Introduction
C10H13NO4 denotes a molecular formula that corresponds to a class of organic compounds containing ten carbon atoms, thirteen hydrogen atoms, one nitrogen atom, and four oxygen atoms. The formula can describe a variety of structural isomers, each featuring distinct arrangements of functional groups such as amides, esters, alcohols, and aromatic rings. Because of its moderate size and functional diversity, C10H13NO4 is represented among pharmaceutical agents, agrochemicals, and industrial intermediates. This article presents an overview of the general characteristics of molecules with this formula, discusses common structural motifs, and surveys notable examples that illustrate the breadth of applications associated with these compounds.
Molecular Characteristics
General Composition
The elemental composition of C10H13NO4 yields a molecular weight of 207.23 g·mol⁻¹ (calculated as 10 × 12.01 + 13 × 1.008 + 14.01 + 4 × 16.00). The presence of a single nitrogen atom typically indicates an amine, amide, or related heteroatom, while the four oxygens can be distributed among alcohol, ether, ester, or carbonyl functionalities. This combination allows for both polar and non‑polar characteristics, depending on the placement of the heteroatoms.
Degree of Unsaturation
The degree of unsaturation (also called double bond equivalents, DBE) for C10H13NO4 is calculated as follows: DBE = C – H/2 + N/2 + 1 = 10 – 13/2 + 1/2 + 1 = 10 – 6.5 + 0.5 + 1 = 5. Thus, any isomer of this formula must contain five rings and/or double bonds. Common arrangements include a single aromatic ring (which accounts for four DBE) combined with one additional double bond or ring elsewhere in the structure. The aromatic ring often participates in conjugation with a carbonyl group, forming a benzoic acid, amide, or ester core.
Polarity and Solubility
Polarity is strongly influenced by the number of heteroatoms and their electronic environments. Compounds with two or more carbonyl groups and at least one hydroxy or amine group are generally more hydrophilic, exhibiting good solubility in water and organic solvents such as methanol or ethanol. In contrast, derivatives that feature only ester or ether linkages and lack ionizable groups tend to be less polar, displaying higher solubility in non‑polar solvents like hexane or dichloromethane. The presence of a protonatable amine allows some isomers to exist in both neutral and protonated forms, which can influence solubility and pharmacokinetics.
Structural Isomerism
Functional Group Distribution
Several structural frameworks can be assembled from the C10H13NO4 scaffold:
- Benzoic acid derivatives featuring an amide or ester side chain (e.g., N‑aryl amides or carboxylate esters).
- Phenylalanine analogues where the side chain includes a hydroxyl or methoxy substituent.
- Amide linkages to aliphatic chains containing secondary or tertiary alcohol groups.
- Tricyclic or bicyclic cores with incorporated nitrogen and oxygen atoms.
Each configuration imposes distinct physicochemical properties such as acidity (pKa), basicity, and hydrogen‑bonding potential.
Common Substituent Patterns
Typical substitution patterns observed among C10H13NO4 compounds include:
- Para‑ or meta‑hydroxy groups on an aromatic ring adjacent to a carboxylate or amide.
- Methylation of nitrogen atoms in amides or amines.
- Formation of cyclic amides (lactams) or cyclic esters (lactones) within the 10‑carbon framework.
- Attachment of aliphatic alcohols to aromatic cores via ether linkages.
These patterns contribute to a range of biological activities, as discussed in the next section.
Notable Compounds with Formula C10H13NO4
Pharmaceutical Agents
Multiple drugs that conform to the C10H13NO4 formula have been developed for therapeutic use. The following examples illustrate the diversity of mechanisms of action and therapeutic areas:
- Paracetamol Derivatives – Certain paracetamol analogues possess an additional hydroxyl group, increasing water solubility and allowing for extended release formulations.
- Selective Serotonin Reuptake Inhibitors (SSRIs) – Some SSRIs contain a phenyl ring linked to an amide side chain, with a methoxy substituent that modulates binding affinity to the serotonin transporter.
- Proton Pump Inhibitors – A subset of these agents features a pyridine ring fused to a benzoic acid core, with a carboxamide substituent that enhances acid‑inhibitory potency.
These molecules exemplify how subtle changes in functional groups can alter pharmacodynamics and pharmacokinetics.
Agricultural Chemicals
Several herbicides and pesticides share the C10H13NO4 formula, typically incorporating a phenoxyacetic acid scaffold with additional functional groups to influence mode of action and environmental persistence. Examples include:
- A phenoxy herbicide featuring a 3,4‑dichloro‑phenyl ring and a carboxamide side chain that interferes with auxin signaling.
- An insecticide based on a pyrazolylbenzamide core that targets nicotinic acetylcholine receptors in insect nervous systems.
These compounds demonstrate the versatility of the C10H13NO4 framework in chemical biology and agrochemical design.
Industrial Intermediates
In the chemical industry, C10H13NO4 derivatives are employed as building blocks for polymer synthesis, surface coatings, and specialty solvents. One common application involves the use of a 2‑hydroxy‑4‑nitrobenzamide derivative as a monomer for polyamide production, where the nitro group is later reduced to an amine during polymerization.
Applications
Medicinal Chemistry
Because the C10H13NO4 scaffold accommodates both hydrophilic and lipophilic features, it is frequently used in medicinal chemistry to tune drug‑like properties. Key strategies include:
- Adding polar hydroxyl groups to improve aqueous solubility without compromising permeability.
- Methylating amide nitrogens to reduce hydrogen‑bond donation, thereby enhancing metabolic stability.
- Incorporating heteroaromatic rings to engage in π‑π stacking with biological targets.
These design principles enable the development of compounds with optimized efficacy, safety, and manufacturability.
Biological Probes
Compounds with the C10H13NO4 formula are often utilized as fluorescent or radiolabeled probes. By attaching a fluorescent dye to the nitrogen atom or incorporating a radioactive isotope into the aromatic ring, researchers can visualize target proteins, monitor enzyme activity, or track drug distribution in vivo.
Materials Science
In materials science, certain C10H13NO4 derivatives serve as cross‑linking agents or compatibilizers in polymer blends. For instance, a benzamide containing a terminal hydroxyl group can act as a reactive site during curing processes, enhancing the mechanical strength of composites used in aerospace or automotive applications.
Synthesis
General Synthetic Routes
Typical synthetic strategies for generating C10H13NO4 molecules involve the following core steps:
- Formation of the aromatic core – Friedel‑Crafts acylation, Suzuki‑Miyaura coupling, or nitration reactions produce a substituted benzene ring.
- Introduction of the nitrogen atom – Amide coupling (using carbodiimide or DCC), reductive amination, or Boc‑protected amine substitution introduce nitrogen functionality.
- Installation of the oxygen atoms – Hydroxyl or methoxy groups are introduced via Williamson ether synthesis, reduction of nitro groups, or oxidation of alcohols to aldehydes/ketones.
- Final functionalization – Esterification, amidation, or oxidation completes the molecule, ensuring the correct distribution of oxygen atoms.
These general approaches are adapted to accommodate the specific demands of each isomer, such as protecting group strategies or reaction condition optimization.
Specific Example: Synthesis of a Phenoxyacetic Acid Derivative
One illustrative example involves the synthesis of a phenoxyacetic acid containing an amide side chain:
- Step 1 – Nitration of benzene yields a nitrobenzene intermediate.
- Step 2 – Reduction of the nitro group to an aniline, followed by acylation with chloroacetyl chloride to introduce the carboxamide side chain.
- Step 3 – Phenylation of the nitrogen via a Buchwald‑Hartwig cross‑coupling generates the final C10H13NO4 scaffold.
Variations of this scheme incorporate alternative protecting groups or catalyst systems to improve yield and selectivity.
Biological Activity
Enzyme Inhibition
Many C10H13NO4 compounds act as inhibitors of enzymes involved in neurotransmission, hormone synthesis, or metabolic pathways. The presence of amide or hydroxyl groups often facilitates hydrogen‑bond interactions with active‑site residues. For example, a lactam derivative can mimic the transition state of peptide bond hydrolysis, thereby blocking protease activity.
Receptor Binding
Phenyl‑lactam molecules with a methoxy substituent frequently exhibit high affinity for G‑protein coupled receptors (GPCRs) such as the 5‑HT_2A or α_2A adrenergic receptors. The aromatic ring engages in hydrophobic contacts, while the amide carbonyl participates in a salt‑bridge with receptor residues.
Metabolic Stability
Structural features that reduce susceptibility to oxidative or hydrolytic degradation are often introduced to improve drug durability. For instance, tertiary alcohols adjacent to a carbonyl group can hinder nucleophilic attack by metabolic enzymes, thereby extending the compound’s half‑life in biological systems.
Safety and Toxicology
Acute Toxicity
Acute toxicity profiles of C10H13NO4 compounds vary widely depending on substituent pattern. Generally, non‑polar derivatives exhibit lower oral LD_50 values in rodent models, whereas polar analogues show higher LD_50 values, reflecting reduced systemic absorption. Inhalation toxicity is typically low for compounds lacking reactive groups that form volatile metabolites.
Chronic Exposure
Chronic exposure studies indicate that compounds with a phenoxyacetic acid core may accumulate in fatty tissues due to their lipophilicity, leading to potential endocrine disruption. In contrast, amide‑protected derivatives with high polar surface area tend to be excreted rapidly via renal pathways, minimizing chronic accumulation.
Environmental Fate
Herbicides and pesticides bearing the C10H13NO4 scaffold often display moderate persistence in soil and aquatic environments. Degradation pathways typically involve hydrolysis of ester bonds, reduction of nitro groups, and microbial oxidation of aromatic rings. Regulatory guidelines require detailed assessment of biodegradability and leaching potential for these compounds before market approval.
Analytical Methods
Chromatographic Techniques
High‑performance liquid chromatography (HPLC) equipped with a reverse‑phase C18 column is commonly employed to separate C10H13NO4 isomers. The detection is usually achieved via ultraviolet (UV) absorption at 210–280 nm, exploiting the π→π* transitions of aromatic systems. For highly polar derivatives, ion‑exchange chromatography provides additional resolution based on charge states.
Spectroscopic Characterization
Proton and carbon‑13 nuclear magnetic resonance (NMR) spectroscopy remains the primary method for confirming the structure of C10H13NO4 compounds. Key diagnostic signals include:
- Aromatic protons appear between 6.5–8.0 ppm, with multiplicity patterns reflecting substitution.
- Amide or carboxamide NH signals typically fall between 7.5–9.5 ppm.
- Hydroxy or methoxy protons appear between 3.0–5.5 ppm, with integration reflecting the number of such groups.
Mass spectrometry (MS) provides complementary confirmation of molecular weight and fragmentation patterns characteristic of amide or ester cleavage.
Conclusion
Compounds with the C10H13NO4 molecular formula encompass a rich array of structures that satisfy a broad spectrum of chemical, biological, and industrial requirements. Their moderate size, high degree of unsaturation, and diverse functional group distribution afford opportunities for fine‑tuning physicochemical properties. Whether employed as pharmaceuticals, agrochemicals, or material science intermediates, molecules in this class demonstrate the power of structural isomerism and rational design to achieve targeted performance across multiple domains.
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