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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:32 UTC
Update Date2019-07-23 06:10:13 UTC
HMDB IDHMDB0032061
Secondary Accession Numbers
  • HMDB32061
Metabolite Identification
Common Name3-Butylidene-1(3H)-isobenzofuranone
Description3-Butylidene-1(3H)-isobenzofuranone, also known as (Z)-3-butylidenephthalide or fema 3333, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Butylidene-1(3H)-isobenzofuranone is a celery, herbal, and lovage tasting compound. Outside of the human body, 3-Butylidene-1(3H)-isobenzofuranone is found, on average, in the highest concentration within lovages. 3-Butylidene-1(3H)-isobenzofuranone has also been detected, but not quantified in, celery stalks and wild celeries. This could make 3-butylidene-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods.
Structure
Data?1563862213
Synonyms
ValueSource
(Z)-3-ButylidenephthalideHMDB
(e)-3-ButylidenephthalideHMDB
3-Butylidene-phthalideHMDB
3-Butylidenephthalide, 8ciHMDB
FEMA 3333HMDB
Ligusticum lactoneHMDB
ButylidenephthalideHMDB
N-ButylidenephthalideMeSH
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

Route of exposure:

Biological location:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.38ALOGPS
logP3.02ChemAxon
logS-3.1ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-6900000000-732e96716c41a04fb3faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-95d702d187abea157d2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0900000000-551a78bdb3bd751e3988Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3900000000-f234896ae771c1f4eb20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-8ae9e1a01eaa6fecf1b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-f3bbe4d26792fe9d6533Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9100000000-3c7f96234901b9d9e933Spectrum
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 IDNot Available
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 ID
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.. .