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acetaldehyde

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acetaldehyde

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Also known as acetic aldehyde, ethanal, ethyl aldehyde, NSC 7594, aldehyde

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula . It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as

OverviewAI-generated

Acetaldehyde is a chemical compound with the formula C₂H₄O and a mass of 44.026. Its canonical SMILES notation is CC=O, and it has a boiling point of 69 and a melting point ranging from -190 to -123. The substance exhibits a density of 0.79, a vapor pressure of 740, and a refractive index of 1.3316. Its electric dipole moment is 2.75, and its ionization energy is 10.23. The standard enthalpy of formation is -166.

Safety data for acetaldehyde indicates a flash point of -36 and an autoignition temperature of 185. The lower flammable limit is 4, while the upper limit is 60. The immediately dangerous to life or health concentration is 3600. Exposure limits include a time-weighted average of 360 and a ceiling limit of 0. Toxicity metrics show a median lethal dose (LD50) of 25000 and a minimal lethal dose of 20000.

Acetaldehyde is associated with alcohol metabolism, as noted by the National Institute on Alcohol Abuse and Alcoholism. It has a PubChem CID of 177 and a NIOSH Pocket Guide ID of 0001. The compound has a xlogp of -0.3, a topological polar surface area of 17.1, and one hydrogen bond acceptor. It is referenced by 705 other encyclopedia articles.

Synthesized by Vinony from 40 facts across 5 sources: Wikidata, PubMed, Firecrawl, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C2H4O
Molecular weight
44.05 g/mol
IUPAC name
acetaldehyde
SMILES
CC=O
InChIKey
IKHGUXGNUITLKF-UHFFFAOYSA-N
XLogP
-0.3
Polar surface area
17.1 Ų
H-bond donors
0
H-bond acceptors
1
Formal charge
0

via PubChem

Research

14,098 papers

via PubMed

Described at

Alcohol Metabolism | National Institute on Alcohol Abuse and Alcoholism (NIAAA)

Drinking heavily puts people at risk for many adverse health consequences, including alcohol use disorder, liver damage, and various cancers. But some people appear to be at greater risk than others for developing these problems. Why do some people drink more than others? And why do some people who drink develop problems, whereas others do not?

niaaa.nih.gov

Official websites use .gov A .gov website belongs to an official government organization in the United States. Secure .gov websites use HTTPS A lock ( Lock Locked padlock icon ) or means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites. Drinking heavily puts people at risk for many adverse health consequences, including alcohol use disorder, liver damage, and various cancers. But some people appear to be at greater risk than others for developing these problems. Why do some people drink more than others? And why do some people who drink develop problems, whereas others do not? Alcohol is metabolized by several processes or pathways. The most common of these pathways involves two enzymes—alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH). These enzymes help break apart the alcohol molecule, making it possible to eliminate it from the body. First, ADH metabolizes alcohol to acetaldehyde, a highly toxic substance and known carcinogen.1 Then, acetaldehyde is further metabolized by ALDH to another, less active byproduct called acetate,1 which then is broken down into water and carbon dioxide for easy elimination.2 The enzymes cytochrome P450 2E1 (CYP2E1) and catalase also break down alcohol to acetaldehyde. However, CYP2E1 only is active after a person has consumed large amounts of alcohol, and catalase metabolizes only a small fraction of alcohol in the body.1 Small amounts of alcohol also are removed by interacting with fatty acids to form compounds called fatty acid ethyl esters (FAEEs). These compounds have been shown to contribute to damage to the liver and pancreas.3 The chemical name for alcohol is ethanol (CH3CH2OH). The body processes and eliminates ethanol in separate steps. Chemicals called enzymes help to break apart the ethanol molecule into other compounds (or metabolites), which can be processed more easily by the body. Some of these intermediate metabolites can have harmful effects on the body. Most of the ethanol in the body is broken down in the liver by an enzyme called alcohol dehydrogenase (ADH), which transforms ethanol into a toxic compound called acetaldehyde (CH3CHO), a known carcinogen. However, acetaldehyde is generally short-lived; it is quickly broken down to a less toxic compound called acetate (CH3COO-) by another enzyme called aldehyde dehydrogenase (ALDH). Acetate then is broken down to carbon dioxide and water, mainly in tissues other than the liver. Ketoacidosis is a condition where the body cannot metabolize glucose and ketones accumulate in the blood. This condition can occur when someone consumes a large amount of alcohol then does not eat enough due to vomiting, nausea, or disordered eating.11 It can be associated with “drunkorexia,” in which someone limits their food intake to compensate for calories from alcohol consumption. Ketoacidosis can be life-threatening and requires treatment. Certain medications can influence the absorption and metabolism of alcohol. The interaction can result in higher blood alcohol concentrations (BACs) and other adverse effects. Alcohol can also affect the metabolism of certain medications, speeding up or slowing down the clearance of the medication from the body. This altered metabolism lowers or raises levels of the medication in the blood. Alcohol can alter the pharmacological effects of a medication, increasing or decreasing the medication's effects on the body. To learn more, please see Harmful Interactions: Mixing Alcohol With Medications .

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Encyclopedic overview

36 sections
Contents
  • History
  • Production
  • Other methods
  • Hydration of acetylene
  • Dehydrogenation of ethanol
  • Hydroformylation of methanol
  • Reactions
  • Tautomerization to vinyl alcohol
  • Addition and condensation reactions
  • Polymeric forms
  • Acetal derivatives
  • Precursor to vinylphosphonic acid
  • Biochemistry
  • Uses
  • Safety
  • Exposure limits
  • Dangers
  • Toxicity
  • Irritation
  • Carcinogenicity
  • DNA crosslinks
  • Aggravating factors
  • Alzheimer's disease
  • Genetic conditions
  • Disulfiram
  • Sources of exposure
  • Indoor air
  • Outdoor air
  • Tobacco smoke
  • Cannabis smoke
  • Alcohol consumption
  • Plastics
  • Candida overgrowth
  • See also
  • References
  • External links

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula . It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

The International Agency for Research on Cancer (IARC) has listed acetaldehyde as a Group 1 carcinogen. Acetaldehyde is "one of the most frequently found air toxins with cancer risk greater than one in a million".

Excerpted from Wikipedia’s “acetaldehyde” article, available under the CC BY-SA 4.0 licence.

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