Record Information
Version1.0
Creation date2010-04-08 22:08:14 UTC
Update date2018-05-29 00:44:08 UTC
Primary IDFDB008742
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzoin
DescriptionBenzoin is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.
CAS Number119-53-9
Structure
Thumb
Synonyms
SynonymSource
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
α-Hydroxy-α-phenylacetophenonebiospider
α-Hydroxybenzyl phenyl ketonebiospider
2-Hydroxy-1,2-diphenylethanone, 9CIdb_source
Acetophenone, 2-hydroxy-2-phenyl-biospider
Phenyl-α-hydroxybenzyl ketonebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H12O2
IUPAC name2-hydroxy-1,2-diphenylethan-1-one
InChI IdentifierInChI=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
Isomeric SMILESOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1
Average Molecular Weight212.2439
Monoisotopic Molecular Weight212.083729628
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.23%; H 5.70%; O 15.08%DFC
Melting Point137 oC
Boiling PointNot Available
Experimental Water Solubility0.3 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
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
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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01408
Pubchem Compound ID8400
Pubchem Substance IDNot Available
ChEBI ID17682
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDVN47-B:DVN47-B
EAFUS ID304
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1011601
SuperScent ID8400
Wikipedia IDBenzoin
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
Flavours
FlavorCitations
vanilla
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference