54337-59-6

Basic information

• Product Name: 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE
• Synonyms: 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE
• CAS NO: 54337-59-6
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Mol File: 54337-59-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 129.5 °C
• Appearance: /
• CAS DataBase Reference: 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE(54337-59-6)
• EPA Substance Registry System: 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE(54337-59-6)

Safety Data

• Hazardous Substances Data: 54337-59-6(Hazardous Substances Data)

Usage

Preparation

Preparation by degradation of 8-acetyl-6-ethyl-7- hydroxy-4-methylcoumarin with refluxing 2 N sodium hydroxide.

Upstream product

• 2163-12-4 2,4-diacetylresorcinol 
• 65490-30-4 8-acetyl-6-ethyl-7-hydroxy-4-methyl coumarin 
• 860714-18-7 3-acetyl-5-ethyl-2,4-dihydroxy-benzoic acid 
• 855875-94-4 3-acetyl-5-ethyl-2,4-dihydroxy-benzoic acid methyl ester 
• 2896-60-8 4-ethyl-1,3-benzenediol 
• 1484-73-7 6-Ethyl-7-hydroxy-4-methylcumarin 
• 109103-15-3 7-acetoxy-6-ethyl-4-methylcoumarin 
• 103324-32-9 5-ethyl-2,4-dihydroxy-benzoic acid methyl ester 
• 856106-66-6 5-ethyl-2,4-dihydroxy-benzoic acid 
• 16555-98-9 6-acetyl-7-hydroxy-4-methylcoumarin 
• 125296-37-9 2-acetyl-4-ethyl-1,3-cyclo-hexanedione 

Downstream Products

• 2896-60-8 4-ethyl-1,3-benzenediol 
• 52959-33-8 2,4-diethyl-resorcinol 
• 257621-37-7 5'-ethyl-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 
• 857080-16-1 ethyl (2-acetyl-4-ethyl-3-hydroxyphenoxy)acetate 
• 857080-28-5 5-ethyl-4-benzyloxy-3-methylbenzofuran-2-carboxylic acid 
• 857080-27-4 5-ethyl-4-benzyloxy-3-methylbenzofuran-2-carboxylic acid ethyl ester 
• 938443-60-8 2-{4'-[(5-ethyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester 
• 938443-57-3 2-{4'-[(5-ethyl-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester 
• 938443-62-0 2-{4'-[(5-ethyl-4-isopropoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester 
• 857076-19-8 N-{[4'-({[4-(benzyloxy)-5-ethyl-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valine 
• 938443-61-9 2-{4'-[(4-benzyloxy-5-ethyl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid tert-butyl ester 

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.