AFCDB: 2-Butanone (FDB003383)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:47 UTC

Update date

2020-09-17 15:34:05 UTC

Primary ID

FDB003383

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Butanone

Description

2-Butanone or Butanone, also known as methylethylketone or MEK, belongs to the class of organic compounds known as ketones. It is an organic compound with the formula CH3C(O)CH2CH3. Ketones 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, butanone is considered to be an oxygenated hydrocarbon lipid molecule. Butanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has been isolated from hop oil (Humulus lupulus), white clover (Trifolium repens), tea, tomatoes, various fruits and other vegetable sources. It is used in the refining and extraction of fats and oils. Butanone is an irritant, but serious health effects in animals have been seen only at very high levels. When inhaled, these effects included birth defects. Butanone occurs as a natural product. It is produced by some trees and found in some fruits and vegetables in small amounts. It is also released to the air from car and truck exhausts. The known health effects to people from exposure to butanone are irritation of the nose, throat, skin, and eyes. This colorless liquid has a sharp, sweet odor, reminiscent of butterscotch and acetone. It is produced industrially at a large scale, and also occurs in trace amounts in nature.

CAS Number

78-93-3

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	93 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.81	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	19.68	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	1	ChemAxon
Refractivity	20.82 m³·mol⁻¹	ChemAxon
Polarizability	8.28 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

Chemical Formula

C4H8O

IUPAC name

butan-2-one

InChI Identifier

InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3

InChI Key

ZWEHNKRNPOVVGH-UHFFFAOYSA-N

Isomeric SMILES

CCC(C)=O

Average Molecular Weight

72.1057

Monoisotopic Molecular Weight

72.057514878

Classification

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:28398 )
dialkyl ketone (CHEBI:28398 )
Oxygenated hydrocarbons (LMFA12000043 )
a methyl-ethyl-ketone (MEK )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 66.63%; H 11.18%; O 22.19%	DFC
Melting Point	Fp -85.9°	DFC
Boiling Point	Bp 79.6°	DFC
Experimental Water Solubility	223 mg/mL at 25 oC	TAFT,RW et al. (1985)
Experimental logP	0.29	HANSCH,C ET AL. (1995)
Experimental pKa	14.7
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 0.81	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-389580382a5be690811f	2014-09-20	View Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb	Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-9d38ccb9b91100a7ec9a	Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c956d364a703ad576f74	Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb	Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-9d38ccb9b91100a7ec9a	Spectrum
GC-MS	2-Butanone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c956d364a703ad576f74	Spectrum
Predicted GC-MS	2-Butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-4e6c1888a6b9f92a7e0c	Spectrum
Predicted GC-MS	2-Butanone, 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)	splash10-05fr-9000000000-ce6384a82cdbc3c32131	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05fr-9000000000-d2220466d540748715a6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-5c396f6150d62df63bf8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-342b15824555f25c17ae	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-9d38ccb9b91100a7ec9a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-9000000000-c956d364a703ad576f74	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-9000000000-df1c4f4393ad8e083cee	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-5db9dc68e554d23fe4ca	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e76aaa16e1218b6b92e0	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-9000000000-df1c4f4393ad8e083cee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-5db9dc68e554d23fe4ca	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e76aaa16e1218b6b92e0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-75ee4bf0cca979df2fee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-a0882d603db69a60cd2b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9000000000-2b71687b4480da0a40a8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-75ee4bf0cca979df2fee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-a0882d603db69a60cd2b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9000000000-2b71687b4480da0a40a8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-1924391f943e092b4486	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b1f7b08e06d7bb20906d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052o-9000000000-d0609c2afd15f75e6cbb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-77e5dcf17bd83eca2c67	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9000000000-91a2cd469019aa3b0b9c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-fa8f185babb9571dbb91	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28398

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00474

CRC / DFC (Dictionary of Food Compounds) ID

CXC70-D:CXC70-D

EAFUS ID

382

Dr. Duke ID

BUTANONE|METHYL-ETHYL-KETONE|2-BUTANONE|BUTAN-2-ONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

78-93-3

GoodScent ID

rw1007581

SuperScent ID

Not Available

Wikipedia ID

Butanone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
ether	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
acetone	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

2-Butanone (FDB003383)

Structure for FDB003383 (2-Butanone)