Diphenolic acid (CHEM016536)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:19 UTC
Update Date2026-04-16 22:37:08 UTC
Accession NumberCHEM016536
Identification
Common NameDiphenolic acid
ClassSmall Molecule
DescriptionDiphenolic acid is a carboxylic acid with molecular formula C17H18O4. Its IUPAC name is 4,4-bis(4-hydroxyphenyl)pentanoic acid, and it can be prepared by the condensation reaction of phenol with levulinic acid in the presence of hydrochloric acid. The equation for this synthesis is: 2 C6H5OH + CH3C(O)CH2CH2COOH → CH3C(p-C6H4OH)2CH2CH2COOH + H2ODiphenolic acid is a solid at room temperature, melting at 168–171 °C and boiling at 507 °C. According to its MSDS, diphenolic acid is soluble in ethanol, isopropanol, acetone, acetic acid, and methyl ethyl ketone, but insoluble in benzene, carbon tetrachloride, and xylene. Diphenolic acid may be a suitable replacement for bisphenol A as a plasticizer.Diphenolate esters have been used to synthesize epoxy resins as a replacement for the digylcidyl ether of bisphenol A.The digylcidyl ethers of n-alkyl diphenolate esters have similar thermomechanical properties to the digylcidyl ether of bisphenol A when cured, but the viscosity and glass transition temperature vary as a function of the ester length. Diphenolate esters have also been used to synthesize polycarbonates with a potential for water solubility.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,4-Bis(4-hydroxyphenyl)pentanoic acidKegg
4,4-Bis(4-hydroxyphenyl)pentanoateGenerator
DiphenolateGenerator
Chemical FormulaC17H18O4
Average Molecular Mass286.327 g/mol
Monoisotopic Mass286.121 g/mol
CAS Registry Number126-00-1
IUPAC Name4,4-bis(4-hydroxyphenyl)pentanoic acid
Traditional Namediphenolic acid
SMILESCC(CCC(O)=O)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C17H18O4/c1-17(11-10-16(20)21,12-2-6-14(18)7-3-12)13-4-8-15(19)9-5-13/h2-9,18-19H,10-11H2,1H3,(H,20,21)
InChI KeyVKOUCJUTMGHNOR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentBisphenols
Alternative Parents
Substituents
  • Bisphenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP3.38ALOGPS
logP3.61ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.14 m³·mol⁻¹ChemAxon
Polarizability30.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-6c2edad8ad814c1feec7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-0090000000-42d74d52b9d28c1118cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01xt-1690000000-cf4ef0088720ffc8c730Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-8fe6b42f334e952f4b19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-bd00c738248df7f713eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4190000000-2d4da42b3808cb41f8d6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiphenolic acid
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID67174
Kegg Compound IDC14294
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available