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P1378

Sigma-Aldrich

Phthaldialdehyde

≥97% (HPLC), powder or crystals

Synonym(s):

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

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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:
24898191
NACRES:
NA.21

Assay

≥97% (HPLC)

form

powder or crystals

color

white to light yellow

mp

55-58 °C

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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Application

Phthaldialdehyde has been used:

  • to detect Arg through spectrophotometry using end-point fluorescent sensitive detection
  • as a reagent stream with the sample to produce a fluorescent product for determining ammonia in seawater
  • in the o-phthaldialdehyde spectrophotometric assay (OPA test) to determine the proteolytic activity (PA)of the strains and the commercial cultures

Biochem/physiol Actions

o-Phthaldialdehyde (OPA) can form fluorescent derivatives while reacting with amino acids.
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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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
Bianca de Moraes Fracasso et al.
PloS one, 14(1), e0209964-e0209964 (2019-01-12)
Circulating advanced glycation end products (AGE) and their receptor, RAGE, are increased after a myocardial infarction (MI) episode and seem to be associated with worse prognosis in patients. Despite the increasing importance of these molecules in the course of cardiac
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
Yi-Jhen Lai et al.
Talanta, 91, 103-109 (2012-03-01)
This study reports a selective and sensitive method for fluorescent detection of total, protein-bound, free, and free oxidized homocysteine (HCys) using tris(2-carboxyethyl)phosphine (TCEP) as a reducing agent, fluorosurfactant-capped gold nanoparticles (FSN-AuNP) as a preconcentrating probe, and o-phthaldialdehyde (OPA) as a
Chien-Chih Shen et al.
Journal of chromatography. A, 1220, 162-168 (2011-12-22)
This study combines Tween 20-capped gold nanoparticles (Tween 20-AuNPs) with capillary electrophoresis (CE) for ultrasensitive detection of thiol-containing peptides, including glutathione (GSH), γ-glutamylcysteine (γ-GCS), and phytochelatin analogs. By forming AuS bonds, Tween 20-AuNPs can selectively extract and enrich these thiols
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