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Showing Compound Ligustilide (FDB012613)

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 found, on average, in the highest concentration within wild celeries (Apium graveolens). Ligustilide has also been detected, but not quantified in, a few different foods, such as celery stalks (Apium graveolens var. dulce), herbs and spices, and lovages (Levisticum officinale). This could make ligustilide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ligustilide.
CAS Number4431-01-0
Structure
Thumb
MOLSDFPDBSMILESInChI
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 RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLigustilide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-6900000000-19a1ca647a7e0491d8e1Spectrum
Predicted GC-MSLigustilide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLigustilide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3900000000-df63f7ba708218730e1c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-6900000000-bb0e90d13b2a41a2f2522016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi3-9100000000-a8552493184912c224392016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-da55f68b7672778c66842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-1900000000-b2cafbc59a05197f25e32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-8900000000-fc5da55ccfb2f546ca152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-02c830ea56178823e1292021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000g-1900000000-ca00aa40e89649e134d32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9100000000-883a9cc29d1cd4ed674d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f778b0a41733b7c667b12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-ce781099c44f51da042b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05s1-3900000000-1cb74a6387e3878f4f592021-09-25View Spectrum
NMRNot Available
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 An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.DUKE
Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
Anti-constrictive52217 An agent that relaxes and dilates blood vessels, airways, or other smooth muscle tissues, reducing constriction and improving blood flow or breathing. Therapeutically, it's used to manage conditions like hypertension, asthma, and angina, helping to alleviate symptoms and prevent complications.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
TracheorelaxantAn agent that relaxes tracheal smooth muscle, easing breathing by reducing airway resistance, commonly used to treat respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD).DUKE
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).