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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:44 UTC
Update Date2023-02-21 17:20:42 UTC
HMDB IDHMDB0031507
Secondary Accession Numbers
  • HMDB31507
Metabolite Identification
Common Name1-Hydroxy-2-butanone
Description1-Hydroxy-2-butanone, also known as 2-oxobutanol or fema 3173, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. 1-Hydroxy-2-butanone is a sweet, butterscotch, and coffee tasting compound. 1-Hydroxy-2-butanone has been detected, but not quantified in, several different foods, such as coffee and coffee products, common mushrooms (Agaricus bisporus), arabica coffees (Coffea arabica), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make 1-hydroxy-2-butanone a potential biomarker for the consumption of these foods. 1-Hydroxy-2-butanone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. Based on a literature review very few articles have been published on 1-Hydroxy-2-butanone.
Structure
Thumb
Synonyms
ValueSource
2-OxobutanolChEBI
Ethyl hydroxymethyl ketoneChEBI
FEMA 3173ChEBI
FEMA no. 3173ChEBI
1-HydroxybutanoneMetaCyc, HMDB
1-Hydroxybutan-2-oneHMDB
2-oxo-1-ButanolHMDB
1-Hydroxy-2-butanoneChEBI
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name1-hydroxybutan-2-one
Traditional Name2-butanone, 1-hydroxy-
CAS Registry Number5077-67-8
SMILES
CCC(=O)CO
InChI Identifier
InChI=1S/C4H8O2/c1-2-4(6)3-5/h5H,2-3H2,1H3
InChI KeyGFAZHVHNLUBROE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxy ketones
Alternative Parents
Substituents
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point152.00 to 154.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility721100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.249 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-11614.916 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-43811.312 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008098
KNApSAcK IDC00052574
Chemspider ID454721
KEGG Compound IDNot Available
BioCyc IDCPD0-2414
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521300
PDB IDNot Available
ChEBI ID88390
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029829
Good Scents IDrw1027461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .