Acetaldehyde

Acetaldehyde
Lewis structure of acetaldehyde	Skeletal structure of acetaldehyde
Ball-and-stick model	Space-filling model
Names
	Preferred IUPAC name Acetaldehyde
	Systematic IUPAC name Ethanal
	Other names Acetic aldehyde; Ethyl aldehyde; Acetylaldehyde
Identifiers
CAS Number	75-07-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:15343 ;
ChEMBL	ChEMBL170365 ;
ChemSpider	172 ;
ECHA InfoCard	100.000.761
EC Number	200-836-8;
IUPHAR/BPS	6277;
KEGG	C00084 ;
PubChem CID	177;
RTECS number	AB1925000;
UNII	GO1N1ZPR3B ;
CompTox Dashboard (EPA)	DTXSID5039224 ;
	InChI InChI=1S/C2H4O/c1-2-3/h2H,1H3 Key: IKHGUXGNUITLKF-UHFFFAOYSA-N ; InChI=1/C2H4O/c1-2-3/h2H,1H3 Key: IKHGUXGNUITLKF-UHFFFAOYAB;
	SMILES O=CC; CC=O;
Properties
Chemical formula	C2H4O
Molar mass	44.053 g·mol−1
Appearance	Colourless gas or liquid
Odor	Ethereal
Density	0.784 g·cm−3 (20 °C) 0.7904–0.7928 g·cm−3 (10 °C)
Melting point	−123.37 °C (−190.07 °F; 149.78 K)
Boiling point	20.2 °C (68.4 °F; 293.3 K)
Solubility in water	miscible
Solubility	miscible with ethanol, ether, benzene, toluene, xylene, turpentine, acetone ; slightly soluble in chloroform
log P	-0.34
Vapor pressure	740 mmHg (20 °C)
Acidity (pKa)	13.57 (25 °C, H2O)
Magnetic susceptibility (χ)	-.5153−6 cm3/g
Refractive index (nD)	1.3316
Viscosity	0.21 mPa-s at 20 °C (0.253 mPa-s at 9.5 °C)
Structure
Molecular shape	trigonal planar (sp2) at C1; tetrahedral (sp3) at C2
Dipole moment	2.7 D
Thermochemistry
Heat capacity (C)	89 J·mol−1·K−1
Std molar; entropy (S⦵298)	160.2 J·mol−1·K−1
Std enthalpy of; formation (ΔfH⦵298)	−192.2 kJ·mol−1
Gibbs free energy (ΔfG⦵)	-127.6 kJ·mol−1
Related compounds
Related aldehydes	Formaldehyde; Propionaldehyde
Related compounds	Ethylene oxide
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen
	GHS labelling:
Pictograms
Hazard statements	H224, H319, H335, H351
Precautionary statements	P210, P261, P281, P305+P351+P338
NFPA 704 (fire diamond)	3 4 3
Flash point	−39.00 °C; −38.20 °F; 234.15 K
Autoignition; temperature	175.00 °C; 347.00 °F; 448.15 K
Explosive limits	4.0–60%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1930 mg/kg (rat, oral)
LC50 (median concentration)	13,000 ppm (rat),; 17,000 ppm (hamster),; 20,000 ppm (rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	200 ppm (360 mg/m3)
IDLH (Immediate danger)	2000 ppm
Safety data sheet (SDS)	HMDB
Supplementary data page
	Acetaldehyde (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH₃CH=O, sometimes abbreviated as MeCH=O. 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,^[11] 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.^[12] Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke.^[13] 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.^[14] Acetaldehyde is "one of the most frequently found air toxins with cancer risk greater than one in a million".^[15]

