This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
678.700 g/mol
XLogP3
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
18
Rotatable Bond Count
10
Exact Mass
678.243 Da
Monoisotopic Mass
678.243 Da
Topological Polar Surface Area
294.000 Ų
Heavy Atom Count
47
Formal Charge
0
Complexity
388.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
3
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
Item-specific tested applications
None provided in the Product Data. No validated protocols, recommended dilutions, or positive control materials are specified for this item.
General guidance (for research use only; develop and validate locally)
Enzyme inhibition assays: Prepare serial dilutions from a filtered stock to generate concentration–response curves against purified DHFR. Include appropriate vehicle controls. Report concentrations as free base equivalents; correct for salt stoichiometry.
Microbial susceptibility studies: When used as a laboratory benchmark compound, prepare fresh aqueous stocks and incorporate into growth media at defined concentrations; verify sterility and stability under incubation conditions. Follow institutional biosafety and antimicrobial stewardship policies; no clinical use.
Analytical standard preparation: For HPLC/LC–MS, prepare accurately weighed standards into Class A volumetrics with water or DMSO, then dilute with mobile phase. Assess stability by bracketed QC checks.
Note
Because no item-specific, validated protocols are provided, users must optimize parameters (solvent, concentration, pH, incubation time) for their systems. Always refer to your organization’s SOPs.
Biological Roles
General biological context (literature; no therapeutic claims)
Primary biochemical target: Trimethoprim is a well-characterized inhibitor of dihydrofolate reductase (DHFR), a key enzyme in folate metabolism that reduces dihydrofolate to tetrahydrofolate, which supports one-carbon transfer reactions in nucleotide biosynthesis.
Selectivity considerations: The compound exhibits preferential activity toward certain microbial DHFR enzymes relative to many eukaryotic homologs (literature). Specific potency and selectivity depend on organismal isoform and assay conditions.
Consequence of DHFR inhibition: Depletion of tetrahydrofolate cofactor pools can reduce thymidylate and purine biosynthesis, impacting DNA replication and cell division in susceptible systems (biochemical pathway level).
Transport and accumulation: Ionization state and transporter expression can influence uptake and intracellular concentration. The sulfate salt form improves aqueous handling but does not change the underlying binding pharmacophore.
Synergy studies: In research, trimethoprim is frequently studied in combination with inhibitors of upstream folate pathway steps to probe metabolic network responses and collateral sensitivities, strictly within laboratory systems.
Item-specific note
This product is designated for research use only. No biological specification data (potency, MIC, Ki, or IC50) are provided for this item; consult primary literature for representative values and verify under your exact assay conditions.
Buffer Applications
Not typically applicable.
Trimethoprim sulfate is not a buffering agent and does not define a standard buffer system. It may be dissolved in biological buffers (e.g., phosphate, HEPES, MOPS) for assays, but it does not itself set pH.
Practical tip: Choose buffer composition and pH to maximize target stability and to keep the compound in a soluble, non-aggregated state. Validate compatibility by small-scale tests.
Item-specific data
No buffer recipes, pH ranges, or compatibility data are provided for this item; refer to your method SOPs and perform pilot solubility/stability checks.
Green Alternatives
Context
This product is a bioactive small-molecule salt, not a process solvent or bulk reagent. “Green alternatives” are therefore less about substituting the compound itself and more about minimizing solvent and waste footprints in its use.
Strategies (general, literature-informed)
Prefer water as solvent when compatible with your assay or reaction. Where organic cosolvent is required, use the minimum DMSO/DMF percentage necessary for solubilization and consider ethanol or water/ethanol mixtures where feasible.
Miniaturize assays (e.g., microplate formats) to reduce material and solvent use; implement automation for precise low-volume dispensing to curb overuse.
Choose buffered aqueous mobile phases in chromatography and reduce halogenated solvent usage; when possible, employ solid-phase extraction (SPE) for sample cleanup to cut solvent volumes.
Waste segregation: Separate aqueous from organic and halogenated streams to enable appropriate treatment and reduce incineration volume.
Illustrative comparison (qualitative)
Solvent for stock solutions: Water or aqueous buffer (greener) vs. high-boiling polar aprotics like DMF (less preferred). Trade-off: Water may limit long-term stability; DMF/DMSO enhance solubility but have higher environmental and health burdens.
Note
No item-specific environmental metrics are provided. Apply your organization’s green chemistry guidelines to optimize solvent choice and scale.
Pharmaceutical Uses
Scope of this section
No therapeutic or clinical claims are made. Content below addresses formulation and manufacturing context from a research/QC perspective.
General context (literature)
Salt selection: The sulfate form of basic small molecules is commonly chosen to enhance aqueous solubility, improve crystallinity, and enable robust solid-state properties for processing. Stoichiometry and hydrate state influence dissolution rate and stability; these must be verified experimentally.
Reference standard/QC use: Trimethoprim salts are used as analytical standards in method development and quality control, including assay, impurities profiling, and dissolution testing in development environments.
Compatibility: Excipients with anionic functionalities (e.g., cellulose derivatives, PVP when acidified) are generally compatible. Avoid strongly basic excipients or high-pH processing that can liberate free base and alter performance.
Item-specific information
Pharmacopeial status, excipient roles, and GMP attributes are not provided for this catalog item. If you require compendial compliance (USP/EP/JP), request documentation and ensure suitability for intended non-clinical applications only.
Physical Properties
Item-specific values
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Other specifications (mp/bp, density, solubility, refractive index, UV cutoff, residuals): Not specified for this item; refer to CoA/Spec Sheet.
General/literature context for trimethoprim sulfate (informational only; verify per lot)
Physical state: typically an off-white to beige crystalline powder (literature).
Salt behavior: inorganic sulfate counterions usually impart markedly higher water solubility relative to the free base (qualitative, literature). Aqueous solubility generally increases with ionic strength and decreases in strong basic conditions where deprotonation of the cation occurs.
Thermal properties: many organic sulfate salts soften and decompose rather than show a sharp melt; decomposition can begin prior to clear melting (literature behavior of amine sulfates).
pKa/logP: The free base contains basic diaminopyrimidine nitrogens (pKa values in the basic range for conjugate acids; literature for the free base). Salt formation shifts apparent pKa and partitioning to favor aqueous phase.
Hygroscopicity: amine sulfate salts may exhibit mild hygroscopicity depending on crystal form (literature). Store tightly closed to minimize moisture uptake.
Important
Do not treat the above as product specifications. For experimental planning, consult the CoA/SDS of this specific item to obtain authoritative values.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality for this compound class
Identity assurance: For small-molecule reference standards and research reagents like trimethoprim sulfate, identity is typically confirmed by NMR, MS, and/or HPLC/GC purity. The sulfate stoichiometry and hydration state (if any) should be clearly indicated on the CoA.
Purity metrics: Reported purity may be by HPLC area % or by titration for salt content. Residual solvents, water content (Karl Fischer), inorganic impurities (sulfate balance), and counterion stoichiometry are common quality attributes.
UV behavior: Diaminopyrimidine/anisole chromophores absorb in the near-UV; low baseline drift solvents are preferred for chromatographic purity checks. If an “HPLC grade” solvent is referenced in your method, verify UV cutoff and background.
Lot-to-lot verification: Salt form and polymorph can influence solubility and assay response. Confirm the exact form (mono-/hemi-/bis-sulfate, hydrate state) for quantitative work.
Recommendations
Request and review the CoA for your lot for: precise salt stoichiometry, purity assay method and result, residual solvent panel, water content, and any metal/elemental impurity data if applicable to your workflow.
Reaction and Applications
Item-specific application text
Manufacturer Applications: Not specified for this item in the catalog entry.
Research uses (general; for laboratory research only)
Enzymology and microbiology research: Widely used as a dihydrofolate reductase (DHFR) inhibitor standard in biochemical assays and microbial susceptibility testing (literature). Useful as a positive control compound when benchmarking DHFR assays, folate pathway studies, or transporter investigations. No clinical/medical claims are made here.
Analytical reference: Serves as a reference material for method development/validation (HPLC/LC–MS) in complex matrices due to its aromatic/heteroaromatic chromophore and ionizable centers.
Supramolecular/host–guest: The cationic nature of the sulfate salt can support studies in ion-pairing chromatography or interactions with polyanionic hosts.
Practical tips
Stock preparation: Prepare fresh aqueous or DMSO stock solutions; filter to remove particulates. Record exact salt form to enable molarity corrections.
Ionization considerations: Activity in enzyme assays depends on free base availability at the active site; maintain physiologically relevant pH (e.g., pH 6–8) and consistent ionic strength.
Controls: Include vehicle controls (e.g., DMSO) and, where relevant, a heat-inactivated enzyme control to distinguish specific from nonspecific effects.
Reminder
This product is for research use only. For precise procedures or validated methods, consult peer-reviewed literature and your institutional SOPs.
Reaction Conditions
Not primarily applicable as a reagent.
Trimethoprim sulfate is generally used as a research standard or bioactive probe rather than as a substrate/reagent in named organic reactions. Consequently, there are no canonical “reaction conditions” associated with its use.
Stock solutions: Prepare at convenient concentrations (e.g., millimolar range) in water, aqueous buffer, or DMSO depending on assay needs. Filter sterilize if required for microbiological or cell-free systems. Record salt form for molarity calculations.
Working solutions: Dilute into assay buffer just before use to minimize adsorption or degradation. Maintain consistent cosolvent levels across controls and treatments.
Temperature/pH: Typical biochemical assays for DHFR and related enzymes are run near neutral pH and ambient to 37 °C; optimize per your enzyme source and SOPs.
Important
No item-specific kinetic parameters, stability, or degradation profiles are provided. Validate conditions empirically and consult the SDS for any incompatibilities.
Safety and Handling
Item-specific safety details
GHS classification: Not specified for this item; refer to SDS.
Signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General safety guidance (informational; defer to SDS)
Likely hazards: organic amine sulfate salts can cause eye/skin irritation and respiratory tract irritation as dusts. Avoid inhalation of powders and contact with eyes/skin.
PPE: wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle solids in a fume hood or ventilated enclosure to control dust.
First aid overview: If inhaled—move to fresh air; if on skin—wash with soap and water; if in eyes—rinse with water for several minutes; if ingested—rinse mouth. Seek medical attention as needed. Follow site-specific EHS procedures.
Fire safety: Although sulfate counterions can dampen combustibility versus free bases, treat as a combustible organic solid. Use CO2, dry chemical, or water spray as appropriate. Combustion may produce nitrogen oxides and sulfur oxides; firefighters should wear SCBA.
Incompatibilities: Strong bases (can liberate free base), strong oxidizers, and strong acids (additional protonation) may be incompatible depending on conditions. Avoid moisture if the material is hygroscopic.
Handling tips: Minimize dust generation, use antistatic precautions when weighing dry powders, and keep container tightly sealed when not in use.
Authoritative information
Always consult the product’s Safety Data Sheet (SDS) for definitive hazard classifications, exposure controls, spill response, and disposal guidance.
Solvent Selection
Applicability
As a protonated amine sulfate salt, trimethoprim sulfate behaves as a polar, ionic compound. Solvent choice is driven by the need to keep the salt ionized (water and polar protic/strongly polar aprotic media) or to convert to the free base for solubility in organic phases.
General guidance (literature/experience)
Highly polar/protic solvents: Water and aqueous buffers generally afford good solubility for the sulfate salt. Methanol and ethanol can also dissolve the salt, especially with a small amount of water present.
Polar aprotic solvents: DMSO and DMF are effective for stock solutions; subsequent dilution into aqueous media is typical for bioassays. Minimize final DMSO to ≤1–2% v/v in enzyme/cell assays as needed.
Nonpolar/medium polarity solvents: Solubility of the sulfate salt in solvents like ethyl acetate, dichloromethane, or toluene is poor. If nonaqueous work-up is required, basify to generate the free base (handle as a separate material and verify identity).
Selection tips
For analytical standards: Prepare concentrated stocks in DMSO or water, filter (0.22 µm) if needed, then dilute into assay buffer.
For extractions/partitioning: Adjust pH to control ionization state—acidic to maintain as salt (aqueous phase), basic to liberate free base (organic phase). Verify recovery and stability after pH shifts.
Note
No item-specific solubility data are provided; consult the CoA/SDS and perform a small-scale solubility check under your exact conditions.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (as provided). Protect from moisture; keep container tightly closed.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling
Solvents: Not specified for this item; refer to CoA/Spec Sheet. In general laboratory practice, the sulfate salt is commonly dissolved in water, aqueous buffer, or DMSO to prepare stock solutions (literature guidance).
Concentration tracking: Record the exact salt form and calculate concentrations as free base equivalents when needed. Use clean, dry glassware. If sterility is required, filter through 0.22 µm membranes; avoid heat sterilization unless stability is verified.
Freeze–thaw: Not specified for this item; refer to CoA/Spec Sheet. If frozen aliquots are prepared for convenience, minimize repeated freeze–thaw cycles by dispensing single-use aliquots.
Stability notes (general)
Avoid prolonged exposure to high pH which may liberate the free base and change solubility. Store away from strong oxidizers and direct light.
Documentation
For definitive shelf life, impurity limits, and reconstitution guidance, consult the product’s CoA and SDS. This product is for research use only.
Structure and Identity
Item-specific identifiers (from Product Data)
SKU: T955040
Product name: Trimethoprim Sulfate
CAS: 56585-33-2
PubChem CID: 64936
InChIKey: 360749 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
General structural description (literature)
Trimethoprim is a 2,4-diaminopyrimidine bearing a 3,4,5-trimethoxybenzyl substituent at C-5 of the pyrimidine ring. The sulfate form is an inorganic acid salt formed by protonation/association with sulfuric acid (stoichiometry varies by supplier; verify on CoA).
Key functional groups: diaminopyrimidine heteroaromatic core, anisole-type aryl trimethoxy substituents, benzylic linker to the heteroarene; sulfate counterion(s) confer ionic character and enhanced aqueous solubility.
2D description: a para-extended system where a substituted phenyl (3,4,5-trimethoxy) connects via a methylene to a pyrimidine ring bearing exocyclic amino groups at C-2 and C-4. The sulfate is not covalently bound to the organic scaffold but present as counterion(s).
Notes
For exact salt stoichiometry, definitive structural identifiers (SMILES, exact InChIKey) and analytical characterization, consult the product’s Certificate of Analysis (CoA) and specification sheet for this specific lot.
Synthetic Utility
Applicability
As an end-use bioactive small molecule, trimethoprim sulfate is not commonly used as a synthetic reagent. Nevertheless, its functional groups allow derivatization for probe development and SAR studies in a research setting.
General reactivity considerations (literature)
Aminopyrimidine core: The exocyclic amino groups can participate in acylation, sulfonylation, or selective protection to modulate binding or physicochemical properties. Electrophilic substitution on the heteroarene is generally low; cross-coupling requires prefunctionalization.
Benzylic position: The methylene linker can be oxidized or converted into linkers (e.g., via halogenation followed by substitution) for affinity probes or conjugates.
Trimethoxyphenyl ring: Methoxy groups can undergo demethylation under strong conditions (e.g., BBr3) to phenols, enabling further diversification (note: such conditions are incompatible with the sulfate salt; transformations are typically performed on the free base).
Salt form considerations: Synthetic manipulations generally begin by liberating the free base (basification and extraction), followed by standard organic synthesis steps. Reconversion to the sulfate can be performed via controlled protonation with sulfuric acid in a suitable solvent system.
Note
No item-specific synthetic procedures or reactivity data are provided. For any modification work, confirm identity and purity at each stage (NMR, LC–MS, HRMS) and document the salt stoichiometry on re-salting.
Target Specificity
Item-specific limitations
Target/antigen specificity, epitope information, clone/isotype, and species reactivity are not applicable to this small-molecule product and are not provided in the Product Data.
General note
In biochemical research, trimethoprim is studied for interaction with dihydrofolate reductase (DHFR). However, no target-binding specifications, potencies, or selectivity data are provided for this catalog item. Users should consult primary literature and determine activity under their experimental conditions.
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