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79760

Sigma-Aldrich

Phthaldialdehyde

for fluorescence, ≥99.0% (HPLC)

Synonym(s):

Benzene-1,2-dicarboxaldehyde, OPA, o-Phthalaldehyde, o-Phthalic dicarboxaldehyde, o-Phthalaldehyde, o-Phthalic dicarboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C8H6O2
CAS Number:
643-79-8
Molecular Weight:
134.13
Beilstein/REAXYS Number:
878317
EC Number:
211-402-2
MDL number:
MFCD00003335
UNSPSC Code:
12352201
PubChem Substance ID:
57652816
NACRES:
NA.32

grade

for fluorescence

assay

≥99.0% (HPLC)

form

solid

impurities

≤0.5% phthalic acid

mp

54-56 °C

fluorescence

λex 334 nm; λem 455 nm (Thiol Adduct)
λex 340 nm; λem 450 nm in reaction buffer (with glycine)

storage temp.

2-8°C

SMILES string

O=Cc1ccccc1C=O

InChI

1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H

InChI key

ZWLUXSQADUDCSB-UHFFFAOYSA-N

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General description

Phthaldialdehyde, also known as o-Phthalaldehyde or OPA, is a pre-column (HPLC) derivatization reagent. OPA reacts with primary amino acids (AA) except cystine to form highly fluorescent adducts. The fluorescence of the derivatives is monitored at excitation and emission wavelengths of 345nm and 455nm, respectively. The HPLC technique efficiently separates the OPA-AA derivatives.

Application

Phthaldialdehyde or OPA determines amino acids in proteins from animal tissue and food samples. Quantification of amino acids adducts of tyramine and phenylethylamine produced by lactic acid bacteria used OPA as the pre-column derivative reagent for HPLC. Intracellular forms of glutathione (GSH/GSSG) are investigated using o-Phthalaldehyde as the pre-column fluorescent agent.

Biochem/physiol Actions

Phthaldialdehyde can be used for the pre-column derivatization of amino acids for high-performance liquid chromatography (HPLC) separation. It may also be used for flow cytometric measurements of protein thiol groups.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

269.6 °F - closed cup

flash_point_c

132 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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José María Landete et al.
International journal of food microbiology, 115(3), 364-368 (2007-02-20)
The ability of wine lactic acid bacteria to produce tyramine and phenylethylamine was investigated by biochemical and genetic methods. An easy and accurate plate medium was developed to detect tyramine-producer strains, and a specific PCR assay that detects the presence
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Zhaolai Dai et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 964, 116-127 (2014-04-16)
Studies of protein nutrition and biochemistry require reliable methods for analysis of amino acid (AA) composition in polypeptides of animal tissues and foods. Proteins are hydrolyzed by 6M HCl (110°C for 24h), 4.2M NaOH (105°C for 20 h), or proteases.
Yun-Bin Han et al.
Applied microbiology and biotechnology, 99(16), 6715-6726 (2015-02-17)
Sphingolipid ceramide N-deacylase (SCDase) catalyzes reversible reactions in which the amide linkage in glycosphingolipids is hydrolyzed or synthesized. While SCDases show great value for the enzymatic synthesis of glycosphingolipids, they are relatively poorly characterized enzymes. In this work, the enzymatic
I Molnár-Perl
Journal of chromatography. A, 913(1-2), 283-302 (2001-05-18)
An overview is presented of HPLC methods currently in use to determine amino acids as their o-phthaldialdyde derivatives in the presence of various SH-group-containing additives. Crucial points that proved to influence the stability of the amino acid OPA derivatives have
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