Formaldehyde (ECMDB01426) (M2MDB000382)
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| Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:52:23 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:11 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Formaldehyde | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Formaldehyde is a highly reactive aldehyde gas. It is the simplest aldehyde. Its chemical formula is H2CO. Although formaldehyde is a gas at room temperature, it is readily soluble in water, and it is most commonly sold as a 37% solution in water called by trade names such as formalin or formol. In water, formaldehyde polymerizes, and formalin actually contains very little formaldehyde in the form of H2CO monomer. Formaldehyde exhibits most of the general chemical properties of the aldehydes, except that is generally more reactive than other aldehydes. Formaldehyde is a potent electrophile. It can participate in electrophilic aromatic substitution reactions with aromatic compounds and can undergo electrophilic addition reactions with alkenes. In E. coli, formaldehyde is formed by the breakdown of N-methyltryptophan and FMNH by their corresponding oxidases. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | CH2O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 30.026 Monoisotopic: 30.010564686 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | WSFSSNUMVMOOMR-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/CH2O/c1-2/h1H2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 50-00-0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | formaldehyde | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | formaldehyde | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | C=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as carbonyl compounds. These are organic compounds containing a carbonyl group, with the general structure RC(=O)R', where R=organyl, R'=H, N, O, organyl group or halide group. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbonyl compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Carbonyl compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Liquid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | -92 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite Water + Oxygen + Sarcosine > Formaldehyde + Glycine + Hydrogen peroxide N-Methyltryptophan + Water + Oxygen > Formaldehyde + Hydrogen peroxide + L-Tryptophan Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione Methanol + Hydrogen peroxide <> Formaldehyde +2 Water Methylamine + Oxygen + Water <> Formaldehyde + Ammonia + Hydrogen peroxide Formaldehyde + Tetrahydrofolic acid > 5,10-Methylene-THF + Water a methylated nucleobase within DNA + Oxygen + Oxoglutaric acid Hydrogen ion + a nucleobase within DNA + Carbon dioxide + Formaldehyde + Succinic acid S-(Hydroxymethyl)glutathione <> Formaldehyde + Glutathione N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acid N3-Methylcytosine + Oxygen + Oxoglutaric acid > Hydrogen ion + Cytosine + Carbon dioxide + Formaldehyde + Succinic acid DNA-base-CH(3) + Oxoglutaric acid + Oxygen > DNA-base + Formaldehyde + Succinic acid + Carbon dioxide N-methyl-L-tryptophan + Water + Oxygen > L-Tryptophan + Formaldehyde + Hydrogen peroxide | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in catalase activity
- Specific function:
- Bifunctional enzyme with both catalase and broad- spectrum peroxidase activity. Displays also NADH oxidase, INH lyase and isonicotinoyl-NAD synthase activity
- Gene Name:
- katG
- Uniprot ID:
- P13029
- Molecular weight:
- 80023
Reactions
| Donor + H(2)O(2) = oxidized donor + 2 H(2)O. |
| 2 H(2)O(2) = O(2) + 2 H(2)O. |
- General function:
- Involved in catalase activity
- Specific function:
- Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
- Gene Name:
- katE
- Uniprot ID:
- P21179
- Molecular weight:
- 84162
Reactions
| 2 H(2)O(2) = O(2) + 2 H(2)O. |
- General function:
- Involved in copper ion binding
- Specific function:
- The enzyme prefers aromatic over aliphatic amines
- Gene Name:
- tynA
- Uniprot ID:
- P46883
- Molecular weight:
- 84378
Reactions
| RCH(2)NH(2) + H(2)O + O(2) = RCHO + NH(3) + H(2)O(2). |
| 2-phenylethylamine + H(2)O + O(2) = phenylacetaldehyde + NH(3) + H(2)O(2). |
- General function:
- Involved in FMN reductase activity
- Specific function:
- Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
- Gene Name:
- ssuE
- Uniprot ID:
- P80644
- Molecular weight:
- 21253
Reactions
| FMNH(2) + NADP(+) = FMN + NADPH. |
- General function:
- Involved in alkanesulfonate monooxygenase activity
- Specific function:
- Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
- Gene Name:
- ssuD
- Uniprot ID:
- P80645
- Molecular weight:
- 41736
Reactions
| An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the oxidative demethylation of N-methyl-L- tryptophan. Can also use other N-methyl amino acids, including sarcosine, which, however, is a poor substrate
- Gene Name:
- solA
- Uniprot ID:
- P40874
- Molecular weight:
- 40902
Reactions
| N-methyl-L-tryptophan + H(2)O + O(2) = L-tryptophan + formaldehyde + H(2)O(2). |
- General function:
- Not Available
- Specific function:
- Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents). Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents).
- Gene Name:
- alkB
- Uniprot ID:
- P05050
- Molecular weight:
- Not Available
Reactions
| DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2). |
| DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2). |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368