Xerocomorubin

Xerocomorubin
Names
	IUPAC name 5,6-Dihydroxy-3-[3-hydroxy-4-(4-hydroxyphenyl)-5-oxo-2(5H)-furanylidene]-2(3H)-benzofuranone
Identifiers
CAS Number	50422-97-4;
3D model (JSmol)	Interactive image;
ChemSpider	129557842;
PubChem CID	162882814;
CompTox Dashboard (EPA)	DTXSID001337189;
	InChI InChI=1S/C18H10O8/c19-8-3-1-7(2-4-8)13-15(22)16(26-17(13)23)14-9-5-10(20)11(21)6-12(9)25-18(14)24/h1-6,19-22H/b16-14+ Key: KSBHFBKGAVZFRD-JQIJEIRASA-N;
	SMILES c1cc(O)ccc1C(=C(O)2)C(=O)OC2=C3C(=O)OC4=C3C=C(O)C(O)=C4;
Properties
Chemical formula	C18H10O8
Molar mass	354.270 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Xerocomorubin is a pigment from the fungus order Boletales. It is the oxidized form of isoxerocomic acid.^[1] Air oxidation is responsible its formation, and it oxidizes faster to a similar pulvinic acid type pigment oxidized variant, variegatorubin.^[1]^[2] The long wavelength has an absorption at 497 nm, 106 nm higher than its precursor isoxerocomic acid. Synthesis experiments have shown tetra-acetylation by acetic anhydride and sulfuric acid. Although xerocomorubin and variegatorubin give off the same deep red color and could simultaneously occur in a mushroom, extracts from the deep red colored mushroom Boletus rubellus Krombh. identified only variegatorubin by thin layer chromatography (TLC), leading to the question the natural abundance of xerocomorubin.

References

^ ^a ^b Gill, M., and 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. PMID 3315906. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link)
^ Edwards and Gill (1973). "Constituents of the Higher Fungi. Part X1l.l Identification of lnvolutin as (-)-cis-5-(3,4-Dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enone and Synthesis of (+)-cis-lnvolutin Trimethyl Ether from Isoxerocomic Acid Derivatives". {{cite journal}}: Cite journal requires |journal= (help)

[Gill-1] Gill, M., and 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. PMID 3315906. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link)

[2] Edwards and Gill (1973). "Constituents of the Higher Fungi. Part X1l.l Identification of lnvolutin as (-)-cis-5-(3,4-Dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enone and Synthesis of (+)-cis-lnvolutin Trimethyl Ether from Isoxerocomic Acid Derivatives". {{cite journal}}: Cite journal requires |journal= (help)

[1]

[2]