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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:02:05 UTC
Update Date2023-02-21 17:29:58 UTC
HMDB IDHMDB0060427
Secondary Accession Numbers
  • HMDB60427
Metabolite Identification
Common NameAcetone cyanohydrin
DescriptionAcetone cyanohydrin, also known as 2-methyllactonitrile, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Crushing the tubers releases these compounds and produces acetone cyanohydrin. It is used as a surrogate in place of HCN, as illustrated by this synthesis of lithium cyanide:(CH3)2C(OH)CN + LiH → (CH3)2CO + LiCN + H2In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by base. Treated with sulfuric acid give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and methyl methacrylate. Acetone cyanohydrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetone cyanohydrin is classified as an extremely hazardous substance in the US Emergency Planning and Community Right-to-Know Act. Acetone cyanohydrin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Acetone cyanohydrin has been detected, but not quantified in, several different foods, such as oregon yampahs, lowbush blueberries, common sages, grapefruits, and chicories. This could make acetone cyanohydrin a potential biomarker for the consumption of these foods. It liberates hydrogen cyanide easily, so it is used as a source of such. Acetone cyanohydrin is a potentially toxic compound. Alternatively, a simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ.
Structure
Thumb
Synonyms
ValueSource
2-HydroxyisobutyronitrileChEBI
2-MethyllactonitrileChEBI
Acetone cyanhydrinChEBI
Acetone-cyanohydrinChEBI
alpha-HydroxyisobutyronitrileChEBI
2-Hydroxy-2-methylpropanenitrileKegg
a-HydroxyisobutyronitrileGenerator
Α-hydroxyisobutyronitrileGenerator
AcetoncyanhydrineHMDB
Acetone cyanohydrin, 14C-labeledHMDB
Chemical FormulaC4H7NO
Average Molecular Weight85.1045
Monoisotopic Molecular Weight85.052763851
IUPAC Name2-hydroxy-2-methylpropanenitrile
Traditional Nameacetone cyanohydrin
CAS Registry NumberNot Available
SMILES
CC(C)(O)C#N
InChI Identifier
InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3
InChI KeyMWFMGBPGAXYFAR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Alpha-hydroxynitrile
  • Cyanohydrin
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02203
Phenol Explorer Compound IDNot Available
FooDB IDFDB030647
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02659
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetone cyanohydrin
METLIN IDNot Available
PubChem Compound6406
PDB IDNot Available
ChEBI ID15348
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Linamarin + Water → Acetone cyanohydrin + D-Glucosedetails