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.

References

• 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

• Media related to Xylindein at Wikimedia Commons