Acetaldehyde (ECMDB00990) (M2MDB000217)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:03:00 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:09 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Acetaldehyde | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Acetaldehyde is a colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. Small amounts of acetaldehyde are produced naturally through gut microbial fermentation. Acetaldehyde is produced through the action of alcohol dehydrogenase on ethanol and is somewhate more toxic than ethanol. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C2H4O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 44.0526 Monoisotopic: 44.02621475 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | IKHGUXGNUITLKF-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C2H4O/c1-2-3/h2H,1H3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 75-07-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | acetaldehyde | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | acetaldehyde | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbonyl compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Short-chain aldehydes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | -123 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Acetaldehyde + Coenzyme A + NAD <> Acetyl-CoA + Hydrogen ion + NADH Ethanol + NAD <> Acetaldehyde + Hydrogen ion + NADH Ethanolamine > Acetaldehyde + Ammonium L-Threonine <> Acetaldehyde + Glycine L-Allothreonine > Acetaldehyde + Glycine 4-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acid Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite Acetaldehyde + Water + NAD > Acetic acid +2 Hydrogen ion + NADH Dihydroneopterin triphosphate + Water > Acetaldehyde + 6-Carboxy-5,6,7,8-tetrahydropterin + Hydrogen ion + Triphosphate Acetaldehyde + Water + NADP > Acetic acid +2 Hydrogen ion + NADPH Deoxyribose 5-phosphate <> Acetaldehyde + D-Glyceraldehyde 3-phosphate Ethanolamine <> Acetaldehyde + Ammonia Acetaldehyde + Pyruvic acid <> 4-Hydroxy-2-oxopentanoate L-Allothreonine <> Glycine + Acetaldehyde Hydrogen ion + Pyruvic acid + Acetaldehyde > acetoin + Carbon dioxide Ethanol + NAD <> Acetaldehyde + NADH + Hydrogen ion Ethanolamine > Hydrogen ion + Acetaldehyde + Ammonia 4-Hydroxy-2-oxopentanoate <> Acetaldehyde + Pyruvic acid Acetaldehyde + NADP + Water > Acetic acid + NADPH + Hydrogen ion DL-allothreonine <> Acetaldehyde + Glycine 1-Ethyladenine + Oxygen + Oxoglutaric acid > Adenine + Carbon dioxide + Acetaldehyde + Succinic acid L-Threonine > Acetaldehyde + Glycine Acetaldehyde + CoA + NAD > Acetyl-CoA + NADH Deoxyribose 5-phosphate > D-Glyceraldehyde 3-phosphate + Acetaldehyde Ethanolamine > Acetaldehyde + Ammonia Dihydroneopterin triphosphate + Water > 6-Carboxy-5,6,7,8-tetrahydropterin + Acetaldehyde + Triphosphate More...4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + Acetaldehyde Acetaldehyde + Coenzyme A + NAD > Hydrogen ion + NADH + Acetyl-CoA 7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate Deoxyribose 5-phosphate > Acetaldehyde + D-Glyceraldehyde 3-phosphate Ethanolamine > Ammonium + Acetaldehyde L-Threonine <> Acetaldehyde + Glycine L-Allothreonine > Acetaldehyde + Glycine Ethanol + NAD <> Acetaldehyde + Hydrogen ion + NADH Ethanolamine <> Acetaldehyde + Ammonia L-Allothreonine > Acetaldehyde + Glycine Ethanol + NAD <> Acetaldehyde + Hydrogen ion + NADH Ethanolamine <> Acetaldehyde + Ammonia | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Wertheim, E. Laboratory preparation of acetaldehyde. Journal of the American Chemical Society (1922), 44 2658-9. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- 2-deoxy-D-ribose 5-phosphate = D- glyceraldehyde 3-phosphate + acetaldehyde
- Gene Name:
- deoC
- Uniprot ID:
- P0A6L0
- Molecular weight:
- 27733
Reactions
2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde. |
- General function:
- Involved in catalytic activity
- Specific function:
- Interconversion of serine and glycine
- Gene Name:
- glyA
- Uniprot ID:
- P0A825
- Molecular weight:
- 45316
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- This enzyme has three activities:ADH, ACDH, and PFL- deactivase. In aerobic conditions it acts as a hydrogen peroxide scavenger. The PFL deactivase activity catalyzes the quenching of the pyruvate-formate-lyase catalyst in an iron, NAD, and CoA dependent reaction
- Gene Name:
- adhE
- Uniprot ID:
- P0A9Q7
- Molecular weight:
- 96126
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH. |
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH. |
- General function:
- Involved in catalytic activity
- Specific function:
- Ethanolamine = acetaldehyde + NH(3)
- Gene Name:
- eutB
- Uniprot ID:
- P0AEJ6
- Molecular weight:
- 49403
Reactions
Ethanolamine = acetaldehyde + NH(3). |
- General function:
- Involved in ethanolamine ammonia-lyase activity
- Specific function:
- Ethanolamine = acetaldehyde + NH(3)
- Gene Name:
- eutC
- Uniprot ID:
- P19636
- Molecular weight:
- 31781
Reactions
Ethanolamine = acetaldehyde + NH(3). |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Involved in the breakdown of putrescine. Was previously shown to have a weak but measurable ALDH enzyme activity that prefers NADP over NAD as coenzyme
- Gene Name:
- puuC
- Uniprot ID:
- P23883
- Molecular weight:
- 53418
Reactions
Gamma-glutamyl-gamma-aminobutyraldehyde + NAD(+) + H(2)O = gamma-glutamyl-gamma-aminobutyrate + NADH. |
An aldehyde + NAD(P)(+) + H(2)O = a carboxylate + NAD(P)H. |
- General function:
- Involved in zinc ion binding
- Specific function:
- Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
- Gene Name:
- frmA
- Uniprot ID:
- P25437
- Molecular weight:
- 39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H. |
An alcohol + NAD(+) = an aldehyde or ketone + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the NADP-dependent oxidation of diverse aldehydes such as chloroacetaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, mafosfamide, 4- hydroperoxycyclophosphamide. Its preferred substrates are acetaldehyde and chloroacetaldehyde
- Gene Name:
- aldB
- Uniprot ID:
- P37685
- Molecular weight:
- 56306
- General function:
- Involved in zinc ion binding
- Specific function:
- Preferred specificity is towards 1-propanol
- Gene Name:
- adhP
- Uniprot ID:
- P39451
- Molecular weight:
- 35379
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH. |
- General function:
- Involved in 4-hydroxy-2-oxovalerate aldolase activity
- Specific function:
- Catalyzes the retro-aldol cleavage of 4-hydroxy-2- oxopentanoate to pyruvate and acetaldehyde. Is involved in the meta-cleavage pathway for the degradation of 3-phenylpropanoate
- Gene Name:
- mhpE
- Uniprot ID:
- P51020
- Molecular weight:
- 36470
Reactions
4-hydroxy-2-oxopentanoate = acetaldehyde + pyruvate. |
- General function:
- Coenzyme transport and metabolism
- Specific function:
- Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
- Gene Name:
- queD
- Uniprot ID:
- P65870
- Molecular weight:
- 13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate. |
- General function:
- Involved in lyase activity
- Specific function:
- Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
- Gene Name:
- ltaE
- Uniprot ID:
- P75823
- Molecular weight:
- 36494
Reactions
L-threonine = glycine + acetaldehyde. |
L-allo-threonine = glycine + acetaldehyde. |
- General function:
- Involved in acetaldehyde dehydrogenase (acetylating) activity
- Specific function:
- Catalyzes the conversion of acetaldehyde to acetyl-CoA, using NAD(+) and coenzyme A. Is the final enzyme in the meta- cleavage pathway for the degradation of 3-phenylpropanoate. Functions as a chaperone protein for folding of mhpE
- Gene Name:
- mhpF
- Uniprot ID:
- P77580
- Molecular weight:
- 33442
Reactions
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH. |
- 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:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- eutE
- Uniprot ID:
- P77445
- Molecular weight:
- Not Available
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- yiaY
- Uniprot ID:
- P37686
- Molecular weight:
- Not Available
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- eutA
- Uniprot ID:
- P76551
- Molecular weight:
- Not Available
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- eutG
- Uniprot ID:
- P76553
- Molecular weight:
- Not Available
- 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