Xylindein

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
CAS Number	3779-11-1;
3D model (JSmol)	Interactive image;
ChemSpider	23078574;
PubChem CID	101293600;
	InChI 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;
	SMILES CCC[C@@H](C0)OC(=O)c(c1O)c0c2Oc3cC(=O)c4c5c3c6c2c1C(=O)cc6Oc5c7c(c4O)C(=O)O[C@H](C7)CCC;
Properties
Chemical formula	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). Infobox references

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

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

Xylindein at Merriam-Webster dictionary
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). Paris. 66: 108–109. ISSN 0001-4036.

Saikawa, Yoko; Watanabe, Takashi; Hashimoto, Kimiko; Nakata, Masaya (October 2000). "Absolute configuration and tautomeric structure of xylindein, a blue-green pigment of Chlorociboria species". Phytochemistry. Elsevier. 55 (3): 237–240. doi:10.1016/S0031-9422(00)00282-X. PMID 11142849.
Donner, Christopher; Cuzzupe, Anthony; Falzon, Cheryl; Gill, Melvyn (April 2012). "Investigations towards the synthesis of xylindein, a blue-green pigment from the fungus Chlorociboria aeruginosa". Tetrahedron. Elsevier. 68 (13): 2799–2805. doi:10.1016/j.tet.2012.02.009.
Robinson, Sara; Tudor, Daniela; Snider, Hilary; Cooper, Paul (March 2012). "Stimulating growth and xylindein production of Chlorociboria aeruginascens in agar-based systems". AMB Express. Springer. 2: 15. doi:10.1186/2191-0855-2-15. PMC 3350399. PMID 22409931.
Ostroverkhova, Oksana; Robinson, Sara; Gutierrez, Sarath Vega; Schenck, Jonathan Van; Giesbers, Gregory (2018). "Fungi-Derived Pigments for Sustainable Organic (Opto)Electronics". MRS Advances. 3 (59): 3459–3464. doi:10.1557/adv.2018.446. ISSN 2059-8521.

External links

Media related to Xylindein at Wikimedia Commons

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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). Paris. 66: 108–109. ISSN 0001-4036.