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Xylindein

From Wikipedia, the free encyclopedia
Xylindein
Names
Preferred IUPAC name
(3S,11S)-8,16-Dihydroxy-3,11-dipropyl-3,4,11,12-tetrahydro-1H,7H-pyrano[4,3-h]pyrano[4′,3′:5,6]xantheno[2,1,9,8-klmna]xanthene-1,7,9,15-tetrone
Other names
Xylindene
(3S,11S)-3,4,11,12-Tetrahydro-8,16-dihydroxy-3,11-dipropyl-1H,7H-dipyrano[4,3-a:4',3'-j]-peri-xanthenoxanthene-1,7,9,15-tetrone

peri-xanthenoxanthene-2,8-dicarboxy-lic acid 4,10-dihydro-3,9-dihydroxy-1,7-bis(2 S-hydroxy-pentyl)-4,10-dioxo-di δ-lactone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C32H24O10/c1-3-5-11-7-13-19(31(37)39-11)27(35)21-15(33)10-18-23-24-17(41-29(13)25(21)23)9-16(34)22-26(24)30(42-18)14-8-12(6-4-2)40-32(38)20(14)28(22)36/h9-12,35-36H,3-8H2,1-2H3/t11-,12-/m0/s1
    Key: BZFKYROURDRMSO-RYUDHWBXSA-N
  • CCC[C@@H](C0)OC(=O)c(c1O)c0c2Oc3cC(=O)c4c5c3c6c2c1C(=O)cc6Oc5c7c(c4O)C(=O)O[C@H](C7)CCC
Properties
C32H24O10
Molar mass 568.534 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Xylindein is a quinone pigment, a dimeric naphthoquinone derivative. It is produced by fungi in the genus Chlorociboria. This pigment causes green staining of wood infected by the fungi.

Etymology

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This pigment was firstly extracted in 1868 by Paul Thénard from wood and resembled indigo, so he called it xylindéine. Combination of xyl- (wood) and indé (indigo) + -ine.[1][2]

References

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  1. ^ Xylindein at Merriam-Webster dictionary
  2. ^ Thenard, Paul; Alphonse Rommier (1868). "Sur un nouvelle matière colorante appelée xylindeine et extraite de certains bois morts". Comptes rendus hebdomadaires des séances de l'Académie des Sciences (in French). 66. Paris: 108–109. ISSN 0001-4036.
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  • Media related to Xylindein at Wikimedia Commons