109103-15-3

Basic information

• Product Name: 6-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate
• Synonyms: 6-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate
• CAS NO: 109103-15-3
• Molecular Formula: C14H14O4
• Molecular Weight: 246.25856
• Mol File: 109103-15-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate(109103-15-3)
• EPA Substance Registry System: 6-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate(109103-15-3)

Safety Data

• Hazardous Substances Data: 109103-15-3(Hazardous Substances Data)

Upstream product

• 16555-98-9 6-acetyl-7-hydroxy-4-methylcoumarin 
• 2896-60-8 4-ethyl-1,3-benzenediol 
• 1484-73-7 6-Ethyl-7-hydroxy-4-methylcumarin 
• 108-24-7 acetic anhydride 

Downstream Products

• 257621-37-7 5'-ethyl-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 
• 54337-59-6 3'-ethyl-2',6'-dihydroxyacetophenone 

Relevant articles and documents

Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents. 4. Synthesis and pharmacological properties of 4'- dehydroxyphlorizin derivatives substituted on the B ring

In our studies of Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents, a series of novel 4'- dehydroxyphlorizin derivatives substituted on the B ring was prepared and their effects on urinary glucose excretion were evaluated in rats. Introduction of only a small alkyl group at the 4'-position increased the activity, and 3-(benzo[b]furan-5- yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D- glucopyranoside (4) showed the most potent effect. To overcome hydrolysis of compound 4 by β-glucosidase in the digestive tract, the OH groups on the glucose moiety of compound 4 were modified. Three prodrugs (5, 42, and 55) were more potent than the parent compound 4 by oral administration, and finally 3- (benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O- (6-O-methoxycarbonyl-β-D-glucopyranoside) (5) was selected as a new promising candidate. Compound 5 was metabolized mainly by liver esterase to the active form (4), which was about 10 times more potent than 5 in inhibiting SGLT. In oral glucose tolerance test in db/db mice, compound 5 dose-dependently suppressed the elevation of glucose levels. Single administration of 5 reduced hyperglycemia concurrently with increase of glucose excretion into urine in diabetic KK-A(y) mice. Furthermore, compound 5 suppressed the elevation of blood glucose levels but did not lower it below the normal level even in fasted conditions in KK- A(y) mice. Additionally, long-term treatment with 5 dose- dependently reduced hyperglycemia and HbA1c in KK-A(y) mice. These pharmacological data strongly suggest that compound 5 has a therapeutic potential in the treatment of NIDDM.