Наименование
Ортофталевый альдегид
Синонимы
орто-фталальдегид; ортофталевый альдегид; ортофталевый ангидрид;
Регистрационный номер CAS
643-79-8
Ортофталевый альдегид
Синонимы: 1,2-бензолдикарбоксиальдегид, o-фтальальдегид; фталевый дикарбоксиальдегид
Формула: C8H6O2
M.B.: 134.1342
Cas №.: 643-79-8
Описание: светложелтые кристаллы.
Применение: полупродукт, биоцид, сырье для дезсредств.
орто-фталевый альдегид
OPA предпочтительнее глутаральдегида для дезинфекции высокого уровня в Соединенных Штатах, потому что он не требует активации, стабилен в широком диапазоне pH, не вызывает раздражения слизистых оболочек и имеет едва уловимый запах. Его активность выше, чем у глутарового альдегида, а дезинфекция высокого уровня достигается при времени контакта 12 минут при 20 ° C или выше.10,11 Основным недостатком OPA является то, что он окрашивает ткани и слизистые оболочки в серый цвет. При работе с раствором необходимо надевать защитное снаряжение, а после обработки тщательно промыть его с предметов. При попадании в глаза может возникнуть раздражение. ОРА также дороже глутаральдегида. 12 Растворы можно использовать повторно в течение максимум 14 дней.
Ортофталевый альдегид
ОРТОФТАЛЕВЫЙ АЛЬДЕГИД
СИНОНИМЫ: 1,2-BENZENDICARBOXALDEHYDE; O-PHTHALDIALDEHYDE; CIDEX OPA; O-PHTHALIC ALDEHYDE; BENZENDICARBOXALDEHYDE; PHTHALIC DICARBOXALDEHYDE
CAS NO.: 643-79-8
ОПИСАНИЕ: СВЕТЛО-ЖЕЛТЫЕ КРИСТАЛЛЫ
Орто-фталевый альдегид: возможная альтернатива глутаральдегиду для дезинфекции высокого уровня !!!
Ортофталевый альдегид (ОРА) был протестирован против ряда организмов, включая устойчивые к глутаральдегиду микобактерии, споры Bacillus subtilis и споры с дефектной шерстью. Глутаральдегид (глутаральдегид) и перуксусная кислота (PAA) были протестированы для сравнительных целей. Испытания как суспензии, так и носителя были выполнены с использованием диапазона концентраций и времени воздействия. Все три биоцида были очень эффективными (≥ 5 log уменьшения) против Escherichia coli, Staphylococcus aureus и Pseudomonas aeruginosa в тестах на суспензию. OPA и глутаральдегид (PAA не тестировался) также были очень эффективны против Staph. aureus и Пс. aeruginosa в тестах-носителях. ОРА продемонстрировал хорошую активность против тестируемых микобактерий, включая два штамма, устойчивых к глутаральдегиду, но 0,5% ОРА (вес / об) не оказал спорицидного действия. Однако была обнаружена ограниченная активность при более высоких концентрациях и значениях pH. Споры с дефектом шерсти были более восприимчивы к OPA, что позволяет предположить, что шерсть может быть ответственной за эту устойчивость. Результаты этого исследования показывают, что OPA эффективен против устойчивых к глутаральдегиду микобактерий и является жизнеспособной альтернативой глутаральдегиду для дезинфекции высокого уровня.
ВВЕДЕНИЕ
Глутаральдегид (глутаральдегид) используется в качестве дезинфицирующего / стерилизующего агента более 30 лет (Russell 1994). Щелочной глутаральдегид (2% об. / Об.) Обладает широким спектром активности и быстрым антимикробным действием, а также не вызывает коррозии металлов, резины и линз. Однако сообщалось о потенциальных мутагенных и канцерогенных эффектах (Hugo & Russell 1999), а также о раздражении кожи и глаз и респираторных заболеваниях (Russell 1994). Риск для персонала и рост числа устойчивых к глутаральдегиду Mycobacterium chelonae (Griffiths et al. 1998a) подчеркивают необходимость замены.
Одной из возможных альтернатив глутаральдегиду является орто-фталевый альдегид (ОРА). OPA уже используется в аминокислотном анализе (Carlomagno et al. 1985; Blundell & Brydon 1987), но 0,5% (мас. / Об.) OPA также продемонстрировали бактерицидное действие. При оценке дезинфекции 100 эндоскопов было обнаружено, что OPA эффективен без активации и стабилен в течение 14-дневного цикла использования (Alfa & Sitter 1994). Микобактерицидная активность была также продемонстрирована против M. bovis с 5-кратным уменьшением после 5-минутного воздействия 0,2% ОРА (Roberts & Chan-Myers 1998).
Другой возможной альтернативой глутаральдегиду является перуксусная кислота (PAA). PAA был представлен как антибактериальный агент в 1955 году; он обладает широким спектром активности, включая бактерии, споры, плесень, дрожжи, водоросли и вирусы (Hugo & Russell 1999). ПАК является сильным окислителем и может вызывать коррозию некоторых металлов. Однако коррозионные проблемы можно уменьшить, используя коммерческие составы, и 13 месяцев использования PAA не дало явно видимых признаков коррозии гибких эндоскопов, использующих систему Steris (DiagMed Ltd, Norby, UK Страница: 2Au: Пожалуйста, предоставьте данные компании / адрес) ( Маннион 1995). Nu-Cidex, равновесная смесь уксусной кислоты, PAA и перекиси водорода, обладает быстрым микобактерицидным действием, в том числе против лекарственно-устойчивых изолятов Mycobacterium tuberculosis и M. avium-intracellulare, всего через 5 минут (Holton et al. . 1995).
Это исследование было инициировано с целью изучения биоцидных свойств OPA против ряда не кислотоустойчивых неспорообразующих организмов, чувствительных к глутаральдегиду и устойчивых микобактерий и спор B. subtilis. Для оценки активности биоцидов использовали тест суспензии и тест носителя; это было сочтено необходимым, поскольку было показано, что дезинфицирующие средства с высокой активностью в тестах на суспензию не обязательно так же активны на загрязненных поверхностях (Best et al. 1988). Также использовали споры, обработанные мочевиной / дитиотреитолом / лаурилсульфатом натрия (UDS), pH 10 · 3. Было показано, что удаление белка из оболочки спор резко увеличивает чувствительность B. subtilis к щелочному глутаровому альдегиду (Gorman et al. 1984), и считалось, что такой же эффект может происходить с OPA. Сравнение с глутаральдегидом и PAA проводилось для оценки активности OPA.
Орто-фталевый альдегид (OPA) - это ароматический диальдегид, используемый в качестве антимикробного дезинфицирующего средства высокого уровня для медицинского оборудования, чувствительного к нормальным процессам тепловой или паровой стерилизации, включая эндоскопы, цистоскопы и некоторые стоматологические инструменты. В течение 40 лет глутаральдегид, другой диальдегид, был основным выбором для дезинфекции термочувствительных медицинских устройств; однако сообщалось, что он является химическим сенсибилизатором. Глутаральдегид, как известно, имеет высокое сродство к биологическим аминам, и его использование в качестве фиксатора тканей извлекает выгоду из этого свойства. Таким образом, глутаральдегид и диальдегиды как химический класс могут связываться с нативными белками, тем самым изменяя их представление иммунной системе. Гаптенизация нативных белков может привести к аберрантному иммунному ответу и развитию аллергии. Несколько исследований на людях продемонстрировали присутствие IgE-антител, специфичных к аддуктам глутарового альдегида, в сыворотке подвергшихся воздействию рабочих с респираторными заболеваниями. Важно отметить, что воздействие глутаральдегида на рабочем месте, как известно, вызывает профессиональную астму и аллергический контактный дерматит, что предполагает необходимость в более безопасных альтернативах. ОРА продемонстрировал превосходную антимикобактерицидную активность по сравнению с глутаральдегидом, что позволяет использовать его в более низких концентрациях. Кроме того, низкая летучесть и отсутствие необходимости в активации увеличили использование OPA в качестве более практичной альтернативы глутаральдегиду.
ortho-Phthalaldehyde
OPA is favored over glutaraldehyde for high-level disinfection in the United States, because it does not require activation, is stable over a wide pH range, does not cause irritation of mucous membranes, and it has a barely perceptible odor. Its activity is greater than that of glutaraldehyde, and high-level disinfection is achieved with a contact time of 12 minutes at or above 20°C.10,11 The primary disadvantage of OPA is that it stains tissues and mucous membranes gray. Protective equipment must be worn when handling the solution, and it must be rinsed thoroughly from items after treatment. Irritation can occur with eye contact. OPA is also more expensive than glutaraldehyde.12 Solutions can be reused for a maximum of 14 days.
Ortho‐phthalaldehyde: a possible alternative to glutaraldehyde for high level disinfection !!!
Ortho‐phthalaldehyde (OPA) was tested against a range of organisms including glutaraldehyde‐resistant mycobacteria, Bacillus subtilis spores and coat‐defective spores. Glutaraldehyde (glutaraldehyde) 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 (≥ 5 log reduction) against Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa in suspension tests. OPA and glutaraldehyde (PAA was not tested) were also very effective against Staph. aureus and Ps. aeruginosa in carrier tests. OPA showed good activity against the mycobacteria tested including the two glutaraldehyde‐resistant strains, but 0·5% w/v OPA was found not to be sporicidal. However, limited activity was found with higher concentrations and pH values. Coat‐defective spores were more susceptible to OPA, suggesting that the coat may be responsible for this resistance. The findings of this study suggest that OPA is effective against glutaraldehyde‐resistant mycobacteria and that it is a viable alternative to glutaraldehyde for high level disinfection.
INTRODUCTION
Glutaraldehyde (glutaraldehyde) has been used as a disinfecting/ sterilizing agent for over 30 years ( Russell 1994). Alkaline glutaraldehyde (2% v/v) has a broad range of activity and rapid antimicrobial action as well being non‐corrosive to metals, rubber and lenses. However, potential mutagenic and carcinogenic effects have been reported ( Hugo & Russell 1999) as well as skin and eye irritation and respiratory disorders ( Russell 1994). The risk to personnel and the increasing frequency of glutaraldehyde‐resistant Mycobacterium chelonae ( Griffiths et al. 1998a ) has highlighted the need for a replacement.
One possible alternative to glutaraldehyde is ortho‐phthalaldehyde (OPA). OPA is already used in amino acid analysis ( Carlomagno et al. 1985 ; Blundell & Brydon 1987) but 0·5% (w/v) OPA has also been demonstrated to be bactericidal. When assessed in the disinfection of 100 endoscopes, OPA was found to be effective without activation and was stable over a 14‐day usage cycle (Alfa & Sitter 1994). Mycobactericidal activity has also been demonstrated against M. bovis with a 5 log reduction after 5 min exposure to 0·2% OPA ( Roberts & Chan‐Myers 1998).
Another possible glutaraldehyde alternative is peracetic acid (PAA). PAA was introduced as an antibacterial agent in 1955; it has a broad spectrum of activity including bacteria, spores, moulds, yeasts, algae and viruses ( Hugo & Russell 1999 ). PAA is a powerful oxidizing agent and can be corrosive to some metals. However, corrosive problems can be reduced by using commercial formulations and 13 months usage of PAA gave no overtly visible signs of corrosion of flexible endoscopes using the Steris system (DiagMed Ltd, Norby, UKPage: 2Au: Please supply company details/address of ) ( Mannion 1995). ‘Nu‐Cidex’, an equilibrium mixture of acetic acid, PAA, and hydrogen peroxide has been shown to be rapidly mycobactericidal, including against drug‐resistant isolates of Mycobacterium tuberculosis and M. avium‐intracellulare, after only 5 min ( Holton et al. 1995 ).
This study was initiated to investigate the biocidal properties of OPA against a range of non‐acid‐fast non‐sporulating organisms, glutaraldehyde‐sensitive and resistant mycobacteria and B. subtilis spores. A suspension test and a carrier test were used to evaluate the activity of the biocides; this was considered necessary as it has been shown that disinfectants with high activity in suspension tests are not necessarily as active on contaminated surfaces ( Best et al. 1988 ). Spores treated with urea/dithiothreitol/sodium lauryl sulphate (UDS), pH 10·3, were also used. The removal of protein from the spore coat has been shown to dramatically increase the sensitivity of B. subtilis to alkaline glutaraldehyde ( Gorman et al. 1984 ) and the same effect was thought likely to occur with OPA. Comparisons with glutaraldehyde and PAA were carried out to assess OPA activity.
Discussion
Despite the high number of bacteria needed to measure large log reductions in these experiments, all three biocides tested were shown to be very effective against non‐acid‐fast nonsporulating organisms. OPA, like the other two biocides, was still very effective at concentrations far lower than its recommended in‐use concentration of 0·5% (w/v) and was equally effective against both the Gram‐negative and Gram‐positive test bacteria.
Due to the increase in the number of organisms tested, a direct comparison between the results of the suspension tests and carrier tests could not be drawn. However, both concentrations of OPA and glutaraldehyde were still effective (≥ 5 log reduction) with only 10 min of exposure time against both of the test organisms, and the recommended in‐use concentrations of 0·5% (w/v) and 2% (v/v) for OPA and glutaraldehyde, respectively, were effective within 2 min. Therefore, it can be concluded that drying of these test organisms did not significantly impair the action of either OPA or glutaraldehyde despite the increased cell numbers.
Due to the worrying increase in isolation of glutaraldehyde‐resistant M. chelonae from washer disinfectors and processed endoscopes ( Griffiths et al. 1998a ), it was encouraging to note a lack of cross‐resistance to OPA in the two glutaraldehyde‐resistant washer isolates tested. OPA (0·5 w/v) and 2% (v/v) alkaline glutaraldehyde were also very effective against M. terrae NCTC 10856, which has been suggested as a possible surrogate testing organism for M. tuberculosis, although M. avium‐intracellulare was found to be more resistant ( Griffiths et al. 1998b ). The other two M. chelonae strains tested were sensitive to both biocides, although glutaraldehyde was slightly more effective against M. chelonae var. abscessus. The rapid action of glutaraldehyde against M. chelonae NCTC 946 ( Jettéet al. 1995 ; Lynam et al. 1995 ) was confirmed with a ≥ 6 log reduction within 1 min of exposure.
The sporicidal activity of glutaraldehyde was confirmed with the same 3 h exposure time found in other studies ( Russell 1990). The lack of any sporicidal effect with 0·5% (w/v) OPA seemed to be connected with the spore coat as there was a large increase in activity when coat‐defective (UDS‐treated) spores were tested. Raising the pH of OPA to 8 increased its efficacy but not to the levels seen with 2% (v/v) alkaline glutaraldehyde. Increasing the concentration of the OPA as well as the pH did produce sporicidal activity, although OPA took longer (preparation of 2% w/v OPA was aided by warming) to dissolve at these higher concentrations.
In conclusion, 0·5% (w/v) OPA is considered to be a viable alternative to glutaraldehyde for high level disinfection where, by definition, the compound need not have a lethal action against high levels of bacterial spores ( Russell 1994; Rutala & Weber 1995). OPA should not be used in situations where sterilization is required, but it might be particularly useful in washer systems where glutaraldehyde‐resistant organisms have developed.
Acknowledgements
The authors thank Prof. S.A. Sattar and Dr V.S. Springthorpe of the Department of Microbiology and Immunology, School of Medicine, University of Ottawa, for their help with the carrier test design. They are also grateful for the financial support of Johnson & Johnson, USA, in providing a research studentship (to S.E.W.).
Comparison between Glutaraldehyde and Ortho-Phthalaldehyde Air Levels during Endoscopic Procedures
Author links open overlay panelC.Marena∗L.LodolaR.LodiL.Zambianchi
https://doi.org/10.1016/j.ajic.2004.04.062Get rights and content
Abstract
BACKGROUND: Glutaraldehyde (glutaraldehyde) has been used as a disinfecting agent for over 30 years, but irritative effects on the skin and respiratory tract have been described. The risk to healthcare personnel and emerging of glutaraldehyde-resistant microorganisms have highlighted the need to develop new agents. One possible alternative to glutaraldehyde is ortho-phthalaldehyde (OPA), which has a similar capacity to kill bacteria and a very good toxicological profile.
OBJECTIVE: To compare air levels of glutaraldehyde and OPA during high-level disinfection of endoscopes.
METHODS: The comparative study was carried out in ten endoscopy units of the San Matteo Hospital, where glutaraldehyde and OPA were routinely used for the low-temperature disinfection of endoscopes. glutaraldehyde and OPA were used under the same operating procedures and for the same exposure time (4 hours). The monitoring of air levels was performed with both HPLC-UV (High Performance Liquid Chromatography with UV detection) and Infrared Spectroscopy (IR).
RESULTS: The HPLC method gave a much lower aldheyde value when using OPA (8.4 mg/m3) compared to that obtained when glutaraldehyde was used to disinfect endoscopes (21279.3 mg/m3). These results were confirmed with IR detection method (the mean values being below 10 mg/m3). In addition, we studied the resistance of various glove types to OPA. Tests showed that OPA-permeated vinyl gloves more rapidly (26628 ng/cm2 per hour) than nitrile gloves (13.9 ng/cm2 per hour).
CONCLUSION: This study showed a very low air concentration of OPA compared to glutaraldehyde. These findings confirm the excellent safety profile of OPA used as a high-level disinfectant in the hospital setting.
Ortho-Phthalaldehyde (OPA) is an aromatic dialdehyde, used as a high-level antimicrobial disinfectant for medical equipment which is sensitive to normal heat or steam sterilization processes, including endoscope, cystoscopes, and certain dental instruments. For 40 years, glutaraldehyde, another dialdehyde, has been the primary choice for disinfecting heat-sensitive medical devices; however, it has been reported to be a chemical sensitizer. Glutaraldehyde is known to have high affinity for biological amines, and its use as a tissue fixative capitalizes on this property. As such, glutaraldehyde and dialdehydes as a chemical class can bind to native proteins, thus, altering their presentation to the immune system. Haptenization of native proteins can lead to an aberrant immune response and the development of allergy. Several human studies have demonstrated the presence of IgE antibodies specific for glutaraldehyde adducts in the serum of exposed workers with respiratory disease [1, 2]. Importantly, workplace exposure to glutaraldehyde is known to induce occupational asthma [2–4] and allergic contact dermatitis [5] suggesting the need for safer alternatives. OPA has shown superior antimycobactericidal activity as compared to glutaraldehyde [6], allowing for its use at lower concentrations. In addition, low volatility and no need for activation have increased the use of OPA as a more practical alternative to glutaraldehyde.
Cas no: 643-79-8;PHTHALALDEHYDE;PHTHARAL; o-Phthaldialdehyde; Benzene-1,2-dicarboxaldehyde; 1,2-Benzenedicarboxaldehyde; Phthaldialdehyde; Phthalic aldehyde; Phthalic dialdehyde; ortho-Phthalaldehyde; Phthalyldicarboxaldehyde; o-Phthaldehyde; benzene-1,2-dicarbaldehyde; Phthalic dicarboxaldehyde; Phthalaldialdehyde
;o-Phthalicdicarboxaldehyde; 1,2-Diformylbenzene; 2-PHTHALALDEHYDE
In chemical sterilant field, phthalaldehyde, compare with glutaraldehyde, is not irritant to the eyes and nasal passages but has excellent stability over a wide range of pH (3-9), which does not require exposure monitoring, and has a barely perceptible odor. But phthaldialdehyde stains proteins gray including unprotected skin. Thus, it must be handled with use of gloves, eye protection, fluid-resistant gowns when handling contaminated instruments, contaminated equipment, and chemicals.
Pure ortho-phthalaldehyde is rarely encountered. When used as a disinfectant, it comes in the form of an aqueous solution with a concentration of approximately 0.55%. Commercial solutions contain additives that help stabilize their pH, such as citric acid and phosphates, preservatives and colorants.
Use and sources of emission:
Ortho-phthalaldehyde is primarily used as a high-efficiency chemical disinfectant for dental or medical instruments, such as endoscopes. It is often considered a safer alternative to glutaraldehyde.
It is also used in the laboratory, as a reagent for fluorometric analyzes of primary amines and thiols.
Phthalaldehyde (sometimes also o-phthalaldehyde or ortho-phthalaldehyde, OPA) is the chemical compound with the formula C6H4(CHO)2. It 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. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.
Phthalaldehyde (sometimes also o-phthalaldehyde or ortho-phthalaldehyde, OPA) is the chemical compound with the formula C6H4(CHO)2. It 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. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.
o-PHTHALALDEHYDE
PRODUCT IDENTIFICATION
CAS NO. 643-79-8
o-PHTHALALDEHYDE
EINECS NO.: 211-402-2
FORMULA: C6H4-1,2-(CHO)2
MOL WT.: 134.12
SYNONYMS: 1,2-Benzenedicarboxaldehyde; 2-Formylbenzaldehyde;1,2-Benzenedialdehyde; 1,2-Phthalic Dicarboxyaldehyde; OPA; PA; Phtalaldehydes (French);
PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE: Light yellow crystalline powder
MELTING POINT: 56 C
Health: 2 ; Flammability: 1 ; Reactivity: 0
REFRACTIVE INDEX
o-Phthalaldehyde Properties
Melting point:55-58 °C(lit.)
Boiling point:83-84 °C (0.7501 mmHg)
Density 1.13
refractive index 1.4500 (estimate)
Flash point:>230 °F
storage temp. 2-8°C
solubility The solubility of o-phthalaldehyde is 3g/100 mL diisopropyl ether, 5g/100mL deionized water, 20g/100mL chloroform, or 20g/100mL acetone at 20°C.
form:powder
color: yellow
Stability:Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.
NIST Chemistry Reference: O-phthalaldehyde(643-79-8)
EPA Substance Registry System: 1,2-Benzenedicarboxaldehyde (643-79-8)
FLASH POINT: 110 C
STABILITY: Stable under ordinary conditions
APPLICATIONS
Phthalaldehyde is used as a disinfectant and as a tanning agent in leather industry. It is useful for the sterilization of endoscopic instruments, thermometers, rubber and plastic equipment which cannot be sterilized by heating system. It is also used as an intermediate in synthesis of pharmaceuticals, medicines, and other organic compounds.
SALES SPECIFICATION
APPEARANCE
Light yellow crystalline powder
PURITY: 99.0% min
INDIVIDUAL IMPURITY: 0.5% max
WATER: 0.5% max
HAZARD CLASS: 8
UN NO.: 1759
REMARKS: In chemical sterilant field, phthalaldehyde, compare with glutaraldehyde, is not irritant to the eyes and nasal passages but has excellent stability over a wide range of pH (3-9), which does not require exposure monitoring, and has a barely perceptible odor. But phthaldialdehyde stains proteins gray including unprotected skin. Thus, it must be handled with use of gloves, eye protection, fluid-resistant gowns when handling contaminated instruments, contaminated equipment, and chemicals.
YELLOW SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.
Synthesis and reactions
The compound was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-ortho-xylene. A more modern synthesis is similar: the hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.
The reactivity of OPA is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively. Its reactions with nucleophiles often involves the reaction of both carbonyl groups
Biochemistry
OPA 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. OPA reacts specifically with primary amines above their isoelectric point Pi in presence of thiols. OPA 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)).
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.
Disinfection
OPA is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex OPA or TD-8. Disinfection with OPA 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.
Poly(phthalaldehyde)
OPA 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.
In winemaking
The Nitrogen by O-Phthaldialdehyde Assay (NOPA) is one of the methods used in winemaking to measure yeast assimilable nitrogen (or YAN) needed by wine yeast in order to successfully complete fermentation.[9]
Ortho-phthalaldehyde (OPA) is a high-level disinfectant that received FDA clearance in October 1999. It contains at least 0.55% 1,2-benzenedicarboxaldehyde or OPA, and it has supplanted glutaraldehyde as the most commonly used “aldehyde” for high-level disinfection in the United States. OPA solution is a clear, pale-blue liquid with a pH of 7.5. The advantages, disadvantages, and characteristics of OPA are listed in Table 301-2.
