Record Information
Version1.0
Creation date2010-04-08 22:09:34 UTC
Update date2019-11-26 03:04:47 UTC
Primary IDFDB011303
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 found, on average, in the highest concentration within olives (Olea europaea). 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. Based on a literature review very few articles have been published on 8-Acetoxypinoresinol.
CAS Number81426-14-4
Structure
Thumb
Synonyms
SynonymSource
1-AcetoxypinoresinolHMDB
1,4-Bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetic acidGenerator
8-Acetoxypinoresinoldb_source
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
Chemical FormulaC22H24O8
IUPAC name1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetate
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C1
Average Molecular Weight416.4212
Monoisotopic Molecular Weight416.147117744
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.45%; H 5.81%; O 30.74%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D +31.4 (c, 0.99 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8-Acetoxypinoresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p9-2794000000-0f8c64f69b2898c77b5aSpectrum
Predicted GC-MS8-Acetoxypinoresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ds-2059050000-56192a8217cf11f20982Spectrum
Predicted GC-MS8-Acetoxypinoresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1009800000-96035af2d5639a162270Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p3-0049200000-a36f0bb00dc7dabf5b99Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-1922000000-9cdc8991b4261f88cc2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2016900000-bfc622bcc0e7b2ad1858Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5029100000-bab16be15bc6bb4c76f6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9113000000-d3202ea73b8d134d3014Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0001900000-7dbb84878068998b9473Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0219700000-92642f49eac57d9252a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-0879000000-bb07bd7c0b3e7af71d73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-c687546442959da0befbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1019000000-2e427bbd2ca4a7c364d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9437100000-b1d20d0cb1e0ebe9d6a7Spectrum
NMRNot Available
ChemSpider ID3682955
ChEMBL IDNot Available
KEGG Compound IDC10544
Pubchem Compound ID4485133
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID603
DrugBank IDNot Available
HMDB IDHMDB33280
CRC / DFC (Dictionary of Food Compounds) IDGMT88-O:GMT89-P
EAFUS IDNot Available
Dr. Duke ID1-ACETOXYPINORESINOL|D-ACETOXPINORESINOL
BIGG IDNot Available
KNApSAcK IDC00002588
HET IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).