Isomuronic acid

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Isomuronic acid
Category Others
Catalog number BBF-05551
CAS 70579-66-7
Molecular Weight 366.49
Molecular Formula C21H34O5

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Description

It is isolated from the lichen Punctelia microsticta.

Specification

Synonyms 3-Furancarboxylic acid, 2,5-dihydro-4-methyl-5-oxo-2-(14-oxopentadecyl)-, (2R)-; (R)-4-Methyl-5-oxo-2-(14-oxo-pentadecyl)-2,5-dihydro-furan-3-carboxylic acid; (2R)-4-methyl-5-oxo-2-(14-oxopentadecyl)-2H-furan-3-carboxylic acid
IUPAC Name (2R)-4-methyl-5-oxo-2-(14-oxopentadecyl)-2,5-dihydrofuran-3-carboxylic acid
Canonical SMILES CC1=C(C(OC1=O)CCCCCCCCCCCCCC(=O)C)C(=O)O
InChI InChI=1S/C21H34O5/c1-16(22)14-12-10-8-6-4-3-5-7-9-11-13-15-18-19(20(23)24)17(2)21(25)26-18/h18H,3-15H2,1-2H3,(H,23,24)/t18-/m1/s1
InChI Key KYSXDEQQOVVLIN-GOSISDBHSA-N

Reference Reading

1. A revised structure for (-)-dihydropertusaric acid, a gamma-butyrolactone acid from the lichen punctelia microsticta
MS Maier, Gonzalez Marimon DI, CA Stortz, MT Adler J Nat Prod. 1999 Nov;62(11):1565-7. doi: 10.1021/np990110n.
The gamma-butyrolactone acid (1) and two known compounds, (-)-isomuronic acid and the tridepside gyrophoric acid, have been isolated from the lichen Punctelia microsticta. The structure and stereochemistry of compound 1 were determined on the basis of spectroscopic evidence and molecular modeling. Spectroscopic and physical data of 1 and (-)-dihydropertusaric acid, previously isolated from the lichen Pertusaria albescens, showed that both are the same compound, although for the latter the epimeric structure 2 has been proposed.

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