^ SciFinderScholar (accessed 4 November 2009). Acetaldehyde (75-07-0) Substance Detail.
^ Shackelford, R.E.; Abdelbaqi, M.Q.; Almhanna, K.; Meredith, K. (2014). "Molecular Pathology and Diagnostics in Esophago-gastric Cancer". In Coppola, D. (ed.). Molecular Pathology and Diagnostics of Cancer. Cancer Growth and Progression. Vol. 16. Springer. pp. 177–210 See p. 190. doi:10.1007/978-94-007-7192-5_6. ISBN 978-94-007-7192-5.
^ ^a ^b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
^ ^a ^b Stoffdaten Acetaldehyd bei Celanese Chemicals. Archived 17 May 2008 at the Wayback Machine as of December 1999.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0001". National Institute for Occupational Safety and Health (NIOSH).
^ Haynes, W.M.; Lide, D.R.; Bruno, T.J., eds. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1-4987-5429-3. OCLC 957751024.
^ "3.2.17 Viscosity". Acetaldehyde (Compound). PubChem.
^ Rumble, J.R.; Lide, D.R.; Bruno, T.J., eds. (2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1-138-56163-2. OCLC 1043763515.
^ ^a ^b ^c Sigma-Aldrich Co., Acetaldehyde. Retrieved on 2022-02-15.
^ ^a ^b ^c "Acetaldehyde". NIOSH. 4 December 2014. Retrieved 12 February 2015.
^ Uebelacker, Michael; Lachenmeier, Dirk (13 June 2011). "Quantitative Determination of Acetaldehyde in Foods Using Automated Digestion with Simulated Gastric Fluid Followed by Headspace Gas Chromatography". Journal of Automated Methods and Management in Chemistry. 2011: 907317. doi:10.1155/2011/907317. PMC 3124883. PMID 21747735.
^ Lacy Perry (12 October 2004). "How Hangovers Work: Biology of a Hangover: Acetaldehyde". health.howstuffworks.com.
^ "Chemicals in the Environment: Acetaldehyde (CAS NO. 75-07-0)". epa.gov. Office of Pollution Prevention and Toxics, United States Environmental Protection Agency. August 1994. Archived from the original on 17 August 2002. Retrieved 22 January 2011.
^ List of IARC Group 1 carcinogens
^ Zhou, Ying; Li, Chaoyang; Huijbregts, Mark A. J.; Mumtaz, M. Moiz (7 October 2015). "Carcinogenic Air Toxics Exposure and Their Cancer-Related Health Impacts in the United States". PLOS ONE. 10 (10): e0140013. Bibcode:2015PLoSO..1040013Z. doi:10.1371/journal.pone.0140013. PMC 4596837. PMID 26444872.

[1] SciFinderScholar (accessed 4 November 2009). Acetaldehyde (75-07-0) Substance Detail.

[2] Shackelford, R.E.; Abdelbaqi, M.Q.; Almhanna, K.; Meredith, K. (2014). "Molecular Pathology and Diagnostics in Esophago-gastric Cancer". In Coppola, D. (ed.). Molecular Pathology and Diagnostics of Cancer. Cancer Growth and Progression. Vol. 16. Springer. pp. 177–210 See p. 190. doi:10.1007/978-94-007-7192-5_6. ISBN 978-94-007-7192-5.

[iupac2013-3] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.

[Celanese-4] Stoffdaten Acetaldehyd bei Celanese Chemicals. Archived 17 May 2008 at the Wayback Machine as of December 1999.

[NIOSH-5] NIOSH Pocket Guide to Chemical Hazards. "#0001". National Institute for Occupational Safety and Health (NIOSH).

[CRC97-6] Haynes, W.M.; Lide, D.R.; Bruno, T.J., eds. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1-4987-5429-3. OCLC 957751024.

[7] "3.2.17 Viscosity". Acetaldehyde (Compound). PubChem.

[crc-8] Rumble, J.R.; Lide, D.R.; Bruno, T.J., eds. (2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1-138-56163-2. OCLC 1043763515.

[sigma-9] Sigma-Aldrich Co., Acetaldehyde. Retrieved on 2022-02-15.

[IDLH-10] "Acetaldehyde". NIOSH. 4 December 2014. Retrieved 12 February 2015.

[:2-11] Uebelacker, Michael; Lachenmeier, Dirk (13 June 2011). "Quantitative Determination of Acetaldehyde in Foods Using Automated Digestion with Simulated Gastric Fluid Followed by Headspace Gas Chromatography". Journal of Automated Methods and Management in Chemistry. 2011: 907317. doi:10.1155/2011/907317. PMC 3124883. PMID 21747735.

[hsf-12] Lacy Perry (12 October 2004). "How Hangovers Work: Biology of a Hangover: Acetaldehyde". health.howstuffworks.com.

[chem-13] "Chemicals in the Environment: Acetaldehyde (CAS NO. 75-07-0)". epa.gov. Office of Pollution Prevention and Toxics, United States Environmental Protection Agency. August 1994. Archived from the original on 17 August 2002. Retrieved 22 January 2011.

[14] List of IARC Group 1 carcinogens

[:0-15] Zhou, Ying; Li, Chaoyang; Huijbregts, Mark A. J.; Mumtaz, M. Moiz (7 October 2015). "Carcinogenic Air Toxics Exposure and Their Cancer-Related Health Impacts in the United States". PLOS ONE. 10 (10): e0140013. Bibcode:2015PLoSO..1040013Z. doi:10.1371/journal.pone.0140013. PMC 4596837. PMID 26444872.

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