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| Formaldehyde ( for-MAL-di-hide, US also fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial systematic names, e.g., for organic compound and chemical formulas.
Formaldehyde also occurs naturally. It is derived from the degradation of polymerises, paraformaldehyde, and resins. particle boards act by converting N-methyl groups to formaldehyde.
Formaldehyde is classified as a group 1 coating and can cause respiratory and skin serine upon exposure. |
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Read full article at Wikipedia
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Saccharomyces cerevisiae
(NCBI:txid4932)
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Source: yeast.sf.net
See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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EC 3.5.1.4 (amidase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of amidase (EC 3.5.1.4).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
disinfectant
An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity.
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View more via ChEBI Ontology
Formaldehyd
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NIST Chemistry WebBook
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Formaldehyde
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KEGG COMPOUND
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formaldehyde
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UniProt
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FORMALDEHYDE
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PDBeChem
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FORMALIN
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ChEMBL
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Formalin
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KEGG COMPOUND
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Methanal
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KEGG COMPOUND
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Methylene oxide
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KEGG COMPOUND
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Oxomethane
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KEGG COMPOUND
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Oxomethylene
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KEGG COMPOUND
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3244
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DrugCentral
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359
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PPDB
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C00067
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KEGG COMPOUND
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c0122
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UM-BBD
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D00017
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KEGG DRUG
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DB03843
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DrugBank
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FOR
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PDBeChem
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Formaldehyde
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Wikipedia
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FORMALDEHYDE
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MetaCyc
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HMDB0001426
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HMDB
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| View more database links |
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1209228
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Reaxys Registry Number
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Reaxys
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445
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Gmelin Registry Number
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Gmelin
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50-00-0
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CAS Registry Number
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KEGG COMPOUND
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50-00-0
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CAS Registry Number
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NIST Chemistry WebBook
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50-00-0
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CAS Registry Number
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ChemIDplus
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Vojdani A, Kharrazian D, Mukherjee PS (2015)
Elevated levels of antibodies against xenobiotics in a subgroup of healthy subjects.
Journal of applied toxicology : JAT 35, 383-397 [PubMed:25042713]
[show Abstract]
In spite of numerous research efforts, the exact etiology of autoimmune diseases remains largely unknown. Genetics and environmental factors, including xenobiotics, are believed to be involved in the induction of autoimmune disease. Some environmental chemicals, acting as haptens, can bind to a high-molecular-weight carrier protein such as human serum albumin (HSA), causing the immune system to misidentify self-tissue as an invader and launch an immune response against it, leading to autoimmunity. This study aimed to examine the percentage of blood samples from healthy donors in which chemical agents mounted immune challenges and produced antibodies against HSA-bound chemicals. The levels of specific antibodies against 12 different chemicals bound to HSA were measured by ELISA in serum from 400 blood donors. We found that 10% (IgG) and 17% (IgM) of tested individuals showed significant antibody elevation against aflatoxin-HSA adduct. The percentage of elevation against the other 11 chemicals ranged from 8% to 22% (IgG) and 13% to 18% (IgM). Performance of serial dilution and inhibition of the chemical-antibody reaction by specific antigens but not by non-specific antigens were indicative of the specificity of these antibodies. Although we lack information about chemical exposure in the tested individuals, detection of antibodies against various protein adducts may indicate chronic exposure to these chemical haptens in about 20% of the tested individuals. Currently the pathological significance of these antibodies in human blood is still unclear, and this protein adduct formation could be one of the mechanisms by which environmental chemicals induce autoimmune reactivity in a significant percentage of the population. | Schena D, Papagrigoraki A, Girolomoni G (2008)
Sensitizing potential of triclosan and triclosan-based skin care products in patients with chronic eczema.
Dermatologic therapy 21 Suppl 2, S35-8 [PubMed:18837732]
[show Abstract]
Triclosan is a lypophilic chlorophenol biocide with broad-spectrum antibacterial and antifungal activity. Triclosan-based topical products have been shown to be tolerated and beneficial in atopic dermatitis. The aim of this study was to evaluate the sensitizing potential of triclosan and triclosan-based creams in patients affected by eczematous dermatitis. Two hundred and seventy-five patients affected by chronic eczema (allergic contact dermatitis, irritant contact dermatitis, atopic eczema, nummular eczema, stasis dermatitis) were patch tested with standard patch test series as well as triclosan and triclosan-based products. Standard patch test series resulted positive in 164 patients (61%), with nickel sulfate, house dust mites, fragrance mix, propolis, thimerosal, myroxylon pereira, potassium dichromate, wool alcohols, and p-phenylenediamine the most common sensitizing haptens. Only two patients developed positive reactions to triclosan (0.7%) and four (1.4%) to triclosan-based products. The present study's results confirm that triclosan is well tolerated and has a very low sensitizing potential even in high-risk patients affected by eczema. | Takeuchi A, Takigawa T, Abe M, Kawai T, Endo Y, Yasugi T, Endo G, Ogino K (2007)
Determination of formaldehyde in urine by headspace gas chromatography.
Bulletin of environmental contamination and toxicology 79, 1-4 [PubMed:17618393]
[show Abstract]
Formaldehyde is a carcinogen to which humans are exposed daily, but few methods are available to quantify formaldehyde in biological samples. We developed a simple, sensitive and rapid technique for the quantification of formaldehyde in urine by derivatization with O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine, using a headspace sampler coupled to a gas chromatograph equipped with an electron capture detector. The detection limit was 1.08 microg/L. The overall recovery of formaldehyde spiked in urine was 99%. The concentration of formaldehyde in urine obtained from healthy volunteers ranged from 56.85 to 144.57 microg/L. This method can be used successfully to measure formaldehyde in urine. | Twardowski ZJ (2006)
Dialyzer reuse-Part I: Historical perspective.
Seminars in dialysis 19, 41-53 [PubMed:16423181]
[show Abstract]
The first apparatus for hemodialysis in animals, made painstakingly by Abel et al. in their laboratory at the beginning of 20th century, was cleaned with acid-pepsin to digest blood, disinfected with thymol, and reused for up to 30 experiments for as long as 8 months. The obvious incentive was saving time. In the early years of hemodialysis in patients, dialyzers and lines were assembled and sterilized immediately before dialysis. Various methods of dry and moist heat sterilization and miscellaneous chemical agents were employed for disinfection. Significant time was required to assemble the dialyzers, so there was an incentive to reuse previously assembled dialyzers to save time, especially for home hemodialysis. Bleach to clean and formaldehyde to disinfect the membranes and lines was used for this purpose. Preassembled dialyzers, commercially introduced in the 1950s, were the most expensive components of hemodialysis systems, therefore reprocessing of these dialyzers was the most effective way to save money. Refrigeration of coil dialyzers with blood, introduced in the mid-1960s, was associated with frequent febrile reactions and was soon abandoned. Preassembled coil and plate dialyzers permitted almost complete return of blood after dialysis and led to the introduction of chemical disinfection for dialyzer reprocessing. A variety of disinfectants have been used. Formaldehyde was the most common disinfectant until the end of the 1970s. Sodium hypochlorite was used to clean the majority of dialyzers and to sterilize dialyzers with polyacrylonitrile membranes. In the early 1980s, peracetic acid and glutaraldehyde started to compete with formaldehyde. By the 1990s, formaldehyde had become less popular than peracetic acid. In the mid-1990s, disinfection and membrane cleaning with acetic acid and heat was introduced. Manual reprocessing was replaced by early reuse machines in the mid-1970s and a more sophisticated second generation of automated hemodialyzer reprocessing machines followed in the late 1970s. Recently disinfection of dialyzers with moist heat has resumed. Saving both time for the patient and money for the provider were the main motivations for designing a new machine for daily home hemodialysis. The machine, developed in the 1990s, cleans and moist-heat disinfects the dialyzer and lines in situ so they do not need to be changed for a month. In contrast, the reuse of dialyzers in home hemodialysis patients treated with other hemodialysis machines has become less popular and is almost extinct. | Nakao H, Umebayashi C, Nakata M, Nishizaki Y, Noda K, Okano Y, Oyama Y (2003)
Formaldehyde-induced shrinkage of rat thymocytes.
Journal of pharmacological sciences 91, 83-86 [PubMed:12686735]
[show Abstract]
To test the possibility that micromolar formaldehyde, a metabolite of methanol derived from aspartame, exerts cytotoxicity, its effect on rat thymocytes was examined under the in vitro condition using a flow cytometer. Incubation of thymocytes with formaldehyde at 100 micro M or more for 24 h significantly increased the populations of shrunken cells and cells with hypodiploid DNA. The peak blood concentration of methanol in human subjects administered abuse doses of aspartame has been reported to exceed 2 mg/dL (625 micro M). It would increase the population of thymocytes undergoing apoptosis if formaldehyde at 100 micro M or more appears in the blood after administration of aspartame. | Bergh M, Magnusson K, Nilsson JL, Karlberg AT (1998)
Formation of formaldehyde and peroxides by air oxidation of high purity polyoxyethylene surfactants.
Contact dermatitis 39, 14-20 [PubMed:9686972]
[show Abstract]
Ethoxylated alcohols are non-ionic surfactants. The majority are used in household cleaners, laundry products, toiletries and in industrial and institutional cleaners. In previous studies, an ethoxylated non-ionic surfactant of technical quality showed allergenic activity in guinea pig experiments. Chemical analysis revealed a content of formaldehyde, a well-known contact allergen, and peroxides in the surfactant. Most cases of occupational contact dermatitis are considered to be of irritant origin, caused by contact with water and surfactants, but if allergenic autoxidation products can be formed, allergic contact dermatitis cannot be excluded. The sensitizing potential of a chemically defined high purity ethoxylated alcohol was investigated and oxidation under various storage and handling conditions was studied for this and a homologous product. The pure surfactant showed no significant allergenic activity on predictive testing in guinea pigs. When ethoxylated alcohols were stored in the refrigerator, their deterioration was limited. At room temperature, their content of peroxides and formaldehyde increased with time. Levels of formaldehyde above those capable of causing positive patch test reactions were found. Since such surfactants have wide applications, resulting exposure to formaldehyde could be more frequent than is generally realized, contributing to persistence of dermatitis in individuals allergic to formaldehyde. | Hansen J, Olsen JH (1995)
Formaldehyde and cancer morbidity among male employees in Denmark.
Cancer causes & control : CCC 6, 354-360 [PubMed:7548723]
[show Abstract]
Formaldehyde, a genotoxic and potent animal carcinogen, is widespread in the working environment as well as in private homes. The risk for cancer morbidity in Denmark during 1970-84 was estimated from standardized proportionate incidence ratios (SPIR) among men whose longest employment had been held since 1964, at least 10 years before diagnosis, in 265 companies in which exposure to formaldehyde was identified. The results do not support the hypothesis that formaldehyde is associated with lung cancer (SPIR = 1.0, 410 cases). Significantly elevated risks were found for cancers of the colon (SPIR = 1.2, 166 cases), kidney (SPIR = 1.3, 60 cases), and sino-nasal cavities (SPIR = 2.3, 13 cases). For sino-nasal cancer, a relative risk of 3.0 (95 percent confidence interval = 1.4-5.7) was found among blue-collar workers with no probable exposure to wood dust, the major confounder. This study provides further evidence that occupational exposure to formaldehyde increases the risk for sino-nasal cancer. | Baez AP, Belmont R, Padilla H (1995)
Measurements of formaldehyde and acetaldehyde in the atmosphere of Mexico City.
Environmental pollution (Barking, Essex : 1987) 89, 163-167 [PubMed:15091529]
[show Abstract]
Ambient levels of carbonyls were measured at the University of Mexico campus, Mexico City. Only formaldehyde and acetaldehyde were measured, since aldehydes with higher molecular weight were not detected. The most abundant aldehyde was formaldehyde, with an overall ratio CH3CHO/H2CO of 0.43. Maximum concentrations occurred for formaldehyde at 10:00 h while for acetaldehyde at 8:00 h. Comparing the concentration measured in this work with those in urban areas it was found that the formaldehyde and acetaldehyde levels in Mexico City are among the highest reported in the literature. | McLaughlin JK (1994)
Formaldehyde and cancer: a critical review.
International archives of occupational and environmental health 66, 295-301 [PubMed:7896413]
[show Abstract]
Formaldehyde is a naturally occurring chemical found in every human cell. It has been in widespread use for over a century as a disinfectant and preservative agent, and more recently in a number of industrial products. Animal studies indicate that formaldehyde is a rat carcinogen at high levels (> or = 10 ppm) of exposure. Results for lower levels of exposure show less clear-cut carcinogenic effects, and some species, such as mice and hamsters, appear much less sensitive to any carcinogenic potential of formaldehyde. Epidemiologic studies of the effects of formaldehyde exposure among humans provide inconsistent results. In general, these nonexperimental studies suffer from a number of biases and flaws. The epidemiologic studies fall into three categories: formaldehyde industry workers, case-control studies, and studies of professionals who use formaldehyde. Studies of industry workers with known exposure to formaldehyde report little evidence of an excess cancer risk. Nasopharyngeal cancer, the one cancer considered most strongly linked to formaldehyde among humans, appears after close examination to be likely a result of multiple subgroup analyses and misclassification. The case-control studies usually lack any direct measure of formaldehyde exposure and rely instead on hypothetical exposure based on occupational exposure matrices. Most of these studies, after adjustment for confounding factors, fail to find a significant association with putative formaldehyde exposure. The studies that do report a significant association suffer from methodologic problems limiting their interpretation.(ABSTRACT TRUNCATED AT 250 WORDS) | Wehner E, Brendel M (1993)
Formaldehyde lacks genotoxicity in formaldehyde-hyperresistant strains of the yeast Saccharomyces cerevisiae.
Mutation research 289, 91-96 [PubMed:7689168]
[show Abstract]
Formaldehyde is a weak mutagen and recombinagen in wild type strains of Saccharomyces cerevisiae. Genotoxicity of formaldehyde is influenced by the activity of the SFA yeast gene. Yeast transformants containing multiple copies of the plasmid-contained SFA gene are hyperresistant to the chemical and grow in the presence of 5 mM formaldehyde, a concentration lethal for the wild type. The SFA-encoded protein mediates the degradation of formaldehyde and its activity is most probably responsible for the low or absent genotoxic effects in formaldehyde-treated cells. Multi-copy vectors containing the SFA gene are retained in yeast transformants growing in complex media supplemented with 5 mM formaldehyde. Cells harboring such multi-copy vectors may, therefore, be propagated in large batch cultures in undefined media in the presence of formaldehyde concentrations toxic to the wild type. | Bodor N, Kaminski JJ, Selk S (1980)
Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials.
Journal of medicinal chemistry 23, 469-474 (Source: ChEMBL) [PubMed:7381846]
[show Abstract]
Strategies for the design of safer drugs are discussed. The various classes of "soft drugs" are designed to avoid undesired metabolic disposition (primarily various oxidative routes, occurring via possible toxic intermediates) and to be metabolized by a predictable manner with controlled rates. As a first example for the "soft analogue" type drugs, a new class of antimicrobial, surface-active quaternary salts of the type RCOOCHR1--N+ comes from X- was developed. These "soft" quaternary salts are isosteric analogues of known "hard" quaternary surfactants and are characterized by predictable and controllable cleavage (metabolism) to nontoxic components, while showing good activity against a wide range of bacteria. Due to their soft nature (low toxicity), the new antimicrobials are much safer than the conventional, hard analogues. | Gregoriou M, Brown PR (1979)
Inhibition of the aliphatic amidase from Pseudomonas aeruginosa by urea and related compounds.
European journal of biochemistry 96, 101-108 [PubMed:110589]
[show Abstract]
The time-dependent inhibition of amidase from Pseudomonas aeruginosa strain AI 3 by urea, hydroxyurea and cyanate displayed saturation kinetics fitting a model for the reaction sequence in which formation of a complex in a reversible step was followed by an irreversible step. Altered amidases from mutant strains AIU 1N and OUCH 4, selected for their resistance to inhibition of growth by urea and hydroxyurea respectively, had altered kinetic constants for inhibition indicating reduced binding capacity for the inhibitors. The substrate acetamide protected AI 3 amidase against inhibition by urea,.and altered Ki values for inhibition of the mutant amidases were paralleled by alterations in Km values for acetamide indicating that urea acted at the active site. Inhibition of AI 3 amidase involved the binding of one molecule of urea per molecule of enzyme. Urea inhibited amidase slowly regained activity at pH 7.2 through release of urea. |
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