6335-27-9

Basic information

• Product Name: 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one
• Synonyms: 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one;2H-1-Benzopyran-2-one, 4,7-dimethyl-5-hydroxy-;5-18-01-00469 (Beilstein Handbook Reference);5-hydroxy-4,7-dimethyl-2-chromenone;5-hydroxy-4,7-dimethyl-chromen-2-one;5-hydroxy-4,7-dimethylchromen-2-one;5-hydroxy-4,7-dimethyl-coumarin;BRN 0163053
• CAS NO: 6335-27-9
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.1953
• Mol File: 6335-27-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 248 °C
• Boiling Point: 371.3°Cat760mmHg
• Flash Point: 167.2°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 4.86E-06mmHg at 25°C
• Refractive Index: 1.599
• PKA: 7.61±0.20(Predicted)
• CAS DataBase Reference: 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one(6335-27-9)
• EPA Substance Registry System: 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one(6335-27-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 6335-27-9(Hazardous Substances Data)

Usage

General Description

5-Hydroxy-4,7-dimethyl-2H-chromen-2-one is a chemical compound with the molecular formula C11H10O3. It is a derivative of coumarin, a natural substance found in many plants. 5-Hydroxy-4,7-dimethyl-2H-chromen-2-one is often used in the synthesis of pharmaceuticals and agrochemicals due to its potential antioxidant and anti-inflammatory properties. It is also being studied for its potential role in the treatment of various diseases, including cancer, due to its reported cytotoxic and anti-proliferative effects. Additionally, it has been explored for its potential as a natural food additive and flavoring agent.

InChI:InChI=1/C11H10O3/c1-6-3-8(12)11-7(2)5-10(13)14-9(11)4-6/h3-5,12H,1-2H3

Upstream product

• 2524-37-0 ethyl orselinate 
• 105-45-3 acetoacetic acid methyl ester 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 88827-62-7 3-benzyl-5,10-dimethyl-3,4-dihydro-2H-chromeno[6,5-e][1,3]oxazin-8-one 
• 109029-09-6 4,7-dimethyl-5-<(2-oxocyclohexyl)oxy>-2H-1-benzopyran-2-one 

Relevant articles and documents

A Reinvestigation of Bicarbonate Induced Oligomerization of Ethyl Acetoacetate: One-pot Biomimetic Synthesis of Dimethylcoumarin, Trimethylcoumarin and Condensed Coumarin Derivatives

In addition to the previously reported products dehydroacetic acid (1) and a pyranopyran derivative, presently revised as 4,7-dimethyl-2H-pyrano-13,2-c]-2H-pyran-2,5-dione (2), seven new polysubstituted coumarin derivatives have been synthesised by NaHCO3 catalyzed self-condensation of ethyl acetoacetate. The new products have been characterized as 3-acetyl-6-carboethoxy-5-hydroxy-4,7-dimethylcoumarin (3), 5-hydroxy-4,7-dimethylcoumarin (4), 3-acetyl-6-carboethoxy-4,5,7-trimethylcoumarin (5), 6-carboethoxy-4,5,7-trimethylcoumarin (6), 9-carboethoxy-10-hydroxy-2,4,8-trimethylbenzo-[3,4]-coumarin (7) and 8-carboethoxy-3,7,9-trimethylfurano-[3,2-c]-coumarin (8) based on their 1H and 13C nmr, and mass spectral studies in conjunction with the mechanistic rationale of their formation and some chemical evidence. In the same way the remaining new product is tentatively assigned 3″-carboethoxy-7,9,10,10′-tetramethyl-tetrahydrofurano-[2,4-de]- 4′,10′-dihydro-[5,6]-naphthopyran-2,5-dione (9) structure. Transformations of 3 to 4, 5 to 6 (minor), 6-carboethoxy-4,5,7-trimethylcoumarin (10) and 4,5,7-trimethylcoumarin (11), and 6 to 11 have been effected by heating with conc. H2SO4. Use of 60% H2SO4 increased the yield of 11. Decarboxylation of 10 affords 11. Sodium bicarbonate mediated self-condensation of methyl acetoacetate affords the methyl ester 12 of 10. Oxidation of the 4-methylcoumarins 6, 11 and 12 with SeO2 gives the corresponding 4-formyl and 4-hydroxymethyl derivatives. The one-pot monosubstrated oligomerization of ethyl acetoacetate thus demonstrates a simple biomimetic type synthesis of a number of new dimethylcoumarin and trimethylcoumarin derivatives.