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Encyclopedia > Acetaldehyde
Acetaldehyde
Chemical structure of acetaldehyde
Systematic name Acetaldehyde
Other name Ethanal
Chemical formula CH3CHO
SMILES CC=O
Molecular mass 44.05 g/mol
Appearance Colorless liquid
Pungent, fruity odor
CAS number [75-07-0]
Properties
Density 0.788 g/cm3
Solubility in water  ? g/100 ml (? °C)
Melting point −124 °C
Boiling point 26 °C
Viscosity  ? cP at ? °C
Structure
Molecular shape  ?
Dipole moment  ? D
Hazards
MSDS External MSDS
EU classification Very flammable (F+)
Harmful (Xn)
Carc. Cat. 3
NFPA 704
Image:nfpa h2.png Image:nfpa f4.png Image:nfpa r2.png
R-phrases R12, R36/37, R40
S-phrases S2, S16, S33, S36/37
Flash point −39 °C
Autoignition temperature 185 °C
RTECS number AB1925000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related aldehydes Formaldehyde
Propionaldehyde
Disclaimer and references

Acetaldehyde, also known as ethanal, is an organic chemical compound. It is an aldehyde with the formula CH3CHO. It is a highly reactive flammable liquid with a strong fruity smell. It melts at -123.5° C and boils at 21 °C. Acetaldehyde occurs naturally in ripe fruit, coffee, and fresh bread and is produced by plants as part of their normal metabolism. Image File history File links Structure of Acetaldehyde, produced with ChemSketch and Gimp, released into the public domain. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The molecular mass (abbreviated MM) of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... It has been suggested that this article or section be merged with Solution. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... The pitch drop experiment at the University of Queensland. ... The poise (P) is the cgs unit of viscosity, 1 P = 1 g·cm-1·s-1 The SI analog is 1 pascal second (Pa·s) = 1 kg·m-1·s-1 = 10 P. It is named after Jean Louis Marie Poiseuille. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... In pathology, a carcinogen is any substance or agent that promotes cancer. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... The autoignition temperature of a substance is the lowest temperature at which it will spontaneously combust in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Mass spectrometry is an analytical technique to measure the mass-to-charge ratio (m/q) of ions. ... An aldehyde is either a functional group consisting of a terminal carbonyl group or a compound containing a terminal carbonyl group. ... The chemical compound formaldehyde (also known as methanal), is a gas with a strong pungent smell. ... Note that propanol is a different compound. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... An aldehyde is either a functional group consisting of a terminal carbonyl group or a compound containing a terminal carbonyl group. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Chalcogens Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... The degree Celsius (also known as Centigrade)) (°C) is a unit of temperature named after the Swedish astronomer Anders Celsius (1701–1744), who first proposed a similar system in 1742. ... Divisions Land plants (embryophytes) Non-vascular plants (bryophytes) Marchantiophyta - liverworts Anthocerotophyta - hornworts Bryophyta - mosses Vascular plants (tracheophytes) Lycopodiophyta - clubmosses Equisetophyta - horsetails Pteridophyta - true ferns Psilotophyta - whisk ferns Ophioglossophyta - adderstongues Seed plants (spermatophytes) †Pteridospermatophyta - seed ferns Pinophyta - conifers Cycadophyta - cycads Ginkgophyta - ginkgo Gnetophyta - gnetae Magnoliophyta - flowering plants Adiantum pedatum (a fern... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms and cells. ...


In the liver, the enzyme alcohol dehydrogenase converts ethanol into acetaldehyde, which is then further converted into harmless acetic acid by acetaldehyde dehydrogenase. Acetaldehyde is more toxic than ethanol and is responsible for many hangover symptoms. N-Acetylcysteine (NAC) is known to assist in processing acetaldehyde in the body and therefore can help to relieve hangover symptoms. L-Cysteine and L-glutamine, which each contain a thiol group, can force conversion back into ethanol, to similar effect. The liver is one of the largest internal organs of the human body. ... Ribbon diagram of the catalytically perfect enzyme TIM. An enzyme is a protein that catalyzes, or speeds up, a chemical reaction. ... Alcohol Dehydrogenase Alcohol dehydrogenases are a group of dehydrogenase enzymes that occur in many organisms and facilitate the conversion between alcohols and aldehydes or ketones. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... Flash point 43 Â°C R-phrases , S-phrases , , , US Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... Acetaldehyde dehydrogenase Acetaldehyde dehydrogenase (EC 1. ... For a list of biologically injurious substances, including toxins and other materials, as well as their effects, see poison. ... A hangover or veisalgia is the unpleasant physical effects following heavy consumption of alcohol or the use of drugs. ... N-acetylcysteine is a chemical, commonly called NAC, produced by the body that enhances the production of the co-enzyme glutathione, a powerful antioxidant. ... A hangover or veisalgia is the unpleasant physical effects following heavy consumption of alcohol or the use of drugs. ... Cysteine is a naturally occurring hydrophobic amino acid which has a sulfhydryl group and is found in most proteins, however only in small quantities. ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom (-SH). ...


