benzoin (YMDB00336)

Identification
YMDB IDYMDB00336
Namebenzoin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Benzoin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • α-Hydroxy-α-phenylacetophenone
  • 2-Hydroxy-1, 2-diphenylethanone
  • 2-Hydroxy-1,2-diphenylethan-1-on
  • 2-Hydroxy-1,2-diphenylethanone
  • 2-Hydroxy-2-phenylacetophenone
  • Acetophenone, 2-hydroxy-2-phenyl-
  • alpha-Hydroxy-alpha-phenylacetophenone
  • alpha-Hydroxybenzyl phenyl ketone
  • Benzoin
  • Benzoin tincture
  • Benzoylphenylcarbinol
  • Bitter almond oil camphor
  • Ethanone, 2-hydroxy-1,2-diphenyl-
  • Fenyl-alpha-hydroxybenzylketon
  • Hydroxy-2-phenyl acetophenone
  • Persian balsam
  • Phenyl-alpha-hydroxybenzyl ketone
  • PHCH(OH)COPH
  • PHCOCH(OH)PH
  • Phenylbenzoyl carbinol
  • a-Hydroxy-a-phenylacetophenone
  • Α-hydroxy-α-phenylacetophenone
  • a-Hydroxybenzyl phenyl ketone
  • Α-hydroxybenzyl phenyl ketone
  • Phenyl-a-hydroxybenzyl ketone
  • Phenyl-α-hydroxybenzyl ketone
  • (+-)-Benzoin
  • (RS)-Benzoin
  • 2-Hydroxy-1,2-diphenylethanone, 9ci
  • 2-Hydroxy-2-phenyl-acetophenone
  • alpha -Hydroxy-alpha -phenylacetophenone
  • alpha -Hydroxybenzyl phenyl ketone
  • alpha-Hydroxy-a-phenylacetophenone
  • DL-Benzoin
  • FEMA 2132
  • Phenyl-alpha -hydroxybenzyl ketone
  • 2 Hydroxy 1,2 diphenylethanone
CAS number119-53-9
WeightAverage: 212.2439
Monoisotopic: 212.083729628
InChI KeyISAOCJYIOMOJEB-UHFFFAOYSA-N
InChIInChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
IUPAC Name2-hydroxy-1,2-diphenylethan-1-one
Traditional IUPAC Name(+-)-benzoin
Chemical FormulaC14H12O2
SMILESOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1
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
Physical Properties
StateSolid
Charge0
Melting point137 °C
Experimental Properties
PropertyValueReference
Water Solubility0.3 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB012830
MedicalFDB012830
MedicinalFDB012830
VanillaFDB012830
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-3ab384278f601cbb4d82JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2900000000-f886e6349d6422a39a61JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000t-0900000000-6b3b67a4498bb2a50054JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001l-0900000000-ba590db9702956fdbc3fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-fc735cf5fddde6b60086JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2490000000-eb9e411954a5de3f1a0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9800000000-d5c6991bbc2cf99c65b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-89224fddc3ce5308d90eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-9460000000-e11b0307b20c79addc26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-73522cae58969d047bcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-3436b87f373d7fbcaf9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-2690000000-7841a53d5c52aa8e2247JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-b4f68180f59549edc6b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-b9f20bd0c9109085d014JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-685098f82765483815acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-e63c1029ad6ef144ad45JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a6r-8900000000-6d617b005827df08dce0JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17682
HMDB IDHMDB0032039
Pubchem Compound ID8400
Kegg IDC01408
ChemSpider ID8093
FOODB IDFDB012830
WikipediaBenzoin
BioCyc IDNot Available

Enzymes

Protein Details
1. Benzil reductase IRC24
General function:
Involved in oxidoreductase activity
Specific function:
Reduces benzil stereospecifically to (S)-benzoin. Is probably involved in a pathway contributing to genomic integrity
Gene Name:
IRC24
Uniprot ID:
P40580
Molecular weight:
28803.90039
Reactions
Benzoin + NADP(+) → benzil + NADPH.