Cannabis Compound Database: Showing Compound Card for Acrolein (CDB000549)

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Record Information

Version

1.0

Created at

2020-03-19 00:43:08 UTC

Updated at

2020-12-07 19:07:31 UTC

CannabisDB ID

CDB000549

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Acrolein

Description

Acrolein, also known as propenal or acrylic aldehyde, belongs to the class of organic compounds known as enals. These are alpha, beta unsaturated aldehydes, with the general chemical formula RC=C-CH=O in which the aldehydic C=O function is conjugated to the C=C double bond located at the alpha beta position. Acrolein 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. Acrolein 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. It is also used as an herbicide and algicide in water treatment. It can be produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and, due to its reactivity it shows high toxicity. It is a good Michael acceptor, making it a useful reaction tool 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 to 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. Acrolein has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Acrolein is found in fruit aromas, black tea, carrot, cooked potato, cheeses, white wine, hydrolyzed soy protein, turkey, pork, beef fat and other foods. Acrolein has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

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 Weight

56.06

Monoisotopic Molecular Weight

56.0262

IUPAC Name

prop-2-enal

Traditional Name

acrolein

CAS Registry Number

107-02-8

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Uremia

Gastrointestinal disorders:

Vomiting

Observation:

Bleeding

Ingestion

Source:

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Organ and components:

Role

Indirect biological role:

Industrial application:

Food and nutrition

Household products:

Pesticide:

Herbicide

Environmental role:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-87.7 °C	Not Available
Boiling Point	53 °C	Wikipedia
Water Solubility	212 mg/mL at 25 °C	Not Available
logP	-0.01	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-34c0891db414206d2b40	2014-09-20	View Spectrum
GC-MS	Acrolein, non-derivatized, GC-MS Spectrum	splash10-0a4i-9000000000-f6aba25388da7855f3eb	Spectrum
GC-MS	Acrolein, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-a667e77a9d666459b411	Spectrum
GC-MS	Acrolein, non-derivatized, GC-MS Spectrum	splash10-0a4i-9000000000-f6aba25388da7855f3eb	Spectrum
GC-MS	Acrolein, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-a667e77a9d666459b411	Spectrum
Predicted GC-MS	Acrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6r-9000000000-4a086c1c9c7836b7b307	Spectrum
Predicted GC-MS	Acrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-cf50f66835baacbc5db4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-abefe6f7a672744326c1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-32a4911454ef635f19ed	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-4740fe3b45257adba96a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-e578c9fb2097eb472d12	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-c28d7e42ec75bd010f50	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-af8a08e40e7604e1b105	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-a0d6dd919aed0acdb715	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-f12145ad941c7b169c50	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, 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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Cyclophosphamide Action Pathway		Not Available
Cyclophosphamide Metabolism Pathway		Not Available
Ifosfamide Action Pathway		Not Available
Ifosfamide Metabolism Pathway		Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0041822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acrolein

METLIN ID

Not Available

PubChem Compound

7847

PDB ID

Not Available

ChEBI ID

15368

References

General References

Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Acrolein (CDB000549)

Structure for CDB000549 (Acrolein)