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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:44 UTC
Update Date2022-03-07 02:53:00 UTC
HMDB IDHMDB0031507
Secondary Accession Numbers
  • HMDB31507
Metabolite Identification
Common Name1-Hydroxy-2-butanone
Description1-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
Data?1563862134
Synonyms
ValueSource
2-OxobutanolChEBI
Ethyl hydroxymethyl ketoneChEBI
FEMA 3173ChEBI
FEMA no. 3173ChEBI
1-HydroxybutanoneMetaCyc, HMDB
1-Hydroxybutan-2-oneHMDB
2-oxo-1-ButanolHMDB
1-Hydroxy-2-butanoneChEBI
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name1-hydroxybutan-2-one
Traditional Name2-butanone, 1-hydroxy-
CAS Registry Number5077-67-8
SMILES
CCC(=O)CO
InChI Identifier
InChI=1S/C4H8O2/c1-2-4(6)3-5/h5H,2-3H2,1H3
InChI KeyGFAZHVHNLUBROE-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxy ketones
Alternative Parents
Substituents
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point152.00 to 154.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility721100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.249 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility569 g/LALOGPS
logP-0.3ALOGPS
logP-0.01ChemAxon
logS0.81ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.52 m³·mol⁻¹ChemAxon
Polarizability9.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.34831661259
DarkChem[M-H]-112.45431661259
DeepCCS[M+H]+128.63830932474
DeepCCS[M-H]-125.8430932474
DeepCCS[M-2H]-162.15830932474
DeepCCS[M+Na]+136.87930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Hydroxy-2-butanoneCCC(=O)CO1303.8Standard polar33892256
1-Hydroxy-2-butanoneCCC(=O)CO705.7Standard non polar33892256
1-Hydroxy-2-butanoneCCC(=O)CO762.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Hydroxy-2-butanone,1TMS,isomer #1CCC(=O)CO[Si](C)(C)C973.2Semi standard non polar33892256
1-Hydroxy-2-butanone,1TMS,isomer #2CCC(=CO)O[Si](C)(C)C998.8Semi standard non polar33892256
1-Hydroxy-2-butanone,1TMS,isomer #3CC=C(CO)O[Si](C)(C)C978.7Semi standard non polar33892256
1-Hydroxy-2-butanone,2TMS,isomer #1CCC(=CO[Si](C)(C)C)O[Si](C)(C)C1133.2Semi standard non polar33892256
1-Hydroxy-2-butanone,2TMS,isomer #1CCC(=CO[Si](C)(C)C)O[Si](C)(C)C1075.0Standard non polar33892256
1-Hydroxy-2-butanone,2TMS,isomer #2CC=C(CO[Si](C)(C)C)O[Si](C)(C)C1166.5Semi standard non polar33892256
1-Hydroxy-2-butanone,2TMS,isomer #2CC=C(CO[Si](C)(C)C)O[Si](C)(C)C1103.9Standard non polar33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #1CCC(=O)CO[Si](C)(C)C(C)(C)C1193.3Semi standard non polar33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #2CCC(=CO)O[Si](C)(C)C(C)(C)C1229.6Semi standard non polar33892256
1-Hydroxy-2-butanone,1TBDMS,isomer #3CC=C(CO)O[Si](C)(C)C(C)(C)C1199.5Semi standard non polar33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #1CCC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1564.7Semi standard non polar33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #1CCC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1509.1Standard non polar33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #2CC=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1568.9Semi standard non polar33892256
1-Hydroxy-2-butanone,2TBDMS,isomer #2CC=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1540.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-411fe857dcb944ac67e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (1 TMS) - 70eV, Positivesplash10-0kl9-9300000000-51971f3b29d9cef53d632017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-2-butanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Positive-QTOFsplash10-0079-9000000000-3f5c3ea36eb88a4dd8f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Positive-QTOFsplash10-00dr-9000000000-cc39ddd976523cf65d9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Positive-QTOFsplash10-0pdl-9000000000-e298c008ce8419015c822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Negative-QTOFsplash10-000i-9000000000-7d5352d5bfb0de735feb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Negative-QTOFsplash10-0a4r-9000000000-6a590e7a03f590f02b1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Negative-QTOFsplash10-0a4i-9000000000-f6d384ee30a191e2650d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Negative-QTOFsplash10-000i-9000000000-6335a435ef469d425a192021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Negative-QTOFsplash10-0a4i-9000000000-cee156eb289b5da03cc92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Negative-QTOFsplash10-052f-9000000000-7b02e4ef9d3783df7e082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 10V, Positive-QTOFsplash10-0fk9-9000000000-a862de210d0cdec00c312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 20V, Positive-QTOFsplash10-006x-9000000000-46be4e4b7739603186812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-2-butanone 40V, Positive-QTOFsplash10-0006-9000000000-97514e0c7d45788738ed2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-11614.916 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-43811.312 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008098
KNApSAcK IDC00052574
Chemspider ID454721
KEGG Compound IDNot Available
BioCyc IDCPD0-2414
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521300
PDB IDNot Available
ChEBI ID88390
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029829
Good Scents IDrw1027461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .