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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:59:36 UTC
Update Date2022-03-07 02:53:39 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 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.
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

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility121.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.25331661259
DarkChem[M-H]-196.25531661259
DeepCCS[M+H]+193.54730932474
DeepCCS[M-H]-191.18930932474
DeepCCS[M-2H]-224.83130932474
DeepCCS[M+Na]+200.05930932474
AllCCS[M+H]+199.032859911
AllCCS[M+H-H2O]+196.332859911
AllCCS[M+NH4]+201.532859911
AllCCS[M+Na]+202.232859911
AllCCS[M-H]-201.632859911
AllCCS[M+Na-2H]-202.132859911
AllCCS[M+HCOO]-202.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-AcetoxypinoresinolCOC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C14795.5Standard polar33892256
8-AcetoxypinoresinolCOC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C13275.1Standard non polar33892256
8-AcetoxypinoresinolCOC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C13439.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Acetoxypinoresinol,1TMS,isomer #1COC1=CC(C2OCC3C(C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OCC23OC(C)=O)=CC=C1O3323.4Semi standard non polar33892256
8-Acetoxypinoresinol,1TMS,isomer #2COC1=CC(C2OCC3(OC(C)=O)C(C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OCC23)=CC=C1O3315.7Semi standard non polar33892256
8-Acetoxypinoresinol,2TMS,isomer #1COC1=CC(C2OCC3(OC(C)=O)C(C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OCC23)=CC=C1O[Si](C)(C)C3301.1Semi standard non polar33892256
8-Acetoxypinoresinol,1TBDMS,isomer #1COC1=CC(C2OCC3C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OCC23OC(C)=O)=CC=C1O3574.6Semi standard non polar33892256
8-Acetoxypinoresinol,1TBDMS,isomer #2COC1=CC(C2OCC3(OC(C)=O)C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OCC23)=CC=C1O3567.1Semi standard non polar33892256
8-Acetoxypinoresinol,2TBDMS,isomer #1COC1=CC(C2OCC3(OC(C)=O)C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OCC23)=CC=C1O[Si](C)(C)C(C)(C)C3760.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Acetoxypinoresinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-2794000000-0f8c64f69b2898c77b5a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Acetoxypinoresinol GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-2059050000-56192a8217cf11f209822017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Acetoxypinoresinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 10V, Positive-QTOFsplash10-014i-1009800000-96035af2d5639a1622702015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 20V, Positive-QTOFsplash10-00p3-0049200000-a36f0bb00dc7dabf5b992015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 40V, Positive-QTOFsplash10-000l-1922000000-9cdc8991b4261f88cc2c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 10V, Negative-QTOFsplash10-014i-2016900000-bfc622bcc0e7b2ad18582015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 20V, Negative-QTOFsplash10-0a4i-5029100000-bab16be15bc6bb4c76f62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 40V, Negative-QTOFsplash10-0a4i-9113000000-d3202ea73b8d134d30142015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 10V, Positive-QTOFsplash10-014i-0001900000-7dbb84878068998b94732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 20V, Positive-QTOFsplash10-014j-0219700000-92642f49eac57d9252a32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 40V, Positive-QTOFsplash10-002r-0879000000-bb07bd7c0b3e7af71d732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 10V, Negative-QTOFsplash10-014i-0001900000-c687546442959da0befb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 20V, Negative-QTOFsplash10-0a4i-1019000000-2e427bbd2ca4a7c364d92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Acetoxypinoresinol 40V, Negative-QTOFsplash10-052f-9437100000-b1d20d0cb1e0ebe9d6a72021-09-25Wishart LabView Spectrum
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 ID172658
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1834441
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.. .