BROMOMETHYL-7-METHOXYCOUMARIN

Other Names 4-(Bromomethyl)-7-methoxy-2//-chromen-2-one 4-(Bromomethyl)-7-methoxy-2//-chromene-2-one 4-Bromomethyl-7-methoxy-2-oxo-2//-benzopyran 4-Bromomethyl-7-methoxycoumarin 7-Methoxy-4-(bromomethyl)coumarin BMC Br-Mmc BrMMC 

Merck Index Number Not listed Chemical/Dye Class Coumarin Molecular Formula CuH9Br03 Molecular Weight 269.09 Physical Form Pale yellow crystals/needles  

Solubility Soluble in acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, methanol 

Revankar, H. M. Kulkarni, M. V. Joshi, S. D. More, U. A. Synthesis, biological evaluation and docking studies of 4-aryloxymethyl coumarins derived from substructures and degradation products of vancomycin. Eur. J. Med. Chem. 2013, 70,750-757. 

Jeyachandran, M. Ramesh, R Sriram, D. Senthilkumar, R Yogeeswari, P. Synthesis and in vitro antitubercular activity of 4-aryl/ alkylsulfonylmethylcoumarins as inhibitors of Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett. 2012, 22,4807-4809. 

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Fluorometric detection has been mainly employed for the determination of aminopenicillins such as amoxicillin and ampicillin in edible animal products because it confers the advantages of selectivity and sensitivity. Fluorometric detection of penicillins, however, necessitates their precolumn derivatization to produce the corresponding fluorescent derivatives. The most commonly used derivatizing reagents are formaldehyde (100, 117, 118), salicylaldehyde (83), and mercury dichloride (91). 4-Bromomethyl-7-methoxycoumarin has also been employed as a fluorescence label for the selective and sensitive detection of seven penicillins in milk (96). 

Lam, S. and Grushka, E., Labeling of fatty acids with 4-bromomethyl-7-methoxycoumarin via crown ether catalyst for fluorimetric detection in high-performance liquid chromatography, J. Chromatogr., 158, 207, 1978. 

Acids, carboxylic O-p-N itrobenzyl-/V, Al -diisopropyliso-urea (PNBDI) p-Bromophenacyl bromide (PBPB) 4-Bromomethyl-7-methoxycoumarin... 

In some cases, precolumn analyte derivatization is applied in bioanalytical LC-MS. Derivatization of L-368,899 with trifluoroacetic anhydride was performed to eliminate carryover and adsorption effects [8]. Derivatization of 5-fluorouracil with 4-bromomethyl-7-methoxycoumarin [9] and conversion of sampatrilat to its dimethyl ester [10] was performed in order to enhance the ionization efficiency. 

Sample preparation Prepare ultrafiltrate from serum with an Amicon Centifree unit by centrifuging at 700 g for 10 min. 25 p,L Ultrafiltrate 475 jlL 10 g,g/mL undecylenic acid in MeCN, centrifuge. Remove 50 g,L supernatant, add 100 jxL 18-crown-6 solution, add 50 (xL 1 mg/mL 4-bromomethyl-7-methoxycoumarin in MeCN, let stand in the dark at 65° for 30 min, ipject a 5 jxL aliquot. (Prepare 18-crown-6 solution by dissolving 100 mg potassium carbonate in 50 p-L water, add 5 mL 20 mM 18-crown-6 in MeCN, sonicate for 30 min, add 5 mL MeCN.)... 

The phenacyl esters are more readily prepared than the other derivatives. The fluorescent tag 4-bromomethyl-7-methoxycoumarin may however offer increased sensitivity. Due to the bulky nature of the fluorescent products, separation factors may be poorer and allow only positive identification of a limited number of fatty acids. 

Diinges, W., 1977. 4-Bromomethyl-7-methoxycoumarin as a new fluorescence label for fatty acids. Anal. Chem., 49 442—445. 

Bromomethyl-7- methoxycoumarin [35231-44-8] 360 (340) 410 (421) Forms fluorescent probes with various compds for TLC/HPLC... 

A wide variety of other esters has been made, or may potentially be accessible, by the type of procedure outlined in this section. To give a couple of examples, the naphthacyl esters were made for improved detectability in HPLC analysis in the same way as the phenacyl esters mentioned earlier [102], the fluorescent esters of 4-methyl-7-methoxycoumarin were made from the 4-bromomethyl-7-methoxycoumarin by the potassium salt procedure [103] and anthrylmethyl esters were obtained by an extractive alkylation procedure [104]. 

Alkylation of carboxylate anions by 4-bromomethyl-7-methoxycoumarin (Br-Mmc) (Figure 19) has been suggested by Dunges [459, 460] as a method for the fluorescence labelling of carboxylic acids and other compounds with acidic functions. Subsequently, a considerable number of related reagents have been suggested. 

PBr derivatives, exhibit fluorescence when excited with at 375 nm, emission wavelength at 470 nm. It is possible to achieve femtomolar detection limits by using 4-bromomethyl-7-methoxycoumarin (BrMMC) derivatives and laser excitation. 

Valproic acid from serum (with an undecylenic acid internal standard) was analyzed as its 4-bromomethyl-7-methoxycoumarin derivative on a 40°C C,g colunm (A = 322 nm, ex 695 nm, em) using an 80/20 methanol/water mobile phase [527]. The authors noted that a 1.6-fold increase in sensitivity was obtained by changing to 228 nm, but more interferences were then detected (i.e., selectivity decreased). The use of methanol rather than acetonitrile resulted in a 2-fold increase in sensitivity. The linear working range was reported as 6-200 pg/mL. 

Evans and McGuffin [824] studied the effect of injecting a 1 pL aliquot of a 5xl0" M 4-(bromomethyl)-7-methoxycoumarin-derivatized C,o fatty acid dissolved in 100% THF onto a C g column eluted with a 90/10 methanol/water mobile phase. A split peak resulted. The authors could not definitively explain the effect but noted that the best solution to the potential problem is to dissolve the sample in the mobile phase itself or in a solvent that is only slightly weaker than the mobile phase. This split peak effect is not uncommon when high percent THF solute solvents are used. 

A less costly alternative to fluorescamine is o-phthaldehyde (OPT) the derivatives of which are more stable and consequently can be stored overnight if necessary. It is used in a similar manner to fluorescamine the detection limits being about 0.1 nanogram (ca. 4 x 10" g/ml). OPT has been used in the analysis of dopamine (24), catecholamines (25) and histamines (26). Other fluorescence reagents sometimes used are 4-bromomethyl-7-methoxycoumarin, diphenylindenonesulfonyl chloride, dansyl-hydrazine and a number of fluorescent isocyanates for details of which the reader is recommended to read the review by Lawrence (11). 

Ertel, K. D. Carstensen, J. T. Quantitative determination of octanoic acid by high-performance liquid chromatography following derivatization with 4-bromomethyl-7-methoxycoumarin. J. Chromatogr. 1987,411, 297-304. 

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