Some people of Far-Eastern descent have a mutation in their acetaldehyde dehydrogenase gene, making this enzyme less effective. In these people, acetaldehyde accumulates after drinking, leading to severe and immediate hangover symptoms. These people are therefore less likely to become alcoholics. The drug Antabuse (disulfiram) also prevents the oxidation of acetaldehyde to acetic acid, with the same unpleasant effects for drinkers. It is used in the treatment of certain alcoholics. Far East is an inexact term often used for East Asia and Southeast Asia combined, sometimes including also the easternmost territories of Russia, i. ... In biology, mutations are changes to the genetic material (usually DNA or RNA). ... Acetaldehyde dehydrogenase Acetaldehyde dehydrogenase (EC 1. ... This stylistic schematic diagram shows a gene in relation to the double helix structure of DNA and to a chromosome (right). ... This article needs cleanup. ... Disulfiram is a drug used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol). ... Disulfiram is a drug used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol. ...


The last steps of alcoholic fermentation in bacteria, plants and yeast involve the conversion of pyruvate into acetaldehyde by the enzyme pyruvate decarboxylase, followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by alcohol dehydrogenase, now operating in the opposite direction. Fermentation typically refers to the conversion of sugar to alcohol using yeast. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Divisions Land plants (embryophytes) Non-vascular plants (bryophytes) Marchantiophyta - liverworts Anthocerotophyta - hornworts Bryophyta - mosses Vascular plants (tracheophytes) Lycopodiophyta - clubmosses Equisetophyta - horsetails Pteridophyta - true ferns Psilotophyta - whisk ferns Ophioglossophyta - adderstongues Seed plants (spermatophytes) †Pteridospermatophyta - seed ferns Pinophyta - conifers Cycadophyta - cycads Ginkgophyta - ginkgo Gnetophyta - gnetae Magnoliophyta - flowering plants Adiantum pedatum (a fern... Yeasts constitute a group of single-celled (unicellular) fungi, a few species of which are commonly used to leaven bread, ferment alcoholic beverages, and even drive experimental fuel cells. ... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... pyruvate decarboxylase is a homotetrameric protein that catalyses decarboxylation as main reaction and carboligation as side reaction. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ...


In the chemical industry, acetaldehyde is mainly used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals. In 1989, US production stood at 740 million pounds (336,000 t). Flash point 43 Â°C R-phrases , S-phrases , , , US Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... General formula of an ester of a carboxylic acid. ...


When exposed to acetaldehyde vapors, humans develop irritation of the eyes, skin and the respiratory tract. Acetaldehyde is an air pollutant, emitted by cars and certain production facilities. It is also contained in tobacco smoke. It is classified as a probable carcinogen. This article is in need of attention from an expert on the subject. ... Various smoking equipment including different pipes, and cigars. ... In pathology, a carcinogen is any substance or agent that promotes cancer. ...


Three molecules of acetaldehyde can form the cyclic paraldehyde, and four can form the cyclic acetaldehyde tetramer. Paraldehyde is the cyclic form of three acetaldehyde molecules (a trimer). ...


See also

Ethyl alcohol, also known as ethanol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... The chemical compound ethylene oxide is an important industrial chemical used as an intermediate in the production of ethylene glycol and other chemicals, and as a sterilant for foodstuffs and medical supplies. ...

External links


  Results from FactBites:
 
Acetaldehyde (1131 words)
Acetaldehyde was tested for carcinogenicity in rats by inhalation exposure and in hamsters by inhalation exposure and by intratracheal instillation.
Acetaldehyde causes gene mutations in bacteria and gene mutations, sister chromatid exchanges, micronuclei and aneuploidy in cultured mammalian cells, without metabolic activation.
Acetaldehyde, chloro-, dimer, hydrate and chloroacetaldehyde monomer hydrate
HHMI Lab Safety: LCSS: ACETALDEHYDE (0 words)
Acetaldehyde is mutagenic and has been shown to be a reproductive toxin in animals.
Acetaldehyde is a reactive substance and on storage in the presence of air may undergo oxidation to form explosive peroxides.
Acetaldehyde should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C, supplemented by the additional precautions for dealing with extremely flammable substances (Chapter 5.F).
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