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Home > Encyclopedia > Phthalaldehyde

Phthalaldehyde

pharmaceutical raw materials
Phthalaldehyde structure

Phthalaldehyde 

structure
  • CAS No:

    643-79-8

  • Formula:

    C8H6O2

  • Chemical Name:

    Phthalaldehyde

  • Synonyms:

    1,2-Benzenedicarboxaldehyde;Phthalaldehyde;o-Phthalaldehyde;o-Phthaldialdehyde;Phthalic aldehyde;Phthalic dialdehyde;Phthalyldicarboxaldehyde;2-Formylbenzaldehyde;Benzene-1,2-dicarbaldehyde;o-Phthalic dialdehyde;1,2-Diformylbenzene;o-Diformylbenzene;CIDEX OPA;OP 100S;OP 100SF;1,2-Phthalaldehyde;o-Benzenedicarbaldehyde;NSC 13394;Phtharal;2-Phthalaldehyde;1,2-Formylbenzene

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

o-Phthalaldehyde is a pale yellow crystalline solid.

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, it has gained popularity as a safe and better alternative to glutaraldehyde.
There are some researches show, pH7.5 contains the sterilizing agent of o-phthalaldehyde 0.5%, and its sterilizing power, sterilization speed, stabilit


YELLOW SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.


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.|A 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.

Phthalaldehyde Basic Attributes

134.13

134.13

878317

211-402-2

4P8QP9768A

1784

13394

2923

DTXSID6032514

Long, pale yellow needles from petroleum ether (MP 56-56.5 °C). Also reported as colorless powder (MP: 54 °C)|Yellow needles or crystals from ligroin

29122900

Characteristics

34.1

1.2

yellow powder

1.2±0.1 g/cm3

55-56 °C

83-84 °C (0.7501 mmHg)

>230 °F

1.623

H2O: soluble

2-8°C

0.0052 mm Hg at 21 °C (0.69 Pa)

Relative vapor density (air = 1): 4.6

LD50 orally in Rabbit: 178 mg/kg LD50 dermal Rat > 2000 mg/kg

Henry's Law constant = 1.8X10-8 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.30X10-11 cu cm/molec-sec at 25 °C)

Safety Information

8

UN29238/PG2

3

36/37/38-43-34-25-50-52/53

26-28-36-45-36/37/39-61-37/39

TH6950000

Xi,T,N,C

Irritant/Air Sensitive

Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.

P273-P280-P301 + P310-P305 + P351 + P338-P310

H301-H314-H317-H400

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Oxidizing agents, amines, strong bases.

Combustible.

|Danger|H228 (41.04%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 212 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P391, P405, and P501|P260, P261, P264, P270, P272, P273, P280, P285, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P307+P311, P310, P314, P321, P330, P333+P313, P342+P311, P363, P391, P405, and P501

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for o-Phthalaldehyde (6 total), please visit the HSDB record page.

Recently, the use of ortho-phthalaldehyde (OPA) has been increasing as an alternative to glutaraldehyde(GA)for endoscope disinfection. We detected development of bronchial asthma and contact dermatitis in health care workers (HCW) employed in an endoscopy unit. ... Two of 83 health care workers described mild eye irritation, but no contact dermatitis or bronchitis had newly developed. ...

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum with specialist equipment or carefully sweep into sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Well closed. Separated from oxidants, amines, strong bases and food and feedstuffs. Ventilation along the floor. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance is corrosive to the eyes and skin. The substance is irritating to the respiratory tract.

Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.

NO open flames.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

URBAN/SUBURBAN: Phthalaldehyde (isomer unspecified) was detected in air samples collected in 1973 from Denver, CO at a median of 130 ng/cu m(1).

Toxicity

IDENTIFICATION AND USE: o-Phthalaldehyde (OPA) is used as disinfectant and reagent in fluorometric determination of primary amines and thiols. HUMAN STUDIES: OPA 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. OPA-induced anaphylaxis following laryngoscopy have also been described. In these patients, OPA-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 OPA, the incidence of disinfection-related complaints were 10% skin, 9% eye, and 16% respiratory symptoms. ANIMAL STUDIES: In male mice, injected OPA induced specific IgE and IgG in the sera, suggesting that OPA acts as a hapten. Overall, OPA caused acute inflammation and acted as a haptenic allergen, although it caused only mild liver injury. In mice sensitized to ovalbumin (OVA), OPA enhanced the OVA-induced recruitment of neutrophils to the lung and the production of allergen-specific IgE, suggesting that OPA acts as an immunological adjuvant. The major targets from OPA 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 OPA inhalation toxicity in male and female rats and mice was significantly increased incidences of nasal cavity lesions (lowest-observable-effect concentration = 0.44 ppm). OPA 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.

Groups of 10 male and 10 female rats and mice were exposed to o-phthalaldehyde at concentrations of 0, 0.44, 0.88, 1.75, 3.5, or 7.0 ppm, 6 hours plus T90 (17 minutes) per day, 5 days per week for 14 weeks; additional groups of 10 male and 10 female clinical pathology study rats were exposed to the same concentrations for 23 days. All rats exposed to 7.0 ppm died by the end of week 2 of the study, and seven males and two females exposed to 3.5 ppm died by week 7 of the study. All mice exposed to 7.0 ppm died during week 1 of the study, and five males and four females exposed to 3.5 ppm died by week 6 of the study. Clinical observations in rats and mice included abnormal breathing, sneezing, and thinness, with increasing frequency in higher exposure groups. In rats, clinical observations also included black discoloration of the appendages (pinnae and/or feet), which was noted throughout the study in male and female rats exposed to 3.5 ppm or greater. Clinical observations in mice also included alopecia. Mean body weights of all surviving exposed groups of male rats and 1.75 and 3.5 ppm female rats were significantly less than those of the chamber controls. Mean body weights of all surviving exposed groups of male and female mice were significantly less than those of the chamber controls, and 3.5 ppm males lost weight during the study. In the hematopoietic system of rats, decreases in lymphocyte counts in males and females coincided with increases in neutrophil counts. These alterations in lymphocyte and neutrophil counts were consistent with stress and inflammation. Decreased lymphocyte counts corresponded to lymphoid atrophy in the thymus and spleen. Within the erythron, the erythrocyte counts, hemoglobin concentrations, hematocrit values, and packed cell volumes were significantly elevated in both male and female rats at all time points. Erythron increases at the earlier time points were consistent with a physiological hemoconcentration, while increases at study termination may have been due to hypoxia with a resultant secondary erythrocytosis. In the hematopoietic system of mice, the total leukocyte and lymphocyte counts, as well as neutrophil and eosinophil counts, were increased in males at study termination. Similarly, female mice had increased total leukocyte, neutrophil, and eosinophil counts. The increases in the leukon were generally consistent with inflammation. Hemoglobin concentrations, erythrocyte counts, hematocrit values, and packed cell volumes were decreased in male and female mice. The decreases in the erythron were most likely due to bone marrow suppression as a result of the chronic inflammation in the respiratory tract. Inhalation exposure to o-phthalaldehyde resulted in a spectrum of lesions at sites of contact within the respiratory tract (nose, larynx, trachea, and lung), skin, and eye that were generally consistent with an irritant effect. In general, exposure of rats and mice to o-phthalaldehyde resulted in lesions throughout the respiratory tract that included necrosis, inflammation, regeneration, hyperplasia, and metaplasia, ranging from minimal to moderate in severity. In general, histologic findings occurred at deeper sites within the respiratory tract with increasing exposure concentration. The first site of contact, the nose, was most affected, with many lesions occurring at the lowest exposure concentration (0.44 ppm) in male and female rats and mice. Laryngeal lesions occurred at all exposure concentrations in rats and at 0.88 ppm or greater in mice. Tracheal findings were first noted at a variety of exposure concentrations. Lung findings were most prevalent at the two highest exposure concentrations (3.5 and 7.0 ppm) in rats and mice. In the skin, there were significant increases in adnexa degeneration and epithelial parakeratosis in both male and female rats and mice. In the eye, there were significant increases in suppurative inflammation of the anterior chamber and cornea, as well as corneal necrosis in male and female rats. Rats exposed to o-phthalaldehyde exhibited lower cauda epididymis, epididymis, and testis weights. In rats, total sperm/cauda exhibited a negative trend and sperm motility was lower. There were no histopathologic correlates identified that could explain the observed responses in sperm parameters, or the weight changes in the testis or epididymis. However, in the higher dose groups where morbidity and mortality were observed, testicular and epididymal histopathologic lesions were noted. In the testes, these lesions included significant increases in the incidences of elongated spermatid degeneration, apoptosis of the germinal epithelium, and interstitial cell atrophy. In the epididymis of male rats, there were significant increases in the incidences of exfoliated germ cells and apoptosis of the epithelium. The mice also displayed decreased sperm motility, and some testicular and epididymal histopathologic lesions, including significantly increased incidences of exfoliated germ cells of the epididymal duct, as well as multifocal cellular depletion of the germinal epithelium, and interstitial cell atrophy of the testis. o-Phthalaldehyde was mutagenic in Salmonella typhimurium strain TA100 in the absence of exogenous metabolic activation (S9 mix); no mutagenicity was seen in TA100 with S9 or in TA98 or Escherichia coli WP2 uvrA/pKM101, with or without S9. Following 3 months of inhalation exposure to o-phthalaldehyde, no increases in the frequencies of micronucleated reticulocytes were observed in male or female Sprague Dawley rats. In B6C3F1/N mice following 3 months of inhalation exposure to o-phthalaldehyde, a small increase in micronucleated reticulocytes was seen in male mice exposed to 3.5 ppm, but no significant increases in micronuclei were seen in erythrocytes of male mice or in reticulocytes or erythrocytes of female mice. A small increase in the percentage of reticulocytes was seen in female mice at the highest dose tested (3.5 ppm). Under the conditions of these 3-month inhalation studies, there were treatment-related lesions in male and female rats and mice. The major targets from o-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 o-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). A no-observed-effect concentration was not reached in rats or mice of either sex.

o-Phthalaldehyde's production and use as a disinfectant(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that o-phthalaldehyde is expected to have very high mobility in soil(SRC). Volatilization of o-phthalaldehyde from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole(SRC) based upon its vapor pressure, 5.2X10-3 mm Hg(3), and water solubility, 5.0X10+4 mg/L(3). o-Phthalaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that o-phthalaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 5.2X10-3 mm Hg(4), and water solubility, 5.0X10+4 mg/L(4). o-Phthalaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of 0.51(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phthalaldehyde, which has a vapor pressure of 5.2X10-3 mm Hg at 21 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phthalaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(3). o-Phthalaldehyde has an absorption peak at 297 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of o-phthalaldehyde with photochemically-produced hydroxyl radicals has been reported as 2.3X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). o-Phthalaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). o-Phthalaldehyde has an absorption peak at 297 nm(1) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for o-phthalaldehyde(SRC), using a log Kow of 0.51(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phthalaldehyde can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phthalaldehyde is expected to have very high mobility in soil(SRC).

The Henry's Law constant for o-phthalaldehyde is estimated as 1.8X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 5.2X10-3 mm Hg(1), and water solubility, 5.0X10+4 mg/L(1). This Henry's Law constant indicates that o-phthalaldehyde is expected to be essentially nonvolatile from water and moist soil surfaces(2). o-Phthalaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER/DRINKING WATER: Phthalaldehyde (isomer unspecified) was detected in groundwater used as a drinking water source collected Oct 17, 1978; it was also detected in finished drinking water from this source(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 3253 workers (2222 of these are female) were potentially exposed to o-phthalaldehyde in the US(1). Occupational exposure to o-phthalaldehyde may occur through dermal contact with this compound at workplaces where o-phthalaldehyde is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to o-phthalaldehyde via dermal contact with devices containing residual disinfectant(SRC). The median time-weighted average exposure to o-phthalaldehyde in manual and automated endoscope disinfection workers was 0.66 and 0.33 ppb, respectively(2).

Drug Information

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)|Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)

Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.


Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aldehydes and Related Compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Aggressive airway management may be necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aldehydes and Related Compounds/|/SRP:/ Advanced treatment: Consider Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Intubation should be considered at the first sign of upper airway obstruction caused by edema. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aldehydes and Related Compounds/

/CASE REPORTS/ Iatrogenic injury from medical disinfectants is an uncommon but potentially devastating complication. We report an unusual, but severe, upper aerodigestive complication from the use of ortho-phthalaldehyde solution, a commonly used endoscope disinfectant.|/CASE REPORTS/ PURPOSE: Ortho-phthalaldehyde (Cidex OPA) is a commonly used solution for rapid sterilization of flexible endoscopic equipment. We report two cases of anaphylaxis following cystoscopy with endoscopes sterilized with this agent. Only a handful of such reactions have been reported in the published literature, the majority of which are in the bladder cancer population undergoing surveillance cystoscopy. PATIENTS AND METHODS: We reviewed the clinical presentation of two cases of anaphylaxis following flexible cystoscopy with instruments sterilized with ortho-phthalaldehyde. We further describe their subsequent evaluation by an allergy and immunology specialist who performed skin testing to confirm a suspected ortho-phthalaldehyde allergy. RESULTS: Both patients were skin test positive to ortho-phthalaldehyde antigen. As a result, sterilization techniques for our flexible endoscopes has been altered. To date, no further anaphylactic reactions have occurred in our bladder cancer patients, including the two cases presented herein following subsequent cystoscopic evaluations. CONCLUSIONS: Ortho-phthalaldehyde-sterilized cystoscopes have been associated with anaphylactic reactions in a small number of patients who have undergone repeated cystoscopy. The manufacturer has already made recommendations to avoid this agent in bladder cancer patients. It may be prudent to extend this practice to other populations undergoing repeat cystoscopy.|/CASE REPORTS/ Ortho-phthalaldehyde (OPA) has recently been used as a disinfectant for various medical apparatuses. OPA is not generally recognized as a potential allergen. CASE SUMMARY: Subsequent to our recent report describing a patient presenting with OPA-induced anaphylaxis following laryngoscopy, we experienced two more such cases. In all three cases, the basophil histamine release test was useful for identifying the allergen as OPA. OPA-specific IgE was successfully detected in the serum of the patients by ELISA. DISCUSSION: Physicians and co-medical workers need to be aware of potential allergens to which patients may be exposed during routine medical procedures.|/CASE REPORTS/ 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 (OPA) 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 OPA. This patient experienced sequelae, which did not improve after more than 1 year of continuous treatment. When using medical devices sterilized with OPA, the use of a probe cover, when applicable, is recommended and complete washing prior to use is required.|For more Human Toxicity Excerpts (Complete) data for o-Phthalaldehyde (10 total), please visit the HSDB record page.

Aldehyde, ortho-Phthalic

Serious local effects on contact with eyes and skin. The substance can be absorbed into the body by inhalation of its vapour or dust and by ingestion.

Cough. Shortness of breath. Headache.


Redness. Pain. Serious skin burns.


Redness. Pain. Severe burns.

Phthalaldehyde Use and Manufacturing

Uses

Disinfectant.Reagent in fluorometric determination of primary amines and thiols.

1,2-Benzenedicarboxaldehyde: ACTIVE

Three sampling and analytical methods have been developed and evaluated for ortho-phthalaldehyde (OPA): (1) an HPLC-UV method for OPA in air, (2) a fluorimetric method for OPA on surfaces, and (3) a colorimetric method for OPA on surfaces. (1) The air sampler contains 350 mg of silica gel coated with 1 mg of acidified 2,4-dinitrophenylhydrazine (DNPH). Air sampling may be conducted at 0.03 to 1.0 L/min for periods up to 8 hr. Samples were eluted with ethyl acetate, and the eluents were allowed to stand for 72 hr. Analysis was by high performance liquid chromatography (HPLC) with a UV detector set at 369 nm. An unusual phenomenon was the observation that the stability of the sample on a sampler at 3 degrees C tends to decrease as the total quantity of OPA collected on the sampler decreases. Elution of the samples within 24 hr of air sampling is required. The detection limit (LOD) is approximately 0.02 ug of OPA per sample. OPA on surfaces may be collected with strips cut from a sheet of polyvinyl alcohol (PVA wipe). (2) In the surface wipe method with analysis by fluorescence measurement, the strips of PVA wipe were placed into dimethyl sulfoxide. An aliquot was treated with aqueous N-acetyl-l-cysteine and ethylenediamine. Analysis was performed with a portable fluorometer (excitation and emission wavelengths = 365 nm and 438 nm, respectively). The LOD is 0.2 ug per sample. (3) In the surface wipe method with visual colorimetric detection, the strips of PVA wipe were placed into 30:70 acetonitrile:water. An aliquot was treated with N-(1-naphthyl)ethylenediamine in 0.1 m sulfuric acid. After color development, the LOD is approximately 48 ug per sample. These methods have been field tested in a hospital.|A simple high performance liquid chromatographic (HPLC) method and a highly sensitive gas chromatography mass spectrometric (GC-MS) method have been established for the determination of ortho-phthalaldehyde (OPA) in water. These methods are based on the derivatization of OPA with hydrazine in water. The following optimum reaction conditions were established: reagent dosage, 20 mg/mL of hydrazine; pH 2; reaction for 20 min at 70 °C. The organic derivative was detected directly by HPLC or after the extraction with methylene chloride/concentration by GC-MS. The limit of detection of OPA in water was 4.0 and 0.3 ug/L by HPLC and GC-MS, respectively. The calibration curve showed good linearity with r2 = 0.9993 and r2 = 0.9994 by HPLC and GC-MS, respectively, the accuracy was in a range of 95-105%, and the precision of the assay was less than 13% in water. The HPLC method was simple and reproducible enough to permit the OPA content analysis in the disinfectant products, and the GC-MS method is sensitive enough to permit reliable analysis of OPA to the ug/L level in environmental water.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Phthalaldehyde is a known environmental transformation product of Dithianon.

Computed Properties

Molecular Weight:134.13
XLogP3:1.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:134.036779430
Monoisotopic Mass:134.036779430
Topological Polar Surface Area:34.1
Heavy Atom Count:10
Complexity:115
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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