Chemistry:3,4-Dimethoxystyrene
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3,4-Dimethoxystyrene (vinylveratrole) is an aromatic organic compound. It is a yellow oily liquid with a pleasant floral odor. Normally, it is supplied with 1-2% of the hydroquinone as an additive to prevent oxidation of the compound.
Occurrence
3,4-Dimethoxystyrene has been identified as a naturally occurring component in the liverwort Cyathodium foetidissimum [1]. 3,4-Dimethoxystyrene is also found in the essential oil of Brazilian propolis[2], as well as cereal and coffee products.[3]
Uses
- 3,4-Dimethoxystyrene is typically used in organic synthesis as a monomer in radical polymerization reactions due to the presence of the electron-deficient double bond.[4] This is similar to the parent compound styrene, which can be polymerized into polystyrene.
- 3,4-dimethoxystyrene can be deprotected using Lewis acid boron tribromide with almost 100% yield. The resulting compound 3,4-dihydroxystyrene is rapidly oxidized in air, which is why 3,4-dimethoxystyrene is preferred as a stable precursor in organic synthesis.
- It is an easily polymerizable precursor to polycatechols as it is less susceptible to oxidation in air than other precursors.[5]
Pharmacology
Pharmacokinetics
Once ingested, 3,4-Dimethoxystyrene is found in the cytoplasm, and extracellularly.[3]
Related compounds
- 3,4-Dihydroxystyrene
- Veratrole
References
- ↑ Sakurai, Tomiyama, Yaguchi, Kawakami, Asakawa (2017). https://www.iseoils.com/images/documents/boa/ISEO_book-of-abstract_2017.pdf https://www.iseoils.com Retrieved 19 November 2025.
- ↑ Kusumoto, Toshihide; Tomofumi, Miyamoto; Ryuichi, Higuchi; Shima, Doi; Hiroyuki, Sugimoto; Hideo, Yamada (2001). "Isolation and Structures of Two New Compounds from the Essential Oil of Brazilian Propolis". Chem. Pharm. Bull. 49 (9): 1207–1209. doi:10.1248/cpb.49.1207. PMID 11558615. http://cpb.pharm.or.jp/cpb/200109/c09_1207.pdf. Retrieved 10 September 2015.
- ↑ 3.0 3.1 "Human Metabolome Database: Showing metabocard for 1,2-Dimethoxy-4-vinylbenzene (HMDB0040359)". https://hmdb.ca/metabolites/HMDB0040359.
- ↑ Rooney, J.M. (1983). "Cationic polymerization of 3,4-dimethoxystyrene by trityl hexachloroantimonate". Polymer Bulletin 10 (9–10): 414–418. doi:10.1007/bf00262183.
- ↑ Daly, William H.; Moulay, Saad (2007). "Synthesis of poly (vinylcatechols)". Journal of Polymer Science: Polymer Symposia 74: 227–242. doi:10.1002/polc.5070740120. https://digitalcommons.lsu.edu/gradschool_disstheses/4197.
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