Butyrolactone I

For research use only. Not for therapeutic Use.

  • CAT Number: R003808
  • CAS Number: 87414-49-1
  • Molecular Formula: C₂₄H₂₄O₇
  • Molecular Weight: 424.44
  • Purity: 95%
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Butyrolactone I(cas 87414-49-1) is one of a family of three butyrolactones isolated from Aspergillus fumigatus, first reported in 1983. Butyrolactone I exhibits antitumor activity, inhibiting the cell cycle at the G1/S and G2/M transitions. Butyrolactone I is a selective inhibitor of cyclin-dependent kinases CDK1/cyclin B, CDK2 and CDK5, and is an important bioprobe for understanding the cellular roles of CDKs.


Catalog Number R003808
CAS Number 87414-49-1
Synonyms

(2R)-2,5-dihydro-4-hydroxy-2-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxo-2-furancarboxylic acid, methyl ester

Molecular Formula C₂₄H₂₄O₇
Purity 95%
Target CDK
Appearance Light yellow solid
Storage -20°C
Analysis method HPLC
IUPAC Name [4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-methyl-5-oxofuran-2-carboxylate
InChI InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-30-23(29)24(3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1
InChIKey FPVUCBMBMUHRDX-XMMPIXPASA-N
SMILES CC(=CCC1=C(C=CC(=C1)COC(=O)C2(C(=C(C(=O)O2)O)C3=CC=C(C=C3)O)C)O)C
Reference

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.<br />
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Butyrolactone I induces cyclin B1 and causes G2/M arrest and skipping of mitosis in human prostate cell lines. Suzuki M. et al. Cancer Lett. 1999, 138, 121.<br />
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Butyrolactone I, a selective inhibitor of cdk2 and cdc2 kinase. Kitagawa M. et al. Oncogene 1993, 8, 2425.
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