| Acetosyringone | |
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4'-Hydroxy-3',5'-dimethoxyacetophenone |
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Other names
Acetosyringenin |
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| Identifiers | |
| CAS number | 2478-38-8 = |
| PubChem | 1 |
| ChemSpider | 16280 |
| ChEBI | CHEBI:2404 |
| ChEMBL | CHEMBL224146 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C10H12O4 |
| Molar mass | 196.19 g/mol 988 |
| Exact mass | 196.073559 u |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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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[1], especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus Agrobacterium. The virA gene on the Ti plasmid in the genome of Agrobacterium tumefaciens and 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[2]. This compound also allows higher transformation efficiency in plants, in A. tumefaciens mediated transformation procedures, and so is of importance in plant biotechnology[3].
Acetosyringone can also be found in Posidonia oceanica[4] and a wide variety of other plants.
The compound is also produced by the male leaffooted bug (Leptoglossus phyllopus) and used in its communication system[5][6][7].
In vitro studies show that acetosyringone increases mycorrhizae formation in the fungus Glomus intraradices[8].
Total synthesis of this simple natural product performed by Crawford et al in 1956,[9] 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.