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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:44:38 UTC
Update Date2018-05-20 10:20:34 UTC
HMDB IDHMDB0031648
Secondary Accession Numbers
  • HMDB31648
Metabolite Identification
Common Name2,4-Pentanedione
Description, also known as acetylacetone or acac, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Thus, is considered to be an oxygenated hydrocarbon lipid molecule. exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, is primarily located in the cytoplasm. Outside of the human body, can be found in papaya. This makes a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
2,4-DioxopentaneChEBI
2,4-PentadioneChEBI
ACACChEBI
AcetoacetoneChEBI
Acetyl 2-propanoneChEBI
CH3-CO-CH2-CO-CH3ChEBI
HacacChEBI
Pentan-2,4-dioneChEBI
2,4-PentandioneHMDB
4-Hydroxy-3-penten-2-oneHMDB
Acetyl acetoneHMDB
Acetyl-2-propanoneHMDB
Acetyl-acetoneHMDB
AcetylacetoneHMDB
Benzil-related compound, 44HMDB
CH3COCH2COCH3HMDB
DiacetylmethaneHMDB
Pentane-2,4-dioneHMDB
PentanedioneHMDB
Pentanedione-2,4HMDB
Indium-111-acetylacetoneMeSH
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Namepentane-2,4-dione
Traditional Nameacetylacetone
CAS Registry Number123-54-6
SMILES
CC(=O)CC(C)=O
InChI Identifier
InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
InChI KeyYRKCREAYFQTBPV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentBeta-diketones
Alternative Parents
Substituents
  • 1,3-diketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-23 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility166 mg/mL at 20 °CNot Available
LogP0.40Not Available
Predicted Properties
PropertyValueSource
Water Solubility140 g/LALOGPS
logP-0.2ALOGPS
logP0.33ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.09 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9100000000-46d8c1174b4626f67753View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-43699b9ce7635de34706View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9100000000-339a18cfa2c9fef9fc0eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-f1c22c3e7618740489d1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-bbf09a0b601d6c1b37f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-d3295daaa18cb9c248cfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9100000000-46d8c1174b4626f67753View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-43699b9ce7635de34706View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9100000000-339a18cfa2c9fef9fc0eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-f1c22c3e7618740489d1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-bbf09a0b601d6c1b37f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-d3295daaa18cb9c248cfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-33ab101159a7d4a6d98eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-7900000000-4812cbafad0eb4f8a68bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9500000000-985f6620ed06341c0d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-926b40c3b86762eb1664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-198e7633acd8394443b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-d23c67af0511dd32e26dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9000000000-ccefb92ad120c18ac6adView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified23.306 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified6.659 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified16.647 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008303
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15499
BioCyc IDCPD-8879
BiGG IDNot Available
Wikipedia LinkAcetylacetone
METLIN IDNot Available
PubChem Compound31261
PDB IDNot Available
ChEBI ID14750
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yuan XH, Liu LM, Ying WB: [Preparation and spectral analysis of Bi(4-x) La(x)Ti3O12 ferroelectric thin films by metal-organic deposition method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jul;27(7):1355-8. [PubMed:17944413 ]
  2. Li C, Wang S, Huang Y, Zheng B, Tian Z, Wen Y, Li F: Synthesis, characterization and electrochemiluminescent properties of cyclometalated platinum(II) complexes with substituted 2-phenylpyridine ligands. Dalton Trans. 2013 Mar 21;42(11):4059-67. doi: 10.1039/c2dt32466k. Epub 2013 Jan 23. [PubMed:23340796 ]
  3. Rao Ch S, Subash Y E: The effect of chronic tobacco smoking and chewing on the lipid profile. J Clin Diagn Res. 2013 Jan;7(1):31-4. doi: 10.7860/JCDR/2012/5086.2663. Epub 2013 Jan 1. [PubMed:23449989 ]
  4. Yao C, Xu X, Wang J, Shi L, Li L: Low-temperature, solution-processed hole selective layers for polymer solar cells. ACS Appl Mater Interfaces. 2013 Feb;5(3):1100-7. doi: 10.1021/am302878m. Epub 2013 Jan 31. [PubMed:23331483 ]
  5. Muyskens KJ, Alsum JR, Thielke TA, Boer JL, Heetderks TR, Muyskens MA: Photochemistry of UV-excited trifluoroacetylacetone and hexafluoroacetylacetone I: infrared spectra of fluorinated methylfuranones formed by HF photoelimination. J Phys Chem A. 2012 Dec 20;116(50):12305-13. doi: 10.1021/jp307725z. Epub 2012 Dec 6. [PubMed:23176295 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .