Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2019-11-26 03:07:12 UTC
Primary IDFDB012613
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLigustilide
DescriptionLigustilide belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Ligustilide is an extremely weak basic (essentially neutral) compound (based on its pKa). Ligustilide is found, on average, in the highest concentration within wild celeries. Ligustilide has also been detected, but not quantified in, a few different foods, such as celery stalks, herbs and spices, and lovages. This could make ligustilide a potential biomarker for the consumption of these foods.
CAS Number4431-01-0
Structure
Thumb
Synonyms
SynonymSource
(e)-LigustilideHMDB
3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone, 9ciHMDB
3-Butylidene-4,5-dihydrophthalide, 8ciHMDB
Z-LigustilideMeSH
Ligustilide, (e)-isomerMeSH
Ligustilide, (Z)-isomerMeSH
LigustilideMeSH
(E)-Ligustilidebiospider
3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone, 9CIdb_source
3-Butylidene-4,5-dihydrophthalide, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP3.48ALOGPS
logP2.73ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.04 m³·mol⁻¹ChemAxon
Polarizability21.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H14O2
IUPAC name(3E)-3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one
InChI IdentifierInChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8+
InChI KeyIQVQXVFMNOFTMU-DHZHZOJOSA-N
Isomeric SMILESCCC\C=C1\OC(=O)C2=C1CCC=C2
Average Molecular Weight190.2384
Monoisotopic Molecular Weight190.099379692
Classification
Description belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsobenzofurans
Sub ClassNot Available
Direct ParentIsobenzofurans
Alternative Parents
Substituents
  • Isobenzofuran
  • 2-furanone
  • Dihydrofuran
  • Enol ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.76%; H 7.42%; O 16.82%DFC
Melting PointNot Available
Boiling PointBp6 168-169°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 320 (e 2400) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-6900000000-19a1ca647a7e0491d8e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3900000000-df63f7ba708218730e1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-6900000000-bb0e90d13b2a41a2f252JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi3-9100000000-a8552493184912c22439JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-da55f68b7672778c6684JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-1900000000-b2cafbc59a05197f25e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-8900000000-fc5da55ccfb2f546ca15JSpectraViewer
ChemSpider ID4731467
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5877292
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34277
CRC / DFC (Dictionary of Food Compounds) IDDWL20-L:HJK13-L
EAFUS IDNot Available
Dr. Duke IDLIGUSTILIDE|TRANS-LIGUSTILIDE|E-LIGUSTILIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSHJK13-L:HJK13-L
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti constrictive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
myorelaxantDUKE
tracheorelaxantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).