Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite
van der Vliet, A., Eiserich, J. P., Halliwell, B., & Cross, C. E. (1997) · Journal of Biological Chemistry · doi:10.1074/jbc.272.12.7617 · Cited by 780 · see citing works
The physiological role of nitric oxide
Butler, A. R., & Williams, D. L. H. (1993) · Chemical Society Reviews · doi:10.1039/cs9932200233 · Cited by 555 · see citing works
A Solution-Phase Chemical Approach to a New Crystal Structure of Cobalt
Dinega, D. P., & Bawendi, M. G. (1999) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19990614)38:12 · Cited by 526 · see citing works
Pryor, W. A., & Lightsey, J. W. (1981) · Science · doi:10.1126/science.214.4519.435 · Cited by 255 · see citing works
The suppression of the N-nitrosating reaction by chlorogenic acid
Kono, Y., Shibata, H., Kodama, Y., & Sawa, Y. (1995) · Biochemical Journal · doi:10.1042/bj3120947 · Cited by 149 · see citing works
Chromatographic behaviour of isomeric long-chain aliphatic compounds
Morris, L. J., Wharry, D. M., & Hammond, E. W. (1967) · Journal of Chromatography A · doi:10.1016/s0021-9673(01)86026-x · Cited by 112 · see citing works
Hata, E., Yamada, T., & Mukaiyama, T. (1995) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.68.3629 · Cited by 79 · see citing works
Rates and mechanisms of reactions of nitrogen dioxide with alkenes in solution
Giamalva, D. H., Kenion, G. B., Church, D. F., & Pryor, W. A. (1987) · Journal of the American Chemical Society · doi:10.1021/ja00257a025 · Cited by 71 · see citing works
Mechanism of Single-Layer Graphite Oxidation: Evaluation by Electron Microscopy
Yang, R. T., & Wong, C. J. (1981) · Science · doi:10.1126/science.214.4519.437 · Cited by 67 · see citing works
Gallon, A. A., & Pryor, W. A. (1994) · Lipids · doi:10.1007/bf02536725 · Cited by 61 · see citing works
Hanessian, S., Dubé, D., & Hodges, P. J. (1987) · Journal of the American Chemical Society · doi:10.1021/ja00257a026 · Cited by 51 · see citing works
Gallon, A. A., & Pryor, W. A. (1993) · Lipids · doi:10.1007/bf02535776 · Cited by 45 · see citing works
Yoshida, Y., Hirose, M., Takaba, K., Kimura, J., & Pito, N. (1994) · International Journal of Cancer · doi:10.1002/ijc.2910560122 · Cited by 43 · see citing works
d’Ischia, M., Rega, N., & Barone, V. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00491-3 · Cited by 23 · see citing works
Self-citationKelly, D. R., Jones, S., Adigun, J. O., Koh, K. S.-V., Hibbs, D. E., Hursthouse, M. B., & Jackson, S. K. (1997) · Tetrahedron · doi:10.1016/s0040-4020(97)10202-2 · Cited by 22 · see citing works
Effects of methyl linoleate hydroperoxide and hydrogen peroxide on N-nitrosation of dimethylamine
Kikugawa, K., Kato, T., Konoe, Y., et al. (1985) · Food and Chemical Toxicology · doi:10.1016/0278-6915(85)90002-x · Cited by 4 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Fatty Acid Transduction of Nitric Oxide Signaling
Baker, P. R. S., Lin, Y., Schopfer, F. J., Woodcock, S. R., Groeger, A. L., Batthyany, C., Sweeney, S., Long, M. H., Iles, K. E., Baker, L. M. S., et al. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m504212200 · Cited by 358 · see citing works
Formation and signaling actions of electrophilic lipids
Schopfer, F. J., Cipollina, C., & Freeman, B. A. (2011) · Chemical Reviews · doi:10.1021/cr200131e · Cited by 299 · see citing works
Reversible Post-translational Modification of Proteins by Nitrated Fatty Acids in Vivo
Batthyany, C., Schopfer, F. J., Baker, P. R. S., Durán, R., Baker, L. M. S., Huang, Y., Cerveñansky, C., Branchaud, B. P., & Freeman, B. A. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m602814200 · Cited by 285 · see citing works
Nitro-fatty acid formation and signaling
Freeman, B. A., Baker, P. R. S., Schopfer, F. J., Woodcock, S. R., Napolitano, A., & d'Ischia, M. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r800004200 · Cited by 265 · see citing works
Self-citationInteractions Between Nitric Oxide and Lipid Oxidation Pathways: Implications for Vascular Disease
O’Donnell, V. B., & Freeman, B. A. (2001) · Circulation Research · doi:10.1161/01.res.88.1.12 · Cited by 257 · see citing works
Nitro-fatty Acid Reaction with Glutathione and Cysteine
Baker, L. M. S., Baker, P. R. S., Golin-Bisello, F., Schopfer, F. J., Fink, M., Woodcock, S. R., Branchaud, B. P., Radi, R., & Freeman, B. A. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m704085200 · Cited by 200 · see citing works
Baker, P. R. S., Schopfer, F. J., Sweeney, S., & Freeman, B. A. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0402587101 · Cited by 201 · see citing works
Conjugated linoleic acid is a preferential substrate for fatty acid nitration
Bonacci, G., Baker, P. R. S., Salvatore, S. R., Shores, D., Khoo, N. K. H., Koenitzer, J. R., Vitturi, D. A., Woodcock, S. R., Golin-Bisello, F., Cole, M. P., et al. (2012) · Journal of Biological Chemistry · doi:10.1074/jbc.m112.401356 · Cited by 147 · see citing works
Lim, D. G., Sweeney, S., Bloodsworth, A., White, C. R., Chumley, P. H., Krishna, N. R., Schopfer, F., O'Donnell, V. B., Eiserich, J. P., & Freeman, B. A. (2002) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.232409599 · Cited by 110 · see citing works
Peroxynitrite-mediated lipid oxidation and nitration: mechanisms and consequences
Rubbo, H., Trostchansky, A., & O’Donnell, V. B. (2009) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2008.11.007 · Cited by 105 · see citing works
Characterization of linoleic acid nitration in human blood plasma by mass spectrometry
Lima, É. S., Di Mascio, P., Rubbo, H., & Abdalla, D. S. P. (2002) · Biochemistry · doi:10.1021/bi025504j · Cited by 103 · see citing works
Nitro-oleic Acid, a Novel and Irreversible Inhibitor of Xanthine Oxidoreductase
Kelley, E. E., Batthyany, C. I., Hundley, N. J., Woodcock, S. R., Bonacci, G., Del Rio, J. M., Schopfer, F. J., Lancaster, J. R., Freeman, B. A., & Tarpey, M. M. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m802402200 · Cited by 81 · see citing works
Napolitano, A., Crescenzi, O., Camera, E., Giudicianni, I., Picardo, M., & d'Ischia, M. (2002) · Tetrahedron · doi:10.1016/s0040-4020(02)00460-x · Cited by 23 · see citing works
Self-citation
- Authors
- Napolitano, A., Camera, E., Picardo, M., & d'Ischia, M.
- Affiliations
- San Gallicano Hospital (IT)
- Department of Organic and Biological Chemistry, University of Naples Federico II, Via Mezzocanone 16, I-80134 Naples, Italy, and Istituto Dermatologico S. Gallicano, Via S. Gallicano 25a, 00153 Rome, Italy
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-07-15
- Volume
- 65
- Issue
- 16
- Pages
- 4853-4860
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1985824649
- Cited by
- 56
- References
- 19
- Citations by year
- 2024: 2 · 2021: 2 · 2019: 2 · 2018: 1 · 2017: 1 · 2016: 1 · 2015: 1 · 2013: 5 · 2012: 1
- FWCI
- 2.32
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Scuola Normale Superiore di Pisa (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Keywords
- ethyl linoleate, nitrite, nitration, nitroalkenes, nitroalcohols, methyl oleate, radical intermediates, regioisomerism
- MeSH terms
- Acids, Cell Line, Humans, Hydrogen-Ion Concentration, Isomerism, Linoleic Acids, Gas Chromatography-Mass Spectrometry, Nitric Oxide, Nitrites, Magnetic Resonance Spectroscopy, Oxygen, Structure-Activity Relationship, Keratinocytes
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review