Benzoin (CED0005106)

Record Information
Version1.0
Creation Date2014-09-11 05:21:43 UTC
Update Date2026-05-14 19:39:32 UTC
Accession NumberCHEM003862
Identification
Common NameBenzoin
ClassSmall Molecule
Description
Benzoin is an exogenous organic compound with the formula C14H12O2 and an average molecular weight of 212.24 g/mol. It exists as a solid at room temperature. Benzoin belongs to the benzoins, a subclass of stilbenes within the organic compounds. Industrially, the compound is utilized as a fragrance, a flavouring and nutrient, and as processing aids not otherwise specified. It is released from polyamide plastics and is found in 41 recorded sources. These include electrical and electronic equipment such as antennas, coils, communication cables or conductors, auxiliary devices, and conductive bodies characterised by the conductive materials. In household cleaning and consumer products, it is present in bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Within food, food processing and cookware, it is associated with food contact materials, food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, and the processing of meats. Additionally, it is found in building and construction materials including ceilings, floors, ladders, and tents or canopies, as well as in drinking water and household items such as rosaries. Recorded exposure routes include inhalation, oral, and touch. At the molecular level, benzoin has two recorded protein targets, acting as an inhibitor of the Androgen receptor (AR) and Liver carboxylesterase 1 (CES1).
Contaminant Type
  • Ester
  • Flavouring Agent
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical 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 diphenylethanoneMeSH, HMDB
Chemical FormulaC14H12O2
Average Molecular Mass212.244 g/mol
Monoisotopic Mass212.084 g/mol
CAS Registry Number119-53-9
IUPAC Name2-hydroxy-1,2-diphenylethan-1-one
Traditional Name(+-)-benzoin
SMILESOC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point137 °C
Boiling Point343°C (649.4°F)
Solubility0.3 mg/mL at 25 °C
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-0900000000-b0ec63ecab48679dd41aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6r-6900000000-2f572dbc9a49f3d86fa6Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0fb9-1900000000-96773244d2cba7c024aeNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-004i-2900000000-ccb5c52e6567e1dffec5Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-0900000000-b0ec63ecab48679dd41aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6r-6900000000-2f572dbc9a49f3d86fa6Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0fb9-1900000000-96773244d2cba7c024aeNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-004i-2900000000-ccb5c52e6567e1dffec5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9700000000-3ab384278f601cbb4d82Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-2900000000-f886e6349d6422a39a61Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-0900000000-6b3b67a4498bb2a50054Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001l-0900000000-ba590db9702956fdbc3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0190000000-fc735cf5fddde6b60086Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2490000000-eb9e411954a5de3f1a0dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9800000000-d5c6991bbc2cf99c65b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-89224fddc3ce5308d90eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-9460000000-e11b0307b20c79addc26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9400000000-73522cae58969d047bcbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-3436b87f373d7fbcaf9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-2690000000-7841a53d5c52aa8e2247Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9210000000-b4f68180f59549edc6b6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0910000000-b9f20bd0c9109085d014Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-685098f82765483815acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-9100000000-e63c1029ad6ef144ad45Not AvailableView Spectrum
MSMS Spectrumsplash10-0a6r-8900000000-6d617b005827df08dce0Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6482.0Log mg/kg[3600:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
575RosariesHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Mandelate racemase structureClick to view 3D structureMandelate racemaseP11444Pseudomonas putidaPredicted (SEA)0.233548
Click to view 3D structureSortase AQ8CM62Streptococcus mutansPredicted (SEA)7.47353
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)211.127
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)234.871
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)3.34752
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)129.775
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)13.7015
Histone deacetylase 4 structureClick to view 3D structureHistone deacetylase 4P56524HumansPredicted (SEA)100.114
Click to view 3D structureLiver carboxylesterase 1P12337Oryctolagus cuniculusPredicted (SEA)0.467095
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)250.519
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)210.426
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)211.594
Histone deacetylase 7 structureClick to view 3D structureHistone deacetylase 7Q8WUI4HumansPredicted (SEA)103.539
Histone deacetylase 5 structureClick to view 3D structureHistone deacetylase 5Q9UQL6HumansPredicted (SEA)128.685
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)255.501
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)4.5931
Click to view 3D structureAlkaline ceramidase 2Q5QJU3HumansPredicted (SEA)16.8154
Click to view 3D structureKynureninaseP70712Rattus norvegicusPredicted (SEA)3.65891
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)92.407
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)173.915
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)374.455
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)733.651
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)166.909
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)1675.39
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)71.3877
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0032039
FooDB IDFDB012830
Phenol Explorer IDNot Available
KNApSAcK IDC00000640
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzoin
Chemspider ID8093
ChEBI ID17682
PubChem Compound ID8400
Kegg Compound IDC01408
YMDB IDYMDB00336
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15828829
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16107154
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17399985
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.