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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:58 UTC
Update Date2019-07-23 06:11:07 UTC
HMDB IDHMDB0032469
Secondary Accession Numbers
  • HMDB32469
Metabolite Identification
Common NamePhthalide
DescriptionPhthalide, also known as 1-phthalanone or isobenzofuranone, belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,. Phthalide is an extremely weak basic (essentially neutral) compound (based on its pKa). Phthalide is a sweet, coconut, and coumarin tasting compound. Outside of the human body, Phthalide has been detected, but not quantified in, a few different foods, such as celeriacs, celery stalks, and evergreen blackberries. This could make phthalide a potential biomarker for the consumption of these foods. A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.
Structure
Data?1563862267
Synonyms
ValueSource
1(3H)-IsobenzofuranoneChEBI
1-PhthalanoneChEBI
2-Hydroxymethylbenzoic acid, gamma-lactoneChEBI
3-oxo-1,3-Dihydro-isobenzofuranChEBI
IsobenzofuranoneChEBI
PhthalolactoneChEBI
2-Hydroxymethylbenzoate, g-lactoneGenerator
2-Hydroxymethylbenzoate, gamma-lactoneGenerator
2-Hydroxymethylbenzoate, γ-lactoneGenerator
2-Hydroxymethylbenzoic acid, g-lactoneGenerator
2-Hydroxymethylbenzoic acid, γ-lactoneGenerator
1-IsobenzofuranoneHMDB
2-Hydroxymethylbenzoic acid, laquo gammaraquo -lactoneHMDB
3-Butylidene-7-hydroxyphthalideHMDB
3H-Isobenzofuran-1-oneHMDB
2-Benzofuran-1(3H)-oneHMDB
PhthalideChEBI
Chemical FormulaC8H6O2
Average Molecular Weight134.132
Monoisotopic Molecular Weight134.036779436
IUPAC Name1,3-dihydro-2-benzofuran-1-one
Traditional Namephthalide
CAS Registry Number87-41-2
SMILES
O=C1OCC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
InChI KeyWNZQDUSMALZDQF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassIsobenzofuranones
Direct ParentPhthalides
Alternative Parents
Substituents
  • Phthalide
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.80Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.95 g/LALOGPS
logP0.99ALOGPS
logP1.53ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)15.36ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.64 m³·mol⁻¹ChemAxon
Polarizability13.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9005020400-2d50f7ae6f3cd7691b4bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9005020400-2d50f7ae6f3cd7691b4bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-8900000000-e2e10448dc354d50b16aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-b82a529519513084f181Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d1e071a72f1a95b3a153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-6900000000-bfb94809be049435fcd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-db8e49fee9cdba16eb19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-79843cf4206508400973Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-452212b0af673745db15Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB010076
KNApSAcK IDNot Available
Chemspider ID6621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalide
METLIN IDNot Available
PubChem Compound6885
PDB IDNot Available
ChEBI ID38085
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .