This compound belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.
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
224.210 g/mol
XLogP3
0.200
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Exact Mass
224.068 Da
Monoisotopic Mass
224.068 Da
Topological Polar Surface Area
91.700 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
383.000
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
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
Manufacturer-tested application protocols are not provided for this SKU. The following are general, literature-informed practices for plant biology assays with trinexapac-class tools; verify and optimize for your system.
Stock and dilution (general):
Prepare 10–50 mM stock in DMSO or ethanol; store aliquots. Immediately before use, dilute into growth medium or buffer; keep final organic solvent ≤0.1–0.5% v/v.
Dose setting and controls:
Establish a pilot range over several orders of magnitude (e.g., 0.01–100 µM, literature-scale) to map response curves. Include vehicle controls and, where relevant, GA add-back (e.g., GA3) to assess pathway specificity.
Application modes:
Seed/seedling exposure on agar or hydroponic media; foliar sprays or droplet application with defined surfactants; petiole feeding for dicots. Record exact developmental stage and environmental conditions (photoperiod, temperature, humidity).
Readouts:
Internode length, leaf sheath length, biomass, and transcript markers of GA signaling; image-based phenotyping improves throughput. Validate uptake and stability analytically when feasible.
Safety and handling:
Prepare solutions in a fume hood, avoid skin contact with concentrated stocks, and dispose of waste properly.
Note: Item-specific solubility, potency, and stability are not specified for this SKU; consult the CoA/SDS and perform system-specific qualification experiments.
Biological Roles
Scope: The following summarizes literature/general knowledge for trinexapac-class compounds; it is not an item-specific claim.
Mode of action (literature): Trinexapac‑ethyl is hydrolyzed in plants to the corresponding acid (trinexapac), which is reported to inhibit a late step in gibberellin (GA) biosynthesis, commonly associated with GA 3-oxidase activity (conversion of GA20 to GA1). The resulting reduction in bioactive GA levels diminishes cell elongation, producing shorter internodes and reduced lodging propensity, especially in grasses and cereals.
Research utility:
Dissecting GA signaling: Used to modulate GA-dependent gene expression, dwarfing phenotypes, and developmental timing; facilitates differential expression and hormone crosstalk studies (e.g., GA–ABA–BR interactions).
Metabolism and fate: Employed to study uptake, hydrolysis kinetics (for the ethyl ester), conjugation, and transport in plant tissues; serves as an analyte in environmental fate assessments (soil/water photolysis, plant metabolism).
Phenotyping: Dose-dependent growth responses (e.g., reductions in leaf sheath elongation) provide quantifiable endpoints for comparing genotype sensitivity or pathway engineering strategies.
Off-target considerations (literature): At high concentrations, broader impacts on primary metabolism and stress responses can occur; include solvent and vehicle controls and, where possible, GA rescue experiments to confirm pathway specificity.
Note: No medical or clinical uses are implied. All uses are for laboratory research only.
Buffer Applications
Not a classical buffering reagent. However, for biological assays with trinexapac-class compounds, preparation and dilution into buffered media is routine.
Practical guidance (general/literature):
Stock solutions: Frequently prepared at 10–50 mM in DMSO or ethanol. Filter-sterilize if required through PTFE (0.2 µm). Record solvent percentage.
Working solutions: Dilute into plant growth media or assay buffers (e.g., 1× MS salts, phosphate or MES-buffered solutions) with final organic solvent typically kept ≤0.1–0.5% v/v to minimize solvent effects.
pH control: If handling the free acid, avoid high pH during prolonged incubations unless testing the anionic form; pH can influence uptake and activity.
Adsorption: To reduce adsorption losses to plastics, use glassware for concentrated stocks and minimize standing times before application.
Item-specific buffer compatibility and solubility are not specified for this SKU; confirm empirically and consult the CoA/SDS.
Green Alternatives
This product is a research chemical/biological tool rather than a process solvent; a “green alternative solvent” discussion is not directly applicable.
Greener practices around its use (general):
Prefer low-toxicity, high-volatility solvents (e.g., acetonitrile over chlorinated solvents) for analytical sample prep to reduce waste persistence; evaluate ethanol or isopropanol where performance allows.
Apply microscale bioassays and analytical methods to minimize chemical use and waste.
Implement efficient solid-phase extraction (SPE) or QuEChERS-type protocols to cut down solvent volume in residue analysis.
Segregate halogenated vs non-halogenated waste streams to maximize recycling options.
If you require an alternative probe for GA-pathway studies with improved environmental profile, survey the literature for newer inhibitors with documented biodegradation/fate data; select based on hazard assessments and effectiveness in your specific plant system.
Pharmaceutical Uses
Not applicable. Trinexapac is a research chemical used predominantly in plant science contexts and as an analytical reference related to plant growth regulation chemistry.
It is not described here as a pharmaceutical active ingredient or excipient. No pharmacopeial status is indicated for this SKU.
For formulation-like considerations in laboratory settings (general): investigators may prepare defined solvent vehicles (e.g., DMSO, ethanol, or PEG-containing aqueous mixtures) for dosing in plant or cell-based assays, but this is strictly for research use.
Physical Properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (BP): Not applicable for many solids; if molten, literature data should be consulted. Item-specific BP: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable for solids; item-specific value not specified.
pKa: Not specified for this item; refer to CoA/Spec Sheet. (General/literature: the free acid of cyclohexenone carboxylates typically has an acidic pKa in the ~3–5 range; consult primary data for trinexapac specifically.)
LogP/LogD: Not specified for this item; refer to CoA/Spec Sheet. (General: growth-regulator cyclohexenones often display moderate hydrophobicity; verify experimentally for your batch and solvent system.)
Solubility: Not specified for this item; refer to CoA/Spec Sheet. Practical note: for assay stock solutions, many users evaluate DMSO, acetone, acetonitrile, methanol/ethanol, or mild aqueous base if handling the acid form. Always confirm with small-scale tests.
Hygroscopicity/photolability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution with conjugated enones and carboxylic acids, minimize prolonged light exposure and moisture until item-specific guidance is confirmed.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
What to expect on the CoA (typical for research chemicals):
Assay/purity by HPLC/GC or qNMR.
Identity by NMR/IR/MS and CAS match.
Water content (e.g., Karl Fischer) and residual solvents (if applicable). For this SKU, specific values are not provided here.
Implications for research use:
Analytical applications (e.g., LC–MS reference standards) benefit from well-characterized purity and known counter-ions/salt forms. Confirm whether the substance is the free acid, an ester, or a salt.
For biological assays, low levels of non-volatile impurities and well-documented stability in chosen solvent are critical; review the CoA and, if needed, perform incoming QC (HPLC purity check, mass confirmation).
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. If stabilizers are present, consider their UV and MS background when planning analytical methods.
Batch-to-batch consistency: Maintain batch records with the CoA to ensure reproducibility across experiments, especially for dose–response or time-course studies.
Reaction and Applications
This SKU is positioned under Life Science; no manufacturer applications were provided. The guidance below reflects typical research uses of trinexapac-class chemistries (literature/general) and not item-specific performance claims.
Research applications (general):
Plant physiology: Probe of gibberellin (GA) biosynthesis. Trinexapac (acid form) is a known active metabolite of trinexapac‑ethyl and is frequently used as a reference standard or tool compound in studies of GA pathway modulation, internode elongation, and lodging resistance phenotypes in grasses. It is associated with inhibition at late GA steps (e.g., GA 3-oxidase activity) in literature.
Analytical: Reference material for LC–MS/GC–MS method development in environmental fate and residue analysis; hydrolysis profiling of the ethyl ester; calibration of metabolite identification workflows.
Chemical reactivity (general for the acid form):
The carboxylic acid can be derivatized to esters (e.g., re-generation of ethyl ester) or converted to amides via standard coupling (EDC/HOBt, DIC/DMAP, etc.), enabling labeled conjugates for analytical or immobilization studies.
The conjugated enone motif (if present) participates in Michael-type additions and can undergo reduction/oxidation under suitable conditions; protect from strong nucleophiles if structural integrity must be preserved for bioassays.
Practical tips:
For bioassay stocks, prepare small aliquots to minimize freeze–thaw; assess stability by LC at intended storage and use conditions.
When quantifying in complex matrices, include isotopically labeled internal standards where available for accurate recovery correction.
Reaction Conditions
No manufacturer-recommended reaction conditions are provided for this SKU. Below are general, literature-informed conditions relevant to handling trinexapac-class compounds in synthesis or analytical preparation.
Hydrolysis/esterification (general):
Ester hydrolysis to acid: Aqueous base (e.g., NaOH, K2CO3) in MeOH/H2O or THF/H2O at 0–40 °C; monitor by LC; then acidify and isolate the free acid.
Re-esterification (acid to ester): Steglich esterification (DCC or DIC, catalytic DMAP) in DCM or acetonitrile at 0–25 °C; or Fischer conditions in anhydrous alcohol with catalytic acid.
Amide coupling (general):
EDC·HCl/HOBt or HATU in DMF or acetonitrile, base (DIPEA), 0–25 °C, 1–18 h; workup and RP-HPLC purification for analytical conjugates.
Stability checks:
Assess solution stability in DMSO, MeOH, and aqueous buffers by LC–UV/MS over intended use timescales; protect from strong base if ester groups are present.
Analytical method development:
RP-LC: Water/acetonitrile with 0.1% formic acid or ammonium formate; monitor 210–230 nm and compound-specific maxima if known; ESI-MS in negative mode often favors acids; positive mode may observe adducts or neutral losses for esters.
These conditions are general guidance from literature/experience; tailor to your verified structure and intended transformation. Item-specific conditions are not specified for this SKU.
Safety and Handling
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General laboratory precautions (good practice):
Handle in a fume hood with appropriate PPE: lab coat, safety glasses, and suitable chemical-resistant gloves.
Avoid inhalation of dust/aerosols and contact with skin/eyes. Prevent environmental release; collect waste appropriately.
If preparing concentrated DMSO/organic stocks, prevent skin contact to avoid enhanced dermal uptake via solvents.
First-aid overview (refer to SDS for authoritative instructions):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities and stability (general):
Avoid strong oxidizers. If working with the ester analogs, avoid strong bases and nucleophiles that can induce rapid hydrolysis/transesterification; for the free acid, strong bases will form salts and alter solubility/partitioning.
Protect from excessive heat and light until item-specific stability is known.
Spill/waste: Absorb small spills with inert material; dispose as organic chemical waste in accordance with institutional and local regulations.
Always defer to the product-specific SDS and institutional EHS guidance for risk assessment and controls.
Solvent Selection
Item-specific solubility is not provided; the following are general, literature-informed practices for cyclohexenone carboxylate growth-regulator chemistries:
Common stock solvents: DMSO (analytical grade), acetone, acetonitrile, methanol or ethanol due to their ability to solubilize moderately lipophilic acids/esters.
Aqueous handling: If the active is the free acid, slight basification (e.g., dilute NaOH or buffered pH > 7) can increase aqueous solubility by forming the carboxylate; avoid strong base if working with ester analogs to prevent hydrolysis.
Nonpolar media: If required, ethyl acetate or isopropyl acetate may dissolve neutrals/esters; verify compatibility with plastics and seals.
Selection strategy for your application:
Bioassays: DMSO stocks (10–50 mM) diluted into aqueous buffers with final DMSO ≤0.1–0.5% v/v to minimize biological solvent effects. Validate precipitation limits empirically.
Chromatography: For reverse-phase LC, mobile phases of water/acetonitrile or water/methanol with 0.1% formic acid or ammonium buffers are typical; verify UV response and ionization in your MS source.
Practical comparison (general):
DMSO: highest solvating power; potential biological effects at >0.5%.
Container and environment: Keep tightly closed in the original container. Until item-specific hygroscopicity/photolability are known, store in a dry place, protected from excessive light.
Long-term stability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, minimize repeated container opening and exposure to ambient humidity.
Reconstitution/stock preparation (general guidance for research use):
Prepare concentrated stocks in dry, high-purity solvent (e.g., DMSO, acetonitrile, ethanol) after confirming solubility. Filter if necessary through PTFE (0.2 µm).
Aliquot working stocks to avoid freeze–thaw cycles; for solution storage beyond a few days, many labs keep aliquots at −20 °C or 2–8 °C protected from light. Verify stability for your solvent and concentration.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Note: All handling is for research use only, as indicated in the Product Data. Always consult the product-specific SDS for authoritative safety and storage guidance.
Structure and Identity
Item-specific identifiers
CAS: 143294-89-7 (from Product Data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data shows an incomplete value)
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.
Naming note (literature/general): “Trinexapac” is commonly used to denote the carboxylic-acid form produced by hydrolysis of the plant growth regulator trinexapac‑ethyl. Many publications discuss biological activity in the context of the ethyl ester as the applied agent and the acid as the active metabolite in planta. Always confirm whether the SKU corresponds to the free acid or an ester/other salt form via the CoA.
Structural features (general/literature): The trinexapac scaffold belongs to the cyclohexenone carboxylate family of growth regulation chemistry. The acid form presents a carboxylic acid moiety capable of forming salts, esters, and amides. The core enone is conjugated and can exhibit keto–enol tautomerism in protic or basic media. Exact stereochemical descriptors and ring substitution pattern must be verified on the item’s CoA/SDS for unambiguous registration and informatics use.
Informatics guidance: For ELN/LIMS registration where full identifiers are required, use the certificate-specific SMILES/InChIKey. If you work across both trinexapac and trinexapac‑ethyl, keep separate compound IDs and cross-reference by CAS and structural identifiers to avoid mix-ups in analytics and inventory.
Synthetic Utility
Item-specific functionalization data are not provided; the following reflects general reactivity patterns of trinexapac-class scaffolds.
Functional group handles (general):
Carboxylic acid (for the acid form): amenable to esterification (Fischer, Steglich), amidation (carbodiimide couplings), and salt formation with inorganic/organic bases. These derivatizations enable conjugation to labels or carriers for analytical and biochemical studies.
Conjugated enone (if present): susceptible to 1,4-additions, reductions (e.g., catalytic hydrogenation or hydride reagents with selectivity control), and reversible Michael adduct formation under certain conditions—consider implications for biological integrity.
Applications in method development:
Synthesis of isotopically labeled standards via incorporation at the carboxylate or ring positions for LC–MS quantitation.
Generation of prodrugs/esters to modulate solubility and uptake in plant systems for mechanistic experiments.
Precautions:
Avoid over-basic conditions when ester integrity must be preserved; conversely, leverage mild base or enzyme catalysis for controlled hydrolysis to the acid.
Protect conjugated systems from prolonged exposure to strong nucleophiles and light to prevent unintended side reactions.
For exact transformations applicable to this SKU, consult detailed structural data on the CoA.
Target Specificity
Not applicable. This product is not an antibody, enzyme prep, or receptor ligand with validated target binding data provided by the manufacturer for this SKU.
Literature context: In plant systems, trinexapac-class compounds are used as chemical probes associated with inhibition within the gibberellin biosynthetic pathway (often attributed to GA 3-oxidase). This is mechanistic background for research planning only and not an item-specific specification.
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