Variegatic acid

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Variegatic acid
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Names
IUPAC name
α-[4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxofuran-2(5H)-ylidene]-3,4-dihydroxybenzeneacetic acid
Other names
3,3',4,4'-tetrahydroxy pulvinic acid
Identifiers
20988-30-1
Jmol 3D model Interactive image
  • InChI=1S/C18H12O9/c19-9-3-1-7(5-11(9)21)13-15(23)16(27-18(13)26)14(17(24)25)8-2-4-10(20)12(22)6-8/h1-6,19-23H,(H,24,25)/b16-14+
    Key: MRRYHTCWZKZVIH-JQIJEIRASA-N
  • O=C(C(C1=CC(O)=C(O)C=C1)=C/2O)OC2=C(C(O)=O)/C3=CC(O)=C(O)C=C3
Properties
C18H12O9
Molar mass 372.29 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Variegatic acid (3,3',4,4'-tetrahydroxypulvinic acid) is a chemical. An orange pigment, 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.[1]

It was first isolated from Suillus variegatus.[2] It has strong antioxidant properties,[3][4] and a nonspecific inhibitory effect on cytochrome P450 enzymes.[5] A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction.[6]

See also

References

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  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  5. ↑ Lua error in package.lua at line 80: module 'strict' not found. open access publication - free to read
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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