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08445

Sigma-Aldrich

7-Amino-4-methyl-3-coumarinylacetic acid

BioReagent, suitable for fluorescence, ~90% (HPLC)

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Synonym(s):
2H-1-Benzopyran-3-acetic acid, AMCA-H, Aminomethyl coumarin acetic acid
Empirical Formula (Hill Notation):
C12H11NO4
CAS Number:
Molecular Weight:
233.22
Beilstein/REAXYS Number:
7927205
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

assay

~90% (HPLC)

form

powder

solubility

DMF: soluble
DMSO: soluble
aqueous base: soluble

fluorescence

λex 350 nm; λem 433 nm in methanol

suitability

suitable for fluorescence

SMILES string

CC1=C(CC(O)=O)C(=O)Oc2cc(N)ccc12

InChI

1S/C12H11NO4/c1-6-8-3-2-7(13)4-10(8)17-12(16)9(6)5-11(14)15/h2-4H,5,13H2,1H3,(H,14,15)

InChI key

QEQDLKUMPUDNPG-UHFFFAOYSA-N

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1 of 4

This Item
2351995.330015.43808
vibrant-m

235199

7-Methoxycoumarin-4-acetic acid

vibrant-m

5.33001

Acetic acid 100%

vibrant-m

5.43808

Acetic acid 100%

assay

~90% (HPLC)

assay

97%

assay

≥99.8% (acidimetric)

assay

≥99.8% (alkalimetric)

form

powder

form

-

form

liquid

form

liquid

solubility

DMF: soluble, DMSO: soluble, aqueous base: soluble

solubility

DMF: soluble 50 mg/mL, clear, colorless to yellow

solubility

-

solubility

-

fluorescence

λex 350 nm; λem 433 nm in methanol

fluorescence

-

fluorescence

-

fluorescence

-

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

Application

AMCA is a useful agent for labeling proteins. Demonstrates a characteristic absorption peak at 345 nm with a fluorescence emission at 440-460 nm (blue region); however, when conjugated with proteins the absorption peak shifts to 355 nm with a fluorescence emission at 440-460 nm. It has a high fluorescence yield with a sufficient Stokes shift (100 nm) and is relatively photostable . Relatively easy to activate and couple to the N-terminal amino group of a peptide resulting in an acid stable amide bond .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Useful blue fluorophore for immunofluorescence, λabs ~350 nm, λem ~440 nm

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Cytometry, 12(6), 537-544 (1991-01-01)
Antibodies coupled to 7-aminocoumarin (AMCA) emit a bright blue fluorescence under ultraviolet (UV) excitation and are therefore ideal for three-color immunofluorescence (IF) with fluorescein (FITC) and phycoerythrin (PE) labeled reagents; however, due to the different absorption spectra, the use of
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The pathogenesis of multiple sclerosis (MS) is currently ascribed in part to a T cell-mediated process targeting myelin components. The T cell response to one candidate autoantigen, myelin basic protein (MBP), in the context of HLA-DR15Dw2, has been previously studied
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The American journal of physiology, 271(1 Pt 1), C210-C217 (1996-07-01)
Dipeptide uptake was studied in primary cultures from rat anterior pituitaries by use of radiolabeled carnosine and the fluorescent dipeptide derivative beta-Ala-Lys-N epsilon-AMCA (AMCA is 7-amino-4-methylcoumarin-3-acetic acid). Fluorescence microscopic studies revealed that the reporter peptide specifically accumulated in the S-100
Melissa J Leyva et al.
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Huntington's Disease (HD) is characterized by a mutation in the huntingtin (Htt) gene encoding an expansion of glutamine repeats on the N terminus of the Htt protein. Numerous studies have identified Htt proteolysis as a critical pathological event in HD postmortem

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