Atromentic acid

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Atromentic acid
Identifiers
3D model (JSmol)
  • InChI=1S/C18H12O7/c19-11-5-1-9(2-6-11)13-15(21)16(25-18(13)24)14(17(22)23)10-3-7-12(20)8-4-10/h1-8,19-21H,(H,22,23)
    Key: QFIPVAAXLHOLFN-PEZBUJJGSA-N
  • (E): InChI=1S/C18H12O7/c19-11-5-1-9(2-6-11)13-15(21)16(25-18(13)24)14(17(22)23)10-3-7-12(20)8-4-10/h1-8,19-21H,(H,22,23)/b16-14+
    Key: QFIPVAAXLHOLFN-JQIJEIRASA-N
  • (Z): InChI=1S/C18H12O7/c19-11-5-1-9(2-6-11)13-15(21)16(25-18(13)24)14(17(22)23)10-3-7-12(20)8-4-10/h1-8,19-21H,(H,22,23)/b16-14-
  • c1cc(O)ccc1C(=C(O)2)C(=O)OC2=C(C(O)=O)c3ccc(O)cc3
  • (E): C1=CC(=CC=C1C2=C(/C(=C(/C3=CC=C(C=C3)O)\C(=O)O)/OC2=O)O)O
Properties
C18H12O7
Molar mass 340.2837
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Atromentic acid is a red-organge pigment found in fungi within the Boletales group. It is the precursor to variegatic acid and xerocomic acid, and is preceded by atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. Variants include homoatromentic acid. This pigment has been studied and elucidated by Wolfgang Steglich and colleagues over decades.[2] When atromentin is oxidised with hydrogen peroxide a yellow product is produced. A sodium hydroxide solution is also yellow, but when this is neutralized with acid the red atromentic acid crystallises.[3] Concentrated potassium hydroxide breaks up the compound to p-hydroxyphenylacetic acid and oxalic acid.[3]

References

  1. ^ "Atromentic acid | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp.
  2. ^ Gill, M., and Steglich, W. (1987) Pigments of fungi (Macromycetes). Prog Chem Org Nat Prod 51: 1–317.
  3. ^ a b NIIR Board of Consultants and Engineers (2005). The Complete book on Natural Dyes & Pigments. ASIA PACIFIC BUSINESS PRESS Inc. ISBN 9788178330327.
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