36651-62-4

Basic information

• Product Name: 7-glycidoxycoumarin
• Synonyms: 7-glycidoxycoumarin
• CAS NO: 36651-62-4
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 0
• Mol File: 36651-62-4.mol

Chemical Properties

• Boiling Point: 414.5°Cat760mmHg
• Flash Point: 189°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 4.44E-07mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 7-glycidoxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-glycidoxycoumarin(36651-62-4)
• EPA Substance Registry System: 7-glycidoxycoumarin(36651-62-4)

Safety Data

• Hazardous Substances Data: 36651-62-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H10O4/c13-12-4-2-8-1-3-9(5-11(8)16-12)14-6-10-7-15-10/h1-5,10H,6-7H2

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 106-89-8 epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 5623-95-0 1-piperazine carboxamide 

Downstream Products

• 1430054-07-1 7-(2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propoxy)-2H-chromen-2-one 

Relevant articles and documents

Biotransformation of newly synthesized coumarin derivatives by Candida albicans as potential antibacterial, antioxidant and cytotoxic agents

In this study, one bioactive coumarin analog was obtained as a result of biotransformation of three inactive coumarin derivatives by free cells of Candida albicans. The bioactive analog was purified by Column chromatography and HPLC. The presence of coumarin moiety in the biotrasformed product was confirmed by λmax at 350–400 nm and FT-IR spectrum. The structure of the purified compound established by LC–MS and 1H NMR suggests the chances of biotransformation of 7-(3-(Cyclopropylamino)-2-hydroxypropoxy)-4-methyl-2H-chromen-2-one (MW 289 Da) into 7-(3-Cyclopropylamino-2-hydroxy-propoxy)-4-methoxymethyl-chromen-2-one or 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-hydroxymethyl-chromen-2-one as a main product (MW 318 Da). The extra peak of 332 Da in LC–MS further confirms the presence of small proportion of 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-methoxymethyl-chromen-2-one apart from the main product. Oxidation followed by methylation reaction might be responsible for this conversion. The biotransformed product showed antimicrobial activity against Bacillus pumilus, Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Salmonella typhi followed by decent antioxidant activity (6.756 μg IC50). The efficacy of coumarin-analog on cellular proliferation was found at 40 μM concentration against human breast cancer MDA-MB-231 cells in MTT assay, which is insignificant against normal breast tissue MCF-10A cells at the same concentration. These findings suggest the potential use of C. albicans for achieving pharmacologically active coumarin analogs showing antibacterial, antioxidant and cytotoxic activity.

COUMARIN-MODIFIED EPOXY ADHESIVES

Coumarin modification of epoxies provide for epoxy adhesives that fluoresce under short wave ultraviolet irradiation while remaining invisible under normal light. Furthermore, these modified epoxy adhesives can have increased adhesive bond strengths. In addition, photochemical curing of an epoxy modified coumarin and a hardening agent with UV irradiation at certain wavelengths affords an epoxy adhesive composition. Further UV irradiation of the composition at certain wavelengths causes photoscission, which breaks the crosslinks that make the cured epoxy adhesive insoluble and intractable.

Resolution, absolute configuration and antifilarial activity of coumarinyl amino alcohols

The resolution of racemic coumarinyl amino alcohols 5–10 was achieved by using the inexpensive and readily accessible chiral resolving agent N-carbethoxy-L-proline (S)-11. Direct esterification of rac-5–10 with (S)-11 furnished diastereomeric esters, which were easily separated by column chromatography. The obtained diastereomers yielded the desired enantiopure coumarinyl amino alcohols (S)-(+)-5–10 and (R)-(?)-5–10 in good yields with high enantiomeric excess on saponification. The absolute configurations were determined by X-ray crystal analysis and/or by comparison of the specific rotations. Furthermore, in in vitro antifilarial motility inhibition assays, enantiopure coumarins (S)-(+)-9, (R)-(?)-9 and (S)-(+)-10, (R)-(?)-10 were found to be less efficient in affecting the viability of macrofilariae of Brugia malayi than their racemic forms 9 and 10, respectively, indicating the synergistic effect of the enantiomers in evoking antifilarial action.

1, 2, 4-triazine-coumarin compound and preparation method and application thereof

The invention discloses a 1, 2, 4-triazine-coumarin compound and a preparation method and application thereof. The compound is of the structure as indicated in the formula (I), and the preparation method comprises the steps that 7-umbelliferone and epoxy chloropropane serve as raw materials, 7-(oxirane-2-methoxyl)-2H-benzopyran-2-ketone is obtained, 1, 2-diphenylethane-1, 2-diketone and thiosemicarbazide serve as raw materials, 5, 6-diaryl-1, 2, 4-triazine-3-thioalcohol is obtained, and finally 7-(oxirane-2-methoxyl)-2H-benzopyran-2-ketone reacts with all types of 5, 6-diaryl-1, 2, 4-triazine-3-thioalcohol, so that the target compound is obtained. The compound can serve as the raw material of anti-diabetic medicine, the preparation method is simple, raw materials are easy to obtain, and operation is convenient.

Non-nucleosidic coumarin derivatives as polynucleotide-crosslinking agents

Novel coumarin derivatives comprising a coumarin moiety linked to a non-nucleosidic backbone moiety are disclosed. The resulting molecules are typically used as photoactivate crosslinking groups when incorporated into polynucleotides as replacements for o

CARBAMYLPIPERAZINE COMPOUNDS

4-(3-Aryloxy-2-hydroxypropyl)piperazines bearing a carbamyl group in the 1-position are β-adrenergic blockers. A typical example is 1-carbamyl-4-{3-2-allyl-3-(2-carbethoxyaminoethyl)phenoxy!-2-hydroxypropyl} piperazine.