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Ethylhexyl triazone's primary mechanism of action is as a physical UV-B filter. It absorbs ultraviolet radiation and dissipates the energy through an ultrafast internal conversion process, returning to its ground state and allowing for multiple absorption cycles. Its large molecular weight is a key property that prevents significant skin penetration, thereby minimizing systemic exposure and potential side effects.
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| ln Vitro |
Ethylhexyltriazone (EHT) has a large molecular weight (823.07 g/mol), which makes it a filter with a lower likelihood of penetrating the skin and a lower potential for side effects. With the highest absorption of ethylhexyltriazone-dioxane and ethylhexyltriazone-methanol at about 311 and 313 nm, respectively, it displays a broad absorption curve in the UV-B region [1].
In vitro studies primarily characterize Ethylhexyl triazone's photoprotective and physicochemical properties. It exhibits antioxidant activity, as demonstrated by DPPH free radical scavenging assays, though this activity is relatively low (3.5% at 400 µM). Its strong UV-B absorption is confirmed via spectrophotometric analysis, with an in vitro SPF value of 3.0 and a UVA to UVB ratio of 0.8. |
| ln Vivo |
In vivo efficacy is established through the compound's application in sunscreen formulations, where it demonstrates effective photoprotection by reducing erythema (sunburn) and preventing UV-induced skin damage, such as photoaging. Its low water solubility makes it suitable for water-resistant sunscreen products, ensuring long-lasting protection.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assay for Ethylhexyl triazone is not standard as it is a UV filter. However, its photoprotective activity is assessed by measuring UV absorption spectra using a spectrophotometer. The compound's absorbance is scanned across the UV spectrum (280-400 nm) in a suitable solvent like ethanol to determine its maximum absorbance wavelength and extinction coefficient, confirming its efficacy as a UV-B filter.
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| Cell Assay |
In vitro cellular assays are not typically performed for Ethylhexyl triazone because it is designed to remain on the skin's surface. Instead, its safety and lack of cytotoxicity can be evaluated using in vitro skin models, such as reconstructed human epidermis (RHE), where the compound is applied topically to assess for cell viability (via MTT assay) and tissue integrity, confirming its low potential for skin irritation.
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| Animal Protocol |
In vivo animal studies are not standard for this compound, as it is a cosmetic ingredient. Historically, phototoxicity and skin sensitization potential may have been evaluated in animal models (e.g., guinea pigs) as part of safety assessments. However, current practice relies on ex vivo human skin models and clinical patch testing in humans for regulatory approval.
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| ADME/Pharmacokinetics |
Ethylhexyl triazone is an oil-soluble, highly lipophilic compound. It is practically insoluble in water, which contributes to its residence on the skin surface and its suitability for water-resistant formulations. It is typically formulated in the oil phase of emulsions. The compound demonstrates excellent photostability, meaning it does not readily degrade upon UV exposure, providing long-lasting protection.
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| Toxicity/Toxicokinetics |
Ethylhexyl triazone is considered to have a low potential for toxicity due to its large molecular weight, which prevents significant skin absorption and systemic exposure. It is not classified as a skin sensitizer or irritant at the low concentrations used in sunscreens. However, like many UV filters, it is an environmental contaminant of concern, and its effects on aquatic life are an area of ongoing research.
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| References | |
| Additional Infomation |
See also: ...View more...
Ethylhexyl triazone is approved as a UV-B filter in sunscreens and cosmetic products under various international regulations. It is often used in combination with other UV filters, such as avobenzone or octocrylene, to provide broad-spectrum (UVA/UVB) protection. It is not a drug and has no therapeutic indications, but its role is exclusively as a preventative agent against sun-induced skin damage. |
| Molecular Formula |
C48H66N6O6
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|---|---|
| Molecular Weight |
823.0743
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| Exact Mass |
822.504
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| CAS # |
88122-99-0
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| PubChem CID |
159201
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
869.5±75.0 °C at 760 mmHg
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| Melting Point |
128°
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| Flash Point |
479.6±37.1 °C
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| Vapour Pressure |
0.0±3.3 mmHg at 25°C
|
| Index of Refraction |
1.576
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| LogP |
15.53
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
30
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| Heavy Atom Count |
60
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| Complexity |
1030
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
JGUMTYWKIBJSTN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C48H66N6O6/c1-7-13-16-34(10-4)31-58-43(55)37-19-25-40(26-20-37)49-46-52-47(50-41-27-21-38(22-28-41)44(56)59-32-35(11-5)17-14-8-2)54-48(53-46)51-42-29-23-39(24-30-42)45(57)60-33-36(12-6)18-15-9-3/h19-30,34-36H,7-18,31-33H2,1-6H3,(H3,49,50,51,52,53,54)
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| Chemical Name |
2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~30 mg/mL (~36.45 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.04 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 (3.04 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (3.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2150 mL | 6.0748 mL | 12.1496 mL | |
| 5 mM | 0.2430 mL | 1.2150 mL | 2.4299 mL | |
| 10 mM | 0.1215 mL | 0.6075 mL | 1.2150 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.
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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