Xerocomic acid

Xerocomic acid
Names
Preferred IUPAC name
(E)-[4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxofuran-2(5H)-ylidene](4-hydroxyphenyl)acetic acid
Identifiers
CAS Number
  • 25287-88-1
3D model (JSmol)
  • Interactive image
ChemSpider
  • 30776773
PubChem CID
  • 54730624
UNII
  • A8AF7UK664 checkY
CompTox Dashboard (EPA)
  • DTXSID601117270 Edit this at Wikidata
InChI
  • InChI=1S/C18H12O8/c19-10-4-1-8(2-5-10)14(17(23)24)16-15(22)13(18(25)26-16)9-3-6-11(20)12(21)7-9/h1-7,19-22H,(H,23,24)/b16-14+
    Key: LJVSOLKVNIGBDE-JQIJEIRASA-N
  • OC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=C(O)C(O)=C1)\C1=CC=C(O)C=C1
Properties
Chemical formula
 C18H12O8
Molar mass 356.286 g·mol−1
Melting point 295 °C (563 °F; 568 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Xerocomic acid is a red-orange pigment found in fungi of the order Boletales (and is named after the genus Xerocomus). It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin.[1] As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. An oxidase acting on xerocomic acid is responsible for the "bluing" reaction seen in mushrooms.

Condensation of two units of xerocomic acid form the pigments sclerocitrin, badione A, and also norbadione A, which are found in the mushroom Scleroderma citrinum Pers.

Variants include isoxerocomic acid and O-methylxerocomic acid.[1][2]

References

  1. ^ a b Gill, M.; Steglich, W. (1987). Pigments of fungi (Macromycetes). Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Vol. 51. pp. 1–317. doi:10.1007/978-3-7091-6971-1_1. ISBN 978-3-7091-7456-2..
  2. ^ Steglich, Wolfgang; Furtner, Willibald; Prox, Axel (1 August 1968). "Neue Pulvinsäure-Derivate aus Xerocomus cbrysenteron (Bull, ex St. Amans) Quél, und Untersuchungen zur Frage des Vorkommens von Anthrachinonpigmenten bei Boletaceen". Zeitschrift für Naturforschung B. 23 (8): 1044–1050. doi:10.1515/znb-1968-0805.