{{Chembox <!-- Images --> | ImageFileL1 = Grevilline A.svg | ImageFileR1 = Grevilline B.svg | ImageFileL2 = Grevilline C.svg | ImageFileR2 = Grevilline D.svg | ImageCaptionL1 = Grevilline A | ImageCaptionR1 = Grevilline B | ImageCaptionL2 = Grevilline C | ImageCaptionR2 = Grevilline D | ImageSizeL1 = 92px <!-- Names --> | IUPACName = | OtherNames = <!-- Sections --> | Section1 = {{Chembox Identifiers | index_label = A | index1_label = B | index2_label = C | index3_label = D | CASNo = 41744-32-5 | CASNo1 = 41744-33-6 | CASNo2 = 41744-34-7 | CASNo3 = 54707-49-2 | ChEBI = 174356 | ChemSpiderID = 4522423 | ChemSpiderID1 = 4527860 | ChemSpiderID2 = 4521898 | ChemSpiderID3 = 4527497 | PubChem = 5372047 | PubChem1 = 5379212 | PubChem2 = 5371346 | PubChem3 = 5378732 | InChI=1S/C18H12O6/c19-12-5-1-10(2-6-12)9-14-16(21)15(17(22)18(23)24-14)11-3-7-13(20)8-4-11/h1-9,19-21H/b14-9+ | InChIKey = HIUMAIHELPNSFG-NTEUORMPSA-N | InChI1=1S/C18H12O7/c19-11-4-2-10(3-5-11)15-16(22)14(25-18(24)17(15)23)8-9-1-6-12(20)13(21)7-9/h1-8,19-22H/b14-8+ | InChIKey1 = OLZRNPOBVWGCKN-RIYZIHGNSA-N | InChI2=1S/C18H12O8/c19-10-3-1-8(5-12(10)21)6-14-16(23)15(17(24)18(25)26-14)9-2-4-11(20)13(22)7-9/h1-7,19-23H/b14-6+ | InChIKey2 = SFYPADSXJOTYIW-MKMNVTDBSA-N | InChI3=1S/C18H12O8/c19-9-2-4-11(20)10(7-9)15-16(23)14(26-18(25)17(15)24)6-8-1-3-12(21)13(22)5-8/h1-7,19-23H/b14-6+ | InChIKey3 = QKEFFIMFIWJNDJ-MKMNVTDBSA-N | SMILES = C1=CC(=CC=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=CC=C(C=C3)O)O)O | SMILES1 = C1=CC(=CC=C1C2=C(/C(=C\C3=CC(=C(C=C3)O)O)/OC(=O)C2=O)O)O | SMILES2 = C1=CC(=C(C=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=CC(=C(C=C3)O)O)O)O)O | SMILES3 = C1=CC(=C(C=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=C(C=CC(=C3)O)O)O)O)O }} | Section2 = {{Chembox Properties | Formula = A: {{chem2|C18H12O6}}<br>B: {{chem2|C18H12O7}}<br>C: {{chem2|C18H12O8}}<br>D: {{chem2|C18H12O8}}<br> | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Grevillines''' (also spelled '''grevillins''') are a group of natural chemical pigments found in certain fungi, notably the tamarack jack mushroom (''Suillus grevillei''). There are four members of the class, named grevilline A through D. Grevillines were first isolated from ''Suillus grevillei'', from which they derive their name, and were characterized by Wolfgang Steglich in 1972.<ref>{{cite journal | last1 = Steglich | first1 = Wolfgang | last2 = Besl | first2 = Helmut | last3 = Prox | first3 = Axel | title = Zur struktur der grevilline, neuartiger pigmente aus dem goldröhrling, suillus grevillei (Boletaceae) | journal = Tetrahedron Letters | date = 1972 | volume = 13 | issue = 48 | pages = 4895–4898 | doi = 10.1016/S0040-4039(01)94459-4 }}</ref>
Grevillines are polyphenolic compounds and contain a keto-pyranone group that is similar to hydroquinone. As pigments, they contribute to yellow, orange, and red coloration of the mushrooms they occur in.
Laboratory syntheses of grevillines have been reported.<ref>{{cite journal | last1 = Gill | first1 = M. | last2 = Kiefel | first2 = MJ | last3 = Lally | first3 = DA | last4 = Ten | first4 = A. | title = Pigments of Fungi. XV. An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and Their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types | journal = Australian Journal of Chemistry | date = 1990 | volume = 43 | issue = 9 | pages = 1497–1518 | doi = 10.1071/CH9901497 }}</ref><ref>{{cite journal | last1 = Gill | first1 = Melvyn | last2 = Kiefel | first2 = Milton J. | title = Synthesis of fungus pigments of the grevillin and pulvinone types from benzylacyloins | journal = Tetrahedron Letters | date = 1988 | volume = 29 | issue = 17 | pages = 2085–2087 | doi = 10.1016/S0040-4039(00)87841-7 }}</ref><ref>{{cite journal | last1 = Pattenden | first1 = Gerald | last2 = Pegg | first2 = Neil A. | last3 = Kenyon | first3 = Ronald W. | title = Synthesis of grevillins and their biogenetic interrelationship with terphenylquinones, xylerythrins and pulvinic acid | journal = Tetrahedron Letters | date = 1987 | volume = 28 | issue = 40 | pages = 4749–4752 | doi = 10.1016/S0040-4039(00)96616-4 }}</ref><ref>{{cite journal | last1 = Lohrisch | first1 = Hans-Joachim | last2 = Steglich | first2 = Wolfgang | title = Synthese von grevillin C und verwandten 2H-pyran-2,5(6H)-dionen | journal = Tetrahedron Letters | date = 1975 | volume = 16 | issue = 33 | pages = 2905–2908 | doi = 10.1016/S0040-4039(00)75026-X }}</ref>
==References== {{reflist}}
Category:Polyphenols Category:Pyrones