Record Information
Version1.0
Creation date2010-04-08 22:13:47 UTC
Update date2019-11-26 03:16:20 UTC
Primary IDFDB018565
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
Description6',7'-Dihydroxybergamottin, also known as lepiochlorin, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. 6',7'-Dihydroxybergamottin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6',7'-Dihydroxybergamottin has been detected, but not quantified in, citrus. This could make 6',7'-dihydroxybergamottin a potential biomarker for the consumption of these foods.
CAS Number71339-34-9
Structure
Thumb
Synonyms
SynonymSource
4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-oneHMDB
LepiochlorinHMDB
6,7-DHBMeSH
6',7'-DihydroxybergamottinMeSH
6',7'-Dihydroxybergamottin (incorr.)db_source
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.4ALOGPS
logP2.67ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.12 m³·mol⁻¹ChemAxon
Polarizability39.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H24O6
IUPAC name4-{[(2Z)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8-
InChI KeyIXZUPBUEKFXTSD-JYRVWZFOSA-N
Isomeric SMILESC\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O2
Average Molecular Weight372.417
Monoisotopic Molecular Weight372.157288493
Classification
Description Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Fatty alcohol
  • Alkyl aryl ether
  • Pyranone
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Furan
  • 1,2-diol
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organooxygen 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 67.73%; H 6.50%; O 25.78%DFC
Melting PointMp 104-106°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +12.7 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9044000000-941ed62632b71a13305dSpectrum
Predicted GC-MS4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kji-8894750000-911d6c503b24adefc3d3Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0219000000-60828bda7a2eb1b2b838Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zni-6898000000-9b3d898ebda6aef35d94Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktr-9230000000-58a1d646ec73e9fb6806Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0029000000-739b06d1a0a3b5242e1bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0395000000-0b1e14b4c9f49fd15767Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2920000000-580ae694ecab81deb640Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39066
CRC / DFC (Dictionary of Food Compounds) IDHBX86-S:LLQ09-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference