Cyclopropanecarboxylic Acid Research Articles

Molecular insights into the inhibition of Leishmania donovaniO-acetylserine sulfhydrylase by cyclopropane carboxylic acid derivatives: a computational study

The study evaluated the inhibitory potential of cyclopropane carboxylic acid derivatives, specifically ICA-2 and ICA-3, against Leishmania donovaniO-acetylserine sulfhydrylase (OASS) using in silico methods. Molecular docking and molecular dynamics (MD) simulations were employed to investigate interactions between compounds and OASS. ADME properties were evaluated using SwissADME and Admetlab 2.0 servers. In the molecular docking study, the binding affinities of various complexes ranged from − 8.7 to − 5.1 kcal/mol. ICA-2 and ICA-3, distinguished by the presence of a phenylpyrazole moiety, demonstrated remarkable stability in MD simulations, with overall binding free energies of − 75 and − 31 kJ/mol, respectively. Analysis of the MD data revealed that ICA-2 induced a global change in the enzyme structure, leading to a closed, inactive conformation. This change was facilitated by frequent interactions with Ser79, Ser80, and Gln152, as indicated by hydrogen bond and residual contribution data. ICA-3, lacking interactions with these residues, likely inhibits the enzyme through a competitive inhibition route. Both compounds adhered to Lipinski’s requirements, exhibiting moderate to high solubility and high absorption in the intestine. Therefore, ICA-2 and ICA-3 have emerged as promising candidates for drug development programs targeting leishmaniasis, demonstrating potential as effective inhibitors of Leishmania donovani OASS.Graphical

New functionally substitutes cyclopropanecarboxylic acids as ethylene biosynthesis innovative regulators

Background: Derivatives of small carbocycles (cyclobutanes and cyclopropanes) are known as bioactive molecules. Both their natural and synthetic representatives have multiple applications. Particularly, 1-aminocyclopropane-1-carboxylic acid (ACC) serves as the well-studied ethylene biosynthesis precursor. The development of new functionally substituted cyclopropane carboxylic acids, which show promise as effective inhibitors of ethylene biosynthesis, is crucial for regulating the plant cycle and preserving the quality of fruits and vegetables. Objectives: This research focused on the in-silico studies aimed at developing a universal and affordable methodology for synthesizing new analogs of ACC and assessing their modulating activity on ethylene biosynthesis in plants. The findings from this in silico research provide a foundation for the upcoming in vitro studies. Results: The elaborated efficient catalytic system [Cu(I) salt/amine/DMSO] enabled the synthesis of model compounds under mild conditions, resulting in increasing yields up to quantitative levels. For bioactivity preliminary assessment we performed in silico research of newly synthesized (E)-2-phenyl-1-chlorocyclopropane-1-carboxylic acid and drug-design an appropriate 1-amino-derivative as the inhibitor of 1-aminocyclopropane-1-carboxylate oxidase 2 (ACO2) of Arabidopsis thaliana. Docking results showed certain advantages of the newly synthesized compound in comparison to well-known inhibitors of ethylene biosynthesis. Conclusions: The recommended synthetic technology has increased efficiency in yield quantification. In silico studies, a high affinity for ACO2 has been demonstrated. The synthesized compounds exhibit superior characteristics compared to widely used market preparations for regulating ethylene biosynthesis. More detailed comparative in vitro studies are planned. Keywords: plant growth regulation, cyclopropane carboxylic acids, ethylene biosynthesis inhibitors, molecular docking, atom transfer radical addition (ATRA), Cu(I) Complex catalyst.

Ionic liquid catalysed synthesis of benzimidazolone from Ortho-Phenylenediamine in the presence of carbon dioxide as a carbonyl source under solvent free condition

In this study, we report synthesis of benzimidazolones from o-phenylene diamine by utilizing carbon dioxide as a carbonyl source under mild reaction conditions in the presence of ionic liquid as a catalyst. Six bifunctional protonic ionic liquids (PILs) were synthesised by reacting superbases 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) and 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) with proton donors such as Trifluoroethanol (TFE), Cyclopropane carboxylic acid (CPCA) and 2,2,2-Trifluoroacetic acid (TFA). Among them, [TBDH+][TFE−] was the most effective, achieving high conversion rates of o-phenylene diamine to 2-benzimidazolone at 1 bar CO2 pressure and 60° C. This PIL could be reused for up to six cycles. Our method offers a green and efficient approach for producing 2-benzimidazolone derivatives, with potential applications in pharmaceuticals and materials science.

Synthesis, spectral elucidation and DNA binding studies of cadmium(II) carboxylates with nitrogen donor heteroligands

A new series of novel homoleptic and heteroleptic Cd(II) complexes using cyclopropanecarboxylic acid (HL1) and cyclopentanecarboxylic acid (HL2) as main ligands and N-donor species like 2,2′-bipyridine (bpy), 1,10-phenanthroline (phen), and 2,9-dimethyl-1,10-phenanthroline (Me2phen) as co-ligands were prepared and characterized by FT-IR, multinuclear (1H and 13C) NMR, and UV–Visible spectroscopies. Furthermore, the crystal structure of the Cd(II) complex coordinated by cyclopentanecarboxylic acid (HL2) and 1,10-phenanthroline (phen) was explored by single crystal X-ray diffraction (SC-XRD) analysis. The crystal structure was binuclear, in which the coordination geometry around each cadmium center was distorted pentagonal bipyramidal coordination geometry. Various intermolecular interactions were accountable for stabilizing the supramolecular associations, which were seen by Hirshfeld surface analysis in terms of interatomic contacts. The spectroanalytical data of the synthesized complexes confirm the absence of the –OH band in the spectra of complexes as compared to the spectra of the free ligands, which favour the formation of complexes. The nature of complex-DNA interaction and the effect of the coordination of heteroligands on the binding strength of complexes were probed through UV–Visible spectroscopy and cyclic voltammetry. The obtained data confirm that the interaction of DNA with the complexes is dual: intercalation as well as groove binding. The DNA binding constants (Kb) and Gibb’s free energy changes (ΔG) were also determined for these complexes. This study aims to project effective drugs with the least harmful effects that could be useful for mankind against dreadful diseases.

Hepatoprotective Effects of Fractions of Adansonia Digitata Leaves on Carbon Tetrachloride (CCL4)- Induced Toxicity in Wistar Rats

Phytochemicals, naturally occurring compounds in plants, offer health benefits to humans. This study aimed to determine the effects of fractions of ethanol extract of Adansonia digitata leaves on carbon tetrachloride (CCl4)-induced toxicity in wistar rats. The extraction was done using absolute ethanol, followed by fractionation with different solvent combination via column chromatography. Elution of extract was done with solvent system by gradually increasing polarity beginning from n-hexane, chloroform, ethyl acetate, methanol, ethanol and finally water. In total, 22 fractions were collected in 200 mL beaker each. The fractions were subjected to total antioxidant analysis using 1, 1-diphenyl-2-picryhydrazyl (DPPH) assay. Total phenolics and total flavonoids content were analyzed by Folin-Ciocalteu. GC-MS, FTIR and HPLC analysis were also carried out. Thirty-six male albino rats were distributed into six groups of six (n = 6). The negative control group received CCl4 only. The standard control group was administered 2 CCl4/kg body weight + 25mg/kg body weight silymarin followed by different doses of ethyl acetate:ethanol fraction-20 mg/kg, 40 mg/kg and 50 mg/kg for 21 days. Induction and treatment were carried out in the beginning of a new week. The animals were fasted for 24 hours, sacrificed and blood samples were collected for biochemical analysis. The administered fraction led to the statistically insignificant (p> 0.05) and statistically significant (p< 0.05) reduction in the levels of Aspartate aminotransferase (AST) and Alanine aminotransferase (ALT) respectively, the reduction in the levels of total protein (TP) and albumin (ALB) were statistically not significant (p> 0.05) in the treated rats as compared to the untreated rats. The phytochemical analysis of the extract revealed the presence of antioxidant and phenolics. From the total antioxidant capacity, fraction 6b (ethyl acetate: ethanol) was selected for GC-MS, FTIR and HPLC analysis. The GC-MS analysis of fraction 6b revealed the presence of 14 compounds from which Bis(2-ethylhexyl) phthalate had the highest percentage constituent (48.30%) while while 2-Methyl-Z,Z-3,13-octadecadienol had the lowest relative abundance of 0.14 %. Dichloroacetic acid, tridecyl este, d-Glycero-d-ido-heptose, Phthalic acid, ethyl pentyl ester, Trifluoroacetoxy hexadecane, 2-Hexene, 6-nitro-, 2-Tetradecanol, 3,5-Dimethyl-2-octanol, Cyclopropanecarboxylic acid, 7,11-Hexadecadienal, 9-Octadecenamide, Squalene and E, E-1,9,17-Docasatriene were the other compounds found in the fraction. FTIR spectral analysis of the fraction showed peaks of various functional groups. The HPLC results showed the presence of quercetin in the fraction.

Organocatalytic Decarboxylative Borylation of Cyclopropane N-Hydroxyphthalimide Esters.

A convenient protocol for the two-step organocatalytic decarboxylative borylation of 1,1-disubstituted, 1,2-disubstituted, and bicyclic cyclopropane carboxylic acids via the corresponding N-hydroxyphthalimide esters is described, using tert-butyl or ethyl isonicotinate as an inexpensive and readily available catalyst. The scope of the method was demonstrated, being limited mainly by electron-poor substrates. The reaction sequence showed good scalability (up to 51.5 g) and excellent trans diastereoselectivity (for the case of 1,2-disubstituted substrates). Therefore, the proposed approach is a very promising alternative to other existing (i.e., metal-catalyzed) methods for borodecarboxylation.

Multigram Synthesis of Chiral Cyclopropane Carboxylic Acids via Tandem Diastereoselective Wadsworth–Emmons Cyclopropanation-Hydrolysis in Continuous Flow

Multigram Synthesis of Chiral Cyclopropane Carboxylic Acids via Tandem Diastereoselective Wadsworth–Emmons Cyclopropanation-Hydrolysis in Continuous Flow

Synthesis of chiral α-amino acids via Pd(ii)-catalyzed enantioselective C-H arylation of α-aminoisobutyric acid.

Non-natural chiral α,α-disubstituted α-amino acids (α,α-AAs) constitute an attractive α-aminoisobutyric acid (Aib) replacement for improving bioavailability of linear peptides as therapeutics due to the ability of these amino acids to induce the peptides to form helical structures. Enantioselective β-C(sp3)-H arylation of Aib could potentially provide a versatile one-step strategy for accessing diverse α,α-AAs, but the installation and removal of external directing groups was found in our previously reported work to reduce the efficiency of this approach. Herein we report a Pd(ii)-catalyzed enantioselective C-H arylation of N-phthalyl-protected Aib enabled by a N-2,6-difluorobenzoyl aminoethyl phenyl thioether (MPAThio) ligand, affording α,α-AAs with up to 72% yield and 98% ee. Use of this newly developed chiral catalyst has also significantly improved enantioselective C(sp3)-H arylation of cyclopropanecarboxylic acids by expanding the substrate scope to heterocyclic coupling partners and increasing enantioselectivity to 99% ee.

QSPR models for predicting the Kovats retention indices of synthetic ester derivatives based on pyrethrin essential oil

ABSTRACT In this study, the chromatographic characteristics of 100 different pyrethroids including ester derivatives of cyclopropanecarboxylic acids were analyzed by measuring their logarithmic kovats retention index (log KRI) using a quantitative structure-retention relationship (QSRR). The log KRI of the studied pyrethroids were modeled by genetic algorithm-structure retention relationships (GA-QSRR) based on linear and nonlinear regression models. The descriptors such as HNar, H0v, and H5p, which express the GETAWAY (geometry, topology, and atom-weights assembly) compound descriptors, have a reasonable correlation with the log KRI. We assessed the predictive strength of the BP-ANN model and demonstrated the potential of the model using various statistical parameters. The statistical parameters such as Q2F1, Q2F2, Q2F3 , AAD, RMSE and CCC were used to evaluate the predictive ability of the BP-ANN model. In predicting the log KRI of pyrethroids, the results indicated that the BP-ANN model is more reliable and accurate than the BW-MLR model.

Antibiofilm, Antimicrobial, Anti-Quorum Sensing, and Antioxidant Activities of Saudi Sidr Honey: In Vitro and Molecular Docking Studies.

Sidr honey is a valuable source of bioactive compounds with promising biological properties. In the present study, antimicrobial, antioxidant, and anti-quorum sensing properties of Saudi Sidr honey were assessed, along with phytochemical analysis, via gas chromatography-mass spectrometry (GC-MS). In silico study was also carried out to study the drug-likeness properties of the identified compounds and to study their affinity with known target proteins assessed using molecular docking approach. The results showed that Saudi Sidr honey exhibited promising antibacterial activity, with MIC values ranging from 50 to 400 mg/mL and MBC values from 50 to >450 mg/mL. Interestingly, the Saudi Sidr honey was active against Candida auris and Candida neoformans, with an MIC value of about 500 mg/mL. Moreover, the Sidr honey showed important antioxidant activities (ABTS assay: IC50 5.41 ± 0.045 mg/mL; DPPH assay: IC50 7.70 ± 0.065 mg/mL) and β-carotene bleaching test results (IC50 ≥ 20 mg/mL). In addition, the Saudi Sidr honey was able to inhibit biofilm formation on glass slides at 1/2 MIC by 77.11% for Bacillus subtilis, 70.88% for Staphylococcus aureus, 61.79% for Escherichia coli, and 56.64% for Pseudomonas aeruginosa. Similarly, violacein production by Chromobacterium violaceum was reduced by about 56.63%, while the production of pyocyanin by P. aeruginosa was decreased to 46.27% at a low concentration of Saudi Sidr honey. ADMET properties showed that five identified compounds, namely, 1-cyclohexylimidazolidin-2-one, 3-Butyl-3-methylcyclohexanone, 4-butyl-3-methoxy-2-cyclo penten-1-one, 2,2,3,3-Tetramethyl cyclopropane carboxylic acid, and 3,5-dihydroxy-2-(3-methylbut-2-en-1-yl showed promising drug-likeness properties. The compound 3,5-dihydroxy-2-(3-methylbut-2-en-1-yl exhibited the highest binding energy against antimicrobial and antioxidant target proteins (1JIJ, 2VAM, 6B8A, 6F86, 2CDU, and 1OG5). Overall, the obtained results highlighted the promising potential of Saudi Sidr honey as a rich source of bioactive compounds that can be used as food preservatives and antimicrobial, antioxidant, and anti-quorum sensing molecules.

N-Ylide Mediated Synthesis and Resolution of a Chiral Pyrimidinyl Cyclopropane Carboxylic Acid

N-Ylide Mediated Synthesis and Resolution of a Chiral Pyrimidinyl Cyclopropane Carboxylic Acid

Gas Chromatography-Mass Spectroscopy(GC-MS) of Chloroform Extract of Ficus exasperata Vahl

Gas Chromatography-Mass Spectrometry (GCMS) analysis of chloroform leaves extract of Ficus exasperate Vahl was performed to identify the composition and percentage abundance of the various phytochemical constituents of Ficus exasperate Vahl. The extract was obtained by fractionating methanol crude leave extract of Ficus exasperate Vahl with in order of increasing polarity, n-Hexane then chloroform. GC-MS analysis was carried out on a GC system comprising a Gas Chromatograph interfaced to a Mass Spectrometer (GC-MS) instrument. The components were compared with the database of spectrum of known components stored in the gas chromatography-mass spectrometry library. Gas Chromatography-Mass Spectrometry analysis of the chloroform leave extract of Ficus exasperate revealed the presence of acyclic olefin which is used for tanning oils and in synthetic fatty acids, Isopryl myristate used in cosmetics, Dibutyl phthalate which is used in cosmetics, textile, safety glass additive, oleic acid used in pharmaceuticals, Cyclopropanecarboxylic acid, 3-(2,2-dichlor used in agrochemicals and pharmaceuticals. The presence of these compounds justifies the use of some parts of the plant for various elements in folklore and can be advised as a plant of phytopharmaceutical and industrial importance.

Short I⋯O Interactions in the Crystal Structures of Two 2-Iodo-Phenyl Methyl-Amides as Substrates for Radical Translocation Reactions

Radical translocation reactions are finding various uses in organic synthesis, in particular the stereospecific formation of complex natural products. In this work, the syntheses and single-crystal structures of two substituted 2-iodo-phenyl methyl-amides are reported, namely cyclo-propane carboxylic acid (2-iodo-phenyl)-methyl-amide, C11H12INO (1), and cyclo-heptane carboxylic acid (2-iodo-phenyl)-methyl-amide, C15H20INO (2). In each case, the methyl-amide group has a syn conformation, and this grouping is perpendicular to the plane of the benzene ring: these solid-state conformations appear to be well setup to allow an intramolecular hydrogen atom transfer to take place as part of a radical translocation reaction. Short intermolecular I⋯O halogen bonds occur in each crystal structure, leading to [010] chains in 1 [I⋯O = 3.012 (2) Å] and isolated dimers in 2 [I⋯O = 3.024 (4) and 3.057 (4) Å]. The intermolecular interactions are further quantified by Hirshfeld surface analyses.

Tribo-induced catalytically active oxide surfaces enabling the formation of the durable and high-performance carbon-based tribofilms

Carbon-containing tribofilms have attracted significant interest in the lubrication research despite a scarcity of information on their high-temperature performance under severe boundary conditions. In this study, high-temperature lubrication of the carbon tribofilm produced from cyclopropane carboxylic acid (CPCa) and NiAl-layered double hydroxide (LDH) nanoparticles was evaluated. NiAl-LDH nanoparticles significantly enhanced the friction stability and antiwear performance of CPCa by over 90% at 50°C and 100°C, comparable to the benchmark zinc dialkyldithiophosphates (ZDDPs). The highly graphitic amorphous carbon tribofilms and the fine-grain intermediate tribolayer constructed by the thermal decomposition products of NiAl-LDH contributed to such excellent lubrication performance. This study paves a pathway in developing functional anti-wear additives for the durable and high-performance carbon-containing tribofilms at high temperatures.

Exposure to non-persistent pesticides and sexual maturation of Spanish adolescent males

BackgroundSeveral non-persistent pesticides are endocrine disrupting chemicals and may impact on sexual maturation. ObjectiveTo examine the association between urinary biomarkers of non-persistent pesticides and sexual maturation in adolescent males in the Environment and Childhood (INMA) Project. MethodsThe metabolites of several pesticides were measured in spot urine samples collected from 201 boys aged 14–17 years, including: 3,5,6-trichloro-2-pyridinol (TCPy), metabolite of chlorpyrifos; 2-isopropyl-4-methyl-6-hydroxypyrimidine (IMPy), metabolite of diazinon; malathion diacid (MDA), metabolite of malathion; diethyl thiophosphate (DETP) and diethyl dithiophosphate, non-specific metabolites of organophosphates; 3-phenoxybenzoic acid (3-PBA) and dimethyl cyclopropane carboxylic acid, metabolites of pyrethroids; 1-naphthol (1-NPL), metabolite of carbaryl; and ethylene thiourea (ETU), metabolite of dithiocarbamate fungicides. Sexual maturation was assessed using Tanner stages, self-reported Pubertal Development Scale, and testicular volume (TV). Multivariate logistic regression was employed to examine associations between urinary pesticide metabolites and the odds of being in Tanner stage 5 of genital development (G5) or pubic hair growth (PH5); stage ≥4 of overall pubertal development, gonadarche, and adrenarche; or having mature TV (≥25 mL). ResultsDETP concentrations>75th percentile (P75) were associated with lower odds of being in stage G5 (OR = 0.27; 95% CI = 0.10–0.70), detectable TCPy with lower odds of gonadal stage≥4 (OR = 0.50; 95% CI = 0.26–0.96), and intermediate detectable MDA concentrations (<P75) with lower odds of adrenal stage≥4 (OR = 0.32; 95% CI = 0.11–0.94). Conversely, detectable concentrations of 1-NPL were associated with higher odds of adrenal stage≥4 (OR = 2.61; 95% CI = 1.30–5.24) but lower odds of mature TV (OR = 0.42; 95% CI = 0.19–0.90). ConclusionExposure to certain pesticides may be associated with delayed sexual maturity in adolescent males.

General and Scalable Approach to Trifluoromethyl-Substituted Cyclopropanes.

CF3-cyclopropanes with aliphatic, aromatic, and even heteroaromatic substituents were prepared on a multigram scale by deoxyfluorination of cyclopropane carboxylic acids or their salts with sulfur tetrafluoride. For labile α-pyridine acetic acids, only the use of their potassium salts allowed to obtain the needed products. Derivatization of CF3-cyclopropanes into building blocks ready for direct use in medicinal chemistry was performed.

In Situ Graphene Formation Induced by Tribochemical Reaction for Sustainable Lubrication

Graphene is widely applied as lubricating materials owing to its superior tribological performances. However, its complex synthesis process causes environmental pollution and increases production cost. In the current work, we developed a facile strategy to construct a sustainable lubricant system by generating graphene in situ, which avoided the complicated graphene synthetic process. The novel lubricant system is constructed by introducing cyclopropanecarboxylic acid (CPCa) and metal particles (nickel and copper) into base oil. CPCa molecules undergo tribochemical reaction to produce hydrocarbons serving as the solid lubricant, and metal particles catalyze the graphitization of hydrocarbons. Importantly, friction products can be reused as lubricating additives for base oil and provide better lubrication performance compared with the original lubricant systems. This fully demonstrates the sustainable lubrication ability of friction products and their potential as recyclable lubricant additives. The present work provides a novel perspective for the design and development of green lubricant additives.

CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes.

Strong reducing agents (<-2.0 V vs saturated calomel electrode (SCE)) enable a wide array of useful organic chemistry, but suffer from a variety of limitations. Stoichiometric metallic reductants such as alkali metals and SmI2 are commonly employed for these reactions; however, considerations including expense, ease of use, safety, and waste generation limit the practicality of these methods. Recent approaches utilizing energy from multiple photons or electron-primed photoredox catalysis have accessed reduction potentials equivalent to Li0 and shown how this enables selective transformations of aryl chlorides via aryl radicals. However, in some cases, low stability of catalytic intermediates can limit turnover numbers. Herein, we report the ability of CdS nanocrystal quantum dots (QDs) to function as strong photoreductants and present evidence that a highly reducing electron is generated from two consecutive photoexcitations of CdS QDs with intermediate reductive quenching. Mechanistic experiments suggest that Auger recombination, a photophysical phenomenon known to occur in photoexcited anionic QDs, generates transient thermally excited electrons to enable the observed reductions. Using blue light-emitting diodes (LEDs) and sacrificial amine reductants, aryl chlorides and phosphate esters with reduction potentials up to -3.4 V vs SCE are photoreductively cleaved to afford hydrodefunctionalized or functionalized products. In contrast to small-molecule catalysts, QDs are stable under these conditions and turnover numbers up to 47 500 have been achieved. These conditions can also effect other challenging reductions, such as tosylate protecting group removal from amines, debenzylation of benzyl-protected alcohols, and reductive ring opening of cyclopropane carboxylic acid derivatives.

Inhibitors of O-Acetylserine Sulfhydrylase with a Cyclopropane-Carboxylic Acid Scaffold Are Effective Colistin Adjuvants in Gram Negative Bacteria.

Antibacterial adjuvants are of great significance, since they allow one to downscale the therapeutic dose of conventional antibiotics and reduce the insurgence of antibacterial resistance. Herein, we report that O-acetylserine sulfhydrylase (OASS) inhibitors could be used as colistin adjuvants to treat infections caused by critical pathogens spreading worldwide, Escherichia coli, Salmonella enterica serovar Typhimurium, and Klebsiella pneumoniae. Starting from a hit compound endowed with a nanomolar dissociation constant, we have rationally designed and synthesized a series of derivatives to be tested against S. Typhimurium OASS isoenzymes, StOASS-A and StOASS-B. All acidic derivatives have shown good activities in the nanomolar range against both OASS isoforms in vitro. Minimal Inhibitory Concentrations (MICs) were then evaluated, as well as compounds’ toxicity. The compounds endowed with good activity in vitro and low cytotoxicity have been challenged as a potential colistin adjuvant against pathogenic bacteria in vitro and the fractional inhibitory concentration (FIC) index has been calculated to define additive or synergistic effects. Finally, the target engagement inside the S. Typhimurium cells was confirmed by using a mutant strain in which the OASS enzymes were inactivated. Our results provide a robust proof of principle supporting OASS as a potential nonessential antibacterial target to develop a new class of adjuvants.

Influences of iron and iron oxides on ultra-thin carbon-based tribofilm lubrication

A molecular dynamics (MD) simulation was used to investigate the influences of iron/iron oxide surface on the lubrication and tribochemistry of C-based tribofilms mixed with cyclopropane carboxylic acid (CPCa). The results revealed that the best tribological performance was found for mixed 1-decene lubricant confined between iron surfaces. In contrast, Fe3O4 was the most beneficial surface for C-based tribofilm formation as this surface resulted in the most significant number of species and molecules, as well as the largest portion of short C-chain molecules, which are intermediate products generated in C-based tribofilm growth. Interestingly, iron oxides resulted in a larger dissociation rate of C−C and C–H bonds than iron in the current thin-film lubrication. The degree of polymerization, reflected by the number and size of polymerized molecules, increases with CPCa concentration on a pure iron surface, while it decreases with an iron oxide surface.