Property | Value |
Chemical Name | 3,5-Diacetoxystyrene (also known as 3,5-Bis(acetyloxy)styrene or 5-Ethenyl-1,3-benzenediol 1,3-diacetate) |
CAS Number | 155222-48-3 |
Molecular Formula | C₁₂H₁₂O₄ |
Molecular Weight | 220.22 g/mol |
Appearance | Not widely reported (likely colorless to pale yellow liquid or low-melting solid, typical for protected styrenes) |
Solubility | Soluble in organic solvents; low water solubility expected |
Stability | Stable under normal conditions; sensitive to polymerization inhibitors may be added; acetoxy groups hydrolyzable under basic/acidic conditions |
Description of 3,5-Diacetoxystyrene
3,5-Diacetoxystyrene (also known as 5-Ethenyl-1,3-benzenediol 1,3-diacetate, CAS: 155222-48-3) is a protected styrene derivative with the molecular formula C₁₂H₁₂O₄. It features acetyl groups protecting the 3,5-dihydroxy positions on the phenyl ring, enhancing stability and solubility during synthesis. It serves as a crucial intermediate in the production of resveratrol (trans-3,4',5-trihydroxystilbene), a natural polyphenol with antioxidant, anti-inflammatory, and potential health benefits.
Application of 3,5-Diacetoxystyrene
Key Intermediate for Resveratrol Synthesis. 3,5-Diacetoxystyrene is widely used as a protected building block in the synthesis of trans-resveratrol (3,4',5-trihydroxystilbene) via palladium-catalyzed Heck coupling with substituted iodobenzenes, followed by deprotection to yield the natural polyphenol with antioxidant properties.
Production of Resveratrol Analogs and Derivatives. It serves as a versatile precursor for preparing stilbene derivatives and resveratrol analogs, enabling structural modifications for pharmaceutical research and development of potential anti-inflammatory, anticancer, and neuroprotective compounds.
Fine Chemical and Pharmaceutical Intermediate. The acetyl-protected dihydroxy styrene unit provides stability during multi-step organic synthesis, making it valuable in medicinal chemistry for constructing polyphenolic frameworks.
Synthesis of Bioactive Stilbenoids. Used in the preparation of natural and synthetic stilbenoids, including combretastatin analogs and other microtubule-targeting agents studied for anticancer activity.
Research and Development Applications. Essential reagent in academic and industrial labs for exploring polyphenolic compounds with applications in nutraceuticals, cosmetics, and therapeutic agents.
Storage of 3,5-Diacetoxystyrene
It should be kept in a cool, dry, well-ventilated area at 2–8°C away from heat, sparks, and direct sunlight. Keep containers tightly sealed under an inert atmosphere (nitrogen preferred) to prevent moisture absorption, hydrolysis of acetoxy groups, and potential polymerization. Protect from strong bases, acids, oxidizers, and radical initiators. Handle in a dark place or amber containers to minimize light exposure.
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