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Sulcotrione

Alias: SC-0051; SC 0051; Sulcotrione
Cat No.:V15449 Purity: ≥98%
Sulcotrione is a beta-triketone herbicide that can inhibit hydroxyphenylpyruvate dioxygenase (HPPD).
Sulcotrione
Sulcotrione Chemical Structure CAS No.: 99105-77-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Sulcotrione is a beta-triketone herbicide that can inhibit hydroxyphenylpyruvate dioxygenase (HPPD).
Sulcotrione (CAS#: 99105-77-8) is a benzoylcyclohexanedione herbicide that inhibits 4-hydroxyphenylpyruvate dioxygenase (HPPD), a key enzyme in the biosynthesis of plastoquinone and tocopherols. It is a selective herbicide used for the control of broadleaf weeds and some grasses in corn and other crops. Sulcotrione is a herbicide (benzoylcyclohexanedione herbicide).
Biological Activity I Assay Protocols (From Reference)
Targets
Sulcotrione targets 4-hydroxyphenylpyruvate dioxygenase (HPPD), an enzyme involved in the biosynthesis of plastoquinone and tocopherols. By inhibiting HPPD, sulcotrione blocks the production of plastoquinone, which is essential for carotenoid biosynthesis and photosynthesis. This leads to the bleaching of plant tissues and eventually plant death.
ln Vitro
The outcomes demonstrate that sultrione functions as a reversible inhibitor independent of time. Comparable outcomes were previously shown for both synthetic β-triketone NTBC and natural β-triketone. Nevertheless, this is the first time that a synthetic β-triketone (sulfotrione) and purified hydroxyphenylpyruvate dioxygenase (HPPD) have been used to examine this behavior. The investigation of inhibition kinetics for concentrations of sulfotrione and 3-hydroxyphenylpyruvate (HPP) revealed that apparent KM rose as sulfotrione concentration increased. This activity is in line with information found in publications characterizing sunotrione as an HPPD competitive inhibitor [1].
In vitro, sulcotrione inhibits HPPD activity. It is a selective herbicide that is effective against a variety of broadleaf weeds and some grasses. Its herbicidal activity is well-characterized.
ln Vivo
In vivo, sulcotrione is used as a post-emergence herbicide for the control of broadleaf weeds and some grasses in corn and other crops. It is applied to the foliage of weeds, where it is absorbed and inhibits HPPD. It is effective against a variety of weeds.
Enzyme Assay
In vitro enzyme/receptor binding assays for sulcotrione typically involve evaluating its inhibitory activity against purified HPPD. The enzyme is incubated with varying concentrations of sulcotrione and its substrate, 4-hydroxyphenylpyruvate. The reaction is monitored by measuring the formation of homogentisate, and the IC₅₀ is determined.
Cell Assay
For in vitro cell-based assays, sulcotrione is dissolved in DMSO or organic solvents and applied to cultured plant cells or algae at concentrations ranging from 0.1-100 µM. The effects on photosynthesis, carotenoid biosynthesis, and cell viability are assessed after 24-72 hours of treatment.
Animal Protocol
In vivo animal studies for sulcotrione are typically toxicological studies conducted in rodents. The compound is administered orally at doses ranging from 100-1000 mg/kg. The effects on body weight, organ weights, hematological parameters, and histopathology are evaluated.
ADME/Pharmacokinetics
Sulcotrione has a molecular formula of C₁₄H₁₃ClO₅S and a molecular weight of 328.77 g/mol. It is a light brown solid with a solubility in water of 165 mg/L at 25°C. It is soluble in acetone and chlorobenzene. It is typically stored at room temperature.
Toxicity/Toxicokinetics
Sulcotrione is considered to have low toxicity to mammals. The oral LD₅₀ in rats is >5000 mg/kg. It may cause skin and eye irritation.
References
[1]. Rocaboy-Faquet E, et al. A novel amperometric biosensor for ß-triketone herbicides based on hydroxyphenylpyruvatedioxygenase inhibition: A case study for sulcotrione. Talanta. 2016;146:510-
Additional Infomation
Sulfonyltrione is an aromatic ketone, a compound in which cyclohexane-1,3-dione is substituted at the 2-position with a 2-chloro-4-(methanesulfonyl)benzoyl group. It is an environmental pollutant, exogenous substance, herbicide, and inhibitor of carotenoid biosynthesis. It is an aromatic ketone, sulfone, cyclohexanone, and β-trione.
Sulcotrione is a benzoylcyclohexanedione herbicide used for the control of broadleaf weeds and some grasses in corn and other crops. It is also known as Milestone. Sulcotrione is approved for agricultural use in many countries. It is supplied by various chemical suppliers for agricultural and research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H13CLO5S
Molecular Weight
328.76
Exact Mass
328.017
CAS #
99105-77-8
PubChem CID
91760
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
574.5±50.0 °C at 760 mmHg
Melting Point
139ºC
Flash Point
301.2±30.1 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.572
LogP
0.21
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
546
Defined Atom Stereocenter Count
0
SMILES
ClC1C([H])=C(C([H])=C([H])C=1C(C1([H])C(C([H])([H])C([H])([H])C([H])([H])C1=O)=O)=O)S(C([H])([H])[H])(=O)=O
InChi Key
PQTBTIFWAXVEPB-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H13ClO5S/c1-21(19,20)8-5-6-9(10(15)7-8)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3
Chemical Name
2-(2-chloro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione
Synonyms
SC-0051; SC 0051; Sulcotrione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~304.16 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0417 mL 15.2087 mL 30.4173 mL
5 mM 0.6083 mL 3.0417 mL 6.0835 mL
10 mM 0.3042 mL 1.5209 mL 3.0417 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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