Milk Composition Database: Showing metabocard for Acetone (BMDB0001659)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:56 UTC

Update Date

2020-06-04 20:23:17 UTC

MCDB ID

BMDB0001659

Secondary Accession Numbers

BMDB01659

Metabolite Identification

Common Name

Acetone

Description

Acetone, also known as dimethyl ketone or 2-propanone, 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. Thus, acetone is considered to be an oxygenated hydrocarbon lipid molecule. Acetone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetone exists in all living organisms, ranging from bacteria to humans. Acetone is a potentially toxic compound.

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

58.0791

Monoisotopic Molecular Weight

58.041864814

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 )

Physical Properties

State

Liquid

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	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	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-14f33068e4ba092deb77	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-23fa1a3953b34b4d17db	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5de48058c986d7c07ac3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-14f33068e4ba092deb77	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-23fa1a3953b34b4d17db	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5de48058c986d7c07ac3	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-bc353e3a40f83275872b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-9000000000-cbc26702df42f89389a4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052f-9000000000-76023af14a12c4b19cf9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-4a0900faf782fa344db9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-052f-9000000000-cd6003561b339cd9243f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-23fa1a3953b34b4d17db	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-5de48058c986d7c07ac3	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-31f47c962fee2ab51810	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-29f0bd4f29c752b098b1	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-44feb4a0693788e21f10	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-e3c53a345dc69a6403f2	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-786aa0674415a8c32182	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3bc848ca563aa39df37e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9251850c7854d63a048f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-7d56b578e5d5ea65f901	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f1d310daeae27abc7672	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3f1c663ba1bd7d012172	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-e24ae6a1f2f0e7aac3e7	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	184 +/- 11 uM	PMID: 11286410	details
Detected and Quantified	3 +/- 1.601 uM	PMID: 12463694	details
Detected and Quantified	2 +/- 1 uM	PMID: 12463694	details
Detected and Quantified	3.61 +/- 1.14 uM	PMID: 12463694	details
Detected and Quantified	17 - 40 uM	PMID: 22098372	details
Detected and Quantified	191 +/- 64 mg/100g dry matter content	Brigitta Gaspardo...	details
Detected and Quantified	244 +/- 123 mg/100g dry matter content	Brigitta Gaspardo...	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	12 - 661 uM	PMID: 20338431	details
Detected and Quantified	17 - 497 uM	PMID: 22098372	details
Detected and Quantified	22 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	23 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	22 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	20 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	12 +/- 1.22 uM	PMID: 29642378	details
Detected and Quantified	19 +/- 3.54 uM	PMID: 29642378	details
Detected and Quantified	13 +/- 4 uM	PMID: 29642378	details

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

Synthesis Reference

Ishizaki, Fumiaki. Acetone and butanol fermentation. Baiomasu Handobukku (2002), 166-175.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. [PubMed:12463694 ]
Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Acetone (BMDB0001659)

Structure for BMDB0001659 (Acetone)