(7-Methoxycoumarin-4-yl)acetic acid

(7-Methoxycoumarin-4-yl)acetic acid is a coumarin-based amino acid derivative featuring a (7-methoxycoumarin-4-yl) substituent attached to the methylene carbon of an acetic acid framework that bears both an amino group and a carboxylic acid group. The coumarin chromophore provides an aromatic, conjugated side-chain functionality, while the amino and carboxyl groups enable formation of amino acid-type intermediates and salt or coupling partners under standard organic synthesis conditions. This molecule is used in chemical biology and analytical chemistry as a fluorescent labeling or probe precursor, where the covalent attachment of the coumarin-bearing amino acid motif supports preparation of tagged peptides, conjugates, or detection reagents.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27291

CAS No:62935-72-2

Synonyms/Alias:2-Aminoheptanedioicacid;627-76-9;2-Aminopimelate;dl-alpha-Aminopimelicacid;Heptanedioicacid,2-amino-;DL-2-Aminopimelate;alpha-Aminopimelicacid;dl-2-Aminopimelicacid;2-Amino-heptanedioicacid;DL-2-Aminoheptanedioicacid;CHEMBL111050;CHEBI:64305;JUQLUIFNNFIIKC-UHFFFAOYSA-N;3721-85-5;heptyline;6382-70-3;2-Aminoheptanedioicacid#;(+-)-2-Aminopimelicacid;D,L-alpha-Aminopimelicacid;(?-2-Aminoheptanedioicacid;d,l-2-aminoheptanedioicacid;dl-.alpha.-Aminopimelicacid;SCHEMBL116556;AC1L2Q56;AC1Q5W38

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M.F/Formula
C7H13NO4
M.W/Mr.
234.21

(7-Methoxycoumarin-4-yl)acetic acid is a coumarin-based aromatic amino-acid-like building block featuring a 7-methoxy substituted coumarin chromophore linked to an acetic acid side chain. Its conjugation-ready aromatic scaffold and carboxylic acid functionality make it useful for constructing fluorescent tags and for preparing coumarin-containing intermediates used in chemical biology and analytical workflows. The coumarin core provides a well-established fluorescence readout, while the acetic acid handle supports downstream coupling to peptides, linkers, or polymer backbones.

1. Fluorescent Tag Building

(7-Methoxycoumarin-4-yl)acetic acid is used to introduce a coumarin fluorophore into labeling reagents and fluorescent conjugates for chemical biology applications. Researchers incorporate this scaffold into peptide or small-molecule constructs where the coumarin chromophore serves as a stable, excitation/emission-active reporter for tracking binding, localization, or reaction progress in vitro. The carboxylic acid functionality supports conversion to activated derivatives for coupling to amines or other nucleophiles during tag assembly, enabling consistent chromophore placement via the acetic acid linker.

2. Peptide And Probe Conjugation

(7-Methoxycoumarin-4-yl)acetic acid supports the preparation of coumarin-functional peptide probes used in biochemical assays and protein studies. In practice, it is selected as a chromophore-bearing building block when a fluorescent readout is required without relying on bulky dye systems, and when a defined linker between the reporter and the biomolecular scaffold is beneficial. The molecule's acid group enables straightforward incorporation into probe design as a pendant fluorescent moiety, supporting workflows such as substrate analog labeling, affinity probe construction, and assay development where fluorescence reporting is used to monitor molecular interactions.

3. Analytical Fluorescence Standards

(7-Methoxycoumarin-4-yl)acetic acid is employed to prepare coumarin-containing analytical standards and calibration materials for fluorescence-based quantification. Laboratories use the chromophore to generate reference solutions or to validate assay performance in instrument settings that monitor coumarin emission. Because the coumarin scaffold is chemically defined and provides a direct optical signal, it is commonly used for method development and routine checks of fluorescence detection systems, including studies that require reproducible reporter behavior across runs.

4. Fluorophore-Linked Intermediate Synthesis

(7-Methoxycoumarin-4-yl)acetic acid is also used as a key intermediate in the synthesis of coumarin-functional linkers, fluorescent reagents, and dye-conjugation building blocks. Development chemists select this scaffold when they need a coumarin reporter with a carboxylic acid handle to enable downstream derivatization into coupling-ready forms. This makes it useful for producing custom fluorescent materials and reagent sets that later feed into peptide labeling, polymer functionalization, or other reporter installation steps in research and industrial R&D environments.

Size
1 g;5 g;
InChI
1S/C7H13NO4/c8-5(7(11)12)3-1-2-4-6(9)10/h5H,1-4,8H2,(H,9,10)(H,11,12)
InChI Key
JUQLUIFNNFIIKC-UHFFFAOYSA-N
Canonical SMILES
C(CCC(=O)O)CC(C(=O)O)N

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