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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:34:59 UTC
Update Date2019-07-23 06:14:24 UTC
HMDB IDHMDB0033812
Secondary Accession Numbers
  • HMDB33812
Metabolite Identification
Common 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 has been found to be an antioxidant that may prevent the spoilage of oils, It also may prevent the spoilage of oils by acting as an antifungal. Sesamol is an extremely weak basic (essentially neutral) compound (based on its pKa). Sesamol is a natural organic compound which is a component of sesame seeds and sesame oil. Outside of the human body, 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. It is sparingly soluble in water, but miscible with most oils. Sesame oil is used in Ayurvedic Medicine. Alexander Shulgin used sesamol in his book PiHKAL to make MMDA-2. It can be used in the synthesis of paroxetine. It can be produced by organic synthesis from heliotropine. It is a white crystalline solid that is a derivative of phenol.
Structure
Data?1563862464
Synonyms
ValueSource
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
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name2H-1,3-benzodioxol-5-ol
Traditional Namesesamol
CAS Registry Number533-31-3
SMILES
OC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChI KeyLUSZGTFNYDARNI-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-f4e897c915ebfdb9b210Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9810000000-5a13228557f3c026594bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-6955e913d40b273c135fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8a0f4bd7021b831ff4e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9600000000-7c190d3c1f9c1e6535b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-bbad8da71ad16993f41cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-fd0c1b0e49ab7cc2952cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000m-9700000000-b88dcfac5372bec38909Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID612
FooDB IDFDB011975
KNApSAcK IDC00002673
Chemspider ID61586
KEGG Compound IDC10832
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSesamol
METLIN IDNot Available
PubChem Compound68289
PDB IDBZX
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang CC, Lu WJ, Chiang CW, Jayakumar T, Ong ET, Hsiao G, Fong TH, Chou DS, Sheu JR: Potent antiplatelet activity of sesamol in an in vitro and in vivo model: pivotal roles of cyclic AMP and p38 mitogen-activated protein kinase. J Nutr Biochem. 2010 Dec;21(12):1214-21. doi: 10.1016/j.jnutbio.2009.10.009. Epub 2009 Dec 16. [PubMed:20015631 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Sesamol → 6-(2H-1,3-benzodioxol-5-yloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails