Peristictic acid

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Peristictic acid
Category Others
Catalog number BBF-05141
CAS 331812-35-2
Molecular Weight 402.31
Molecular Formula C19H14O10

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Description

Peristicic acid is a β-Orcinol depsidone isolated from the lichens Relicina sydneyensis and Xanthoparmelia.

Specification

Synonyms 1,3-Dihydro-1,4-dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxylic acid
IUPAC Name 13,17-dihydroxy-5-methoxy-7,12-dimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-4-carboxylic acid
Canonical SMILES CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3C)O)C(=O)OC4O)C(=O)O)OC
InChI InChI=1S/C19H14O10/c1-5-4-7(26-3)9(16(21)22)14-8(5)17(23)28-13-6(2)12(20)10-11(15(13)27-14)19(25)29-18(10)24/h4,19-20,25H,1-3H3,(H,21,22)
InChI Key HIPOOOQGJTVSMG-UHFFFAOYSA-N

Properties

Boiling Point 801.0±65.0°C (Predicted)
Density 1.652±0.06 g/cm3 (Predicted)

Reference Reading

1. NMR reassignment of stictic acid isolated from a Sumatran lichen Stereocaulon montagneanum (Stereocaulaceae) with superoxide anion scavenging activities
Friardi Ismed, Françoise Lohézic-Le Dévéhat, Isabelle Rouaud, Solenn Ferron, Amri Bakhtiar, Joël Boustie Z Naturforsch C J Biosci. 2017 Jan 1;72(1-2):55-62. doi: 10.1515/znc-2016-0148.
The phytochemical study of Stereocaulon montagneanum harvested in Sumatra (Indonesia) led to the isolation of 11 known compounds including two metabolites not previously described in the genus Stereocaulon, peristictic acid (8) and menegazziaic acid (10). The complete 1H and 13C NMR spectral assignments of stictic acid derivatives are reported with some revisions. Five depsidones belonging to the stictic acid chemosyndrome were superoxide anion scavengers as potent as ascorbic acid and with no toxicity on two human cell lines.
2. Comparative metabolite profiling and chemical study of Ramalina siliquosa complex using LC-ESI-MS/MS approach
Delphine Parrot, Saleem Jan, Nicolas Baert, Sylvain Guyot, Sophie Tomasi Phytochemistry. 2013 May;89:114-24. doi: 10.1016/j.phytochem.2013.02.002. Epub 2013 Mar 13.
A chemical study of the lichen Ramalina siliquosa complex found in Brittany was conducted. Eight chemotypes were considered and their chemical composition was elucidated for the first time by LC-MS analysis. Ten main compounds were identified: conhypoprotocetraric acid (1), salazinic acid (2), peristictic acid (3), cryptostictic acid (4), protocetraric acid (5), stictic acid (6), norstictic acid (7), hypoprotocetraric acid (8), 4-O-demethylbarbatic acid (9), (+)-usnic acid (10) and 22 minor compounds were reported. The MS/MS fragmentation patterns of each compound of R. siliquosa complex were determined and proposed.

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