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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:32 UTC
Update Date2021-10-13 06:21:03 UTC
HMDB IDHMDB0032061
Secondary Accession Numbers
  • HMDB32061
Metabolite Identification
Common Name3-Butylidene-1(3H)-isobenzofuranone
Description3-Butylidene-1(3H)-isobenzofuranone, also known as 3-butylidenephthalide, belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position. 3-Butylidene-1(3H)-isobenzofuranone is a celery, herbal, and lovage tasting compound. 3-Butylidene-1(3H)-isobenzofuranone is found, on average, in the highest concentration within lovages (Levisticum officinale). 3-Butylidene-1(3H)-isobenzofuranone has also been detected, but not quantified in, celery stalks (Apium graveolens var. dulce) and wild celeries (Apium graveolens). This could make 3-butylidene-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Butylidene-1(3H)-isobenzofuranone.
Structure
Data?1563862213
Synonyms
ValueSource
3-ButylidenephthalideMeSH
ButylidenephthalideMeSH
N-ButylidenephthalideMeSH
(Z)-3-ButylidenephthalideChEMBL, HMDB
(e)-3-ButylidenephthalideHMDB
3-Butylidene-phthalideHMDB
3-Butylidenephthalide, 8ciHMDB
FEMA 3333HMDB
Ligusticum lactoneHMDB
3-Butylidene-1(3H)-isobenzofuranoneMeSH
Chemical FormulaC12H12O2
Average Molecular Weight188.2225
Monoisotopic Molecular Weight188.083729628
IUPAC Name(3E)-3-butylidene-1,3-dihydro-2-benzofuran-1-one
Traditional Namebutylidenephthalide
CAS Registry Number551-08-6
SMILES
CCC\C=C1\OC(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+
InChI KeyWMBOCUXXNSOQHM-DHZHZOJOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassIsobenzofuranones
Direct ParentIsobenzofuranones
Alternative Parents
Substituents
  • Isobenzofuranone
  • Benzenoid
  • Enol ester
  • 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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point319.00 to 321.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP3.388 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP10(3.38) g/LALOGPS
logP10(3.02) g/LChemAxon
logS10(-3.1) g/LALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.28 m³·mol⁻¹ChemAxon
Polarizability20.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.64131661259
DarkChem[M-H]-144.07231661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-6900000000-732e96716c41a04fb3fa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Positive-QTOFsplash10-000i-2900000000-8ae9e1a01eaa6fecf1b42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Positive-QTOFsplash10-000i-5900000000-f3bbe4d26792fe9d65332016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Positive-QTOFsplash10-0pbc-9100000000-3c7f96234901b9d9e9332016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Negative-QTOFsplash10-000i-0900000000-95d702d187abea157d2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Negative-QTOFsplash10-000f-0900000000-551a78bdb3bd751e39882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Negative-QTOFsplash10-0006-3900000000-f234896ae771c1f4eb202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Negative-QTOFsplash10-000i-0900000000-0efd5563391c35d6cf2a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Negative-QTOFsplash10-000i-0900000000-03cc6cd126f49f6326542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Negative-QTOFsplash10-0a4i-2900000000-fe566d20babcbcbca0ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Positive-QTOFsplash10-000i-0900000000-18975ec6e59c754be61e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Positive-QTOFsplash10-000b-0900000000-6eebf85402bef8698a162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Positive-QTOFsplash10-0ar9-9600000000-82c62a98392b22d4237c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB008768
KNApSAcK IDC00029489
Chemspider ID4509715
KEGG Compound IDC16924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352899
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1027291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .