4,4'-Dihydroxydiphenylmethane (CED0021858)

Record Information
Version1.0
Creation Date2016-05-19 04:08:25 UTC
Update Date2026-04-17 18:00:26 UTC
Accession NumberCHEM013141
Identification
Common Name4,4'-Dihydroxydiphenylmethane
ClassSmall Molecule
Description
4,4'-Dihydroxydiphenylmethane (C13H12O2) is a compound with an average molecular weight of 200.24 g/mol. 4,4'-Dihydroxydiphenylmethane belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. It is classified as an endocrine disruptor (biological) (PMC13416212) and an environmental contaminant (environmental) (PMC13296130). The compound is unspecified in polycarbonate plastics. This substance is released from 24 recorded sources, including indoor air, building and construction materials such as ceilings and tents or canopies, and household cleaning and consumer products including soap detergents, bleaching agents, and perfumes within detergents and soaps. Other sources include food contact materials and the processing of fish and meats, as well as electrical and electronic equipment such as antennas, coils, communication cables or conductors, conductive bodies characterised by the conductive materials, and cores yokes or armatures. Recorded exposure routes include oral, inhalation, and touch. Health effects associated with 4,4'-Dihydroxydiphenylmethane include breast cancer (PMC12649852), thyroid cancer (PMC6944215), cancer (PMC9918139), and miscarriage (PMC12613030). It is linked to osteoporosis (PMC13416212), allergic contact dermatitis (PMC6944215), depression (PMC9329846), heart disease (PMC9918139), and hypertension (PMC10669689, PMC9329846). Additionally, it is associated with asthma (PMC9918139) and an increase in asthma (PMC10877704, PMC9329846). The compound is linked to overweight (PMC8147950, PMC8632231) and obesity (PMC10538013, PMC10669689, PMC5974368, PMC7983487, PMC8632231, PMC9329846). Furthermore, levels of the compound are elevated in the blood in cases of cryptorchidism (PMC8654277).
Contaminant Type
  • Phenolic Antioxidant
Chemical Structure
Synonyms
ValueSource
4,4'-Bisphenol FChEBI
4,4'-DihydroxydiphenylmethaneChEBI
4,4'-Methylenebis(phenol)ChEBI
4,4'-MethylenediphenolChEBI
Bis(4-hydroxyphenyl)methaneChEBI
Bis(p-hydroxyphenyl)methaneChEBI
Bis(para-hydroxyphenyl)methaneChEBI
BPFChEBI
p,P'-bis(hydroxyphenyl)methaneChEBI
p-(p-Hydroxybenzyl)phenolChEBI
Para-(para-hydroxybenzyl)phenolChEBI
p-HydroxydiphenylmethaneHMDB
4,4'-Methylenebis(phenol), disodium saltHMDB
Bisphenol FKEGG
Chemical FormulaC13H12O2
Average Molecular Mass200.237 g/mol
Monoisotopic Mass200.084 g/mol
CAS Registry Number620-92-8
IUPAC Name4-[(4-hydroxyphenyl)methyl]phenol
Traditional Namebis(4-hydroxyphenyl)methane
SMILESOC1=CC=C(CC2=CC=C(O)C=C2)C=C1
InChI IdentifierInChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
InChI KeyPXKLMJQFEQBVLD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.61ALOGPS
logP3.46ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.84ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.76 m³·mol⁻¹ChemAxon
Polarizability21.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-d5d25429146e5db52ae5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0690000000-e9c9f9ab405e91a93786Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a7i-4900000000-2d488377fb7682ae2dd0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-4e94a3f79c8823327fb0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-7c09a1963726f69076a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-3900000000-2438ce185772421e7603Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-01d8d5f74b31bc5d92efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-5890000000-ecf48cefe9bb2e62e373Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-7900000000-c1a0e100b1b01e4d0a03Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-85db899e345a8672fcfeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-fd0f19a2393be50a2fceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-4900000000-27a6f8c98ff0f8315528Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2801.0Log mg/kg[1600:5000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionassociated_withNot AvailablePMC10669689 , PMC9329846 , PMC9329846
cancerassociated_withNot AvailablePMC9918139
breast cancerassociated_withNot AvailablePMC12649852
overweightassociated_withNot AvailablePMC8147950 , PMC8632231 , PMC8632231
osteoporosisassociated_withNot AvailablePMC13416212 , PMC13416212 , PMC13416212 , PMC13416212 , PMC13416212 , PMC13416212
asthmaassociated_withincreasePMC10877704 , PMC9329846
asthmaassociated_withNot AvailablePMC9918139
depressionassociated_withNot AvailablePMC9329846
obesityassociated_withNot AvailablePMC10538013 , PMC10669689 , PMC5974368 , PMC7983487 , PMC8632231 , PMC8632231 , PMC9329846 , PMC9329846
allergic contact dermatitisassociated_withNot AvailablePMC6944215
thyroid cancerassociated_withNot AvailablePMC6944215 , PMC6944215
heart diseaseassociated_withNot AvailablePMC9918139
miscarriageassociated_withNot AvailablePMC12613030
cryptorchidismelevated_in_blood_inNot AvailablePMC8654277
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
491Industrial manufacturing & chemical processingNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & 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
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
582Aircraft CarriersMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, 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
654Sleeve LinksTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, 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
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)64.3035
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)20.7857
Click to view 3D structureTrace amine-associated receptor 1Q923Y9Rattus norvegicusPredicted (SEA)4.67095
Click to view 3D structureHTH-type transcriptional regulator MgrAP0C1S0Staphylococcus aureusPredicted (SEA)0.934191
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 2P11507Rattus norvegicusPredicted (SEA)0.467095
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)8.64126
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)13.935
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)16.3483
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)88.2032
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)110.935
Click to view 3D structureTyR1H9TVJ1Chilo suppressalisPredicted (SEA)0.389246
Click to view 3D structureTyrosinaseO42713Agaricus bisporusPredicted (SEA)5.3716
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)101.827
Click to view 3D structureTrace amine-associated receptor 1Q923Y8Mus musculusPredicted (SEA)8.32987
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)56.7521
Click to view 3D structureCarbonic anhydraseQ2PCB5Dicentrarchus labraxPredicted (SEA)1.01204
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)56.0514
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)28.415
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 3Q64518Mus musculusPredicted (SEA)1.24559
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)1.40129
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)18.9952
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)41.1044
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)109.067
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)1.47914
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)69.0523
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0240711
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBisphenol_F
Chemspider ID11614
ChEBI ID34575
PubChem Compound ID12111
Kegg Compound IDC14298
YMDB IDNot Available
ECMDB IDM2MDB004901
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18024680
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18973785
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25475787
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25965889
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26555822
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26766355
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26838047
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26945833
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26957022
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27154708