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F9015

Sigma-Aldrich

Fluorescamine

≥98% (TLC), powder, used for detection of primary amines

Synonym(s):

4-Phenylspiro-[furan-2(3H),1-phthalan]-3,3′-dione

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About This Item

Empirical Formula (Hill Notation):
C17H10O4
CAS Number:
38183-12-9
Molecular Weight:
278.26
Beilstein:
921143
EC Number:
253-814-5
MDL number:
MFCD00005928
UNSPSC Code:
12352204
PubChem Substance ID:
24894984
NACRES:
NA.32

Assay

≥98% (TLC)

form

powder

color

off-white to yellow

mp

153-157 °C (lit.)

solubility

acetone: 50 mg/mL

storage temp.

room temp

SMILES string

O=C1OC2(OC=C(C2=O)c3ccccc3)c4ccccc14

InChI

1S/C17H10O4/c18-15-13(11-6-2-1-3-7-11)10-20-17(15)14-9-5-4-8-12(14)16(19)21-17/h1-10H

InChI key

ZFKJVJIDPQDDFY-UHFFFAOYSA-N

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General description

Fluorescamine, a heterocyclic dione, reacts with primary amines, amino acids, peptides, and protein to form a fluorescent product. Excess reagent and its degradation products are non-fluorescent. The fluorescence of a solution containing protein plus fluorescamine is equivalent to the quantity of free amine groups present. This is the basic principle of a fluorescent protein assay. Fluorescamine is used as a derivatizing agent for the identification of various compounds used in the pharmaceutical industry, such as oseltamavir, penicillamine, sulfonamide residues, lisinopril, methotrexate, vigabatrin, and gabapentin.

Application

Fluorescamine has been used as a stain to localize granular proteins on the surface of foxtail millet starch as well as protein in foxtail millet flour through confocal scanning laser microscopy (CSLM). It has also been used for photometric determination of para-aminobenzoic acid.
Non-fluorescent reagent that reacts readily under mild conditions with primary amines in amino acids and peptides to form stable, highly fluorescent compounds. Low background due to hydrolysis. Useful for the fluorometric assay of amino acids, protein, and proteolytic enzymes. Effectively blocks newly generated amino termini in protein sequence analyses.

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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Hai-Teng Li et al.
Food chemistry, 330, 127328-127328 (2020-06-23)
Granular protein is an important structural feature in determining starch digestibility. High-amylose wheat starch (HAWS) with >80% amylose content contains more granular protein than wild-type starch. As analyzed by mass spectrometry-based proteomics, granular-bound starch synthase (GBSS) is the major granular
S Udenfriend et al.
Science (New York, N.Y.), 178(4063), 871-872 (1972-11-24)
Fluorescamine is a new reagent for the detection of primary amines in the picomole range. Its reaction with amines is almost instantaneous at room temperature in aqueous media. The products are highly fluorescent, whereas the reagent and its degradation products
S Udenfriend et al.
Science (New York, N.Y.), 178(4063), 871-872 (1972-11-24)
Fluorescamine is a new reagent for the detection of primary amines in the picomole range. Its reaction with amines is almost instantaneous at room temperature in aqueous media. The products are highly fluorescent, whereas the reagent and its degradation products
P C Hollman et al.
The American journal of clinical nutrition, 62(6), 1276-1282 (1995-12-01)
Quercetin is a dietary antioxidant that prevents oxidation of low-density lipoproteins in vitro. Intake of quercetin was inversely associated with coronary heart disease mortality in elderly Dutch men. However, the extent of absorption of quercetin in humans is unclear. The
Min Jia et al.
Analytical chemistry, 81(19), 8033-8040 (2009-10-01)
Fluorescamine derivatized 3-amino-2,2,5,5,-tetramethyl-1-pyrrolidinyloxy (I) is shown to undergo an irreversible reaction with peroxyl radicals and other radical oxidants to generate a more highly fluorescent diamagnetic product (II) and thus can be used as a highly sensitive and versatile probe to
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