Acetaldehyde
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Basic Info
| Common Name | Acetaldehyde(F04842) |
| 2D Structure | |
| Description | Acetaldehyde is a colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. In the chemical industry, acetaldehyde is used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals. it is also an air pollutant resulting from combustion, such as automotive exhaust and tobacco smoke. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis. 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. Acetaldehyde is linked to most of the negative clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver, multiple forms of cancer, and alcoholism. |
| FRCD ID | F04842 |
| CAS Number | 75-07-0 |
| PubChem CID | 177 |
| Formula | C2H4O |
| IUPAC Name | acetaldehyde |
| InChI Key | IKHGUXGNUITLKF-UHFFFAOYSA-N |
| InChI | InChI=1S/C2H4O/c1-2-3/h2H,1H3 |
| Canonical SMILES | CC=O |
| Isomeric SMILES | CC=O |
| Wikipedia | Acetaldehyde |
| Synonyms |
acetic aldehyde
Aldeide acetica
acetaldehyde
ethanal
ethyl aldehyde
75-07-0
Acetaldehyd
Acetylaldehyde
aldehyde
Acetic ethanol
|
| Classifies |
Plant Toxin
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Aldehydes |
| Direct Parent | Short-chain aldehydes |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Organic oxide - Hydrocarbon derivative - Short-chain aldehyde - Aliphatic acyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 44.053 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 10.3 |
| Monoisotopic Mass | 44.026 |
| Exact Mass | 44.026 |
| XLogP | -0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 3 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9833 |
| Human Intestinal Absorption | HIA+ | 0.9942 |
| Caco-2 Permeability | Caco2+ | 0.7557 |
| P-glycoprotein Substrate | Non-substrate | 0.8268 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9712 |
| Non-inhibitor | 0.9820 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9246 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4845 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7858 |
| CYP450 2D6 Substrate | Non-substrate | 0.9309 |
| CYP450 3A4 Substrate | Non-substrate | 0.8027 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8641 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9741 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9791 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9800 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9876 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9511 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9511 |
| Non-inhibitor | 0.9805 | |
| AMES Toxicity | Non AMES toxic | 0.6375 |
| Carcinogens | Carcinogens | 0.6803 |
| Fish Toxicity | Low FHMT | 0.6158 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8581 |
| Honey Bee Toxicity | High HBT | 0.7938 |
| Biodegradation | Ready biodegradable | 0.7562 |
| Acute Oral Toxicity | III | 0.8284 |
| Carcinogenicity (Three-class) | Non-required | 0.6767 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.8143 | LogS |
| Caco-2 Permeability | 1.5492 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8556 | LD50, mol/kg |
| Fish Toxicity | 1.6543 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3413 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Expression of Gre2p improves tolerance of engineered xylose-fermenting Saccharomyces cerevisiae to glycolaldehyde under xylose metabolism. | Appl Microbiol Biotechnol | 2018 Sep | 30027490 |
| Development of an LC-MS/MS Determination Method for T-2 Toxin and Its Glucoside and Acetyl Derivatives for Estimating the Contamination of Total T-2 Toxins in Staple Flours. | J AOAC Int | 2018 May 1 | 29070164 |
| Effects of aldehyde products of lipid oxidation on the color stability andmetmyoglobin reducing ability of bovine Longissimus muscle. | Anim Sci J | 2018 May | 29460317 |
| Reference values for acetyl and butyrylcholinesterases in cattle under actual management conditions, hepatic and renal function by application of chlorpyrifos. | J Environ Sci Health B | 2018 Mar 4 | 29293401 |
| Advances in Enzyme-Based Biosensors for Pesticide Detection. | Biosensors (Basel) | 2018 Mar 22 | 29565810 |
| Analysis of changes in volatile constituents and expression of genes involved in terpenoid metabolism in oleocellosis peel. | Food Chem | 2018 Mar 15 | 29146338 |
| Particulate matter emissions and gaseous air toxic pollutants from commercial meat cooking operations. | J Environ Sci (China) | 2018 Mar | 29548387 |
| Interactions between ALDH2 rs671 polymorphism and lifestyle behaviors on coronaryartery disease risk in a Chinese Han population with dyslipidemia: A guide totargeted heart health management. | Environ Health Prev Med | 2018 Jun 30 | 29960587 |
| Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia OrangeJuices Not from Concentrate (NFC) during Chilled Storage. | J Agric Food Chem | 2018 Jul 18 | 29889522 |
| Synergic effect of curcumin and its structural analogue (Monoacetylcurcumin) onanti-influenza virus infection. | J Food Drug Anal | 2018 Jul | 29976394 |
| Abundance of DNA adducts of 4-oxo-2-alkenals, lipid peroxidation-derived highlyreactive genotoxins. | J Clin Biochem Nutr | 2018 Jan | 29362517 |
| Contribution of Histidine and Lysine to the Generation of Volatile Compounds inJinhua Ham Exposed to Ripening Conditions Via Maillard Reaction. | J Food Sci | 2018 Jan | 29194607 |
| Development of blueberry liquor: influence of distillate, sweetener and fruitquantity. | J Sci Food Agric | 2018 Feb | 28722782 |
| Enhancement of α,ω-Dicarboxylic Acid Production by the Expression of XyloseReductase for Refactoring Redox Cofactor Regeneration. | J Agric Food Chem | 2018 Apr 4 | 29537267 |
| Occupational exposures of flour dust and airborne chemicals at bakeries inTaiwan. | J Occup Environ Hyg | 2018 Apr 30:1-25 | 29708861 |
| Increased chemical acetylation of peptides and proteins in rats after dailyingestion of diacetyl analyzed by Nano-LC-MS/MS. | PeerJ | 2018 Apr 25 | 29713565 |
| A colorimetric assay for vanillin detection by determination of the luminescence of o-toluidine condensates. | PLoS One | 2018 Apr 20 | 29677193 |
| Mannanase hydrolysis of spruce galactoglucomannan focusing on the influence ofacetylation on enzymatic mannan degradation. | Biotechnol Biofuels | 2018 Apr 19 | 29713374 |
| Extraction, structure, and emulsifying properties of pectin from potato pulp. | Food Chem | 2018 Apr 1 | 29120771 |
| PR Toxin - Biosynthesis, Genetic Regulation, Toxicological Potential, Prevention and Control Measures: Overview and Challenges. | Front Pharmacol | 2018 | 29651243 |
Targets
- General Function:
- Aldehyde dehydrogenase [nad(p)+] activity
- Specific Function:
- Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
- Gene Name:
- ALDH3B1
- Uniprot ID:
- P43353
- Molecular Weight:
- 51839.245 Da
References
- Marchitti SA, Brocker C, Orlicky DJ, Vasiliou V: Molecular characterization, expression analysis, and role of ALDH3B1 in the cellular protection against oxidative stress. Free Radic Biol Med. 2010 Nov 15;49(9):1432-43. doi: 10.1016/j.freeradbiomed.2010.08.004. Epub 2010 Aug 10. [20699116 ]