Studies have demonstrated excellent microbicidal activity in in vitro studies,74,75,93,111,147-152 including superior mycobactericidal activity (5-log10 reduction in 5 minutes) compared with glutaraldehyde. Walsh and colleagues also found OPA effective (>5-log10 reduction) against a wide range of microorganisms, including glutaraldehyde-resistant mycobacteria and Bacillus atrophaeus spores.150
OPA has several potential advantages compared with glutaraldehyde. It has excellent stability over a wide pH range (pH 3 to 9), is not a known irritant to the eyes and nasal passages, does not require exposure monitoring, has a barely perceptible odor, and requires no activation. OPA, like glutaraldehyde, has excellent material compatibility. A potential disadvantage of OPA is that it stains proteins gray (including unprotected skin) and thus must be handled with caution.93 However, skin staining would indicate improper handling that requires additional training and/or personal protective equipment (gloves, eye and mouth protection, fluid-resistant gowns). OPA residues remaining on inadequately water-rinsed transesophageal echocardiographic probes may leave stains on the patient's mouth. Meticulous cleaning, use of the correct OPA exposure time (e.g., 12 minutes), and copious rinsing of the probe with water should eliminate this problem. Because OPA has been associated with several episodes of anaphylaxis after cystoscopy,153 the manufacturer has modified its instructions for use of OPA and contraindicates the use of OPA as a disinfectant for reprocessing all urologic instrumentation for patients with a history of bladder cancer. Personal protective equipment should be worn when handling contaminated instruments, equipment, and chemicals.148 In addition, equipment must be thoroughly rinsed to prevent discoloration of a patient's skin or mucous membrane. The MEC of OPA is 0.3%, and that concentration is monitored by test strips designed specifically for the OPA solution. OPA exposure level monitoring found that the concentration during the disinfection process was significantly higher in the manual group (median, 1.43 ppb) than in the automatic group (median, 0.35 ppb). These findings corroborate other findings that show it is desirable to introduce automatic endoscope reprocessors to decrease disinfectant exposure levels among scope reprocessing technicians
Isomeric phthalaldehydes
Related to phthalaldehyde are:
isophthalaldehyde (benzene-1,3-dicarbaldehyde; m.p. 87–88 °C, CAS# 626-19-7)
terephthalaldehyde (benzene-1,4-dicarbaldehyde; m.p. 114–116 °C, CAS# 623-27-8)
IUPAC name: Phthalaldehyde
Preferred IUPAC name: Benzene-1,2-dicarbaldehyde
Other names: Benzene-1,2-dicarboxaldehyde; o-Phthalaldehyde; o-Phthalic dicarboxaldehyde; Phthaldialdehyde
CAS Number: 643-79-8
CHEBI:70851
ChemSpider: 4642
ECHA InfoCard 100.010.367
Properties
Chemical formula: C8H6O2
Molar mass: 134.134 g·mol−1
Appearance:Yellow solid
Density:1.19 g/mL
Melting point: 55.5 to 56 °C (131.9 to 132.8 °F; 328.6 to 329.1 K)
Boiling point: 266.1 °C (511.0 °F; 539.2 K)
Solubility in water: Low
Hazards
Main hazards: Toxic, Irritant
R-phrases (outdated): R25 R34 R43 R50
S-phrases (outdated): S26 S36/37/39
o-Phthalaldehyde, vapor fraction
Phthalaldehyde.IUPAC names: 1,2-Benzenedicarboxaldehyde;o-Phthalaldehyde;o-Phthalaldehyde;Phthaldialdehyd;o-Phthalaldehyde;o-Phthaldialdehyde;643-79-8
Aldehyde, ortho-Phthalico Phthalaldehydeo Phthaldialdehydeo-Phthalaldehydeo-Phthaldialdehydeortho Phthalaldehydeortho Phthalic Aldehydeortho-Phthalaldehydeortho-Phthalic AldehydeOrthophthaldialdehyde
benzene-1,2-dicarbaldehyde
o-Phthalaldehyde [for HPLC Labeling]
o-Phthalaldehyde
Cas no: 643-79-8
PHTHALALDEHYDE;PHTHARAL; o-Phthaldialdehyde; Benzene-1,2-dicarboxaldehyde; 1,2-Benzenedicarboxaldehyde; Phthaldialdehyde; Phthalic aldehyde; Phthalic dialdehyde; ortho-Phthalaldehyde; Phthalyldicarboxaldehyde; o-Phthaldehyde; benzene-1,2-dicarbaldehyde; Phthalic dicarboxaldehyde; Phthalaldialdehyde
;o-Phthalicdicarboxaldehyde; 1,2-Diformylbenzene; 2-PHTHALALDEHYDE
O-PHTHALALDEHYDE
PHTHARAL
O-PHTHALDIALDEHYDE
1,2-BENZENEDICARBOXALDEHYDE
1,2-Phthalic dicarboxaldehyde
ortho Phthalaldehyde
o-Phthalic dicarboxaldehyde
1,2-BENZENEDICARBALDEHYDE
OPA
OPTA
Phtalaldehydes [French]
2-PHTHALDIALDEHYDE
EINECS 211-402-2
Phtalaldehydes
1,2-Phthalic dicarboxaldehyde, 98+%
CAS-643-79-8
Orthophthaldialdehyde
ortho-Phthalic Aldehyde
phthalaldehyd
o-Phthalaldehyd
o-phthal aldehyde
orthophthalaldehyde
Phtharal (JAN)
Disopa (TN)
2-PHTHALDEHYDE
Phthaldialdehyde Reagent
PubChem17402
ORTHO-PHTHALADEHYDE
phthalaldehyde;Phthalaldehyde
O-PHTHALIC DIALDEHYDE
2-Phthaldehyde, High purity
Benzene-1,2-dicarboxakdehyde
1,2-Benzenedialdehyde;Phthalaldehyde
FLUORALDEHYDE(TM) O-PHTHALALDEHYDE
Phthaldialdehyde Reagent, Solution Complete
Phthaldialdehyde Reagent, Solution Incomplete
Phthaldialdehyde, for fluorescence, >=99.0% (HPLC)
6-Oxomethylene-5-[(E)-hydroxymethylene]cyclohexa-1,3-diene
6-Oxomethylene-5-[(Z)-hydroxymethylene]cyclohexa-1,3-diene
Phthaldialdehyde, >=97% (HPLC), powder (may contain lumps)
Phthaldialdehyde, suitable for HPLC fluorimetric detection of amino acids, >=99% (HPLC), powder
ortho-Phthalaldehyde
1,2-Benzenedicarboxaldehyde [ACD/Index Name]
211-402-2 [EINECS]
4-07-00-02138 (Beilstein Handbook Reference) [Beilstein]
643-79-8 [RN]
Benzene-1,2-dicarbaldehyde [ACD/IUPAC Name]
Benzene-1,2-dicarboxaldehyde [ACD/IUPAC Name]
Benzol-1,2-dicarbaldehyd [German]
o-Phthalaldehyde
o-Phthaldialdehyde
Phtalaldéhyde [French] [ACD/IUPAC Name]
Phthalaldehyd [German] [ACD/IUPAC Name]
Phthalaldehyde [ACD/IUPAC Name]
Phthaldialdehyde
VHR BVH [WLN]
[643-79-8]
o-phthalaldehyde
o-phthaldialdehyde
o-phthalicdicarboxaldehyde
1,2-Diformylbenzene
4P8QP9768A
68234-47-9 [RN]
BR-44048
CHEBI 70851
D03470
Disopa
Disopa (TN)
MFCD00003335 [MDL number]
NCGC00166206-01
OPA
OPTA
P-6600
Phtalaldehydes [French]
Phthalic dicarboxaldehyde
Phthalyldicarboxaldehyde
Phtharal
Phtharal (JAN)
SBB008450
SS-7380
STR01056
TH6950000 [RTECS]
UNII-4P8QP9768A
オルトフタルアルデヒド [Japanese]
IUPAC Name
benzene-1,2-dicarbaldehyde
Synonyms
1,2-Benzenedicarboxaldehyde
1,2-Diformylbenzene
o-phthalaldehyde
o-Phthaldehyde
o-Phthaldialdehyde
o-Phthaldialdehyde
o-Phthalicdicarboxaldehyde
OPA ChEBI
OPTA ChEBI
Phthalaldialdehyde
Phthaldialdehyde
Phthalic aldehyde
Phthalic dialdehyde
Phthalic dicarboxaldehyde
Phthalyldicarboxaldehyde
OPA;OPD;o-PhthaL;Phtharal;CIDEX-OPA;phthaldehyde;PHTHALALDEHYDE;2-PHTHALDEHYDE;Phthaldialdehy;phtalaldehydes
CAS NO: 643-79-8
METATAGS:ortho-Phthalaldehyde; 1,2-BENZENEDICARBALDEHYDE; 1,2-Benzenedicarboxaldehyde [ACD/Index Name]; 1,2-Phthalic dicarboxaldehyde
2-Phthalaldehyde; 4-07-00-02138 (Beilstein Handbook Reference) [Beilstein]; 643-79-8 [RN]; benzene-1,2-dicarbaldehyde; Benzene-1,2-dicarboxaldehyde; BENZENEDICARBOXALDEHYDE; Benzol-1,2-dicarbaldehyd; OPA; o-Phthalaldehyde; o-Phthaldehyde; o-Phthaldialdehyde; o-Phthalic aldehyde; p-Benzenedicarboxaldehyde; Phtalaldéhyde [French] ; Phthalaldehyd [German] ; Phthalaldehyde [ACD/IUPAC Name]; Phthalic dialdehyde; [643-79-8]; 1,2-Diformylbenzene; 211-402-2 [EINECS]; 2-Phthaldehyde; 2-Phthaldialdehyde; Benzene-1,2-dicarboxaldehyde; OPA; Disopa; Disopa (TN); MFCD00003335 [MDL number]; NCGC00166206-01; o-Phthalaldehyde (en); o-Phthalaldehyde | o-Phthalic dicarboxaldehyde |; Benzene-1,2-dicarboxaldehyde | OPA; O-Phthalaldialdehyde; o-Phthalic dicarboxaldehyde, o-Phthalicdicarboxaldehyde; OPTA; Ortho-Phthalic Aldehyde (OPA); P-6600; Phtalaldehydes [French]; Phthalaldialdehyde; Phthaldialdehyde; PHTHALIC ALDEHYDE; Phthalic dicarboxaldehyde; Phthalyldicarboxaldehyde; Phtharal; Phtharal (JAN); オルトフタルアルデヒド [Japanese];ortofitalaldehit; orto fital aldehit; o fital aldehit; orto, fital, aldehit; ortho, fital, aldehit; orto, phthalal, aldehyde; ortho, phthalal, aldehyde; ortho fitaldehit.
O-Fitalaldehit veya orto-ftalaldehit (OPA), C6H4 (CHO) 2 formülüne sahip kimyasal bileşiktir. Genellikle kısaltılmış OPA, molekül bir benzen halkasında komşu karbon merkezlerine bağlı iki formil (CHO) grubundan oluşan bir dialdehittir. Soluk sarı renkli bu katı, heterosiklik bileşiklerin sentezinde bir yapı taşı ve amino asitler analizinde bir reaktiftir. OPA, pH <11.5 olan su çözeltisinde erir. Solüsyonları UV aydınlatması ve havaya maruz kalma üzerine bozunur.
OPA polimerize edilebilir. Polimerde, oksijen atomlarından biri, aynı fitalaldehit biriminin diğer halka-olmayan karbonuna köprü oluştururken, diğer köprüler başka bir fitalaldehit biriminin halka-olmayan karbonuna köprü oluşturur. Poli (ftalaldehit), bir fotorezist oluşturmada kullanılır.
Ortofitalaldehit veya OPA, heterosiklik bileşiklerin sentezinde kullanılan bir dialdehid ve amino asitlerin analizinde bir reaktiftir. OPA, hastanelerde tıbbi bir dezenfektan olarak ve hasta bakımı için cerrahi alet sterilizasyon çözümü olarak yaygın olarak kullanılmaktadır. Ortofitalaldehit, geniş bir endoskop yelpazesini ve diğer ısıya hassas kritik yarı tıbbi cihazları dezenfekte etmeye yardımcı olabilir.
Ortho-Phthalaldehyde (OPA), endoskop, sistoskoplar ve bazı diş araçlarını da içeren normal ısı veya buhar sterilizasyonu süreçlerine duyarlı tıbbi ekipman için üst düzey bir antimikrobiyal dezenfektan olarak kullanılan bir aromatik dialdehittir. 40 yıldır, başka bir dialdehit olan glutaraldehit, ısıya duyarlı tıbbi cihazların dezenfekte edilmesi için birincil tercih olmuştur; Bununla birlikte, kimyasal bir sensitizör olduğu bildirilmiştir. Glutaraldehidin biyolojik aminlere karşı yüksek afiniteye sahip olduğu bilinmektedir ve bir doku fiksatif maddesi olarak kullanımı bu mülkiyetten yararlanmaktadır. Bu nedenle, bir kimyasal sınıf olan glutaraldehit ve dialdehitler doğal proteinlere bağlanabilir, böylece sunumlarını bağışıklık sistemine değiştirirler.
Floraldehit Reaktif Çözeltisi, floresan algılama ve kantitatif etkinleştirmek için amino asitler, peptit ve proteinlerin birincil aminleri ile reaksiyona giren OPA (o-ftalaldehit) içerir. Bir protein veya peptit tahlil reaktifi olarak veya amino asit analizi (HPLC) için bir ön veya son sütun tespit reaktifi olarak kullanılabilen reaktif. OPA'nın proteinler ve peptidlerle reaksiyonu, geniş bir konsantrasyon yelpazesinde doğrusal sonuçlar verir. Fluoraldehyde Reaktif Çözümü, kullanıma hazır olarak tedarik edilir ve çözeltideki proteinlerin veya peptidlerin hızlı bir şekilde nicelenmesini sağlar.
Moleküler Formül: C8H6O2
Moleküler Ağırlık: 134.13
Yoğunluk: 1.19 g / mL
Erime Noktası: 55.5-56 ° C
Görünüş: Sarı katı
Nakliye Bilgileri: 25kgs
o-Phthalaldehyde or ortho-phthalaldehyde (OPA) is the chemical compound with the formula C6H4(CHO)2. Often abbreviated OPA, the molecule is a dialdehyde, consisting of two formyl (CHO) groups attached to adjacent carbon centres on a benzene ring. This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.
OPA 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 or OPA is a dialdehyde used in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids. OPA is commonly used as a medical disinfectant in hospitals and as a surgical instrument sterilization solution for patient care. Ortho-phthalaldehyde can help disinfect a wide range of endoscopes and other heat sensitive semi-critical medical devices.
Ortho-Phthalaldehyde (OPA) is an aromatic dialdehyde, used as a high-level antimicrobial disinfectant for medical equipment which is sensitive to normal heat or steam sterilization processes, including endoscope, cystoscopes, and certain dental instruments. For 40 years, glutaraldehyde, another dialdehyde, has been the primary choice for disinfecting heat-sensitive medical devices; however, it has been reported to be a chemical sensitizer. Glutaraldehyde is known to have high affinity for biological amines, and its use as a tissue fixative capitalizes on this property. As such, glutaraldehyde and dialdehydes as a chemical class can bind to native proteins, thus, altering their presentation to the immune system.
Fluoraldehyde Reagent Solution contains OPA (o-phthalaldehyde), which reacts with primary amines of amino acids, peptide and proteins to enable fluorescent detection and quantitation. The reagent that can be used as a protein or peptide assay reagent or as a pre- or post-column detection reagent for amino acid analysis (HPLC). Reaction of OPA with proteins and peptides yields linear results over a wide range of concentrations. The Fluoraldehyde Reagent Solution is supplied ready to use and enables fast quantitation of proteins or peptides in solution.
Molecular Formula:C8H6O2
Molecular Weight:134.13
Density:1.19 g/mL
Melting Point:55.5-56 °C
Appearance:Yellow solid
Transport Information:25kgs
