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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:53 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034277
Secondary Accession Numbers
  • HMDB34277
Metabolite Identification
Common 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.
Structure
Data?1563862538
Synonyms
ValueSource
(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
Chemical FormulaC12H14O2
Average Molecular Weight190.2384
Monoisotopic Molecular Weight190.099379692
IUPAC Name(3E)-3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one
Traditional NameZ-ligustilide
CAS Registry Number4431-01-0
SMILES
CCC\C=C1\OC(=O)C2=C1CCC=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point377.00 to 378.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility125.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.710 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.48131661259
DarkChem[M-H]-142.41531661259
DeepCCS[M+H]+146.73230932474
DeepCCS[M-H]-144.37430932474
DeepCCS[M-2H]-179.08430932474
DeepCCS[M+Na]+154.55730932474
AllCCS[M+H]+143.632859911
AllCCS[M+H-H2O]+139.332859911
AllCCS[M+NH4]+147.532859911
AllCCS[M+Na]+148.732859911
AllCCS[M-H]-147.832859911
AllCCS[M+Na-2H]-148.232859911
AllCCS[M+HCOO]-148.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LigustilideCCC\C=C1\OC(=O)C2=C1CCC=C22643.4Standard polar33892256
LigustilideCCC\C=C1\OC(=O)C2=C1CCC=C21752.9Standard non polar33892256
LigustilideCCC\C=C1\OC(=O)C2=C1CCC=C21729.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ligustilide GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-6900000000-19a1ca647a7e0491d8e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ligustilide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ligustilide 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 - Ligustilide 10V, Negative-QTOFsplash10-000i-0900000000-da55f68b7672778c66842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 20V, Negative-QTOFsplash10-000j-1900000000-b2cafbc59a05197f25e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 40V, Negative-QTOFsplash10-004l-8900000000-fc5da55ccfb2f546ca152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 10V, Negative-QTOFsplash10-000i-0900000000-f778b0a41733b7c667b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 20V, Negative-QTOFsplash10-000i-0900000000-ce781099c44f51da042b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 40V, Negative-QTOFsplash10-05s1-3900000000-1cb74a6387e3878f4f592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 10V, Positive-QTOFsplash10-0006-3900000000-df63f7ba708218730e1c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 20V, Positive-QTOFsplash10-0006-6900000000-bb0e90d13b2a41a2f2522016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 40V, Positive-QTOFsplash10-0zi3-9100000000-a8552493184912c224392016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 10V, Positive-QTOFsplash10-0006-0900000000-02c830ea56178823e1292021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 20V, Positive-QTOFsplash10-000g-1900000000-ca00aa40e89649e134d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ligustilide 40V, Positive-QTOFsplash10-00or-9100000000-883a9cc29d1cd4ed674d2021-09-23Wishart 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 IDFDB012613
KNApSAcK IDC00051275
Chemspider ID4731467
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5877292
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lu Q, Qiu TQ, Yang H: Ligustilide inhibits vascular smooth muscle cells proliferation. Eur J Pharmacol. 2006 Aug 7;542(1-3):136-40. Epub 2006 May 11. [PubMed:16806164 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .