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301450

Sigma-Aldrich

4-Bromomethyl-6,7-dimethoxycoumarin

96%

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About This Item

Empirical Formula (Hill Notation):
C12H11BrO4
CAS Number:
88404-25-5
Molecular Weight:
299.12
Beilstein:
4750487
MDL number:
MFCD00011570
UNSPSC Code:
12352100
PubChem Substance ID:
24858188
NACRES:
NA.22

Assay

96%

mp

212-216 °C (lit.)

fluorescence

λex 322; λem 395 (Reaction product with acetic acid)
λex 354 nm; λem 435 nm in methanol

SMILES string

COc1cc2OC(=O)C=C(CBr)c2cc1OC

InChI

1S/C12H11BrO4/c1-15-10-4-8-7(6-13)3-12(14)17-9(8)5-11(10)16-2/h3-5H,6H2,1-2H3

InChI key

JGODLBJJCNQFII-UHFFFAOYSA-N

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Application

4-Bromomethyl-6,7-dimethoxycoumarin was used as fluorescent labeling reagent for the reversed-phase HPLC separation and detection of carboxylic acids. It was also used as derivatization reagent:
  • for quantitation of clofibric, bezafibric and fenofibric acids in liver by liquid chromatography
  • in determination of the concentration of tripeptide glutathione by matrix-assisted laser desorption ionization time-of-flight mass spectrometry
  • for determination of carboxylic acids in chromatographic detection

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A P Starling et al.
The Biochemical journal, 304 ( Pt 2), 569-575 (1994-12-01)
On reconstitution of the Ca(2+)-ATPase of skeletal muscle sarcoplasmic reticulum into bilayers of dimyristoleoylphosphatidylcholine [di(C14:1)PC] or dinervonylphosphatidylcholine [di(C24:1)PC] the stoichiometry of Ca2+ binding changes from the usual two Ca2+ ions bound per ATPase molecule to one Ca2+ ion bound per
H I Stefanova et al.
Biochemistry, 31(26), 6023-6031 (1992-07-07)
The (Ca(2+)-Mg2+)-ATPase of sarcoplasmic reticulum was labeled with 4-(bromomethyl)-6,7-dimethoxycoumarin. It was shown that a single cysteine residue (Cys-344) was labeled on the ATPase, with a 25% reduction in steady-state ATPase activity and no reduction in the steady-state rate of hydrolysis
K A Dalton et al.
The Biochemical journal, 329 ( Pt 3), 637-646 (1998-03-07)
The sarcoplasmic reticulum of skeletal muscle contains anionic phospholipids as well as the zwitterionic phosphatidylcholine and phosphatidylethanolamine. Here we study the effects of anionic phospholipids on the activity of the Ca2+-ATPase purified from the membrane. Reconstitution of the Ca2+-ATPase into
4-Bromomethyl-6,7-dimethoxycoumarin as a fluorescence reagent for precolumn derivatization of 5-fluorouracil compounds in high-performance liquid chromatography.
S Yoshida et al.
Journal of chromatography, 430(1), 156-162 (1988-08-19)
A M Mata et al.
Biochimica et biophysica acta, 1147(1), 6-12 (1993-04-08)
4-Bromomethyl-6,7-dimethoxy-coumarin labels the (Ca(2+)-Mg(2+)-ATPase of skeletal muscle sarcoplasmic reticulum at Cys-344. Resonance energy transfer has been used to measure the distance between this site and Lys-515 labelled with fluorescein isothiocyanate as about 37 A. The height of Cys-344 above the
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