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O-Phthalaldehyde is a dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring. It has a role as an epitope. It is a dialdehyde and a member of benzaldehydes. O-Phthalaldehyde is mainly used as a high-level disinfectant (a low-temperature chemical method) for heat-sensitive medical and dental equipment such as endoscopes and thermometers; in recent years, O-Phthalaldehyde has gained popularity as a safe and better alternative to glutaraldehyde.
CAS NO: 643-79-8
IUPAC NAME:
1,2-Benzenedicarboxaldehyde; Aldehyde, ortho-Phthalico Phthalaldehydeo Phthaldialdehydeo-Phthalaldehydeo-Phthaldialdehydeortho Phthalaldehydeortho Phthalic Aldehydeortho-Phthalaldehydeortho-Phthalic AldehydeOrthophthaldialdehyde; benzene-1,2-dicarbaldehyde; o-Phthalaldehyde; o-Phthalaldehyde; Phthalaldehyde; phthalaldehyde; Phthaldialdehyd
TRADE NAME:
Phthalaldialdehyde; Phthaldialdehyde; Phthalic aldehyde; Phthalic dialdehyde; Phthalic dicarboxaldehyde; Phthalyldicarboxaldehyde
OTHER NAME :
643-79-8
SYNONYM:
643-79-8; PHTHALALDEHYDE; o-Phthaldialdehyde; 1,2-Benzenedicarboxaldehyde; Benzene-1,2-dicarboxaldehyde; Phthaldialdehyde; Phthalic aldehyde; Phthalic dialdehyde; ortho-Phthalaldehyde; Phthalyldicarboxaldehyde; Phthalic dicarboxaldehyde; o-Phthaldehyde; benzene-1,2-dicarbaldehyde; Phthalaldialdehyde; o-Phthalicdicarboxaldehyde; 1,2-Diformylbenzene; 2-PHTHALALDEHYDE; 1,2-Phthalic dicarboxaldehyde; ortho Phthalaldehyde; o-Phthalic dicarboxaldehyde; 1,2-BENZENEDICARBALDEHYDE; OPA; OPTA; Phtalaldehydes; MFCD00003335; NSC 13394; UNII-4P8QP9768A; CHEBI:70851; 2-PHTHALDIALDEHYDE; EINECS 211-402-2; BRN 0878317; 4P8QP9768A; NCGC00166206-01; DSSTox_CID_12514; DSSTox_RID_78962; DSSTox_GSID_32514; Phtalaldehydes;1,2-Phthalic dicarboxaldehyde, 98+%; CAS-643-79-8; Orthophthaldialdehyde; ortho-Phthalic Aldehyd; phthalaldehyd; o-Phthalaldehyd; o-phthal aldehyde
There are some researches show, pH7.5 contains the sterilizing agent of O-Phthalaldehyde 0.5%, and its sterilizing power, sterilization speed, stability and toxicity all are better than glutaraldehyde, can kill mycobacterium in the 5min, the bacterium number reduces by 5 logarithmic value, and O-Phthalaldehyde is very stable, tasteless in pH3～9 scopes, non-stimulated to human nose, eye mucosa, and need not activate before using, various materials are had good consistency, have tangible microbiocidal activity. O-Phthalaldehyde can be widely used for precolumn derivatization of amino acids in HPLC separation or Capillary electrophoresis. For flow cytometric measurements of protein thiol groups.
O-Phthalaldehyde can be used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups. Precolumn derivatization reagent for primary amines and amino acids. The fluorescent derivative can be detected by reverse-phase HPLC. The reaction requires O-Phthalaldehyde , primary amine and a sulfhydryl. In the presence of excess sulfhydryl, amines can be quantitated. In the presence of excess amine, sulfhydryls can be quantitated. O-Phthalaldehyde is a high-level chemical disinfectant that is commonly used for disinfection of dental and medical instruments as an alternative to glutaraldehyde, which is a known skin and respiratory sensitizer. A variety of processes for manufacturing O-Phthalaldehyde have been reported in the literature. O-Phthalaldehyde is produced by heating pure benzaldehyde and chloroform with potassium hydroxide solution. The resulting solution is further acidified with hydrochloric acid and cooled to yield a colorless powder of o-phthalaldehyde. O-Phthalaldehyde is also produced by ozonization of naphthalene in alcohol followed by catalytic hydrogenation. Catalytic oxidation of various chemicals is also used in manufacturing o-phthalaldehyde.
