Record Information
Version1.0
Creation date2010-04-08 22:09:50 UTC
Update date2015-10-09 22:32:08 UTC
Primary IDFDB011799
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetoin
DescriptionConstit. of beer, wine, fresh or cooked apple, fresh or cooked leak, corn, honey, cocoa, butter, cheeses, roasted coffee and other foodstuffs. Flavouring ingredient. [DFC] Acetoin is a colorless or pale yellow to green yellow liquid with a pleasant, buttery odor. 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 used as a food flavoring (in baked goods) and a fragrance. It can be found in apples, butter, yogurt, asparagus, black currants, blackberry, wheat, broccoli, brussels sprouts, cantaloupe. [Wikipedia]
CAS Number513-86-0
Structure
Thumb
Synonyms
SynonymSource
(R)-2-AcetoinHMDB
(R)-3-Hydroxybutan-2-oneHMDB
(R)-DimethylketolHMDB
(S)-2-AcetoinChEBI
1-Hydroxyethyl methyl ketonedb_source
2-AcetoinChEBI
2-Butanol-3-oneHMDB
2-Hydroxy-3-butanoneChEBI
2-Hydroxy-3-oxobutaneHMDB
2,3-ButanoloneChEBI
3-Hydroxy-2-butanonemanual
3-Hydroxybutan-2-oneChEBI
3-Hydroxyl-2-butanoneHMDB
Acetoindb_source
AcetoineHMDB
Acetylmethylcarbinoldb_source
b-OxobutaneHMDB
beta-oxobutanebiospider
Butan-2-one 3-hydroxybiospider
Dimethylketoldb_source
FEMA 2008db_source
g-Hydroxy-b-oxobutaneGenerator
gamma-Hydroxy-beta-oxobutaneChEBI
gamma-hydroxy-beta;-oxobutanebiospider
Methylacetylcarbinoldb_source
γ-hydroxy-β-oxobutaneGenerator
Predicted Properties
PropertyValueSource
Water Solubility473 g/LALOGPS
logP-0.66ALOGPS
logP-0.14ChemAxon
logS0.73ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H8O2
IUPAC name3-hydroxybutan-2-one
InChI IdentifierInChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
InChI KeyInChIKey=ROWKJAVDOGWPAT-UHFFFAOYSA-N
Isomeric SMILESCC(O)C(C)=O
Average Molecular Weight88
Monoisotopic Molecular Weight88
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 54.53%; H 9.15%; O 36.32%DFC
Melting Point15 oC
Boiling PointNot Available
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-62904abc1fc33ec40dfaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-be498c13cd64980f1f35View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00kf-9500000000-79fa75cf570cd4a3de14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-9000000000-3bc66270ca4dc0f2c444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ac710258a11f0566c38aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-94fbec9f0efb37d8aa39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0005-9000000000-eaafc4c4d8cb29864f1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-ebb7996f3f82cc069f12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9000000000-4043204b04ec3b5823ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-1e66901c3375433b1693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-9d60c7f29d91e72ce0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-35eb749498333af99296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-9000000000-ce5e7eaa33d4f9d4fa86View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0005-9000000000-74d60654cdf23dfc35acView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID21105851
ChEMBL IDNot Available
KEGG Compound IDC00466
Pubchem Compound ID179
Pubchem Substance IDNot Available
ChEBI ID15688
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03243
CRC / DFC (Dictionary of Food Compounds) IDGZG79-M:GZG79-M
EAFUS ID20
Dr. Duke ID3-HYDROXY-2-BUTANONE|ACETOIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet ID513-86-0
GoodScent IDrw1007331
SuperScent ID179
Wikipedia IDAcetoin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
butter
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cream
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
creamy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buttery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dairy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
milky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).