939-19-5

Basic information

• Product Name: 3-HYDROXYCOUMARIN
• Synonyms: 2,3-DIHYDROXYCOUMARIN;3-HYDROXY-2H-CHROMEN-2-ONE;3-HYDROXYCOUMARIN;HYDROXYCOUMARIN, 3-;AURORA KA-3736;3-hydroxy-2h-1-benzopyran-2-on;3-hydroxy-2h-1-benzopyran-2-one;3-hydroxy-coumari
• CAS NO: 939-19-5
• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14
• EINECS: 213-355-3
• Product Categories: Coumarins;Fused Ring Systems;Building Blocks;Heterocyclic Building Blocks
• Mol File: 939-19-5.mol

Chemical Properties

• Melting Point: 153-157 °C(lit.)
• Boiling Point: 369.9 °C at 760 mmHg
• Flash Point: 174.7 °C
• Appearance: /
• Density: 1.446 g/cm³
• Vapor Pressure: 4E-06mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.24±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYCOUMARIN(939-19-5)
• EPA Substance Registry System: 3-HYDROXYCOUMARIN(939-19-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: GN6797000
• Hazardous Substances Data: 939-19-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxycoumarin is used as a precursor in the synthesis of anticoagulant pharmaceuticals like coumadin and potent anticoagulant rodenticides. Its ability to inhibit α-glucosidase enzymes plays a crucial role in its effectiveness in these applications.
Used in Diabetes Management:
3-Hydroxycoumarin is used as a diabetes management agent due to its potent α-glucosidase inhibitory properties. By inhibiting these enzymes, it helps regulate the breakdown and absorption of carbohydrates, thus managing blood sugar levels effectively.

InChI:InChI=1/C9H6O3/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5,10H

Upstream product

• 52900-70-6 4-((E)-2-acetoxy-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 90-02-8 salicylaldehyde 
• 91-64-5 coumarin 
• 92714-81-3 1-acetyl-(Z)-3-salicylidene-2,5-piperazinedione 
• 89-95-2 2-methyl-benzyl alcohol 
• 782503-73-5 2-methyl-4-(2-methoxyphenylmethylene)-5(4H)-oxazolone 
• 135-02-4 ortho-anisaldehyde 
• 207910-76-7 (Z)-2-hydroxy-3-(2-methoxy-phenyl)-acrylic acid 
• 334022-78-5 2-hydroxy-3-(2-methoxyphenyl)acrylic acid 
• 543-24-8 N-acetylglycine 
• 92714-82-4 3-(N-acetylglycyl)aminocoumarin 
• 92714-81-3 1-Acetyl-3-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione 
• 1473-60-5 3-[(2-hydroxy-benzylidene)amino]chromen-2-one 
• 2549-08-8 3-benzamidocoumarin 

Downstream Products

• 73844-51-6 cinnamyloxycoumarin 
• 93866-51-4 3-Hydroxy-4-phenyl-cumarin 
• 131575-43-4 3-Hydroxy-4-(4-methoxy-phenyl)-chromen-2-one 
• 131575-44-5 4-(2,4-Dimethoxy-phenyl)-3-hydroxy-chromen-2-one 
• 108462-41-5 6H,8H,14H-chloro-bis<1>benzopyrano<3,4-b:4',3'-e>pyran-6,8-dione 
• 108462-37-9 4,4'-p-nitrobenzal-bis-(3-hydroxycoumarin) 
• 131575-45-6 3-Hydroxy-4-(3-methoxy-phenyl)-chromen-2-one 
• 108462-36-8 4,4'-p-methoxybenzal-bis-(3-hydroxycoumarin) 
• 108462-42-6 6H,8H,14H-hydroxy-bis<1>benzopyrano<3,4-b:4',3'-e>pyran-6,8-dione 
• 108462-38-0 4,4'-p-bromobenzal-bis-(3-hydroxycoumarin) 
• 155620-96-5 3-(benzyloxycarbonyloxy)-1-benzopyran-2-one 
• 84693-51-6 3-(cyclohex-2-enyloxy)coumarin 
• 108462-40-4 6H,8H,14H-nitro-bis<1>benzopyrano<3,4-b:4',3'-e>pyran-6,8-dione 
• 2549-07-7 3-methoxycoumarine 

Relevant articles and documents

Novel coupled molecules from active structural motifs of synthetic and natural origin as immunosuppressants

Introduction: Nitric oxide (NO) is an important mediator in the pathogenesis and control of immune system-related disorders and its levels are modulated by inducible NO synthase (iNOS). Oxidative stress is another pathological indication in majority of autoimmune disorders. The present study aims at the development of coupled molecules via selection of pharmacophores for both immunomodulatory and antioxidant activities through iNOS inhibition. Methods: Variedly substituted coumarin moieties are coupled with naturally occurring phenols through an amide linkage and were predicted for activities using computer-based program PASS. The compounds predicted to have dual activities were synthesized. Docking studies were carried out against iNOS (PDB 1R35) and compounds having good docking score were evaluated for immunomodulatory and antioxidant activities. Results: The synthesized compounds were found to be pure and were obtained in good yields. Compounds with maximum docking score (YR1a, YR2e, YR2c and YR4e) were selected for evaluation by in vitro models. Compounds YR2e and YR2c markedly inhibited the reduction of NBT dye and showed maximum percent iNOS inhibition. In DPPH assay, compound YR4e was observed as the most potent antioxidant (EC50 0.33 μM/mL). Based on these studies, compounds YR2e and YR2c were selected for haemagglutination test. Compound YR2e was observed as the most active immunosuppressant with maximal inhibitory ability of iNOS and NBT reduction and lower HAT value of 3.5. Conclusion: Compound YR2e can be utilized as a pharmacological agent in the prevention or treatment of immunomodulatory diseases such as tumors, rheumatoid arthritis, ulcerative colitis, organ transplant and other autoimmune disorders.

Hydroxycoumarin derivatives: Novel and potent α-glucosidase inhibitors

A novel class of hydroxycoumarin derivatives were found to be potent α-glucosidase inhibitors. Their syntheses were reported and the structure-activity relationship was established. Kinetic enzymatic assays indicated that compound 10 was a slow-binding and noncompetitive inhibitor with a Ki value of 589 nM, while compound 11 was a competitive inhibitor with a Ki value of 4.810 μM. Among all hydroxycoumarin derivatives studied, compounds 10 and 11 exhibited the highest activities, were specific inhibitors of α-glucosidase, and could be exploited as the lead compounds for the development of potent α-glucosidase inhibitors. Compounds 10 and 11 were also selected for further discussion for the mechanism of enzymatic inhibition.

Engineering bacterial cytochrome P450 (P450) BM3 into a prototype with human P450 enzyme activity using indigo formation

Human cytochrome P450 (P450) enzymes metabolize a variety of endogenous and xenobiotic compounds, including steroids, drugs, and environmental chemicals. In this study, we examine the possibility that bacterial P450 BM3 (CYP102A1) mutants with indole oxidation activity have the catalytic activities of human P450 enzymes. Errorprone polymerase chain reaction was carried out on the heme domain-coding region of the wild-type gene to generate a CYP102A1 DNA library. The library was transformed into Escherichia coli for expression of the P450 mutants. A colorimetric colony-based method was adopted for primary screening of the mutants. When the P450 activities were measured at the whole-cell level, some of the blue colonies, but not the white colonies, possessed apparent oxidation activity toward coumarin and 7-ethoxycoumarin, which are typical human P450 substrates that produce fluorescent products. Coumarin is oxidized by the CYP102A1 mutants to produce two metabolites, 7-hydroxycoumarin and 3-hydroxycoumarin. In addition, 7-ethoxycoumarin is simultaneously oxidized to 7-hydroxycoumarin by O-deethylation reaction and to 3-hydroxy,7-ethoxycoumarin by 3-hydroxylation reactions. Highly active mutants are also able to metabolize several other human P450 substrates, including phenacetin, ethoxyresorufin, and chlorzoxazone. These results indicate that indigo formation provides a simple assay for identifying CYP102A1 mutants with a greater potential for human P450 activity. Furthermore, our computational findings suggest a correlation between the stabilization of the binding site and the catalytic efficiency of CYP102A1 mutants toward coumarin: the more stable the structure in the binding site, the lower the energy barrier and the higher the catalytic efficiency. Copyright

Synthesis and biological evaluation of alkoxycoumarins as novel nematicidal constituents

We synthesized all of the monomethoxycoumarins, 5-alkoxycoumarins and their derivatives, and investigated their nematicidal activity against the phytopathogenic nematode, Bursaphelenchus xylophilus. Among the compounds, 5-ethoxycoumarin showed the highest nematicidal activity. Furthermore, 5-ethoxycoumarin was comparatively harmless against both the brine shrimps, Artemia salina, and the Japanese killifish, Oryzias latipes.

Antioxidant properties of 3-hydroxycoumarin derivatives

A series of hydroxylated 3-hydroxycoumarins was synthesised and evaluated for their antioxidant properties. The compounds substituted on the C-7 position were almost as antioxidant as quercetin or vitamin C. The antioxidant properties were related by an EPR study to their abilities to give stable semiquinonic or polyhydroxylated radicals. A series of hydroxylated 3-hydroxycoumarins was synthesised by the reaction of 3-aryl-2-hydroxypropenoic derivatives with boron tribromide. They were evaluated for their ability to scavenge the 2,2-diphenyl-1-picrylhydrazyl radical, the superoxide anion radical, the hydroxyl radical and the peroxynitrite anion and to inhibit copper-induced human LDL peroxidation. The physicochemical results were in accordance to establish the compounds hydroxylated on C-6 and C-7 positions as the most active of the series with antioxidant potencies comparable to those of quercetin and vitamin C. These compounds form o- and p-quinonoid derivatives upon radical scavenging and may serve as new lead compounds for pharmacological investigations.

New efficient synthesis of pyrido[2,3-c] and pyrido[3,2-c]coumarin derivatives

Various substituted pyrido[2,3-c] and pyrido[3,2-c]coumarins are efficiently prepared in three steps from 3- and 4-hydroxycoumarins, respectively and protected β-aminoketones.

Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide

(Z)-Mono, di or trimethoxyphenyl-2-hydroxypropenoic acids 1a-d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a-d when treated with boron tibromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs, and 3-hydroxycoumarins 3 and benzofuran-2-carboxylic acids 4 can be obtained. 3-Hydroxycoumarin 3a can also be obtained almost quatitatively from the reaction of methyl 3-(2-methoxyphenyl)-2,3-epoxypropanoate with boron tribromide.

Synthesis of 2-methyl-9-oxo-9H-furo[2,3-c]benzo pyrans and 2-methyl- 3H,4H[1]benzopyrano[3,4-b]pyrrol-4-ones

3:4-Fused furocoumarins and pyrrolocoumarins are synthesised from 3- hydroxy and 3-benzamido- substituted coumarins by a novel two step sequence.

Palladium(II) catalyzed oxidation reactions of coumarin derivatives

A few substituted allyl and allyloxy coumarins have been converted into their carbonyl derivatives in the presence of catalytic amount of palladium(II) chloride in oxygen atmosphere.However cyclization occurs for compounds where a free adjacent hydroxy group is present.

A Facile Synthesis of 3-Acylaminocoumarins

2-Methyl/phenyl-2-oxazolin-5-ones (2a,b), generated by cyclising aceturic and hippuric acids respectively with benzenesulphonyl chloride and triethylamine in benzene, undergo condensation with salicylaldehyde to give 3-acetyl/benzoylaminocoumarins (4a,b) which afford 3-aminocoumarin (5) on acid hydrolysis.Hydrolysis of 4b with KOH gives 3-hydroxycoumarin (6) and/or 2-benzoylamino-o-hydroxycinnamic acid (9).