AFCDB: Acetaldehyde (FDB008297)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2020-09-17 15:29:56 UTC

Primary ID

FDB008297

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetaldehyde

Description

Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are aldehydes with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol; which is mediated by the enzyme alcohol dehydrogenase 1B. In addition, acetaldehyde can be converted into acetic acid; which is mediated by mitochondrial aldehyde dehydrogenases. Industrially, the main method of production of acetaldehyde is via the oxidation of ethylene via the Wacker process. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process for producing acetaldehyde exceeded 2 million tonnes annually. Acetaldehyde is found in a number of different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine), Acetaldehyde has also been detected, but not quantified in, several different foods, such as malabar plums, malus (crabapple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. As a food constituent, acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and Crohn's disease. Acetaldehyde has also been linked to several inborn metabolic disorders including aldehyde dehydrogenase deficiency (III). The level at which an average consumer can detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Plastics Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. Acetaldehyde is known to be the most abundant carcinogen in tobacco smoke; it is easily dissolved in saliva while smoking (PMID:17382522, PMID:21556207).

CAS Number

75-07-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	225 g/L	ALOGPS
logP	-0.01	ALOGPS
logP	-0.38	ChemAxon
logS	0.71	ALOGPS
pKa (Strongest Acidic)	16.73	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	11.72 m³·mol⁻¹	ChemAxon
Polarizability	4.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C2H4O

IUPAC name

acetaldehyde

InChI Identifier

InChI=1S/C2H4O/c1-2-3/h2H,1H3

InChI Key

IKHGUXGNUITLKF-UHFFFAOYSA-N

Isomeric SMILES

CC=O

Average Molecular Weight

44.0526

Monoisotopic Molecular Weight

44.02621475

Classification

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Short-chain aldehydes

Alternative Parents

Substituents

Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aldehyde (CHEBI:15343 )
an <i>n</i>-alkanal (ACETALD )

Ontology

Physiological effect

Health effect:

Health condition:

Cancer

Metabolism and nutrition disorders:

Aldehyde dehydrogenase deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Environmental:

Biological:

Animal

Microbe:

Helicobacter:

Helicobacter pylori

Water disinfection

Naturally occurring process:

Biological process:

Biochemical pathway:

Alcoholism

Role

Indirect biological role:

Industrial application:

Food and nutrition

Environmental role:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 21°	DFC
Charge	0
Density	d204 0.78	DFC
Experimental logP	-0.34	TSCATS
Experimental pKa	pKa1 13.57 (25°,hydrate)	DFC
Experimental Water Solubility	1000 mg/mL at 25 oC	RIDDICK,JA et al. (1986)
Isoelectric point	Not Available
Mass Composition	C 54.53%; H 9.15%; O 36.32%	DFC
Melting Point	Mp -121°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-002f-9000000000-65d53ef91644a0bacd6c	2014-09-20	View Spectrum
Predicted GC-MS	Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-69e31ccd415894a68912	Spectrum
Predicted GC-MS	Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-9000000000-f1274d4b6066776ca898	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001l-9000000000-c1e37abbf2ad6054dc10	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000t-9000000000-2289ead4f7210282cd87	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-cf54221d95714f5478c4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-8d8afe7422ae76f7ebb9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9000000000-d68dec9f846cfe9acc72	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-4430d6a790eca4132aa4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-607a755de038203a6b68	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-63c9f623d8dc4b1e60a2	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-0d922cdfd7f6947230c0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2758497e574a09010547	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15343

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00990

CRC / DFC (Dictionary of Food Compounds) ID

DFR74-T:DFR74-T

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Potato	Expected but not quantified	Not Available	DUKE, HMDB
White cabbage	Expected but not quantified	Not Available	DUKE, HMDB
Barley	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Broccoli	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, Charles F. Forney and Michael A. Jordan. Induction of Volatile Compounds in Broccoli by Postharvest Hot-Water Dips. J. Agric. Food Chem. 1998, 46, 5295-5301, Charles F. Forney, James P. Mattheis, and Rodney K. Austin. Volatile Compounds Produced by Broccoli under Anaerobic Conditions. J. Agric. Food Chem., 1991, 39 (12), pp 2257-2259, HMDB
Common pea	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Cucumber	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Dill	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Eggplant	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Garden onion	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Garden tomato	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB

Showing 1 to 10 of 40 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
addictive			DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	CHEBI
fungicide	24127	A substance used to destroy fungal pests.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
respiraparalytic			DUKE
tyrosinase inhibitor	59997	Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.	DUKE

Showing 1 to 7 of 7 entries

Enzymes

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Showing 1 to 3 of 3 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
aldehydic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ether	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
ethereal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
whiskey	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695

Showing 1 to 6 of 6 entries

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Acetaldehyde (FDB008297)

Structure for FDB008297 (Acetaldehyde)