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| Names | |
|---|---|
| IUPAC name 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide | |
| Systematic IUPAC name 2-Amino-4-{N'-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid | |
| Other names β-N-[γ-glutamyl]-4-hydroxymethylphenylhydrazine N2-(γ-glutamyl)-4-hydroxymethylphenylhydrazine | |
| Identifiers | |
3D model (JSmol) | |
| Abbreviations | AGT |
| 757731 | |
| ChEBI | |
| ChemSpider |
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| KEGG |
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| MeSH | Agaritine |
| RTECS number |
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| UNII | |
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| Properties | |
| C12H17N3O4 | |
| Molar mass | 267.285 g·mol−1 |
| Melting point | 203 °C (397 °F; 476 K) |
| Acidity (pKa) | 3.4 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Toxic |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Agaritine is an aromatichydrazine-derivativemycotoxin inmushroom species of the genusAgaricus.[1] It is anα-aminoacid and a derivative ofphenylhydrazine.
Agaritine is present as a naturalmycotoxin in fresh samples of at least 24 species of the generaAgaricus,Leucoagaricus, andMacrolepiota.[1][2] Mushrooms of these species are found around the world.[3] These mushrooms grow in a wide range of habitats; indeed, one species alone,Agaricus bisporus, is cultivated in over 70 countries and on every continent except Antarctica.[4]A. bisporus, also known as the common button mushroom, is of particular socio-economic importance in developed countries.[4]
Agaritine content varies between individual mushrooms and across species.[2] Agaritine content (% fresh weight) in rawAgaricus bisporus, for example, ranges from 0.033% to 0.173%, with an average of 0.088%.[5] The highest amount of agaritine is found in the cap and gills of the fruiting body, and the lowest in the stem.[6] Agaritine oxidizes rapidly upon storage, however, and is totally degraded after 48 hours in aqueous solution with exposure to extraction with water or methanol and isolation from the extract by one of several methods.[7] It has also been shown to decompose readily upon cooking (up to 90% reduction) as well as upon freezing (up to 75% reduction).[8]
Agaritine occurs naturally in mushrooms and can beextracted from cultivatedAgaricus bisporus mushrooms with water or methanol.[1]
Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.[9]
Although recognized as an experimentalcarcinogen when used in high laboratory doses, there is inadequate evidence to classify Agaritine as carcinogenic to humans in amounts ingested from consuming mushrooms.[1]
