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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:57 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033876
Secondary Accession Numbers
  • HMDB33876
Metabolite Identification
Common NameDehydrodiferulic dilactone
DescriptionDehydrodiferulic dilactone belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Dehydrodiferulic dilactone has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make dehydrodiferulic dilactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydrodiferulic dilactone.
Structure
Data?1563862474
SynonymsNot Available
Chemical FormulaC20H18O8
Average Molecular Weight386.3521
Monoisotopic Molecular Weight386.100167552
IUPAC Name3,6-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1,4-dione
Traditional Name3,6-bis(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1,4-dione
CAS Registry Number13962-76-0
SMILES
COC1=C(O)C=CC(=C1)C1OC(=O)C2C(OC(=O)C12)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C20H18O8/c1-25-13-7-9(3-5-11(13)21)17-15-16(20(24)27-17)18(28-19(15)23)10-4-6-12(22)14(8-10)26-2/h3-8,15-18,21-22H,1-2H3
InChI KeyDNJFYRXUTBVKIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassNot Available
Direct ParentLignan lactones
Alternative Parents
Substituents
  • Lignan lactone
  • Furanoid lignan
  • Furofuran lignan skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Furofuran
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility24870 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.88ALOGPS
logP2.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.7 m³·mol⁻¹ChemAxon
Polarizability37.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.80731661259
DarkChem[M-H]-189.23531661259
DeepCCS[M-2H]-220.04930932474
DeepCCS[M+Na]+195.23230932474
AllCCS[M+H]+191.832859911
AllCCS[M+H-H2O]+188.932859911
AllCCS[M+NH4]+194.632859911
AllCCS[M+Na]+195.432859911
AllCCS[M-H]-192.232859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-192.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydrodiferulic dilactoneCOC1=C(O)C=CC(=C1)C1OC(=O)C2C(OC(=O)C12)C1=CC(OC)=C(O)C=C15205.9Standard polar33892256
Dehydrodiferulic dilactoneCOC1=C(O)C=CC(=C1)C1OC(=O)C2C(OC(=O)C12)C1=CC(OC)=C(O)C=C13277.0Standard non polar33892256
Dehydrodiferulic dilactoneCOC1=C(O)C=CC(=C1)C1OC(=O)C2C(OC(=O)C12)C1=CC(OC)=C(O)C=C13593.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydrodiferulic dilactone,1TMS,isomer #1COC1=CC(C2OC(=O)C3C(C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC(=O)C23)=CC=C1O3543.8Semi standard non polar33892256
Dehydrodiferulic dilactone,2TMS,isomer #1COC1=CC(C2OC(=O)C3C(C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC(=O)C23)=CC=C1O[Si](C)(C)C3517.5Semi standard non polar33892256
Dehydrodiferulic dilactone,1TBDMS,isomer #1COC1=CC(C2OC(=O)C3C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC(=O)C23)=CC=C1O3829.7Semi standard non polar33892256
Dehydrodiferulic dilactone,2TBDMS,isomer #1COC1=CC(C2OC(=O)C3C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC(=O)C23)=CC=C1O[Si](C)(C)C(C)(C)C4060.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrodiferulic dilactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0923000000-656ab2b02a0a0651c23f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrodiferulic dilactone GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-1191320000-4d4aed020a332249d4682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrodiferulic dilactone 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 - Dehydrodiferulic dilactone 10V, Positive-QTOFsplash10-000i-0109000000-3b2d174ec2d5f39a445a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 20V, Positive-QTOFsplash10-000i-0119000000-8ae00deab42d273cd70b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 40V, Positive-QTOFsplash10-0uk9-0900000000-7929ecee5842f77703df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 10V, Negative-QTOFsplash10-000i-0009000000-62c361ca3913caf561682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 20V, Negative-QTOFsplash10-000i-0009000000-3ce4a2d99d5857114b672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 40V, Negative-QTOFsplash10-0abj-0936000000-0f3921768ad8368ee1e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 10V, Negative-QTOFsplash10-000i-0009000000-aa7b6e6005c5fbeadf5d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 20V, Negative-QTOFsplash10-052s-0296000000-19eee765805c64019d672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 40V, Negative-QTOFsplash10-0541-1395000000-68a2f47a2682f7c9469e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 10V, Positive-QTOFsplash10-000i-0009000000-67d41a0aa2404c067a572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 20V, Positive-QTOFsplash10-000i-0239000000-40c98b585920d6a6aefb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodiferulic dilactone 40V, Positive-QTOFsplash10-0079-1839000000-a976508541a3e06417342021-09-23Wishart 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 IDFDB012069
KNApSAcK IDNot Available
Chemspider ID2935494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3703882
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839011
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.. .