Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:44 UTC
Update Date2021-10-13 04:41:00 UTC
HMDB IDHMDB0003243
Secondary Accession Numbers
  • HMDB03243
Metabolite Identification
Common NameAcetoin
DescriptionAcetoin, also known as dimethylketol or 2,3-butanolone, 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, acetoin is considered to be an oxygenated hydrocarbon lipid molecule. Acetoin is used as an external energy store by a number of fermentive bacteria. Acetoin, along with diacetyl, is one of the compounds giving butter its characteristic flavor. Acetoin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Acetoin is used as a food flavoring (in baked goods) and a fragrance. Acetoin is a sweet, buttery, and creamy tasting compound. Outside of the human body, Acetoin has been detected, but not quantified in several different foods, such as cocoa and cocoa products, evergreen blackberries, orange bell peppers, tortilla chips, and pomes. This could make acetoin a potential biomarker for the consumption of these foods. Constituent of beer, wine, fresh or cooked apple, fresh or cooked leak, corn, honey, cocoa, butter, cheeses, roasted coffee and other foodstuffs. Acetoin, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and ulcerative colitis; acetoin has also been linked to the inborn metabolic disorder celiac disease. Acetoin is a colorless or pale yellow to green yellow liquid with a pleasant, buttery odor. It can be found in apples, butter, yogurt, asparagus, black currants, blackberry, wheat, broccoli, brussels sprouts, cantaloupe.
Structure
Data?1582752267
Synonyms
ValueSource
(S)-2-AcetoinChEBI
1-Hydroxyethyl methyl ketoneChEBI
2,3-ButanoloneChEBI
2-AcetoinChEBI
2-Hydroxy-3-butanoneChEBI
3-Hydroxy-2-butanoneChEBI
3-Hydroxybutan-2-oneChEBI
Acetyl methyl carbinolChEBI
DimethylketolChEBI
gamma-Hydroxy-beta-oxobutaneChEBI
g-Hydroxy-b-oxobutaneGenerator
Γ-hydroxy-β-oxobutaneGenerator
3H-2b ButanoneMeSH
AcetylmethylcarbinolMeSH
(R)-2-AcetoinHMDB
(R)-3-Hydroxy-2-butanoneHMDB
(R)-3-Hydroxybutan-2-oneHMDB
(R)-AcetoinHMDB
(R)-DimethylketolHMDB
2-Butanol-3-oneHMDB
2-Hydroxy-3-oxobutaneHMDB
3-Hydroxyl-2-butanoneHMDB
AcetoineHMDB
b-OxobutaneHMDB
beta-OxobutaneHMDB
AcetoinMeSH
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name3-hydroxybutan-2-one
Traditional Nameacetoin
CAS Registry Number513-86-0
SMILES
CC(O)C(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
InChI KeyROWKJAVDOGWPAT-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 effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling Point147.00 to 148.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.360The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility473 g/LALOGPS
logP10(-0.66) g/LALOGPS
logP10(-0.14) g/LChemAxon
logS10(0.73) g/LALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability9.14 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]+116.86931661259
DarkChem[M-H]-110.31931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetoinCC(O)C(C)=O1239.6Standard polar33892256
AcetoinCC(O)C(C)=O678.5Standard non polar33892256
AcetoinCC(O)C(C)=O713.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetoin,1TMS,isomer #1CC(=O)C(C)O[Si](C)(C)C896.7Semi standard non polar33892256
Acetoin,1TMS,isomer #2CC(O)=C(C)O[Si](C)(C)C1000.8Semi standard non polar33892256
Acetoin,1TMS,isomer #3C=C(O[Si](C)(C)C)C(C)O862.6Semi standard non polar33892256
Acetoin,2TMS,isomer #1CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C1137.2Semi standard non polar33892256
Acetoin,2TMS,isomer #1CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C1103.3Standard non polar33892256
Acetoin,2TMS,isomer #1CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C1025.7Standard polar33892256
Acetoin,2TMS,isomer #2C=C(O[Si](C)(C)C)C(C)O[Si](C)(C)C1040.9Semi standard non polar33892256
Acetoin,2TMS,isomer #2C=C(O[Si](C)(C)C)C(C)O[Si](C)(C)C1062.2Standard non polar33892256
Acetoin,2TMS,isomer #2C=C(O[Si](C)(C)C)C(C)O[Si](C)(C)C1031.2Standard polar33892256
Acetoin,1TBDMS,isomer #1CC(=O)C(C)O[Si](C)(C)C(C)(C)C1131.9Semi standard non polar33892256
Acetoin,1TBDMS,isomer #2CC(O)=C(C)O[Si](C)(C)C(C)(C)C1218.1Semi standard non polar33892256
Acetoin,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C(C)O1094.3Semi standard non polar33892256
Acetoin,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C1553.0Semi standard non polar33892256
Acetoin,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C1538.2Standard non polar33892256
Acetoin,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C1371.1Standard polar33892256
Acetoin,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(C)O[Si](C)(C)C(C)(C)C1457.5Semi standard non polar33892256
Acetoin,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(C)O[Si](C)(C)C(C)(C)C1508.3Standard non polar33892256
Acetoin,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(C)O[Si](C)(C)C(C)(C)C1370.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetoin EI-B (Non-derivatized)splash10-0005-9000000000-62904abc1fc33ec40dfa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoin EI-B (Non-derivatized)splash10-0005-9000000000-62904abc1fc33ec40dfa2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-be498c13cd64980f1f352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin GC-MS (1 TMS) - 70eV, Positivesplash10-00kf-9500000000-79fa75cf570cd4a3de142017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0005-9000000000-74d60654cdf23dfc35ac2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-006x-9000000000-3bc66270ca4dc0f2c4442012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9000000000-ac710258a11f0566c38a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-94fbec9f0efb37d8aa392012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0005-9000000000-eaafc4c4d8cb29864f1d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin 35V, Negative-QTOFsplash10-000i-9000000000-f6eb75cfea26ad71fa572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoin 35V, Negative-QTOFsplash10-000i-9000000000-9a52f81ee533956236322021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 10V, Positive-QTOFsplash10-000i-9000000000-ebb7996f3f82cc069f122015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 20V, Positive-QTOFsplash10-0079-9000000000-4043204b04ec3b5823ff2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 40V, Positive-QTOFsplash10-0uk9-9000000000-1e66901c3375433b16932015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 10V, Negative-QTOFsplash10-000i-9000000000-9d60c7f29d91e72ce0bc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 20V, Negative-QTOFsplash10-000i-9000000000-35eb749498333af992962015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 40V, Negative-QTOFsplash10-00xr-9000000000-ce5e7eaa33d4f9d4fa862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 10V, Positive-QTOFsplash10-0fk9-9000000000-c5e178ac425b271910a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 20V, Positive-QTOFsplash10-0006-9000000000-f43d429661b310e7148a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 40V, Positive-QTOFsplash10-0006-9000000000-160fee6a321df2fa7b052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 10V, Negative-QTOFsplash10-000i-9000000000-4b3590a18d40d4d58a012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 20V, Negative-QTOFsplash10-000i-9000000000-bc260446b65990487a672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin 40V, Negative-QTOFsplash10-0006-9000000000-0c841ea6edf8e31c3df02021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.06 +/- 1.54 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected and Quantified56.75 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified11.35 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified41.617 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-478519.405 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.497 +/- 2.989 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0-3877982.0918 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected and Quantified5.516 +/- 5.604 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011799
KNApSAcK IDC00050424
Chemspider ID21105851
KEGG Compound IDC00466
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetoin
METLIN ID103
PubChem Compound179
PDB IDNot Available
ChEBI ID15688
Food Biomarker OntologyNot Available
VMH IDACTN_R
MarkerDB IDMDB00013447
Good Scents IDrw1007331
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. [PubMed:3275321 ]
  2. Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
  3. Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73. [PubMed:2589871 ]
  4. Otsuka M, Ohmori S: Simple and sensitive determination of diacetyl and acetoin in biological samples and alcoholic drinks by gas chromatography with electron-capture detection. J Chromatogr. 1992 Jun 10;577(2):215-20. [PubMed:1400754 ]