ContaminantDB: Acrolein

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (29)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:58 UTC

Update Date

2026-03-31 17:59:10 UTC

Accession Number

CHEM000033

Identification

Common Name

Acrolein

Class

Small Molecule

Description

Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. Acrolein is an herbicide and algicide used in water treatment. It is produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and a reactive one, hence its high toxicity. It is a good Michael acceptor, hence its useful reaction with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 mg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram.

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 3
OECD HPV Chemicals
OSHA Hazardous Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Aldehyde
Food Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Lachrymator
Metabolite
Organic Compound
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acrylaldehyde	ChEBI
Acrylic aldehyde	ChEBI
Propenal	ChEBI
2-Propen-1-one	HMDB
2-Propenal	HMDB, MeSH
2-Propenaldehyde	HMDB
Acquinite	HMDB
Acraldehyde	HMDB, MeSH
Acroleina	HMDB
Aldehyde, acrylic	HMDB, MeSH
Aldehyde, allyl	HMDB, MeSH
Aldehyde, ethylene	HMDB, MeSH
Allyl aldehyde	HMDB, MeSH
Aqualin	HMDB, MeSH
Aqualine	HMDB
Biocide	HMDB
CH2=chcho	HMDB
Crolean	HMDB
Ethylene aldehyde	HMDB, MeSH
Magnacide	HMDB
Magnacide H	HMDB
Magnacide H and b	HMDB
Papite	HMDB
Prop-2-en-1-al	HMDB
Prop-2-enal	HMDB
Propenaldehyde	HMDB
Propylene aldehyde	HMDB
Slimicide	HMDB
trans-Acrolein formylethylene	HMDB
2 Propenal	MeSH, HMDB

Chemical Formula

C₃H₄O

Average Molecular Mass

56.063 g/mol

Monoisotopic Mass

56.026 g/mol

CAS Registry Number

107-02-8

IUPAC Name

prop-2-enal

Traditional Name

acrolein

SMILES

C=CC=O

InChI Identifier

InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2

InChI Key

HGINCPLSRVDWNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:15368 )
Pesticides (C01471 )
a small molecule (ACROLEIN )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

Not Available

Applications

herbicide

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Greenish-yellow when impure

Experimental Properties

Property	Value
Melting Point	-87.7°C
Boiling Point	52°C
Solubility	212 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	107 g/L	ALOGPS
logP	0.18	ALOGPS
logP	0.37	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Basic)	-4.3	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	1	ChemAxon
Refractivity	16.37 m³·mol⁻¹	ChemAxon
Polarizability	5.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-f6aba25388da7855f3eb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-a667e77a9d666459b411	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-f6aba25388da7855f3eb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-a667e77a9d666459b411	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-4a086c1c9c7836b7b307	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-cf50f66835baacbc5db4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-abefe6f7a672744326c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-32a4911454ef635f19ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-4740fe3b45257adba96a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-e578c9fb2097eb472d12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-c28d7e42ec75bd010f50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-af8a08e40e7604e1b105	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-a0d6dd919aed0acdb715	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-f12145ad941c7b169c50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-34c0891db414206d2b40	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

Acrolein rapidly and irreversibly binds to lysine moieties and sulfhydryl groups found on many cellular molecules forming thiol ethers. By this mechanism acrolein can bind to messenger compounds to produce direct cytotoxic effects or secondary effects from interrupted cell signaling pathways. Perturbation of inflammatory responses in bronchial epithelial cells was demonstrated by direct action of acrolein on the inhibitor of nuclear factor kappa-B (IκB) kinase, which inhibits activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) transcription factor and suppresses interleukin 8 (IL-8) production. Rapid binding of acrolein to neural receptors in the corneal and nasal mucosa results in rapid depolarization of the associated neurons to produce ocular and nasal irritation. Acrolein also binds rapidly to glutathione, which may be inhibitory to the enzyme glutathione peroxidase and result in a lower level of cellular protection against oxygen radical toxicity. Further, the adduction of glutathione generates GS-propionaldehyde, which produces oxygen and possibly hydroxy radicals via cytosolic aldehyde dehydrogenase. Acrolein inhibits thioredoxin and thioredoxin reductase, which disrupts the cellular thiol redox balance necessary for cell survival. It interferes with normal reverse cholesterol transport by high density lipoprotein (HDL) by modifying specific sites in apolipoprotein A-I. Acrolein also inhibits aldehyde dehydrogenases and activates the transient receptor potential cation channel. (5, 1, 2, 3)

Metabolism

Acrolein can be absorbed though oral, inhalation, or dermal routes. In the liver and kidneys, acrolein forms conjugates with glutathione, cysteine, N-acetylcysteine, and/or thioredoxin. Acrolein can also be transformed into acrylic acid by liver cytosol or microsomes, or it can be oxidized to glycidaldehyde by lung or liver microsomes. Acrolein metabolites are excreted in the urine. (5)

Toxicity Values

LC50: 130 ppm over 30 minutes (Inhalation, Rat) (10) LD50: 562 mg/kg (Dermal, Rabbit) (11) LD50: 46 mg/kg (Oral, Rat) (11) LD50: 30 mg/kg (Subcutaneous, Rat) (11) High levels of acrolein (>7 mg/m3) cause injury to lungs after short term exposures.

Lethal Dose

10 ppm for an adult human. (9)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (8)

Uses/Sources

Acrolein is used as a pesticide to control algae, weeds, bacteria, and mollusks. It is also used to make other chemicals, such as polyester resin, polyurethane, propylene glycol, acrylic acid, acrylonitrile, and glycerol. Small amounts of acrolein can be formed when trees, tobacco, other plants, gasoline, and oil are burned. (5)

Minimum Risk Level

Acute Inhalation: 0.003 ppm (7) Intermediate Inhalation: 0.00004 ppm (7) Intermediate Oral: 2 mg/kg/day (7)

Health Effects

Acrolein is a severe pulmonary irritant and lachrymatory agent. Breathing large amounts of acrolein damages the lungs and could cause death. (5, 6)

Symptoms

Ingestion of acrolein causes stomach irritation, vomiting, stomach ulcers and bleeding. Breathing acrolein may cause eye watering, burning of the nose and throat and a decreased breathing rate. (5)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041822

FooDB ID

FDB008307

Phenol Explorer ID