o-Phthalaldehyde

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H6O2
Molecular Weight	134.132
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=CC1=C(C=O)C=CC=C1

InChI

InChIKey=ZWLUXSQADUDCSB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C8H6O2
Molecular Weight	134.132
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.fda.gov/MedicalDevices/DeviceRegulationandGuidance/GuidanceDocuments/ucm093943.htm
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/20427143 http://www.fda.gov/MedicalDevices/DeviceRegulationandGuidance/GuidanceDocuments/ucm093943.htm; http://www.accessdata.fda.gov/cdrh_docs/reviews/k050077.pdf; https://www.ncbi.nlm.nih.gov/pubmed/21785612; https://clinicaltrials.gov/ct2/show/NCT02611648?term=O-PHTHALALDEHYDE&rank=1; http://wolfson.huji.ac.il/purification/PDF/Protein_Quantification/PIERCE_Fluorescence_Assay.pdf; https://www.ncbi.nlm.nih.gov/pubmed/24366628; https://www.ncbi.nlm.nih.gov/pubmed/20176622

O-Phthalaldehyde (OPA) is a chemical reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids. O-Phthalaldehyde is approved by FDA for use in test systems to detect blood urea nitrogen (BUN) for the diagnosis and treatment of certain renal and metabolic diseases. OPA is also a known desinfectant and has been approved for high-level sterilization of heat-sensitive medical instruments and is increasingly being used as a replacement in the healthcare industry for glutaraldehyde. OPA has also been approved for use as an indoor antimicrobial pesticide; an intermediate for the synthesis of pharmaceuticals, medicines, and other organic compounds.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Urea Nitrogen 1 Target ID: Urea Nitrogen Sources: http://www.accessdata.fda.gov/cdrh_docs/reviews/k050077.pdf	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Metabolic disease 3 Sources: http://www.fda.gov/MedicalDevices/DeviceRegulationandGuidance/GuidanceDocuments/ucm093943.htm	Diagnostic		Approved 8583	Urea Nitrogen Test System Approved Use Measurements obtained by this device are used in the diagnosis and treatment of certain renal and metabolic diseases. The intended patient population may be adult, pediatric, and neonatal, while the environment of use may be a hospital (e.g., respiratory care or laboratory department), urgent care situations (e.g., intensive care unit, surgery, emergency department), or bedside/near patient care situations. Launch Date 1998
Kidney disease 6 Sources: http://www.fda.gov/MedicalDevices/DeviceRegulationandGuidance/GuidanceDocuments/ucm093943.htm	Diagnostic		Approved 8583	Urea Nitrogen Test System Approved Use Measurements obtained by this device are used in the diagnosis and treatment of certain renal and metabolic diseases. The intended patient population may be adult, pediatric, and neonatal, while the environment of use may be a hospital (e.g., respiratory care or laboratory department), urgent care situations (e.g., intensive care unit, surgery, emergency department), or bedside/near patient care situations. Launch Date 1998

Doses

Dose	Population	Adverse events
0.55 % 1 times / day multiple, respiratory Recommended Dose: 0.55 %, 1 times / day Route: respiratory Route: multiple Dose: 0.55 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25780032/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25780032/	Disc. AE: Asthma... AEs leading to discontinuation/dose reduction: Asthma Sources: https://pubmed.ncbi.nlm.nih.gov/25780032/
0.55 % single, topical Recommended Dose: 0.55 % Route: topical Route: single Dose: 0.55 % Sources: https://pubmed.ncbi.nlm.nih.gov/18811577/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18811577/	Other AEs: Anaphylaxis... Other AEs: Anaphylaxis Sources: https://pubmed.ncbi.nlm.nih.gov/18811577/

AEs

AE	Significance	Dose	Population
Asthma	Disc. AE	0.55 % 1 times / day multiple, respiratory Recommended Dose: 0.55 %, 1 times / day Route: respiratory Route: multiple Dose: 0.55 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25780032/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25780032/
Anaphylaxis		0.55 % single, topical Recommended Dose: 0.55 % Route: topical Route: single Dose: 0.55 % Sources: https://pubmed.ncbi.nlm.nih.gov/18811577/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18811577/

PubMed

Title	Date	PubMed
Liquid chromatographic determination of 1-adamantanamine and 2-adamantanamine in human plasma after pre-column derivatization with o-phthalaldehyde and 1-thio-beta-D-glucose.	2004-01-25	14670755
Coordination modes vs. antitumor activity: synthesis and antitumor activity of novel platinum(II) complexes of N-substituted amino dicarboxylic acids.	2004-01	14659638
Simultaneous detection of arginine, asymmetric dimethylarginine, symmetric dimethylarginine and citrulline in human plasma and urine applying liquid chromatography-mass spectrometry with very straightforward sample preparation.	2003-12-25	14643502
Analysis of the stability of amino acids derivatized with naphthalene-2,3-dicarboxaldehyde using high-performance liquid chromatography and mass spectrometry.	2003-11-01	14705782
A versatile route to 3-benzoheteroepines containing group 15 and 16 heavier elements involving several novel ring systems, and their thermal stabilities.	2003-11	14600373
Chemical burn injury secondary to intraoperative transesophageal echocardiography.	2003-11	14570634
Effect of different concentrations of ortho-phthalaldehyde on biofilms formed by Pseudomonas fluorescens under different flow conditions.	2003-10	14650083
ESGE/ESGENA technical note on cleaning and disinfection.	2003-10	14551869
Efficacy of some neutralizers in suspension tests determining the activity of disinfectants.	2003-10	14529639
Perioral stains after ortho-phthalaldehyde disinfection of echo probes.	2003-10	14508346
Monitoring of beta-lactoglobulin dry-state glycation using various analytical techniques.	2003-09-01	12895479
Multiple effects of chemical reagent on enzyme: o-phthalaldehyde-induced inactivation, dissociation and partial unfolding of lactate dehydrogenase from pig heart.	2003-09	12957316
Acute effects of decreased glutamine supply on protein and amino acid metabolism in hepatic tissue: a study using isolated perfused rat liver.	2003-08	12898474
[Monitoring air dispersed concentrations of aldehydes during the use of ortho-phthalaldehyde and glutaraldehyde for high disinfection of endoscopes].	2003-07-23	12872495
Liquid chromatographic determination of hydroxyproline in tissue samples.	2003-07-05	12798203
High-performance liquid chromatographic assay of asymmetric dimethylarginine, symmetric dimethylarginine, and arginine in human plasma by derivatization with naphthalene-2,3-dicarboxaldehyde.	2003-07-01	12782025
A photoactivated diazopyruvoyl cross-linking agent for bonding tissue containing type-I collagen.	2003-07	12929744
An evaluation of Cidex OPA (0.55% ortho-phthalaldehyde) as an alternative to 2% glutaraldehyde for high-level disinfection of endoscopes.	2003-07	12855240
Simultaneous determination of inorganic nitrogen species by microcolumn ion chromatography.	2003-06-27	12899309
Endoscope disinfection by ortho-phthalaldehyde in a clinical setting: an evaluation of reprocessing time and costs compared with glutaraldehyde.	2003-06-18	12811321
Enhancement of the fluorescence and stability of o-phthalaldehyde-derived isoindoles of amino acids using hydroxypropyl-beta-cyclodextrin.	2003-06-15	12758262
Studies on the behaviour of Pseudomonas fluorescens biofilms after Ortho-phthalaldehyde treatment.	2003-06	14619283
Characterisation and quantification of the reaction(s) catalysed by transglutaminase using the o-phthaldialdehyde reagent.	2003-06	12866625
A rapid and sensitive fluorometric assay method for the determination of nitrilase activity.	2003-06	12549980
A novel chiral thiol reagent for automated precolumn derivatization and high-performance liquid chromatographic enantioseparation of amino acids and its application to the aspartate racemase assay.	2003-04-15	12689836
HPLC method for determining ethylenediamine migration from epoxy-amine food packaging coatings into EU food simulants.	2003-03	12623657
Effects of ortho-phthalaldehyde, glutaraldehyde and chlorhexidine diacetate on Mycobacterium chelonae and Mycobacterium abscessus strains with modified permeability.	2003-03	12615857
New aspects of the simultaneous analysis of amino acids and amines as their o-phthaldialdehyde derivatives by high-performance liquid chromatography. Analysis of wine, beer and vinegar.	2003-02-14	12613825
