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Human Metabolome Database Version 3.5

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Showing metabocard for Acetoin (HMDB03243)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:44 -0600
Update Date 2013-02-08 17:12:23 -0700
HMDB ID HMDB03243
Secondary Accession Numbers None
Metabolite Identification
Common Name Acetoin
Description Acetoin is a product of fermentation. It is a component of the butanediol cycle in microorganisms. In mammals it is oxidized to carbon dioxide. -- Pubchem; '3-Hydroxybutanone, also known as acetoin or acetyl methyl carbinol, is a chemical compound composed of carbon, hydrogen and oxygen. Its formula is C4H8O2. It is a colourless or pale yellow to green yellow liquid with a pleasant buttery odour. It is used as a food flavoring and a fragrance. -- Wikipedia.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (R)-2-acetoin
  2. (R)-3-hydroxy-2-butanone
  3. (R)-3-hydroxybutan-2-one
  4. (R)-acetoin
  5. (R)-dimethylketol
  6. 1-Hydroxyethyl methyl ketone
  7. 2,3-Butanolone
  8. 2-Acetoin
  9. 2-Butanol-3-one
  10. 2-Hydroxy-3-butanone
  11. 2-Hydroxy-3-oxobutane
  12. 3-Hydroxy-2-butanone
  13. 3-Hydroxybutan-2-one
  14. 3-Hydroxyl-2-butanone
  15. Acetoine
  16. Acetyl methyl carbinol
  17. b-Oxobutane
  18. beta-Oxobutane
  19. Dimethylketol
Chemical Formula C4H8O2
Average Molecular Weight 88.1051
Monoisotopic Molecular Weight 88.0524295
IUPAC Name 3-hydroxybutan-2-one
Traditional IUPAC Name acetoin
CAS Registry Number 513-86-0
SMILES CC(O)C(C)=O
InChI Identifier InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
InChI Key ROWKJAVDOGWPAT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Acyloins
Sub Class N/A
Other Descriptors
  • acetoin(Cyc)
  • methyl ketone(ChEBI)
Substituents
  • Alpha Ketoaldehyde
  • Ketone
  • Secondary Alcohol
Direct Parent Acyloins
Ontology
Status Detected and Quantified
Origin
  • Plant
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 15 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000 mg/mL at 20 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 473 g/L ALOGPS
LogP -0.66 ALOGPS
LogP -0.14 ChemAxon
LogS 0.73 ALOGPS
pKa (strongest acidic) 13.72 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 22.39 ChemAxon
Polarizability 9.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80B)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.06 +/- 1.54 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011799
KNApSAcK ID Not Available
Chemspider ID 21105851 Link_out
KEGG Compound ID C00466 Link_out
BioCyc ID CPD-255 Link_out
BiGG ID Not Available
Wikipedia Link Acetoin Link_out
NuGOwiki Link HMDB03243 Link_out
Metagene Link HMDB03243 Link_out
METLIN ID 103 Link_out
PubChem Compound 179 Link_out
PDB ID Not Available
ChEBI ID 15688 Link_out
References
Synthesis Reference Not 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  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 Link_out