Acetosyringone
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IUPAC name
4'-Hydroxy-3',5'-dimethoxyacetophenone
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| Other names
Acetosyringenin
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3D model (Jmol)
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| ECHA InfoCard | 100.017.828 |
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PubChem CID
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| Properties | |
| C10H12O4 | |
| Molar mass | 196.20 g·mol−1 |
| Melting point | 125.5 °C (257.9 °F; 398.6 K) |
| Boiling point | 335 °C (635 °F; 608 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Acetosyringone is a phenolic natural product, and is a chemical compound related to acetophenone and 2,6-dimethoxyphenol. It was first described in relation to lignan/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.
Historically, this substance has been best known for its involvement in plant-pathogen recognition, especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus Agrobacterium. The virA gene on the Ti plasmid of Agrobacterium tumefaciens and the Ri plasmid of Agrobacterium rhizogenes is used by these soil bacteria to infect plants, via its encoding for a receptor for acetosyringone and other phenolic phytochemicals exuded by plant wounds. This compound also allows higher transformation efficiency in plants, in A. tumefaciens-mediated transformation procedures, and so is of importance in plant biotechnology.
Acetosyringone can also be found in Posidonia oceanica and a wide variety of other plants. It is secreted at wounded site of dicotyledons. This compound enhances the Agrobacterium-mediated gene transformation in dicot. Monocotyledons lack this wound response and it is considered as the limiting factor in Agrobacterium-mediated gene transformation in monocots.
The compound is also produced by the male leaffooted bug (Leptoglossus phyllopus) and used in its communication system.
In vitro studies show that acetosyringone increases mycorrhizae formation in the fungus Glomus intraradices.
Total synthesis of this simple natural product performed by Crawford et al. in 1956, but is of limited contemporary synthetic interest. A variety of acetosyringone analogs are available, including some which are covalent inactivators of cellular processes that involve acetosyringone.
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