| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C16H17N3O5S |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Topramezone is a potent inhibitor of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD). It is a herbicide used for post-emergence control of broadleaf and grass weeds in corn[1]. It is supplied as a light yellow to yellow solid (C16H17N3O5S, MW 363.39) at 99.95% purity.
Physical & Chemical Properties
| CAS Number | 210631-68-8 |
|---|---|
| Molecular Formula | C16H17N3O5S |
| Molecular Weight | 363.39 g/mol |
| Purity | 99.95% |
| Appearance | Solid |
| Color | Light yellow to yellow |
| SMILES | O=C(C1=CC=C(S(=O)(C)=O)C(C2=NOCC2)=C1C)C3=C(O)N(C)N=C3 |
| Signaling Pathway | NF-κB; Metabolic Enzyme/Protease; Immunology/Inflammation |
| Solubility | In Vitro: DMSO: 116.67 mg/mL (321.06 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) H2O: < 0.1 mg/mL (insoluble) |
| Storage | 4°C, protect from light. In solvent: -80°C, 6 months; -20°C, 1 month (protect from light). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 116.67 mg/mL (321.06 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
| H2O | < 0.1 mg/mL | insoluble |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); protect from light; avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
Topramezone (5, 10, 20, 30, 45 mg/L; 24-96 h) inhibits growth of the alga C. vulgaris by triggering oxidative stress and damaging cell morphology and photosynthetic activity during exposure[1]. Topramezone (20 mg/L; 24, 48, 72 and 96 h) impairs the photosynthetic system by lowering photosynthetic pigment content, and induces ROS (oxidative stress) with a time-dependent increase in MDA[1]. Topramezone (20 mg/L; 96 h) compromises cell integrity, damages chloroplasts and membranes of algal cells, and triggers apoptosis[1]. Topramezone shows selectivity and inhibits 4-HPPD (recombinant enzyme protein) activity in vitro (0.1 nM-0.1 mM; 30 min), with IC50 values of 15 nM for Setaria faberi, 23 nM for Arabidopsis thaliana, and 180 nM for Corn[2]. Corn metabolizes foliar-applied Topramezone (containing [14C]topramezone of 0.29 μg; 24 and 48 h) faster than the weeds do[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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