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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:24 UTC
Update Date2018-03-12 21:57:36 UTC
HMDB IDHMDB0032039
Secondary Accession Numbers
  • HMDB32039
Metabolite Identification
Common NameBenzoin
Description(±)-Benzoin is a flavouring ingredient.Benzoin 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. (Wikipedia
Structure
Thumb
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
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 diphenylethanoneMeSH
Chemical FormulaC14H12O2
Average Molecular Weight212.2439
Monoisotopic Molecular Weight212.083729628
IUPAC Name2-hydroxy-1,2-diphenylethan-1-one
Traditional Name(+-)-benzoin
CAS Registry Number119-53-9
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
DescriptionThis compound 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
Disposition

Biological location:

Source:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point137 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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
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
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008742
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)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Benzoin → (2-oxo-1,2-diphenylethoxy)sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Benzoin → 3,4,5-trihydroxy-6-(2-oxo-1,2-diphenylethoxy)oxane-2-carboxylic aciddetails