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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

Feces (PMID: 21970810)

Cellular substructure

Extracellular (HMDB: HMDB0031507)
Cytoplasm (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)

Exogenous (HMDB: HMDB0031507)

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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.72 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3952 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	83.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1170.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	349.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	683.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	221.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	905.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	512.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	281.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	144.2 seconds	40023050

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra