Record Information
Version1.0
Creation date2015-05-07 19:41:51 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030647
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameacetone cyanohydrin
DescriptionAcetone cyanohydrin, also known as 2-hydroxyisobutyronitrile or 2-methyllactonitrile, is a member of the class of 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 ). Acetone cyanohydrin is soluble (in water) and a very weakly acidic compound (based on its pKa). Acetone cyanohydrin can be found in a number of food items such as burdock, sweet marjoram, rice, and garland chrysanthemum, which makes acetone cyanohydrin a potential biomarker for the consumption of these food products. Acetone cyanohydrin is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number75-86-5
Structure
Thumb
Synonyms
SynonymSource
2-HydroxyisobutyronitrileChEBI
2-MethyllactonitrileChEBI
Acetone cyanhydrinChEBI
Acetone-cyanohydrinChEBI
alpha-HydroxyisobutyronitrileChEBI
2-Hydroxy-2-methylpropanenitrileKegg
a-HydroxyisobutyronitrileGenerator
Α-hydroxyisobutyronitrileGenerator
AcetoncyanhydrineHMDB
Acetone cyanohydrin, 14C-labeledHMDB
Predicted Properties
PropertyValueSource
Water Solubility26 g/LALOGPS
logP-0.29ALOGPS
logP0.019ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.53 m³·mol⁻¹ChemAxon
Polarizability8.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H7NO
IUPAC name2-hydroxy-2-methylpropanenitrile
InChI IdentifierInChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3
InChI KeyMWFMGBPGAXYFAR-UHFFFAOYSA-N
Isomeric SMILESCC(C)(O)C#N
Average Molecular Weight85.1045
Monoisotopic Molecular Weight85.052763851
Classification
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 effect

Health effect:

Disposition

Route of exposure:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-9aa3eca8406a4215b9c3Spectrum
Predicted GC-MSacetone cyanohydrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9000000000-770359d0721cdfdd25e7Spectrum
Predicted GC-MSacetone cyanohydrin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-9300000000-c28dcd8adee9c59078bbSpectrum
Predicted GC-MSacetone cyanohydrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSacetone cyanohydrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a225990200c17c1d5ec3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-033fac0cf5145b432726Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-08c60cd373cc9c8fca19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-2f152ee4137e9704b5dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-8f021cb12cf136adfbbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-9000000000-9744197fabb953390cf8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-4ce5c5d615ae500b11a1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-9dd1d03e9fcbf20e267eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9000000000-4044392e4dc24f3fc09aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-7a143ae4298ec77ebd35Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-87949a2afd28ecc4b7f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-9382fb51ed20c37c2c5aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference