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08445

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

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

Synonym(s):

2H-1-Benzopyran-3-acetic acid, AMCA-H, Aminomethyl coumarin acetic acid

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$131.00

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$454.00

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About This Item

Empirical Formula (Hill Notation):
C12H11NO4
CAS Number:
106562-32-7
Molecular Weight:
233.22
NACRES:
NA.32
PubChem Substance ID:
329748585
UNSPSC Code:
12352106
MDL number:
MFCD00081051
Beilstein/REAXYS Number:
7927205

Key Documents

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Product Name

7-Amino-4-methyl-3-coumarinylacetic acid, BioReagent, suitable for fluorescence, ~90% (HPLC)

SMILES string

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

InChI key

QEQDLKUMPUDNPG-UHFFFAOYSA-N

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)

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

Quality Level

100

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1 of 4

This Item
2351995.330015.43808
7-Amino-4-methyl-3-coumarinylacetic acid BioReagent, suitable for fluorescence, ~90% (HPLC)

Sigma-Aldrich

08445

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

7-Methoxycoumarin-4-acetic acid 97%

Sigma-Aldrich

235199

7-Methoxycoumarin-4-acetic acid

Acetic acid 100% for LC-MS LiChropur™

Supelco

5.33001

Acetic acid 100%

Acetic acid 100% for HPLC LiChropur™

Supelco

5.43808

Acetic acid 100%

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

fluorescence

λex 350 nm; λem 433 nm in methanol

fluorescence

-

fluorescence

-

fluorescence

-

form

powder

form

-

form

liquid

form

liquid

solubility

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

solubility

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

solubility

-

solubility

-

assay

~90% (HPLC)

assay

97%

assay

≥99.8% (acidimetric)

assay

≥99.8% (alkalimetric)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

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 [1]. Relatively easy to activate and couple to the N-terminal amino group of a peptide resulting in an acid stable amide bond [2][3].

Other Notes

Useful blue fluorophore for immunofluorescence, λabs ~350 nm, λem ~440 nm[4]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2244
BCCG2235
BCCD4043
BCBW7473
BCBT3244

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D Delia et al.
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
Meera Mohan et al.
British journal of haematology, 189(1), 67-71 (2019-12-11)
Gain of chromosome 1q21 and the gene expression-based GEP70 risk score are established prognostic markers for newly diagnosed Multiple Myeloma (MM) patients. Here we addressed the prognostic impact of these two markers in 81 relapsed/refractory (RR) MM patients treated with
B Ulfhake et al.
Journal of neuroscience methods, 40(1), 39-48 (1991-11-01)
This paper describes the implementation of an ultraviolet (UV) laser (Spectra Physics 171-18 with 3 lines: 334, 351 and 364 nm in UV) as light source for fluorescence confocal scanning microscopy. With this instrument it is possible to use fluorophores
M W Wessendorf et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 38(1), 87-94 (1990-01-01)
7-Amino-4-methylcoumarin-3-acetic acid (AMCA) has been found to be a useful fluorophore for immunofluorescence. The present study describes a spectrophotometric method for determining the ratio of moles AMCA to moles protein (or the f/p ratio) in an AMCA-conjugated IgG. The concentration
C Otto et al.
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
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