Variegatic acid
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IUPAC name
α-[4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxofuran-2(5H)-ylidene]-3,4-dihydroxybenzeneacetic acid
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| Other names
3,3',4,4'-tetrahydroxy pulvinic acid
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3D model (JSmol)
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| Properties | |
| C18H12O9 | |
| Molar mass | 372.29 g·mol−1 |
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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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| Infobox references | |
Variegatic acid (3,3',4,4'-tetrahydroxypulvinic acid) is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form (due to the production of a second lactone ring) is variegatorubin, similar to xerocomorubin.
It was first isolated from Suillus variegatus. It has strong antioxidant properties, and a nonspecific inhibitory effect on enzymes. A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction. It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg. It is recognized as an Fe3+-reducant in Fenton chemistry as part of the initial attack of dead plant matter as part of the brown-rot saprobic lifestyle.
3-O-Methyl variegatic acid methyl ester is a red-orange pigment found in Boletales.
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