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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:43:44 UTC

Update Date

2023-02-21 17:20:42 UTC

HMDB ID

HMDB0031507

Secondary Accession Numbers

HMDB31507

Metabolite Identification

Common 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 coffee and coffee products, common mushrooms (Agaricus bisporus), arabica coffees (Coffea arabica), mushrooms, 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

1-hydroxybutan-2-one

Traditional Name

2-butanone, 1-hydroxy-

CAS Registry Number

5077-67-8

SMILES

CCC(=O)CO

InChI Identifier

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

InChI Key

GFAZHVHNLUBROE-UHFFFAOYSA-N

Chemical Taxonomy

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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031507)
Cytoplasm (HMDB: HMDB0031507)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031507)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031507)

Source

Endogenous

Endogenous (HMDB: HMDB0031507)

Plant

Plant (HMDB: HMDB0031507)
Coffea (HMDB: HMDB0031507)

Exogenous

Food

Food (HMDB: HMDB0031507)

Vegetable

Mushroom

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031507)

Pharmaceutical industry

Biomarker

Celiac disease (MarkerDB: MDB00029829)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	152.00 to 154.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	721100 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.249 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	117.348	31661259
DarkChem	[M-H]-	112.454	31661259
DeepCCS	[M+H]+	128.638	30932474
DeepCCS	[M-H]-	125.84	30932474
DeepCCS	[M-2H]-	162.158	30932474
DeepCCS	[M+Na]+	136.879	30932474
AllCCS	[M+H]+	123.6	32859911
AllCCS	[M+H-H2O]+	119.1	32859911
AllCCS	[M+NH4]+	127.7	32859911
AllCCS	[M+Na]+	128.9	32859911
AllCCS	[M-H]-	126.9	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxy-2-butanone	CCC(=O)CO	1303.8	Standard polar	33892256
1-Hydroxy-2-butanone	CCC(=O)CO	705.7	Standard non polar	33892256
1-Hydroxy-2-butanone	CCC(=O)CO	762.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxy-2-butanone,1TMS,isomer #1	CCC(=O)CO[Si](C)(C)C	973.2	Semi standard non polar	33892256
1-Hydroxy-2-butanone,1TMS,isomer #2	CCC(=CO)O[Si](C)(C)C	998.8	Semi standard non polar	33892256
1-Hydroxy-2-butanone,1TMS,isomer #3	CC=C(CO)O[Si](C)(C)C	978.7	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TMS,isomer #1	CCC(=CO[Si](C)(C)C)O[Si](C)(C)C	1133.2	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TMS,isomer #1	CCC(=CO[Si](C)(C)C)O[Si](C)(C)C	1075.0	Standard non polar	33892256
1-Hydroxy-2-butanone,2TMS,isomer #2	CC=C(CO[Si](C)(C)C)O[Si](C)(C)C	1166.5	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TMS,isomer #2	CC=C(CO[Si](C)(C)C)O[Si](C)(C)C	1103.9	Standard non polar	33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #1	CCC(=O)CO[Si](C)(C)C(C)(C)C	1193.3	Semi standard non polar	33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #2	CCC(=CO)O[Si](C)(C)C(C)(C)C	1229.6	Semi standard non polar	33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #3	CC=C(CO)O[Si](C)(C)C(C)(C)C	1199.5	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #1	CCC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1564.7	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #1	CCC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1509.1	Standard non polar	33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #2	CC=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1568.9	Semi standard non polar	33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #2	CC=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1540.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-411fe857dcb944ac67e5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (1 TMS) - 70eV, Positive	splash10-0kl9-9300000000-51971f3b29d9cef53d63	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Positive-QTOF	splash10-0079-9000000000-3f5c3ea36eb88a4dd8f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Positive-QTOF	splash10-00dr-9000000000-cc39ddd976523cf65d9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Positive-QTOF	splash10-0pdl-9000000000-e298c008ce8419015c82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Negative-QTOF	splash10-000i-9000000000-7d5352d5bfb0de735feb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Negative-QTOF	splash10-0a4r-9000000000-6a590e7a03f590f02b1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Negative-QTOF	splash10-0a4i-9000000000-f6d384ee30a191e2650d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Negative-QTOF	splash10-000i-9000000000-6335a435ef469d425a19	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Negative-QTOF	splash10-0a4i-9000000000-cee156eb289b5da03cc9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Negative-QTOF	splash10-052f-9000000000-7b02e4ef9d3783df7e08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Positive-QTOF	splash10-0fk9-9000000000-a862de210d0cdec00c31	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Positive-QTOF	splash10-006x-9000000000-46be4e4b773960318681	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Positive-QTOF	splash10-0006-9000000000-97514e0c7d45788738ed	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	0-11614.916 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	0-43811.312 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details

Associated Disorders and Diseases

Disease References

Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008098

KNApSAcK ID

C00052574

Chemspider ID

454721

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2414

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

521300

PDB ID

Not Available

ChEBI ID

88390

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029829

Good Scents ID

rw1027461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1-Hydroxy-2-butanone (HMDB0031507)

MOL for HMDB0031507 (1-Hydroxy-2-butanone)

3D MOL for HMDB0031507 (1-Hydroxy-2-butanone)

3D SDF for HMDB0031507 (1-Hydroxy-2-butanone)

3D-SDF for HMDB0031507 (1-Hydroxy-2-butanone)

PDB for HMDB0031507 (1-Hydroxy-2-butanone)

3D PDB for HMDB0031507 (1-Hydroxy-2-butanone)

SMILES for HMDB0031507 (1-Hydroxy-2-butanone)

INCHI for HMDB0031507 (1-Hydroxy-2-butanone)

Structure for HMDB0031507 (1-Hydroxy-2-butanone)

3D Structure for HMDB0031507 (1-Hydroxy-2-butanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra