Record Information
Version1.0
Creation date2010-04-08 22:09:55 UTC
Update date2019-11-26 03:05:51 UTC
Primary IDFDB011975
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSesamol
DescriptionSesamol, also known as 5-benzodioxolol or sesamol lithium, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Sesamol is an extremely weak basic (essentially neutral) compound (based on its pKa). Sesamol is found, on average, in the highest concentration within sesames. Sesamol has also been detected, but not quantified in, fats and oils. This could make sesamol a potential biomarker for the consumption of these foods.
CAS Number533-31-3
Structure
Thumb
Synonyms
SynonymSource
1, 3-Benzodioxol-5-olHMDB
1,2,4-Benzenetriol methylene etherHMDB
1,3-Benzodioxol-5-olHMDB
1,3-Benzodioxol-5-ol, 9ciHMDB
3,4-(Methylenedioxy)-phenolHMDB
3,4-(Methylenedioxy)phenolHMDB
5-BenzodioxololHMDB
5-Hydroxy-1, 3-benzodioxoleHMDB
5-Hydroxy-1,3-benzodioxoleHMDB
Methylene ether OF oxyhydroquinoneHMDB
Sesamol lithiumHMDB
Sesamol sodiumHMDB
Sesamol titanium (+4)HMDB
Sesamol, ion (1+)HMDB
3,4-MethylenedioxyphenolHMDB
1,3-benzodioxol-5-olbiospider
1,3-Benzodioxol-5-ol, 9CIdb_source
Methylene ether of oxyhydroquinonebiospider
Phenol, 3,4-(methylenedioxy)-biospider
Sesamoldb_source
sesamol titanium (+4)biospider
sesamol, ion (1+)biospider
Predicted Properties
PropertyValueSource
Water Solubility77.3 g/LALOGPS
logP0.89ALOGPS
logP1.29ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.81 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O3
IUPAC name2H-1,3-benzodioxol-5-ol
InChI IdentifierInChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChI KeyLUSZGTFNYDARNI-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(OCO2)C=C1
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
Classification
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.87%; H 4.38%; O 34.75%DFC
Melting PointMp 65.8°DFC
Boiling PointBp13 135-140°DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSesamol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-3900000000-f4e897c915ebfdb9b210Spectrum
Predicted GC-MSSesamol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-9810000000-5a13228557f3c026594bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-6955e913d40b273c135fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8a0f4bd7021b831ff4e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9600000000-7c190d3c1f9c1e6535b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-bbad8da71ad16993f41cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-fd0c1b0e49ab7cc2952cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000m-9700000000-b88dcfac5372bec38909Spectrum
NMRNot Available
ChemSpider ID61586
ChEMBL IDCHEMBL1517998
KEGG Compound IDC10832
Pubchem Compound ID68289
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID612
DrugBank IDNot Available
HMDB IDHMDB33812
CRC / DFC (Dictionary of Food Compounds) IDHCD74-Y:HCD74-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002673
HET IDBZX
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 IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.