AFCDB: 3-Hexanone (FDB008080)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:55 UTC

Update date

2020-09-17 15:38:42 UTC

Primary ID

FDB008080

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Hexanone

Description

3-Hexanone, also known as 3-oxohexane or hexan-3-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, 3-hexanone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is hexane in which the two methylene protons at position 3 have been replaced by an oxo group. 3-Hexanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexanone is an ether and grape tasting compound. Outside of the human body, 3-Hexanone has been detected, but not quantified in, several different foods, such as yellow bell peppers, pili nuts, almonds, spirulina, and redcurrants. This could make 3-hexanone a potential biomarker for the consumption of these foods. 3-Hexanone, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease, perillyl alcohol administration for cancer treatment, pervasive developmental disorder not otherwise specified, and autism; 3-hexanone has also been linked to the inborn metabolic disorder celiac disease.

CAS Number

589-38-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	12.6 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.95	ChemAxon
logS	-0.9	ALOGPS
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	3	ChemAxon
Refractivity	30.05 m³·mol⁻¹	ChemAxon
Polarizability	12.2 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

C6H12O

IUPAC name

hexan-3-one

InChI Identifier

InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3

InChI Key

PFCHFHIRKBAQGU-UHFFFAOYSA-N

Isomeric SMILES

CCCC(=O)CC

Average Molecular Weight

100.1589

Monoisotopic Molecular Weight

100.088815006

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

Oxygenated hydrocarbons (LMFA12000049 )
a ketone (CPD-13223 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 71.95%; H 12.08%; O 15.97%	DFC
Melting Point	-55.5 oC
Boiling Point	Bp 123-123.5°	DFC
Experimental Water Solubility	14.7 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d20 0.81	DFC
Refractive Index	n20D 1.4004	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	3-Hexanone, non-derivatized, GC-MS Spectrum	splash10-054o-9000000000-5f5fc7b9733f9b4cffbb	Spectrum
GC-MS	3-Hexanone, non-derivatized, GC-MS Spectrum	splash10-054o-9000000000-7166c2e59f557283534f	Spectrum
GC-MS	3-Hexanone, non-derivatized, GC-MS Spectrum	splash10-054o-9000000000-5f5fc7b9733f9b4cffbb	Spectrum
GC-MS	3-Hexanone, non-derivatized, GC-MS Spectrum	splash10-054o-9000000000-7166c2e59f557283534f	Spectrum
Predicted GC-MS	3-Hexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9000000000-92da37904e089295c380	Spectrum
Predicted GC-MS	3-Hexanone, 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)	splash10-0udi-4900000000-fba23bcfce6e0fc8d0bf	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9200000000-ab391fe484d74d2e5d7b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-d37048707f60af4c3dde	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-054o-9000000000-f480eb2f152de94dc887	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-054o-9000000000-f6d606fe82c5b1172d55	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3900000000-83aa81dd024ae863ad54	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9400000000-85cfd66144075267b694	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f04b6b76a11b3ebd4f73	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-0e54355e695222772a5f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-79a882c98147bad72249	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05nf-9000000000-5bb39fbe03acc5ce93df	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-1f4e3fa1bc2ad21156e9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-29d5d7016d7db880eba3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-1997bcb1b30062474eed	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9100000000-93a3b6f541e915ace8fc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-702a378a0b227d3cdc43	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-b014a0bc6ce7cff19a56	2021-09-23	View Spectrum

NMR

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18351

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00753

CRC / DFC (Dictionary of Food Compounds) ID

DBR38-J:DBR38-J

EAFUS ID

1631

Dr. Duke ID

3-HEXANONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

589-38-8

GoodScent ID

rw1005661

SuperScent ID

11509

Wikipedia ID

Not Available

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

Not Available

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
grape	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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	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.
waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rum	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).

3-Hexanone (FDB008080)

Structure for FDB008080 (3-Hexanone)