Scytalone

Scytalone or Scytolone is a cyclic beta hydroxy ketone substituted by hydroxy groups at positions 3, 6, and 8. It is a natural product found in various fungal species including Cytospora populina and Ceratocystis fimbriata.^[2]

Scytalone

Names
IUPAC name (3R)-3,6,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
Other names 3,4-Dihydro-3,6,8-trihydroxy-1(2H)naphthalenone SCYTALON Scytolone
Identifiers
CAS Number	49598-85-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16945 Y
ChEMBL	ChEMBL4081370
ChemSpider	142729
KEGG	C00779
MeSH	scytalone
PubChem CID	162567
UNII	1MQ5L1414D
CompTox Dashboard (EPA)	DTXSID50964289
InChI InChI=1S/C10H10O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1,3,7,11-13H,2,4H2/t7-/m1/s1 Key: RTWVXIIKUFSDJB-SSDOTTSWSA-N
SMILES C1[C@H](CC(=O)C2=C1C=C(C=C2O)O)O
Properties
Chemical formula	C10H10O4
Molar mass	194.18 g/mol
log P	0.9[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Properties

Scytalone is a chemical compound with a cyclic structure consisting of a benzene ring fused to a cyclohexenone ring. It is a simple derivative of 1-tetralone with hydroxy groups at 3, 6 and 8th positions.^[3] It contains one stereocenter^[4][5] and therefore exists in R- and S- forms.

Biological significance

Scytalone is a natural product found in species of fungal genus Scytalidium.^[6] It is also found in many other fungal species like Phialocephala lagerbergii,^[7] Cytospora populina,^[8] Verticillium dahliae,^[9] Phialophora lagerbergii^[7] and Pestalotiopsis fici.^[10]

It is a pivotal intermediate in the biosynthesis of melanin in fungi, the pigment responsible for fungal coloration.^[11][12][13] Melanin production in fungi is crucial for several biological processes like protection against UV radiation, defense against pathogens, regulation of cell wall integrity and protection against other physical and chemical stresses.^[14]

See also

• Scytalone dehydratase