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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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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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