Record Information
Version1.0
Creation date2010-04-08 22:06:00 UTC
Update date2019-11-26 02:59:39 UTC
Primary IDFDB003895
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-N-Butyl-4,5-dihydrophthalide
Description3-n-butyl-4,5-dihydrophthalide, also known as nbpa or sedanenolide, is a member of the class of compounds known as isobenzofurans. Isobenzofurans are organic aromatic compounds containing an isobenzofuran moiety. 3-n-butyl-4,5-dihydrophthalide is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-n-butyl-4,5-dihydrophthalide is a herbal tasting compound found in dill, lovage, parsley, and wild celery, which makes 3-n-butyl-4,5-dihydrophthalide a potential biomarker for the consumption of these food products.
CAS Number62006-39-7
Structure
Thumb
Synonyms
SynonymSource
3-N-Butyl-4,5-dihydrophthalide, (S)-isomerMeSH
SedanenolideMeSH
SenkyunolideMeSH
NBPAMeSH
Senkyunolide aMeSH
3-butyl-4,5-dihydro-3H-2-benzofuran-1-onemanual
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP3.47ALOGPS
logP3.07ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)15.49ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.55 m³·mol⁻¹ChemAxon
Polarizability21.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H16O2
IUPAC name3-butyl-1,3,4,5-tetrahydro-2-benzofuran-1-one
InChI IdentifierInChI=1S/C12H16O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,11H,2-4,6,8H2,1H3
InChI KeyZPIKVDODKLJKIN-UHFFFAOYSA-N
Isomeric SMILESCCCCC1OC(=O)C2=C1CCC=C2
Average Molecular Weight192.2542
Monoisotopic Molecular Weight192.115029756
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
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Dihydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-a1158f039671b5997791JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-4900000000-b662d4b24ab550bdc49eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-9200000000-4895b56617eb5732e535JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c22a777084b86bdcc0ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-1900000000-7420f09891f2bf426f6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9700000000-45de4fd4ff3df8020719JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID3-N-BUTYL-4,5-DIHYDROPHTHALIDE|SENKYUNOLIDE|SEDANENOLIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1588071
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Yi T, Leung KS, Lu GH, Zhang H, Chan K: Identification and comparative determination of senkyunolide A in traditional Chinese medicinal plants Ligusticum chuanxiong and Angelica sinensis by HPLC coupled with DAD and ESI-MS. Chem Pharm Bull (Tokyo). 2005 Nov;53(11):1480-3. Pubmed [Senkyunolide A] [Sructure]
  2. Qi H, Siu SO, Chen Y, Han Y, Chu IK, Tong Y, Lau AS, Rong J: Senkyunolides reduce hydrogen peroxide-induced oxidative damage in human liver HepG2 cells via induction of heme oxygenase-1. Chem Biol Interact. 2010 Feb 12;183(3):380-9. Epub 2009 Dec 2. Pubmed [Senkyunolide H and I] [Structure]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).