Picrolichenic acid

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Picrolichenic acid
Category Others
Catalog number BBF-05395
CAS 466-34-2
Molecular Weight 442.50
Molecular Formula C25H30O7

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Description

It is a 3-spirobenzofuran heterocyclic compound isolated from Variolaria amara.

Specification

Synonyms 6-Hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[benzofuran-3(2H),1'-[2,5]cyclohexadiene]-5-carboxylic acid; Pikrolichenic acid; Spiro[benzofuran-3(2H),1'-[2,5]cyclohexadiene]-5-carboxylic acid, 6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentyl-; picrolichenin; NSC 43331; 6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentyl-2H-spiro[benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid
IUPAC Name 6-hydroxy-1'-methoxy-2,3'-dioxo-4,5'-dipentylspiro[1-benzofuran-3,6'-cyclohexa-1,4-diene]-5-carboxylic acid
Canonical SMILES CCCCCC1=CC(=O)C=C(C12C3=C(C=C(C(=C3CCCCC)C(=O)O)O)OC2=O)OC
InChI InChI=1S/C25H30O7/c1-4-6-8-10-15-12-16(26)13-20(31-3)25(15)22-17(11-9-7-5-2)21(23(28)29)18(27)14-19(22)32-24(25)30/h12-14,27H,4-11H2,1-3H3,(H,28,29)
InChI Key LOGCRVAWKCZXQM-UHFFFAOYSA-N

Properties

Boiling Point 629.2±55.0°C at 760 mmHg
Melting Point 181°C (dec.)
Density 1.3±0.1 g/cm3

Reference Reading

1. Circumscription of the genus Lepra, a recently resurrected genus to accommodate the "Variolaria"-group of Pertusaria sensu lato (Pertusariales, Ascomycota)
Xinli Wei, Imke Schmitt, Brendan Hodkinson, Adam Flakus, Martin Kukwa, Pradeep K Divakar, Paul M Kirika, Jürgen Otte, Anjuli Meiser, H Thorsten Lumbsch PLoS One. 2017 Jul 11;12(7):e0180284. doi: 10.1371/journal.pone.0180284. eCollection 2017.
Pertusarialean lichens include more than 300 species belonging to several independent phylogenetic lineages. Only some of these phylogenetic clades have been comprehensively sampled for molecular data, and formally described as genera. Here we present a taxonomic treatment of a group of pertusarialean lichens formerly known as "Pertusaria amara-group", "Monomurata-group", or "Variolaria-group", which includes widespread and well-known taxa such as P. amara, P. albescens, or P. ophthalmiza. We generated a 6-locus data set with 79 OTUs representing 75 species. The distinction of the Variolaria clade is supported and consequently, the resurrection of the genus Lepra is followed. Thirty-five new combinations into Lepra are proposed and the new species Lepra austropacifica is described from mangroves in the South Pacific. Lepra is circumscribed to include species with disciform ascomata, a weakly to non-amyloid hymenial gel, strongly amyloid asci without clear apical amyloid structures, containing 1 or 2, single-layered, thin-walled ascospores. Chlorinated xanthones are not present, but thamnolic and picrolichenic acids occur frequently, as well as orcinol depsides. Seventy-one species are accepted in the genus. Although the distinction of the genus from Pertusaria is strongly supported, the relationships of Lepra remain unresolved and the genus is tentatively placed in Pertusariales incertae sedis.

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