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[edit]

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[edit]

^ 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). 66. Paris: 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. 55 (3). Elsevier: 237–240. Bibcode:2000PChem..55..237S. 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. 68 (13). Elsevier: 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. 2. Springer: 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. S2CID 53646580.

External links[edit]

Media related to Xylindein at Wikimedia Commons

[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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