79760

Phthaldialdehyde

suitable for fluorescence, ≥99.0% (HPLC)

• Synonym(s): Benzene-1,2-dicarboxaldehyde, OPA, o-Phthalaldehyde, o-Phthalic dicarboxaldehyde, o-Phthalaldehyde, o-Phthalic dicarboxaldehyde
• 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

Properties

• Quality Level: 100
• Assay: ≥99.0% (HPLC)
• form: solid
• mol wt: 134.13 g/mol
• concentration: ≤100% (o-phthaldialdehyde)
• impurities: ≤0.5% phthalic acid
• color: white to light yellow
• bp: 83 °C/1.067 hPa
• mp: 54-56 °C
• solubility: ethanol: 0.5 g/10 mL, clear, colorless to greenish-yellow; water: 37.7 g/L at 20 °C (OECD Test Guideline 105)
• density: 1.13 g/cm³ at 20 °C
• fluorescence: λ_ex 334 nm; λ_em 455 nm (Thiol Adduct); λ_ex 340 nm; λ_em 450 nm in reaction buffer (with glycine)
• suitability: suitable for fluorescence
• 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

Description

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.[1]

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.[2] Intracellular forms of glutathione (GSH/GSSG) are investigated using o-Phthalaldehyde as the pre-column fluorescent agent.[3]

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.

Safety Information

• Pictograms: GHS06,GHS05,GHS09
• Signal Word: Danger
• Hazard Statements: H301,H314,H317,H335,H410
• Precautionary Statements: P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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