Hypostictic acid

Hypostictic acid
Names
IUPAC name
13,17-dihydroxy-5-methoxy-4,7,12-trimethyl-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-9,15-dione
Other names
Hypostictinsäure
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H16O8/c1-6-5-9(24-4)7(2)14-10(6)17(21)26-15-8(3)13(20)11-12(16(15)25-14)19(23)27-18(11)22/h5,19-20,23H,1-4H3
    Key: PGRWVCGZKIXMQW-UHFFFAOYSA-N
  • CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3C)O)C(=O)OC4O)C)OC
Properties
C19H16O8
Molar mass 372.3 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

Hypostictic acid is a lichen secondary metabolite belonging to the depsidone class of aromatic compounds. It was first prepared in 1933 by catalytic hydrogenation of stictic acid isolated from the foliose lichen Lobaria pulmonaria, and as a natural product was later reported from an undescribed species of the crustose lichen genus Thelotrema collected in Venezuelan cloud forest. As a lichen metabolite it has been detected as a minor or trace component in several foliose and crustose lichen genera, including Pseudoparmelia, Xanthoparmelia, Nephroma, Aspicilia, Clandestinotrema, Porpidia and Rinodina. Hypostictic acid forms colourless crystals with a relatively high melting point and has been used as a model substrate in electrochemical studies that investigate the reduction behaviour of lichen depsidones.