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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:47:24 UTC
Update Date2022-09-22 18:34:57 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
Data?1563862210
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 diphenylethanoneMeSH, HMDB
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
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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point137 °CNot Available
Boiling Point194.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility0.3 mg/mL at 25 °CNot Available
LogP2.130The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.51131661259
DarkChem[M-H]-147.4831661259
DeepCCS[M+H]+145.74730932474
DeepCCS[M-H]-143.35230932474
DeepCCS[M-2H]-176.62830932474
DeepCCS[M+Na]+151.6630932474
AllCCS[M+H]+148.332859911
AllCCS[M+H-H2O]+143.932859911
AllCCS[M+NH4]+152.432859911
AllCCS[M+Na]+153.532859911
AllCCS[M-H]-149.432859911
AllCCS[M+Na-2H]-149.332859911
AllCCS[M+HCOO]-149.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzoinOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C12594.8Standard polar33892256
BenzoinOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C11836.5Standard non polar33892256
BenzoinOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C11801.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzoin,1TMS,isomer #1C[Si](C)(C)OC(C(=O)C1=CC=CC=C1)C1=CC=CC=C11832.3Semi standard non polar33892256
Benzoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)C1=CC=CC=C1)C1=CC=CC=C12056.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzoin EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024ae2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin EI-B (Non-derivatized)splash10-0a4i-0900000000-b0ec63ecab48679dd41a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin EI-B (Non-derivatized)splash10-0a6r-6900000000-2f572dbc9a49f3d86fa62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin GC-EI-TOF (Non-derivatized)splash10-0fb9-1900000000-96773244d2cba7c024ae2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzoin GC-EI-TOF (Non-derivatized)splash10-004i-2900000000-ccb5c52e6567e1dffec52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-3ab384278f601cbb4d822016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoin GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2900000000-f886e6349d6422a39a612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-8900000000-6d617b005827df08dce02014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzoin Linear Ion Trap , positive-QTOFsplash10-000t-0900000000-6b3b67a4498bb2a500542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzoin Linear Ion Trap , positive-QTOFsplash10-001l-0900000000-ba590db9702956fdbc3f2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 10V, Positive-QTOFsplash10-03di-0190000000-fc735cf5fddde6b600862016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 20V, Positive-QTOFsplash10-03di-2490000000-eb9e411954a5de3f1a0d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 40V, Positive-QTOFsplash10-0a4i-9800000000-d5c6991bbc2cf99c65b42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 10V, Negative-QTOFsplash10-03di-0090000000-89224fddc3ce5308d90e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 20V, Negative-QTOFsplash10-01t9-9460000000-e11b0307b20c79addc262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 40V, Negative-QTOFsplash10-004i-9400000000-73522cae58969d047bcb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 10V, Negative-QTOFsplash10-03di-0090000000-3436b87f373d7fbcaf9c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 20V, Negative-QTOFsplash10-08fr-2690000000-7841a53d5c52aa8e22472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 40V, Negative-QTOFsplash10-004i-9210000000-b4f68180f59549edc6b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 10V, Positive-QTOFsplash10-0002-0910000000-b9f20bd0c9109085d0142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 20V, Positive-QTOFsplash10-0002-0900000000-685098f82765483815ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoin 40V, Positive-QTOFsplash10-004l-9100000000-e63c1029ad6ef144ad452021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012830
KNApSAcK IDC00000640
Chemspider ID8093
KEGG Compound IDC01408
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzoin
METLIN IDNot Available
PubChem Compound8400
PDB IDNot Available
ChEBI ID17682
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011601
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