Fatty Amines Research Articles

Comparative analysis of oral saliva microbiomes and metabolites in Han population at different altitudes

ObjectiveThis study investigated the differences in oral saliva microbiota composition and metabolic products among Han Chinese populations living at different altitudes, as well as their correlations.MethodThe analysis was conducted using the 16S rRNA gene sequencing method and untargeted metabolomics.Results16S gene sequencing results showed significant differences in bacterial diversity and composition between HH (High altitude Han) group and LH (Low altitude Han) group. LEfSe analysis showed that Selenomonas, Leptotrichia, Veillonella, Prevotella relatively abundant are higher in HH group, Haemophilus, Neisseria, Actinobacillus, Aggregatibacter are higher in LH group (p<0.05). Furthermore, as depicted in the phylogenetic tree, there are differences observed between the two groups at all taxonomic levels: 4 phyla, 6 classes, 6 orders, 9 families, 9 genera and 8 species (p<0.05). After conducting PICRUSt functional prediction analysis, we identified 11 significantly different KEGG categories (level 2) between the two groups. These categories primarily encompass energy metabolism, amino acid metabolism, and carbohydrate metabolism. Furthermore, non-targeted metabolomics analysis revealed a total of 997 distinct metabolites in the two groups. These differentiated metabolites can be classified into 13 Class I categories including amino acids and their metabolites, benzene and its derivatives, organic acids and their derivatives, heterocyclic compounds, aldehydes, ketones and esters, nucleotides and their metabolites among others. Additionally, fatty acyl compounds, alcohols and amines as well as glycerophospholipids are present along with carbohydrates and other physiologically active components such as hormones. Finally, Pearson correlation analysis of the top 20 differential metabolites with microorganisms demonstrated an interaction between them; however further experimental verification is required to elucidate the specific mechanism of action.ConclusionTherefore, this study revealed the effect of altitude on oral saliva microbes and metabolites, as well as their correlations.

Designing invert emulsion drilling fluids for high temperature and high-pressure conditions.

Good and optimal rheology is a primary requisite for a drilling fluid to achieve better hole-cleaning and barite sag resistance. Conventional thickeners like organophilic clay that provide rheology to invert emulsion fluids degrade with time and thereby fail to maintain sufficient rheology of the drilling fluid. Generally, excess amount of organophilic clay or low gravity solids (LGS) is added to the drilling fluid to enhance rheology. However, addition of excess amount of organoclay or low gravity solids not only increases the cost of drilling but also may severely affect other drilling fluid properties, which will require further treatment. In addition, addition of organoclay or low gravity solids increases the plastic viscosity, decreases the rate of penetration thereby ultimately increasing the cost of drilling. Thus, there was a need to develop a drilling fluid with optimal rheology sufficient to give good hole cleaning and barite sag resistance. This paper describes the formulation of 70pcf, 90pcf and 120pcf organoclay-free invert emulsion drilling fluids formulated with a novel rheology modifier combination of RM1 and RM2. The paper describes the synergistic effect of RM1 and RM2 which is a combination of fatty acid and fatty amine respectively. The fluids were hot rolled at 250°F, 250°F and 350°F respectively and the temperature effect on the rheological and filtration properties were studied. The paper also describes the static aging and contamination studies of 90pcf and 120pcf fluids at 250°F and 350°F respectively. Rheology of the 90pcf invert emulsion fluid was measured across high temperature and high pressure (HTHP) conditions to observe their effects on the fluid properties. 70pcf, 90pcf and 120pcf organoclay-free invert emulsion drilling fluids formulated with the novel rheology modifier combination of RM1 and RM2 showed optimal rheology and low HTHP fluid loss. Static aging studies of 90pcf IEFs at 250°F respectively showed that the fluids are sag-resistant with low top-oil separation. Contamination studies of 90pcf fluid showed that the contaminants have minimal effect on the rheology and filtration properties of the invert emulsion fluid. HTHP rheology of the 90pcf invert emulsion fluid shows consistent rheology across high temperatures and pressures. The paper thus demonstrates the superior performance of the rheology modifier combination to achieve good rheological and filtration properties.

Sea urchin-like Fe3O4 hollow microspheres/fatty amines composites phase change materials for highly efficient light-to-thermal conversion and heat storage

Pure phase change materials (PCMs) have limited photothermal conversion capabilities. To improve the photothermal conversion capability of PCMs, we developed composite phase change materials (FHS@PCMs) of sea urchin-like Fe3O4 hollow spheres (FHS) loaded with fatty amines (hexadecylamine (HDA) and octadecylamine (ODA)). The material composition and the surface nano-raised structure of FHS enable FHS@PCMs to exhibit excellent light absorption (up to 90 %, without any additional modification) and thermal conductivity. Moreover, the internal hollow spherical structure would prevent the leakage of PCM during the phase change process. Interestingly, FHS and FHS@PCMs exhibit inherent superhydrophobic properties with a water contact angle greater than 150°, thus endowing them with self-cleaning properties. FHS possesses strong magnetic properties that aid in material collection. Furthermore, the prepared FHS@PCMs exhibited exceptional thermal properties. The latent heat of FHS@HDA and FHS@ODA was 139.21 J∙g−1 and 140.13 J∙g−1, respectively. Additionally, FHS@PCMs maintained their excellent thermal properties even after 50 and 100 thermal cycles. Under one solar radiation, FHS@PCMs show a photothermal conversion efficiency of 89.63 % and 88.02 %, respectively. Taking of these advantages, the as-prepared composite phase change material may have significant potential in the fields of solar energy conversion and storage.

Development of an efficient biocatalytic three-component reaction for synthesizing pyrrole derivatives

Multi-component reactions (MCRs) enable the development of efficient and atom-economic methods for synthesizing pyrrole derivatives. However, the current MCRs methods for synthesizing pyrrole derivatives in the enzymatic process have been unexploited. Herein, we developed a one-pot three-component enzymatic promiscuous catalytic system with green, efficient, and atom-economic to construct pyrrole derivatives. In this system, amines and 1,3-dicarbonyl compounds formed enamines with subsequent Michael addition with nitroolefins catalyzed by trypsin. A series of pyrrole derivatives were successfully obtained with moderate to good yield (up to 92 %). In addition, molecular simulations were conducted to gain insight into the source of differing tolerance of aromatic amides and fatty amines and the intrinsic effect of solvents in this system. This enzymatic catalytic one-pot three-component system has excellent functional tolerance, simple operation, and application potential for industrial production demonstrated by the gram scale experiment.

Deciphering the Entropy-Driven Host-Guest Interactions within Single Covalent Organic Frameworks for Trapping of 131I.

By combining dark-field optical microscopy with an in situ thermochemical aqueous solution system, we report a single-particle imaging strategy to investigate the host-guest interactions between covalent organic framework-300 (COF-300) as a representative COF host and a series of linear-chain fatty amines. The thermodynamic parameters, such as dissociation constant, Gibbs free energy changes, enthalpy changes, and entropy changes for the binding events within COF-300 are quantified. Correlation between the hydrophobicity of various amines and other data suggests that the mechanism of the host-guest bindings arises from the entropy-driven noncovalent interactions such as hydrogen bonds and van der Waals forces. These mechanistic insights allow for the rational design and preparation of COF-300-encapsulated n-octylamine with enhanced trapping performance of radioactive 131I-. This study not only provides thermodynamic insights into the host-guest interactions within the COF framework but also establishes a structure-property relationship between fatty amines and energetic magnitude information.

Determination of insecticidal potential of selected plant extracts against fall armyworm (Spodoptera frugiperda) larvae

The fall armyworm, Spodoptera frugiperda (J.E. Smith), is a devastating pest that attacks a wide range of crops, including sugarcane, rice, and maize. The purpose of this study is to evaluate the toxicity potential of native plant extracts (Azadirachta indica, Eucalyptus globulus, Parthenium hysterophorus, Cannabis sativa, Citrullus colocynthis, Nicotiana tabacum) against S. frugiperda. Four different concentrations (50, 100, 200, and 400ppm) of the ethanolic plant extracts was evaluated against S. frugiperda third-instar larvae to determine their median lethal concentration (LC50). After 72 hours of exposure, the LC50 values of A. indica, E. globulus, P. hysterophorus, C. sativa, C. colocynthis, N. tabacum, and positive control (Spinetoram) were 186.104, 518.438, 320.027, 334.259, 252.651, 720.980 and 189.369 ppm respectively. The maximum percent mortality was caused by the highest concentration (400 ppm) of A. indica (64±0.18), E. globulus (48±0.22), P. hysterophorus (56±0.18), C. sativa (56±0.18), C. colocynthis (60±0.00), and N. tabacum (40±0.28), after 72 hours of treatment while Spinetoram induced 100±0.00 percent mortality of S. frugiperda and only 4±0.18 percent mortality was recorded in a control group. Results showed that all plant extracts were found to be effective against S. frugiperda. The compounds from the two most effective ethanolic plant extracts were identified by using Gas chromatography-mass spectrometry analysis (GC-MS). The key compounds identified in neem leaf extract and kortuma fruit extract are predominantly biologically active molecules. Many of them were volatile compounds that belonged to different chemical categories, such as fatty acids, hydrocarbons, esters, terpenoids, phenolic compounds, and amines. Terpenes exhibited a wide range of different biological activities, such as serving as insecticides and antifeedant. The presence of various functional groups in the plant extract was determined by conducting a Fourier Transform Infrared Spectroscopy (FTIR). Farmers should employ these kinds of environmental friendly insecticides to lessen the impact of fall armyworm because these products are cheaper to use and better for the economy and the environment.

Albusamides A-G: Hydroxylated Fatty Amine Derivatives from the Deep-Sea-Derived Actinomycete Streptomyces albus 228DD-066 and Their Cytotoxic Activity.

A series of new hydroxylated fatty amine derivatives, albusamides A-G (1-7), along with four known compounds (8-11), which are reported for the first time from a natural source, were isolated from the culture broth of Streptomyces albus 228DD-066 derived from a deep-sea sediment sample gathered off the coast of Dokdo Island, Republic of Korea. Their structures were elucidated through the comprehensive analysis of 1D and 2D NMR spectra and HRESIMS, and absolute configurations were determined using the modified Mosher's method. Biological evaluations against solid and blood cancer cell lines revealed that these new metabolites have moderate to strong cytotoxic activity. Compound 3 exhibited high cytotoxic activity with GI50 values ranging from 0.4 to 0.6 μM against solid cancer cell lines and exhibited the strongest cytotoxicity (GI50 value = 0.2 μM) against the WSU-DLCL2 blood cancer cell line.

Increasing the Thermal Resistance of Water-Based Mud for Drilling Geothermal Wells

Energy demand and growing environmental concerns have fueled increased interest in geothermal drilling in recent decades. The high temperature and pressure in the boreholes present significant challenges to drilling, particularly in terms of the selection of suitable drilling mud, cement slurry, and drilling equipment. Drilling mud is regarded as one of the primary factors that affect the cost and success of geothermal drilling. This paper presents experimental studies aimed at assessing the thermal stability of drilling muds for geothermal drilling. Research on the antidegradation of polymers contained in drilling muds is presented. The thermal stability of drilling fluids was evaluated on the basis of changes in rheological and filtration parameters under the influence of a temperature of 160 °C. Attempts were made to increase the thermal resistance of drilling fluids by using antioxidants and glycol compounds. The effectiveness of increasing the thermal resistance of muds by adding synthetic polymers, nanomaterials, and graphite was tested. A new way of increasing the thermal resistance of drilling muds by using fatty amine compounds in combination with the amine agent ‘TEA’ was proposed. Tests showed that the addition of polyglycol and the antioxidant agent sodium ascorbate to the mud did not protect the polymers from decomposition at 160 °C. There was no effect of increasing the thermal conductivity on improving the thermal resistance of the scrubber. Based on the analysis of results from laboratory tests, a composition of a water-based drilling mud without bentonite was developed for drilling geothermal wells. The developed drilling mud is characterized by thermal resistance up to 160 °C, stable rheological parameters, low filtration, and appropriate thermal conductivity characteristics.

Synthesis and quantitative structure–activity relationship of unsaturated fatty acid amide propyl dimethyl tertiary amines and their application in clean fracturing fluid thickener in low temperature environment

Solve the problem of freezing and blocking of clean fracturing fluid thickener during winter fracturing operations in the north, which is conducive to improving the efficiency of fracturing operations and oil and gas production rate. In this paper, four kinds of fatty acid amidopropyl dimethyl tertiary amine were successfully prepared and characterized with FT-IR and 1H NMR. Their acid values and Krafft temperature are discussed. The molecular structures of the four kinds of fatty acid amidopropyl dimethyl tertiary amine salts were optimized using Gaussian09 software, then their single point energies were calculated. A quantitative structure–property relationship (QSPR) model was established to predict Krafft temperature of the four kinds of fatty acid amidopropyl dimethyl tertiary amine salts. N-(3-(Dimethylamino)propyl)oleamide (PKO-O), (9Z,12Z)-N-(3-(dimethylamino)propyl)octadeca-9,12-dienamide (PKO-LO) were selected as the main agent. The optimal thickener formulation O1-8 and O2-1 were optimized by single factor experiment and orthogonal test respectively. O2-1 thickener has high low-temperature stability at −5 °C. The viscosity increase property, gel breaking property, rheological property, and viscoelasticity of the clean fracturing fluid obtained by cross-linking O1-8 with O2-1 thickener were evaluated and the properties of O1-8 thickener are better. The result shows that the O1-8 thickener basically meets the conditions of the winter fracturing construction site, and has more practical application significance.

Solvent management and Li+/Mg2+ co-doping enable efficient n-i-p NiOx-based perovskite solar cells

Spin-coating pre-fabricated NiOx nanocrystals using an annealing-free process is a compatible technique for fabricating the hole transport layer in n-i-p structured perovskite solar cells. The solvothermal method, assisted by long-chain fatty acids or amines such as oleic acid and oleylamine, has demonstrated the applicability of fabricating NiOx nanoparticles with uniform morphology and size. However, the long-chain fatty acids or amines covering the NiOx nanoparticles cannot be removed at low temperature, obstructing the transport of photo-generated holes due to their insulating characteristics. Herein, triphenylphosphine is employed to replace a portion of oleylamine in the solvothermal reaction solution. Experimental results demonstrate that the introduction of triphenylphosphine does not affect the dispersion of the synthesized NiOx nanoparticles in toluene. The as-fabricated n-i-p structured device receives an efficiency of 12.63 %. Thereafter, Li+ doping and Li+-Mg2+ co-doping strategies are used to further enhance the devices' performance. The best-behaved device with Li+-Mg2+ co-doping NiOx hole transport layer acquires an efficiency of 16.20 %. This research provides a practical approach for fabricating efficient NiOx hole transport materials for n-i-p structured perovskite solar cells.

Tandem hydroformylation-amine condensation and reduction of canola fatty acid methyl esters for production of diesel renewable antioxidant additives

A canola fatty acid methyl esters (FAME) mixture was synthesized through transesterification and modified by rhodium homogeneous tandem hydroformylation-amine condensation, with primary amines, yielding imine products. The obtained imines were reduced by maceration with sodium borohydride and alumina, yielding secondary amine products. The synthesized fatty imines and amines were evaluated as additives for commercial diesel and biodiesel on concentrations of 0.5 and 1.0 %, while tested for oxidative stability fallowing the EN14112 standard method. The tested amino products exhibited higher oxidative stability, which justifies its application as antioxidant additives, while the diesel blends did not show expressive physicochemical modifications. The modified amino-FAME antioxidant performance, justifies a renewable biorefinery application, extend the biodiesel shelf-life prior to diesel blending, complies with UN’s Sustainable Development Goals (SDGs) and if prepared from residues, enhance the circular economy appeal.

Multicolor Anti‐counterfeiting Strategy and Synchronous High Capacity Storage Based on Acidochromic Organic Fluorescent Materials

Comprehensive SummaryMany industries are plagued by economic losses and product failures caused by counterfeit goods. Therefore, advanced anti‐counterfeiting techniques are continuously needed. In this study, we constructed a series of acid‐base sensitive cyclic chalcone dyes A—F by modifying different electron‐donating groups. Differences in acid sensitivity of different structures are well rationalised by NMR and theoretical calculations. Aniline is difficult to protonate than fatty amines, so there is a difference in fluorescence. Hiding and anti‐counterfeiting of information is achieved by this phenomenon. Powder X and Y are the anti‐counterfeit fluorescent powder containing montmorillonite and cyclic chalcone, which have orange fluorescence and the very similar appearance. However, under the influence of acid the Powder X containing triphenylamine modified cyclic chalcone shows red shifted fluorescence and Powder Y containing morpholino and diethylamino groups modified cyclic chalcone shows blue shifted fluorescence. Therefore, the anti‐counterfeiting strategy based on cyclic chalcone is not only limited to UV‐irradiated fluorescence development, but also has more colorization and pattern variations with the aid of acid developer. Data encryption and decryption of numbers, English alphabets and Chinese characters have been realized using A—F, which have great potential for practical applications.

Continuous Homogeneously Catalyzed Production of Fatty Amines in Microemulsions─Proof of Concept in a Mini-Plant

Continuous Homogeneously Catalyzed Production of Fatty Amines in Microemulsions─Proof of Concept in a Mini-Plant

Structure and functionality of surface-active amylose-fatty amine salt inclusion complexes

Novel value-added starch-based materials can be produced by forming amylose inclusion complexes (AIC) with hydrophobic compounds. There is currently little research on AIC use as polymeric emulsifiers, particularly for AIC with fatty amine salt ligands. This work evaluated AIC emulsifiers by studying the structure and functionality of AIC composed of high amylose corn starch and fatty amine salts (10–18 carbons, including a mixture simulating vegetable oil composition) produced via steam jet cooking. X-ray scattering verified successful AIC formation, with peaks located near 7.0°, 12.8° and 19.9° 2θ. AIC were easily dispersed in water (80–85 °C) and remained in suspension at room temperature for weeks, unlike the uncomplexed ligands or starch. AIC were highly effective emulsifying agents, with emulsifying activity indexes of 213–229 m2g−1 at pH 5, and zeta potentials, a measure of electrostatic repulsion, as high as 43.4 mV. AIC dispersions had surface tension ranging from 24 to 41 mN/m and displayed surface-active properties superior to amylose complexes formed from fatty acid salts and competitive with common starch-based emulsifiers. These findings demonstrate that fatty amine salt AIC are effective emulsifiers that can be made from low-cost sources of fatty amine salts, such as vegetable oil derivatives.

Bacterial membrane-induced disassembly of fluorescein aggregates enables selective imaging and killing of Gram-positive bacteria

The escalating health threats posed by bacteria and the pressing issue of antibiotic resistance underscore the urgent need for selective detection technologies and antimicrobial reagents. Fluorescein's biocompatibility renders it the preferred fluorescent dye for in vivo imaging. This study reveals that compounds from the aliphatic chain-derived fluorescein series (BMP-alkyl) not only selectively stain and fluorescently image Gram-positive bacteria but also demonstrate the ability to rapidly eliminate them. The discovery of fluorescein's antibacterial properties is poised to have applications in antibiotic research due to its excellent biocompatibility. These amphiphilic BMP-alkyl compounds were easily synthesized through a one-step amidation process involving dicarboxyfluorescein and long-chain fatty amines. In aqueous solutions, the formed aggregates exhibited complete fluorescence quenching. Upon encountering the Gram-positive bacterial membrane, BMP-alkyl compounds underwent depolymerization, resulting in a single fluorescent molecule and the activation of fluorescence. Subsequently, as these amphiphilic fluoresceins continuously combined and entered the bacterial interior, the potential for bacterial membrane depolarization, membrane structure damage, and ultimately bacterial death ensued.

Reverse calcite flotation applied for the beneficiation of the Queguay Formation limestone

Limestone is a significant resource for the Uruguayan mining industry. The Queguay Formation hosts a sedimentary limestone deposit containing quartz inclusions as its primary impurity, which limits its use in applications other than cement. In this work, a representative sample from Queguay Formation was characterized and subjected to flotation tests. The application of reverse froth flotation is proposed to reject quartz from the sample. A specific reagent scheme, with fatty amines as collectors and starch as depressor was evaluated through microflotation and bench scale flotation. Microflotation test results evidenced the selectiveness of the process. Bench scale tests presented new practical challenges, which are discussed in this work.

Covalent Adaptable Networks with Tailorable Material Properties Based on Divanillin Polyimines.

Covalent adaptable networks (CANs) are being developed as future replacements for thermosets as they can retain the high mechanical and chemical robustness inherent to thermosets but also integrate the possibility of reprocessing after material use. Here, covalent adaptable polyimine-based networks were designed with methoxy and allyloxy-substituted divanillin as a core component together with long flexible aliphatic fatty acid-based amines and a short rigid chain triamine, yielding CANs with a high renewable content. The designed series of CANs with reversible imine functionality allowed for fast stress relaxation and tailorability of the thermomechanical properties, as a result of the ratio between long flexible and short rigid amines, with tensile strength (σb) ranging 1.07-18.7 MPa and glass transition temperatures ranging 16-61 °C. The CANs were subsequently successfully reprocessed up to three times without determinantal structure alterations and retained mechanical performance. The CANs were also successfully chemically recycled under acidic conditions, where the starting divanillin monomer was recovered and utilized for the synthesis of a recycled CAN with similar thermal and mechanical properties. This promising class of thermosets bearing sustainable dynamic functionalities opens a window of opportunity for the progressive replacement of fossil-based thermosets.

Effect of synthesized warm mix additive and rejuvenator on performance of recycled warm asphalt mixtures

In this study, a warm mix additive (composed of diamine and fatty acid amine) and a rejuvenator (consisting of styrene-butadiene-styrene and aromatic elements) were synthesized to facilitate the incorporation of 50% recycled asphalt pavement (RAP) in warm mix asphalt for the surface layer and 100% RAP in cold asphalt mixtures for the base layer. The effect of WMA and rejuvenator-modified asphalt binder was performed through rotation viscosity, dynamic shear rheometer, and bending beam rheometer. Simultaneously, the performances of RAP-modified asphalt mixtures were assessed using dynamic modulus, overlay test, and flow number test. Constructing two testbed roads provided a real-world evaluation of two surface mixtures and two base mixtures. The results indicated that modifying asphalt binder PG 64–22 with 2.0% warm mix additive (WMA) and 5.0% rejuvenator upgraded the performance grade to PG 76–22, significantly improving rutting resistance, and reducing 40% creep stiffness. The asphalt mixture with 50% RAP, modified with WMA and rejuvenator, demonstrated a better resistance to rutting and low-temperature cracking compared to the original mixture. Both surface and base mixtures met field application specifications, exhibiting excellent performance after a year of service, as confirmed by pavement condition surveys, and falling weight deflectometer tests, thus highlighting the potential for sustainable and high-performance recycled asphalt solutions in road construction.

Adsorption study of the charge distribution features of highly charged smectites

The study examines the results of assessing the charge density distribution of smectite layers from the bentonite province of the Republic. Kazakhstan (Taganskoye and Dinosaurovoye fields) by alkylammonium method. The method is based on the study of the interaction of a homologous series of fatty amines with the surface of smectites. Organic cations form monomolecular and bimolecular adsorption layers on the basal surfaces. This allows the analysis of the dependence of the position of the diffraction maximum in the small-angle region on the bounding area of the organic cation and to obtain the charge density distribution over the smectite layers. The results obtained for the studied samples show a similar composition of montmorillonite: in all cases, smectites were characterized by a significant charge density with a different proportion of highly charged layers (cation exchange capacity – 120-130 mEq/100 g). The obtained data on charge distribution were compared with some adsorption and colloid-chemical characteristics of smectites, including the values of their cation exchange capacities. At the same time, such technological parameters as the effective viscosity of aqueous dispersions, despite the close charge distribution, differed significantly and showed a sharp dependence on the proportion of sodium cations in the exchange complex.

Structural elucidation of derivatives of polyfunctional metabolites after methyl chloroformate derivatization by high-resolution mass spectrometry gas chromatography. Application to microbiota metabolites

Metabolomics has become an essential discipline in the study of microbiome, emerging gas chromatography coupled to mass spectrometry as the most mature, robust, and reproducible analytical technique. Silylation is the most widely used chemical derivatization strategy, although it has some limitations. In this regard, alkylation by alkyl chloroformate offers some advantages, such as a rapid reaction, milder conditions, better reproducibility, and the generation of more stable derivatives. However, commercial spectral libraries do not include many of the alkyl derivatives, mainly for polyfunctional metabolites, which can form multiple derivatives. That introduces a huge bias in untargeted metabolomics leading to common errors such as duplicates, unknowns, misidentifications, wrong assignations, and incomplete results from which non-reliable findings and conclusions will be retrieved. For this reason, the purpose of this study is to overcome these shortcomings and to expand the knowledge of metabolites in general and especially those closely related to the gut microbiota through the thorough study of the reactivity of the different functional groups in real matrix derivatized by methyl chloroformate, a common representative alkylation reagent. To this end, a systematic workflow has been developed based on exhaustive structural elucidation, along with computational simulation, and taking advantage of the high sensitivity and high-resolution gas chromatography-mass spectrometry. Several empirical rules have been established according to chemically different entities (free fatty acids, amino acids, polyols, sugars, amines, and polyfunctional groups, etc.) to predict the number of derivatives formed from a single metabolite, as well as their elution order and structure. In this work, some methyl chloroformate derivatives not previously reported as well as the mechanisms to explain them are given. Extremely important is the interconversion of E- and Z- geometric isomers of unsaturated dicarboxylic acids (case of fumaric-maleic and case of citraconic-mesaconic acids), or the formation of cycled derivatives for amino acids, as well as common metabolites, as in the case of serine and cysteine, and many others.