Showing Compound 1-Hydroxy-2-butanone (FDB008098)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:55 UTC

Update date

2019-11-26 03:02:05 UTC

Primary ID

FDB008098

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1-Hydroxy-2-butanone

Description

1-Hydroxy-2-butanone, also known as 2-oxobutanol or fema 3173, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. 1-Hydroxy-2-butanone is a sweet, butterscotch, and coffee tasting compound. 1-Hydroxy-2-butanone has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), mushrooms, arabica coffees (Coffea arabica), coffee and coffee products, and oyster mushrooms (Pleurotus ostreatus). This could make 1-hydroxy-2-butanone a potential biomarker for the consumption of these foods. 1-Hydroxy-2-butanone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. Based on a literature review very few articles have been published on 1-Hydroxy-2-butanone.

CAS Number

5077-67-8

Structure

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

Synonyms

Synonym	Source
2-Oxobutanol	ChEBI
Ethyl hydroxymethyl ketone	ChEBI
FEMA 3173	ChEBI
FEMA no. 3173	ChEBI
1-Hydroxybutanone	MetaCyc, HMDB
1-Hydroxybutan-2-one	HMDB
2-oxo-1-Butanol	HMDB
1-Hydroxy-2-butanone	ChEBI
2-Butanone, 1-hydroxy-	biospider
2-Oxo-1-butanol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	569 g/L	ALOGPS
logP	-0.3	ALOGPS
logP	-0.01	ChemAxon
logS	0.81	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.52 m³·mol⁻¹	ChemAxon
Polarizability	9.17 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

C4H8O2

IUPAC name

1-hydroxybutan-2-one

InChI Identifier

InChI=1S/C4H8O2/c1-2-4(6)3-5/h5H,2-3H2,1H3

InChI Key

GFAZHVHNLUBROE-UHFFFAOYSA-N

Isomeric SMILES

CCC(=O)CO

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

Classification

Description

Belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydroxy ketones

Alternative Parents

Substituents

Alpha-hydroxy ketone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (CPD0-2414 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Coffea

Biological location:

Biofluid and excreta:

Feces

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.53%; H 9.15%; O 36.32%	DFC
Melting Point	Not Available
Boiling Point	Bp 160°	DFC
Experimental Water Solubility	Not Available
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	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	1-Hydroxy-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9000000000-411fe857dcb944ac67e5	Spectrum
Predicted GC-MS	1-Hydroxy-2-butanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kl9-9300000000-51971f3b29d9cef53d63	Spectrum
Predicted GC-MS	1-Hydroxy-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1-Hydroxy-2-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-9000000000-3f5c3ea36eb88a4dd8f6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9000000000-cc39ddd976523cf65d9e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pdl-9000000000-e298c008ce8419015c82	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-7d5352d5bfb0de735feb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9000000000-6a590e7a03f590f02b1f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-f6d384ee30a191e2650d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-6335a435ef469d425a19	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-cee156eb289b5da03cc9	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-7b02e4ef9d3783df7e08	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-9000000000-a862de210d0cdec00c31	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-46be4e4b773960318681	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-97514e0c7d45788738ed	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

454721

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

521300

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31507

CRC / DFC (Dictionary of Food Compounds) ID

DBV18-X:DBV18-X

EAFUS ID

1729

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1027461

SuperScent ID

Not Available

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
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coffee	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grain	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
malt	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
butterscotch	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.