O-Phthalaldehyde can be manufactured by oxidation of phthalan by nitrogen monoxide in acetonitrile with N-hydroxyphthalimide as the catalyst to yield 80% to 90%. O-phthalaldehyde(OPA) is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups. Used for fluorometric determination of histamine, histidine and other amino acids. Also O-Phthalaldehyde is used for cholesterol assay in the picomole range. Phthaldialdehyde has been used; in the preparation of O-phthaldialdehyde reagent for analysing gentamycin content, in the preparation of reagent for determining the degree of hydrolysis of milk proteins, in the measurement of free amino acids of milk samples by o-phthaldialdehyde/N-acetyl-L-cysteine (OPA/NAC) assay, in the derivatization of putrescine samples.
The primary routes of human exposure to O-Phthalaldehyde are by inhalation and through the skin, which may occur through accidental or occupational exposures. Along with its increasing popularity as a chemical sterilizer, O-Phthalaldehyde has many applications in analytical methods and in diagnostic kits. O-Phthalaldehyde is also used as an intermediate in the synthesis of pharmaceuticals and as a reagent in the tanning industry, hair colorings, wood treatment, and antifouling paints. O-Phthalaldehyde was approved for use as an indoor antimicrobial pesticide in 1997; however, O-Phthalaldehyde is no longer registered with the United States Environmental Protection Agency (USEPA) for this use. Phthalaldehyde (sometimes also o-phthalaldehyde or ortho-phthalaldehyde, Ortho phthalaldehyde) is the chemical compound with the formula C6H4(CHO)2. O-Phthalaldehyde is one of three isomers of benzene dicarbaldehyde, related to phthalic acid. This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
Ortho phthalaldehyde dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air. Ortho phthalaldehyde was tested against a range of organisms including glutaraldehyde-resistant mycobacteria, Bacillus subtilis spores and coat-defective spores. Glutaraldehyde (GTA) and peracetic acid (PAA) were tested for comparative purposes. Both suspension and carrier tests were performed using a range of concentrations and exposure times. All three biocides were very effective (> or = 5 log reduction) against Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa in suspension tests. Ortho phthalaldehyde and GTA (PAA was not tested) were also very effective against Staph. aureus and Ps. aeruginosa in carrier tests. Ortho phthalaldehyde showed good activity against the mycobacteria tested including the two GTA-resistant strains, but 0.5% w/v Ortho phthalaldehyde was found not to be sporicidal. However, limited activity was found with higher concentrations and pH values. Coat-defective spores were more susceptible to Ortho phthalaldehyde, suggesting that the coat may be responsible for this resistance. The findings of this study suggest that Ortho phthalaldehyde is effective against GTA-resistant mycobacteria and that O-Phthalaldehyde is a viable alternative to GTA for high level disinfection.
Ortho phthalaldehyde is used in a very sensitive fluorescent reagent for assaying amines or sulfhydryls in solution, notably contained in proteins, peptides, and amino acids, by capillary electrophoresis and chromatography. Ortho phthalaldehyde reacts specifically with primary amines above their isoelectric point Pi in presence of thiols. Ortho phthalaldehyde reacts also with thiols in presence of an amine such as n-propylamine or 2-aminoethanol. The method is spectrometric (fluorescent emission at 436-475 nm (max 455 nm) with excitation at 330-390 nm (max. 340 nm)). Ortho phthalaldehyde is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex Ortho phthalaldehyde or TD-8. Disinfection with Ortho phthalaldehyde is indicated for semi-critical instruments that come into contact with mucous membranes or broken skin, such as specula, laryngeal mirrors, and internal ultrasound probes.
Ortho phthalaldehyde can be polymerized. In the polymer, one of the oxygen atoms forms a bridge to the other non-ring carbon of the same phthalaldehyde unit, while the other bridges to a non-ring carbon of another phthalaldehyde unit. Poly(phthalaldehyde) is used in making a photoresist. Ortho phthalaldehyde is a pale, yellow crystal or colorless powder. Ortho phthalaldehyde is soluble in water. Ortho phthalaldehyde is used as a disinfectant, mainly for dental and medical equipment. Workers that produce or use Ortho phthalaldehyde may have direct skin contact. The general population may be exposed by contact with residual disinfectant. If Ortho phthalaldehyde is released to the environment, will be broken down in air by reaction with hydroxyl radicals. Ortho phthalaldehyde may be broken down in the air by sunlight. Ortho phthalaldehyde will not volatilize into air from soil or water surfaces. Ortho phthalaldehyde is expected to move easily through soil. Ortho phthalaldehyde is not expected to build up in fish. Irritation to the skin, eyes, and respiratory tract as well as asthma and allergic skin rashes have been reported in some healthcare workers that routinely use Ortho phthalaldehyde to disinfect equipment.
Severe anaphylactic allergic reactions have been reported in some patients exposed to equipment disinfected with Ortho phthalaldehyde. Discoloration of the mouth and throat, burning of the throat, nausea, vomiting, and diarrhea may occur with ingestion. Damage to the nose, throat, lung, skin, and eyes were observed in laboratory animals following repeated exposure to low air levels of Ortho phthalaldehyde, damage was severe at moderate air levels and some animals died. Several alterations in the blood were also observed. Damage to the gastrointestinal tract, irregular breathing, impaired movement, and changes in the blood were observed in laboratory animals given moderate oral doses. Some animals died at high oral doses. No evidence of abortion or birth defects were noted in laboratory animals exposed to Ortho phthalaldehyde during pregnancy, but delayed bone development was observed at high doses that made the mothers sick. Data on the potential for Ortho phthalaldehyde to cause infertility in laboratory animals were not available. However, damage to the testis and reduced sperm counts and motility were observed in male animals following repeated exposure to low air levels of Ortho phthalaldehyde.
Data on the potential for Ortho phthalaldehyde to cause cancer in laboratory animals were not available. The potential for Ortho phthalaldehyde to cause cancer in humans has not been assessed by the U.S. EPA IRIS program, the International Agency for Research on Cancer, or the U.S. National Toxicology Program 14th Report on Carcinogens. Ortho Phthalaldehyde (Ortho phthalaldehyde) is used as disinfectant and reagent in fluorometric determination of primary amines and thiols. Ortho phthalaldehyde is a commonly used solution for rapid sterilization of medical equipment. Cases of anaphylaxis following cystoscopy with endoscopes sterilized with this agent have been reported. Ortho phthalaldehyde-induced anaphylaxis following laryngoscopy have also been described. In these patients, Ortho phthalaldehyde-specific IgE was detected in the serum. Contact dermatitis occurred in 4 workers of the endoscopy unit, one of whom also developed asthma. Among 80 female disinfection workers who used only antiseptic solutions containing Ortho phthalaldehyde, the incidence of disinfection-related complaints were 10% skin, 9% eye, and 16% respiratory symptoms. In male mice, injected Ortho phthalaldehyde induced specific IgE and IgG in the sera, suggesting that Ortho phthalaldehyde acts as a hapten.
Overall, Ortho phthalaldehyde caused acute inflammation and acted as a haptenic allergen, although it caused only mild liver injury. In mice sensitized to ovalbumin , Ortho phthalaldehyde enhanced the induced recruitment of neutrophils to the lung and the production of allergen-specific IgE, suggesting that Ortho phthalaldehyde acts as an immunological adjuvant. The major targets from Ortho phthalaldehyde exposure in rats and mice included the respiratory system (nasal cavity, larynx, trachea, and lung), skin, eye, testis, and epididymis. The most sensitive measure of Ortho phthalaldehyde inhalation toxicity in male and female rats and mice was significantly increased incidences of nasal cavity lesions (lowest-observable-effect concentration = 0.44 ppm). Ortho phthalaldehyde was mutagenic in Salmonella typhimurium strain TA100 in the absence of exogenous metabolic activation; no mutagenicity was seen in TA100 with metabolic activation or in TA98 or Escherichia coli WP2 uvrA/pKM101, with or without metabolic activation.
Ortho Phthalaldehyde's production and use as a disinfectant may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 5.2X10-3 mm Hg at 21 °C indicates Ortho Phthalaldehyde will exist solely as a vapor in the atmosphere. Vapor-phase Ortho Phthalaldehyde will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 17 hours. Ortho Phthalaldehyde has an absorption peak at 297 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, Ortho Phthalaldehyde is expected to have very high mobility based upon an estimated Koc of 10. Volatilization from moist soil surfaces is not expected based upon an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole. Ortho Phthalaldehyde is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data in soil or water were not available. If released into water, Ortho Phthalaldehyde is not expected to adsorb to suspended solids and sediment based upon the estimated Koc.
Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to Ortho Phthalaldehyde may occur through dermal contact with this compound at workplaces where Ortho Phthalaldehyde is produced or used. Monitoring and use data indicate that the general population may be exposed to Ortho Phthalaldehyde via contact with products containing residual disinfectant.
Because body fluids and blood have a tendency to adhere to transesophageal echo devices, a high level of sterilization is required when cleaning them. Ortho phthalaldehyde has been widely used in Japan since being approved as a high-level sterilant. The authors report a patient with widespread, severe skin and mucous membrane damage of the lip, tongue, pharynx and esophagus areas that was attributed to inadequate washing after the sterilization of a transesophageal echo device with Ortho phthalaldehyde. This patient experienced sequelae, which did not improve after more than 1 year of continuous treatment. When using medical devices sterilized with Ortho phthalaldehyde, the use of a probe cover, when applicable, is recommended and complete washing prior to use is required.
