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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:
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.

Signal Word

Danger

Hazard Statements

H301,H314,H317,H335,H410

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 Code

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

WGK

WGK 3

Flash Point(F)

269.6 °F - closed cup

Flash Point(C)

132 °C - closed cup

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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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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