Record Information
Version1.0
Creation date2010-04-08 22:08:57 UTC
Update date2020-02-24 19:10:58 UTC
Primary IDFDB010076
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 a sweet, coconut, and coumarin tasting compound. Phthalide has been detected, but not quantified in, several different foods, such as blackberries (Rubus), celeriacs (Apium graveolens var. rapaceum), celery stalks (Apium graveolens var. dulce), and evergreen blackberries (Rubus laciniatus). This could make phthalide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phthalide.
CAS Number87-41-2
Structure
Thumb
Synonyms
SynonymSource
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-Benzofuran-1(3H)-oneHMDB
2-Hydroxymethylbenzoic acid, laquo gammaraquo -lactoneHMDB
3-Butylidene-7-hydroxyphthalideHMDB
3H-Isobenzofuran-1-oneHMDB
PhthalideChEBI
2-Hydroxymethylbenzoic acid, «gamma»-lactonebiospider
3-oxo-1,3-dihydro-IsobenzofuranChEBI
3H-isobenzofuran-1-onebiospider
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
Chemical FormulaC8H6O2
IUPAC name1,3-dihydro-2-benzofuran-1-one
InChI IdentifierInChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
InChI KeyWNZQDUSMALZDQF-UHFFFAOYSA-N
Isomeric SMILESO=C1OCC2=CC=CC=C12
Average Molecular Weight134.132
Monoisotopic Molecular Weight134.036779436
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point75 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP0.80HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhthalide, non-derivatized, GC-MS Spectrumsplash10-0udi-9005020400-2d50f7ae6f3cd7691b4bSpectrum
GC-MSPhthalide, non-derivatized, GC-MS Spectrumsplash10-0udi-9005020400-2d50f7ae6f3cd7691b4bSpectrum
Predicted GC-MSPhthalide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-8900000000-e2e10448dc354d50b16aSpectrum
Predicted GC-MSPhthalide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-b82a529519513084f181Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d1e071a72f1a95b3a153Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-6900000000-bfb94809be049435fcd7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-db8e49fee9cdba16eb19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-79843cf4206508400973Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-452212b0af673745db15Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-763f3be528f491ee0dd5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4900000000-097b37d9d5e7c9652393Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-a7e77f83a48982f6438aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-91ef080a1daaff255358Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-1900000000-51fa67a737dba49d390bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-8e75af6c7c6fee98529fSpectrum
NMRNot Available
ChemSpider ID6621
ChEMBL IDCHEMBL2391738
KEGG Compound IDC09921
Pubchem Compound ID6885
Pubchem Substance IDNot Available
ChEBI ID479525
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32469
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID3035
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1274731
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coumarin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lactonic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference