13544-37-1

Basic information

• Product Name: 7-O-Prenylscopoletin
• Synonyms: 6-Methoxy-7-prenyloxycoumarin;7-(3-Methyl-2-butenyloxy)-6-methoxycoumarin;7-O-Prenylscopoletin;Prenyletin methyl ether;6-Methoxy-7- isoprenyloxycoumarin
• CAS NO: 13544-37-1
• Molecular Formula: C15H16O4
• Molecular Weight: 260.28514
• Mol File: 13544-37-1.mol

Chemical Properties

• Melting Point: 80-81 °C
• Boiling Point: 422.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.159
• CAS DataBase Reference: 7-O-Prenylscopoletin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-Prenylscopoletin(13544-37-1)
• EPA Substance Registry System: 7-O-Prenylscopoletin(13544-37-1)

Safety Data

• Hazardous Substances Data: 13544-37-1(Hazardous Substances Data)

Upstream product

• 92-61-5 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one 
• 870-63-3 prenyl bromide 
• 14382-91-3 2-hydroxy-4,5-dimethoxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 15870-92-5 8-(1,1-Dimethylallyl)-scopoletin 

Relevant articles and documents

Synthesis of virgatol and virgatenol, two naturally occurring coumarins from Pterocaulon virgatum (L.) DC, and 7-(2,3-epoxy-3-methylbutoxy)-6- methoxycoumarin, isolated from Conyza obscura DC

The synthesis of a number of naturally occurring coumarins from Pterocaulon virgatum (L.) and Conyza obscura DC is described for the first time. It concerns the synthesis of 7-(2-hydroxy-3-methoxy-3-methylbutoxy)-6- methoxycoumarin (virgatol, 1), 7-(2-hydroxy-3-methyl-3-butenyloxy)-6- methoxycoumarin (virgatenol, 2) and 7-(2,3-epoxy-3-methylbutoxy)-6- methoxycoumarin (3). In addition, a straightforward synthesis of scopoletin (4) (7-hydroxy-6-methoxycoumarin) is reported and the synthesis of a new coumarin derivative, 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin (7), is described.

Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity.