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Showing metabocard for Benzoin (BMDB0063675)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-02-10 19:45:45 UTC
Update Date2020-04-22 15:54:39 UTC
BMDB IDBMDB0063675
Secondary Accession Numbers
  • BMDB63675
Metabolite Identification
Common NameBenzoin
DescriptionBenzoin, also known as PHCH(OH)COPH or benzoin tincture, belongs to the class of organic compounds known as benzoins. These are organic compounds containing a 1,2-hydroxy ketone attached to two phenyl groups. Benzoin is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzoin is a potentially toxic compound. It appears as off-white crystals, with a light camphor-like odor. It is a hydroxy ketone attached to two phenyl groups. Benzoin is synthesized from benzaldehyde in the benzoin condensation.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Hydroxy-1,2-diphenylethanoneChEBI
2-Hydroxy-2-phenylacetophenoneChEBI
alpha-Hydroxy-alpha-phenylacetophenoneChEBI
alpha-Hydroxybenzyl phenyl ketoneChEBI
BenzoylphenylcarbinolChEBI
Hydroxy-2-phenyl acetophenoneChEBI
PHCH(OH)COPHChEBI
PHCOCH(OH)PHChEBI
Phenyl-alpha-hydroxybenzyl ketoneChEBI
Phenylbenzoyl carbinolChEBI
Benzoin tinctureKegg
a-Hydroxy-a-phenylacetophenoneGenerator
Α-hydroxy-α-phenylacetophenoneGenerator
a-Hydroxybenzyl phenyl ketoneGenerator
Α-hydroxybenzyl phenyl ketoneGenerator
Phenyl-a-hydroxybenzyl ketoneGenerator
Phenyl-α-hydroxybenzyl ketoneGenerator
(+-)-BenzoinHMDB
(RS)-BenzoinHMDB
2-Hydroxy-1,2-diphenylethanone, 9ciHMDB
2-Hydroxy-2-phenyl-acetophenoneHMDB
alpha -Hydroxy-alpha -phenylacetophenoneHMDB
alpha -Hydroxybenzyl phenyl ketoneHMDB
alpha-Hydroxy-a-phenylacetophenoneHMDB
DL-BenzoinHMDB
FEMA 2132HMDB
Phenyl-alpha -hydroxybenzyl ketoneHMDB
2 Hydroxy 1,2 diphenylethanoneHMDB
Chemical FormulaC14H12O2
Average Molecular Weight212.2439
Monoisotopic Molecular Weight212.083729628
IUPAC Name2-hydroxy-1,2-diphenylethan-1-one
Traditional Name(+-)-benzoin
CAS Registry NumberNot Available
SMILES
OC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
InChI KeyISAOCJYIOMOJEB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoins. These are organic compounds containing a 1,2-hydroxy ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassBenzoins
Direct ParentBenzoins
Alternative Parents
Substituents
  • Benzoin
  • Alkyl-phenylketone
  • Phenylketone
  • Benzoyl
  • Aryl ketone
  • Aryl alkyl ketone
  • Acyloin
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.64ALOGPS
logP2.65ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.62ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.52 m³·mol⁻¹ChemAxon
Polarizability22.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024aeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024aeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-3ab384278f601cbb4d82View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2900000000-f886e6349d6422a39a61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000t-0900000000-6b3b67a4498bb2a50054View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001l-0900000000-ba590db9702956fdbc3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-fc735cf5fddde6b60086View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2490000000-eb9e411954a5de3f1a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9800000000-d5c6991bbc2cf99c65b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-89224fddc3ce5308d90eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-9460000000-e11b0307b20c79addc26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-73522cae58969d047bcbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a6r-8900000000-6d617b005827df08dce0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0032039
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012830
KNApSAcK IDNot Available
Chemspider ID8093
KEGG Compound IDC01408
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzoin
METLIN IDNot Available
PubChem Compound8400
PDB IDNot Available
ChEBI ID17682
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available