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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

AI overview

Acetaldehyde is a common organic chemical that exists as a colorless liquid or gas and occurs naturally in foods like coffee, bread, and ripe fruit, while also being produced in large quantities by industry. It's notable because your liver produces it when breaking down alcohol—a process that contributes to hangovers—and because it's one of the most important aldehydes found throughout nature and the environment.

AI-generated from the Wikipedia summary — may 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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Wikidata facts

Mass
44.026
Autonomy
185
Show 22 more facts
immediately dangerous to life or health
2000
Commons category
Acetaldehyde
boiling point
20.1
melting point
-123
vapor pressure
740
NIOSH Pocket Guide ID
0001
density
0.79
flash point
-36
upper flammable limit
60
lower flammable limit
4
ionization energy
10.23
time-weighted average exposure limit
5
ceiling exposure limit
0
median lethal dose (LD50)
3540
minimal lethal dose
1200
canonical SMILES
CC=O
chemical formula
C₂H₄O
standard enthalpy of formation
-166
refractive index
1.3316
electric dipole moment
2.750
pKa
13.57
Sources (12)

via Wikidata · CC0

~20 min read

Article

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".

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