Milk Composition Database: Showing metabocard for 2-Heptanone (BMDB0003671)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:05:50 UTC

Update Date

2020-06-04 19:04:10 UTC

MCDB ID

BMDB0003671

Secondary Accession Numbers

BMDB03671

Metabolite Identification

Common Name

2-Heptanone

Description

2-Heptanone, also known as butylacetone or heptan-2-one, 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, 2-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone has been found to be associated with several diseases known as hepatic encephalopathy, crohn's disease, ulcerative colitis, and perillyl alcohol administration for cancer treatment; also 2-heptanone has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Butylacetone	ChEBI
Methyl N-amyl ketone	ChEBI
Methyl pentyl ketone	ChEBI
N-Amyl methyl ketone	ChEBI
N-Pentyl methyl ketone	ChEBI
Heptan-2-one	Kegg
Methyl-N-amyl ketone	MeSH
1-Methylhexanal	HMDB
2-Oxoheptane	HMDB
Amyl methyl ketone	HMDB
Methyl amyl ketone	HMDB
Methyl N-pentyl ketone	HMDB
Pentyl methyl ketone	HMDB
2-Heptanone	ChEBI

Chemical Formula

C₇H₁₄O

Average Molecular Weight

114.1855

Monoisotopic Molecular Weight

114.10446507

IUPAC Name

heptan-2-one

Traditional Name

2-heptanone

CAS Registry Number

110-43-0

SMILES

CCCCCC(C)=O

InChI Identifier

InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3

InChI Key

CATSNJVOTSVZJV-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:5672 )
dialkyl ketone (CHEBI:5672 )
Oxygenated hydrocarbons (C08380 )
Oxygenated hydrocarbons (LMFA12000004 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-35 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.3 mg/mL at 25 °C	Not Available
LogP	1.98	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.92	ALOGPS
logP	2.14	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-7.3	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	4	ChemAxon
Refractivity	34.62 m³·mol⁻¹	ChemAxon
Polarizability	14.31 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-9000000000-91b562632b96c4162a98	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-67e38b971af9b3c9eab2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-91a94dcd78168a9329dd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-91b562632b96c4162a98	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-67e38b971af9b3c9eab2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-91a94dcd78168a9329dd	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-bce74b4c35b3b9e36244	2016-09-22	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)	splash10-00di-9000000000-340ccee799fd50ab5a33	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-0fd345f1dea8cedcab42	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-f99f3bb1427948d03185	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-97b7fddf959ef5d3b440	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-67e38b971af9b3c9eab2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0a4i-9000000000-91a94dcd78168a9329dd	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-6a3dc0c3384cd6612eff	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9200000000-5a05142154c02577b232	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-2d6778d58ba8e8ea00a8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-ed3177cddff3fa618b12	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6900000000-25ce7fee81ab8707f58b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9000000000-5ada47c45a2fe1735d19	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-87ba7764343ecec4c93f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-5900000000-f86b22df61c18f43f2a1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-60d871af25b43ebc5562	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4m-9000000000-5a65545c973f8321f4b1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-dfada72bb790844e1ef7	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-29ce8ae76e2c33b1b8ac	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-e42425c6c304ff44687b	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	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	0.002 +/- 0.001 uM	PMID: 12463694	details
Detected and Quantified	0.0013 +/- 0.0011 uM	PMID: 12463694	details
Detected and Quantified	0.0014 +/- 0.0011 uM	PMID: 12463694	details
Detected and Quantified	0.17 +/- 0.16 mg/100g dry matter content	Brigitta Gaspardo...	details
Detected and Quantified	0.09 +/- 0.09 mg/100g dry matter content	Brigitta Gaspardo...	details

External Links

HMDB ID

HMDB0003671

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Heptanone

METLIN ID

Not Available

PubChem Compound

8051

PDB ID

Not Available

ChEBI ID

5672

References

Synthesis Reference

Johnson, J. R.; Hager, F. D. Methyl amyl ketone. Organic Syntheses (1927), 7 60-2. CODEN: ORSYAT ISSN:0078-6209. CAN 21:32500 AN 1927:32500

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 .

Showing metabocard for 2-Heptanone (BMDB0003671)

Structure for BMDB0003671 (2-Heptanone)