Structural studies on Santalin (cas 1397-70-2) permethyl ether☆

Add time:09/06/2019    Source:sciencedirect.com

The chloroform extract of the heartwood of Pterocarpus Santalin (cas 1397-70-2)us yielded a mixture of red pigments which could be separated by polyamide column chromatography into two major compounds, santalin-A and santalin-B. Both gave the same permethyl ether, C38H36O10 which had 8 methoxyls and formed a number of derivatives typical of anhydrobenzopyranols. IR and UV spectra confirmed the same. NMR and MS suggested the presence of homoveratrayl group supported by the formation of veratraldehyde in alkali degradation. Permanganate oxidation gave 2,4-dimethoxy benzoic acid, veratric acid and 3,4,6-trimethoxy phthalic acid. On a basic fluorone skeleton, the substituents in the A ring are indicated by 2,4-dihydroxy-5-methoxy benzaldehyde, an alkali fission product and, further, 2,4-dimethoxy phenyl and homoveratryl units are located in ring C based on NMR, MS and biogenetic considerations. The residues constitute another benzene ring fused to ring C leading to the complete structures of the permethyl ether as (VII) which explains all its degradations and which constitutes a highly condensed biflavonoid of a new type.

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