Dihydropergillin

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Category Bioactive by-products
Catalog number BBF-01410
CAS
Molecular Weight 262.30
Molecular Formula C15H18O4

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Description

Dihydropergillin is produced by the strain of Aspergillus ustus. It can inhibit the growth of plants.

Specification

IUPAC Name (7R)-7-hydroxy-7-methyl-2-propan-2-yl-6,9-dihydrofuro[3,2-h]isochromen-3-one
Canonical SMILES CC(C)C1C(=O)C2=C(O1)C3=C(CC(OC3)(C)O)C=C2
InChI InChI=1S/C15H18O4/c1-8(2)13-12(16)10-5-4-9-6-15(3,17)18-7-11(9)14(10)19-13/h4-5,8,13,17H,6-7H2,1-3H3/t13?,15-/m1/s1
InChI Key CYPMCDMSUWADNK-AWKYBWMHSA-N

Properties

Appearance Crystalline
Melting Point 122-126°C

Reference Reading

1. Synthesis and structural characterization of natural benzofuranoids
Kouji Kuramochi, Kazunori Tsubaki J Nat Prod. 2015 May 22;78(5):1056-66. doi: 10.1021/np5010483. Epub 2015 Apr 23.
The synthesis of ustusoranes A, B, and E, pergillin, dihydropergillin, (±)-penicisochroman A, and (-)-brassicadiol, starting from optically active (R)-benzolactone, is described. The synthesis of ustusoranes A and E established the absolute configurations of these natural products. The synthesis of pergillin and (±)-penicisochroman A led to the structural revision of aspergiones E and F. This study clearly indicates that (R)-benzolactone is a potential intermediate in the synthesis of natural benzofuranoids.

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