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2,3-Butanedione (FDB011930)

Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2019-11-26 03:05:45 UTC
Primary IDFDB011930
Secondary Accession Numbers
  • FDB030818
Chemical Information
FooDB Name2,3-Butanedione
DescriptionConstituent of butter; formed during fermentation. A common constituent of plant oils, production of breakdown of carbohydrates. Flavouring additive used in food industryand is also present in apple, orange, plum, okra, walnut, Bourbon vanilla, clary sage, soybean, coffee, honey, rose wine, port wine, cocoa and scallop Beer sometimes undergoes a diacetyl rest, in which its temperature is raised slightly for two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavor it imparts. It is present in many California chardonnays known as "Butter Bombs," although there is a growing trend back toward the more traditional French styles.[citation needed]; Diacetyl (IUPAC systematic name: butanedione or 2,3-butanedione) is a natural byproduct of fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. Diacetyl occurs naturally in alcoholic beverages and is added to some foods to impart a buttery flavor.; Diacetyl is a natural by-product of secondary or malolactic fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2.; Carrier of aroma of butter, vinegar, coffee, and other foods.; Beer sometimes undergoes a diacetyl rest, which entails waiting two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavors it imparts. 2,3-Butanedione is found in many foods, some of which are capers, linden, sweet marjoram, and brazil nut.
CAS Number431-03-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility129 g/LALOGPS
logP0.07ALOGPS
logP0.4ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.54 m³·mol⁻¹ChemAxon
Polarizability8.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H6O2
IUPAC namebutane-2,3-dione
InChI IdentifierInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
InChI KeyQSJXEFYPDANLFS-UHFFFAOYSA-N
Isomeric SMILESCC(=O)C(C)=O
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
Classification
Description Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Role

Industrial application:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.81%; H 7.02%; O 37.17%DFC
Melting PointFp 7°DFC
Boiling PointBp 88°DFC
Experimental Water Solubility200 mg/mL at 15 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-1.34HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.94DFC
Refractive Indexn18.5D 1.3933DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8d1a3988261033033e032014-09-20View Spectrum
GC-MS2,3-Butanedione, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-eeaaf8aa838a1d6a7ddeSpectrum
GC-MS2,3-Butanedione, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-622030119adee3079d84Spectrum
GC-MS2,3-Butanedione, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-eeaaf8aa838a1d6a7ddeSpectrum
GC-MS2,3-Butanedione, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-622030119adee3079d84Spectrum
Predicted GC-MS2,3-Butanedione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-58f4b3973bdf0094a5e3Spectrum
Predicted GC-MS2,3-Butanedione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4e7132ef8eb6971544b12012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00r5-9000000000-0cc5c90a4394d550268f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-06dj-9000000000-a74bfecfcdb93a5c3e072012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-eeaaf8aa838a1d6a7dde2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-171c3774c90fd50b6d6b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-6e218d8c4f1cb3a012542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-9000000000-c27bd416a10df3c9c1d32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-49c29114e2316ba16f022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9000000000-0c5000d8f4b14cdc5b052021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f3362015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb3922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f3362015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb3922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b3322015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b3322015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-ec20127c74818b1f634d2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID630
ChEMBL IDCHEMBL365809
KEGG Compound IDC00741
Pubchem Compound ID650
Pubchem Substance IDNot Available
ChEBI ID16583
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03407
CRC / DFC (Dictionary of Food Compounds) IDHBW35-X:HBW35-X
EAFUS ID871
Dr. Duke IDBUTANEDIONE|BIACETYL|DIACETYL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID431-03-8
GoodScent IDrw1014611
SuperScent ID650
Wikipedia IDDiacetyl
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
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
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strong
  1. 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.
creamy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  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).