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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:47 UTC
Update Date2022-03-07 02:53:00 UTC
HMDB IDHMDB0031516
Secondary Accession Numbers
  • HMDB31516
Metabolite Identification
Common Name3-Hydroxy-2-pentanone
Description3-Hydroxy-2-pentanone belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thus, 3-hydroxy-2-pentanone is considered to be an oxygenated hydrocarbon. 3-Hydroxy-2-pentanone is a herbal and truffle tasting compound. 3-Hydroxy-2-pentanone is found, on average, in the highest concentration within beer. 3-Hydroxy-2-pentanone has also been detected, but not quantified in, asparagus (Asparagus officinalis). This could make 3-hydroxy-2-pentanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxy-2-pentanone.
Structure
Data?1563862135
Synonyms
ValueSource
2-oxo-3-PentanolHMDB
AcetylethylcarbinolHMDB, MeSH
FEMA 3550HMDB
3-Hydroxy-2-pentanoneMeSH
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name3-hydroxypentan-2-one
Traditional Name3-hydroxypentan-2-one
CAS Registry Number3142-66-3
SMILES
CCC(O)C(C)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3
InChI KeyHDKKRASBPHFULQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAcyloins
Alternative Parents
Substituents
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point105.00 to 107.00 °C. @ 50.00 mm HgThe Good Scents Company Information System
Water Solubility290700 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.211 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility283 g/LALOGPS
logP-0.1ALOGPS
logP0.38ChemAxon
logS0.44ALOGPS
pKa (Strongest Acidic)13.43ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.91 m³·mol⁻¹ChemAxon
Polarizability11.03 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]+121.03731661259
DarkChem[M-H]-117.21631661259
DeepCCS[M+H]+126.73230932474
DeepCCS[M-H]-124.83730932474
DeepCCS[M-2H]-160.53630932474
DeepCCS[M+Na]+134.9930932474
AllCCS[M+H]+126.632859911
AllCCS[M+H-H2O]+122.232859911
AllCCS[M+NH4]+130.732859911
AllCCS[M+Na]+131.832859911
AllCCS[M-H]-125.732859911
AllCCS[M+Na-2H]-129.632859911
AllCCS[M+HCOO]-133.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2-pentanoneCCC(O)C(C)=O1294.3Standard polar33892256
3-Hydroxy-2-pentanoneCCC(O)C(C)=O774.9Standard non polar33892256
3-Hydroxy-2-pentanoneCCC(O)C(C)=O814.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2-pentanone,1TMS,isomer #1CCC(O[Si](C)(C)C)C(C)=O965.4Semi standard non polar33892256
3-Hydroxy-2-pentanone,1TMS,isomer #2CCC(O)=C(C)O[Si](C)(C)C1071.1Semi standard non polar33892256
3-Hydroxy-2-pentanone,1TMS,isomer #3C=C(O[Si](C)(C)C)C(O)CC963.7Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TMS,isomer #1CCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C1192.8Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TMS,isomer #1CCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C1165.8Standard non polar33892256
3-Hydroxy-2-pentanone,2TMS,isomer #2C=C(O[Si](C)(C)C)C(CC)O[Si](C)(C)C1118.4Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TMS,isomer #2C=C(O[Si](C)(C)C)C(CC)O[Si](C)(C)C1115.1Standard non polar33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(C)=O1190.8Semi standard non polar33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #2CCC(O)=C(C)O[Si](C)(C)C(C)(C)C1300.7Semi standard non polar33892256
3-Hydroxy-2-pentanone,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C(O)CC1179.6Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C1631.8Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C1586.0Standard non polar33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C1529.6Semi standard non polar33892256
3-Hydroxy-2-pentanone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C1558.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2-pentanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-08027296f0a19b4180962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2-pentanone GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9300000000-9793ae3a0b4ddfd1a1bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2-pentanone 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 - 3-Hydroxy-2-pentanone 10V, Positive-QTOFsplash10-0udr-8900000000-fc4f2e76ee03f2fc544e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Positive-QTOFsplash10-0f79-9300000000-238db97e31076c69deff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Positive-QTOFsplash10-05mx-9000000000-855a711689fd0df6f9432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Negative-QTOFsplash10-0udi-2900000000-90004bd938f6ba2db6032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Negative-QTOFsplash10-0pb9-9300000000-bbce80bdc4443df17ffc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Negative-QTOFsplash10-0abc-9000000000-fbdf3bdb47ac16ffd5b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Positive-QTOFsplash10-0006-9000000000-54a3eb88039ed7669fac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Positive-QTOFsplash10-0006-9000000000-9d059a8148178f54694d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Positive-QTOFsplash10-0006-9000000000-3560c1d8216f72208cc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 10V, Negative-QTOFsplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 20V, Negative-QTOFsplash10-0536-9000000000-cc8ee3e9af5120834aef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2-pentanone 40V, Negative-QTOFsplash10-0a4l-9000000000-c5ff37f832fb731002892021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008110
KNApSAcK IDNot Available
Chemspider ID56264
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62484
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036801
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.. .