Cannabis Compound Database: Showing Compound Card for 2-Propanone (CDB000698)

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Record Information

Version

1.0

Created at

2020-03-19 00:51:46 UTC

Updated at

2020-12-07 19:07:42 UTC

CannabisDB ID

CDB000698

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Propanone

Description

Acetone or 2-propanone, also known as dimethyl ketone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Acetone is neutral molecule that is miscible in water. It readily dissolves in other organic solvents such as ethanol, methanol and diethyl ether. It occurs naturally in plants, trees, volcanic gases, forest fires, and is present in vehicle exhaust, alcoholic beverages, tobacco smoke, and landfill sites. Within the body small amounts of acetone are produced by the decarboxylation of ketone bodies (acetoacetate, beta-hydroxybutyrate). Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue. More specifically, acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals. In humans acetone can be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate (PMID 4285478 ). In addition to its presence in humans, acetone is found in a variety of foods and plants. Acetone¬¨‚Ä†has been rated as a generally recognized as safe (GRAS) substance when present in beverages, baked¬¨‚Ä†foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L. It is used as a flavor enhancer for sweetners in pickling mixes. Acetone is one of several ketones that are found in Cannabis sativa (PMID: 6991645 ). Acetone is widely used as an organic solvent and is the active ingredient in nail polish remover and as paint thinner. Acetone has been studied extensively and is believed to exhibit only slight toxicity in normal use. There is no strong evidence of chronic health effects if basic precautions are followed

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Propanone	ChEBI
Aceton	ChEBI
Azeton	ChEBI
beta-Ketopropane	ChEBI
Dimethyl ketone	ChEBI
Dimethylcetone	ChEBI
Dimethylketon	ChEBI
Dimethylketone	ChEBI
Methyl ketone	ChEBI
Propanon	ChEBI
Propanone	ChEBI
Pyroacetic ether	ChEBI
b-Ketopropane	Generator
Β-ketopropane	Generator
Dimethylformaldehyde	HMDB

Chemical Formula

C₃H₆O

Average Molecular Weight

58.08

Monoisotopic Molecular Weight

58.0419

IUPAC Name

propan-2-one

Traditional Name

acetone

CAS Registry Number

67-64-1

SMILES

CC(C)=O

InChI Identifier

InChI=1S/C3H6O/c1-3(2)4/h1-2H3

InChI Key

CSCPPACGZOOCGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:15347 )
propanone (CHEBI:15347 )
ketone body (CHEBI:15347 )
Oxygenated hydrocarbons (LMFA12000057 )
a methyl-ethyl-ketone (ACETONE )

Ontology

Ingestion

Metabolite

Environmental role:

Industrial application:

Personal care products

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-94.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL at 25 °C	Not Available
logP	-0.24	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.29	ALOGPS
logP	0.11	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	19.51	ChemAxon
pKa (Strongest Basic)	-7.2	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	16.19 m³·mol⁻¹	ChemAxon
Polarizability	6.41 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)	splash10-0006-9000000000-e24ae6a1f2f0e7aac3e7	2014-09-20	View Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-14f33068e4ba092deb77	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-23fa1a3953b34b4d17db	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-5de48058c986d7c07ac3	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-14f33068e4ba092deb77	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-23fa1a3953b34b4d17db	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-5de48058c986d7c07ac3	Spectrum
GC-MS	Acetone, non-derivatized, GC-MS Spectrum	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	Spectrum
Predicted GC-MS	Acetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9000000000-bc353e3a40f83275872b	Spectrum
Predicted GC-MS	Acetone, 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)	splash10-0a4i-9000000000-cbc26702df42f89389a4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052f-9000000000-76023af14a12c4b19cf9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-4a0900faf782fa344db9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-052f-9000000000-cd6003561b339cd9243f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-23fa1a3953b34b4d17db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-5de48058c986d7c07ac3	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-31f47c962fee2ab51810	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-29f0bd4f29c752b098b1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-44feb4a0693788e21f10	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-e3c53a345dc69a6403f2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-786aa0674415a8c32182	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3bc848ca563aa39df37e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9251850c7854d63a048f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-7d56b578e5d5ea65f901	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f1d310daeae27abc7672	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3f1c663ba1bd7d012172	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Ketone Body Metabolism
Succinyl CoA: 3-ketoacid CoA transferase deficiency		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

HMDB0001659

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15347

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Miller ON, Bazzano G: Propanediol metabolism and its relation to lactic acid metabolism. Ann N Y Acad Sci. 1965 Jul 31;119(3):957-73. doi: 10.1111/j.1749-6632.1965.tb47455.x. [PubMed:4285478 ]
Kalapos MP: Possible physiological roles of acetone metabolism in humans. Med Hypotheses. 1999 Sep;53(3):236-42. doi: 10.1054/mehy.1998.0752. [PubMed:10580530 ]
Abou-Zeid AA, Fouad M, Yassein M: Microbiological production of acetone-butanol by Clostridium acetobutylicum. Zentralbl Bakteriol Naturwiss. 1978;133(2):125-34. doi: 10.1016/s0323-6056(78)80023-8. [PubMed:685531 ]

Showing Compound Card for 2-Propanone (CDB000698)

Structure for CDB000698 (2-Propanone)