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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:59:36 UTC
Update Date2019-07-23 06:13:00 UTC
HMDB IDHMDB0033280
Secondary Accession Numbers
  • HMDB33280
Metabolite Identification
Common Name8-Acetoxypinoresinol
Description8-Acetoxypinoresinol belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. 8-Acetoxypinoresinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8-Acetoxypinoresinol is found, on average, in the highest concentration within olives. 8-Acetoxypinoresinol has also been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and pomes. This could make 8-acetoxypinoresinol a potential biomarker for the consumption of these foods.
Structure
Data?1563862380
Synonyms
ValueSource
1-AcetoxypinoresinolHMDB
1,4-Bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetic acidGenerator
Chemical FormulaC22H24O8
Average Molecular Weight416.4212
Monoisotopic Molecular Weight416.147117744
IUPAC Name1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetate
Traditional Name1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-yl acetate
CAS Registry Number81426-14-4
SMILES
COC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C22H24O8/c1-12(23)30-22-11-29-20(13-4-6-16(24)18(8-13)26-2)15(22)10-28-21(22)14-5-7-17(25)19(9-14)27-3/h4-9,15,20-21,24-25H,10-11H2,1-3H3
InChI KeyNATDFORNCKZPCI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative Parents
Substituents
  • Furanoid lignan
  • Furofuran lignan skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Furofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP2.53ALOGPS
logP2.17ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.13 m³·mol⁻¹ChemAxon
Polarizability42.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-2794000000-0f8c64f69b2898c77b5aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-2059050000-56192a8217cf11f20982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1009800000-96035af2d5639a162270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p3-0049200000-a36f0bb00dc7dabf5b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-1922000000-9cdc8991b4261f88cc2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2016900000-bfc622bcc0e7b2ad1858Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5029100000-bab16be15bc6bb4c76f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9113000000-d3202ea73b8d134d3014Spectrum
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 IDFDB011303
KNApSAcK IDC00002588
Chemspider ID3682955
KEGG Compound IDC10544
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4485133
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .