Butyrolactone II

• CAT Number: R000148
• CAS Number: 87414-44-6
• PubChem Substance ID: 16745402
• Molecular Formula: C19H16O7
• Molecular Weight: 356.3
• Purity: 95%
• Synonyms: Methyl 4-hydroxy-3-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-5-oxofuran-2-carboxylate
• Target: Endogenous Metabolite
• Appearance: Yellow solid
• Analysis method: HPLC
• IUPAC Name: methyl 4-hydroxy-3-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-5-oxofuran-2-carboxylate
• InChI: InChI=1S/C19H16O7/c1-25-18(24)19(10-11-2-6-13(20)7-3-11)15(16(22)17(23)26-19)12-4-8-14(21)9-5-12/h2-9,20-22H,10H2,1H3
• InChIKey: AEKPZNDJHWFONI-UHFFFAOYSA-N
• SMILES: COC(=O)C1(C(=C(C(=O)O1)O)C2=CC=C(C=C2)O)CC3=CC=C(C=C3)O

Butyrolactone II(cas 87414-44-6) is one of a family of four butyrolactones isolated from the fungus, Aspergillus terreus, by Yamamoto and collaborators at Kanazawa University, Japan in 1983. Butyrolactone II inhibits soybean lipoxygenase (LOX) and α-glucosidase. Butyrolactone II has antioxidant activity via DPPH radical-scavenging.

Reference

1. Metabolic products of Aspergillus terreus. IX. Biosynthesis of butyrolactone derivatives isolated from strains IFO 8835 and 4100. Nitta K. et al., Chem. Pharm. Bull. 1983, 31, 1528.
2. Soybean lipoxygenase inhibitory and DPPH radical-scavenging activities of aspernolide A and butyrolactones I and II. Sugiyama Y. et al., Biosci. Biotechnol. Biochem. 2010, 74, 881.
3. Effect on α-glucosidase inhibition and antioxidant activities of butyrolactone derivatives from Aspergillus terreus MC751. Dewi T.R. et al., Med. Chem. Res. 2014, 23, 454.