Quantitation of amino acids and amines in the same matrix by high-performance liquid chromatography, either simultaneously or separately.	2003-02-14	12613824
Changes in the ornithine cycle following ionising radiation cause a cytotoxic conditioning of the culture medium of H35 hepatoma cells.	2003-02-10	12569390
Lactic acid bacteria: inhibition of angiotensin converting enzyme in vitro and in vivo.	2003	12755477
Oligonucleotides incorporating 7-(aminoalkynyl)-7-deaza-2'-deoxyguanosines: duplex stability and phosphodiester hydrolysis by exonucleases.	2002-11-21	12440863
Comparative study of naphthalene-2,3-dicarboxaldehyde and o-phthalaldehyde fluorogenic reagents for chromatographic detection of sphingoid bases.	2002-11-15	12456096
Chemical synthesis of cyclodextrins by using intramolecular glycosylation.	2002-11-15	12423149
Automated column-switching high-performance liquid chromatography system for quantifying N-methyl-D- and -L-aspartate.	2002-11-01	12413481
Proteolytic specificity of Lactobacillus delbrueckli subsp. bulgaricus influences functional properties of mozzarella cheese.	2002-11	12487442
SPPS of protected peptidyl aminoalkyl amides.	2002-11	12487429
Photoactivated coumaryl-diazopyruvate fluorescent label for amine functional groups of tissues containing type-I collagen.	2002-11	12462640
O- and m-Benzenedicarbaldehyde.	2002-11	12415166
Determination of bone and tissue concentrations of teicoplanin mixed with hydroxyapatite cement to repair cortical defects.	2002-10-31	12406586
A new sensitive HPLC assay for methoxyamine and its analogs.	2002-10-15	12367666
Measurement of the intracellular distribution of reduced glutathione in cultured rat hepatocytes using monochlorobimane and confocal laser scanning microscopy.	2002-10	12206828
Gentamicin sulphate release from a modified commercial acrylic surgical radiopaque bone cement. I. Influence of the gentamicin concentration on the release process mechanism.	2002-09	12237536
Derivatization reactions of carbamate pesticides in supercritical carbon dioxide.	2002-09	12207247
High-performance liquid chromatographic method to quantify total cysteine excretion in urine.	2002-08-01	12137797
Change in plasma glutamate concentration during cardiac surgery is a poor predictor of cognitive outcome.	2002-08	12154420
Selective detection of biogenic amines using capillary electrochromatography with an on-column derivatization technique.	2002-07-15	12139055
Automated capillary liquid chromatography for simultaneous determination of neuroactive amines and amino acids.	2002-07-12	12198955
Chemical modification of specific active site amino acid residues of Enterobacter aerogenes glycerol dehydrogenase.	2002-02	12365461
Efficient heterogeneous catalytic intramolecular Tishchenko reaction of o-phthalaldehyde to phthalide with alkaline earth oxides.	2001-12-07	12240039

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Highly differentiated epidermis tissue derived from normal, human-derived epidermal keratinocytes, were used to determine the skin irritation potential of OPA and glutaraldehyde. Treatment with 0.4125% and 0.55% OPA induced irritation, while glutaraldehyde exposure at these concentrations did not.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:46 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:46 GMT 2025`
Record UNII	4P8QP9768A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

o-Phthalaldehyde

Common Name

English

Orthophthalaldehyde

Preferred Name

English

Phtharal [JAN]

Common Name

English

o-Phthaldialdehyde

Common Name

English

NSC-13394

Code

English

1,2-Benzenedicarboxaldehyde

Systematic Name

English

Orthophthalaldehyde [VANDF]

Common Name

English

o-Phthaldialdehyde [MART.]

Common Name

English

DISOPA

Brand Name

English

OPA

Common Name

English

Phtharal

Common Name

English

CIDEX

Common Name

English

o-Phthalaldehyde [MI]

Common Name

English

ortho-Phthalaldehyde

Common Name

English

ortho-Phthaldialdehyde

Common Name

English

Phthalaldehyde

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

129017