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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:44:04 UTC
Update Date2022-03-07 02:56:52 UTC
HMDB IDHMDB0041089
Secondary Accession Numbers
  • HMDB41089
Metabolite Identification
Common Name4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol
Description4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol has been detected, but not quantified in, beverages and herbs and spices. This could make 4-(3-hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol.
Structure
Data?1563863622
Synonyms
ValueSource
1-(3,4-Dihydroxyphenyl)-7-phenyl-6-hepten-3-olHMDB
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol, 9ciHMDB
Chemical FormulaC19H22O3
Average Molecular Weight298.3762
Monoisotopic Molecular Weight298.15689457
IUPAC Name4-[(6E)-3-hydroxy-7-phenylhept-6-en-1-yl]benzene-1,2-diol
Traditional Name4-[(6E)-3-hydroxy-7-phenylhept-6-en-1-yl]benzene-1,2-diol
CAS Registry Number158697-56-4
SMILES
OC(CC\C=C\C1=CC=CC=C1)CCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C19H22O3/c20-17(9-5-4-8-15-6-2-1-3-7-15)12-10-16-11-13-18(21)19(22)14-16/h1-4,6-8,11,13-14,17,20-22H,5,9-10,12H2/b8-4+
InChI KeyOELWYQGRQUQQPD-XBXARRHUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Fatty alcohol
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point100 - 102 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility23 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP4.19ALOGPS
logP4.46ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.15 m³·mol⁻¹ChemAxon
Polarizability34.67 ųChemAxon
Number of Rings2ChemAxon
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]+171.88831661259
DarkChem[M-H]-171.00931661259
DeepCCS[M+H]+174.630932474
DeepCCS[M-H]-172.24230932474
DeepCCS[M-2H]-205.12830932474
DeepCCS[M+Na]+180.69330932474
AllCCS[M+H]+176.532859911
AllCCS[M+H-H2O]+172.932859911
AllCCS[M+NH4]+179.932859911
AllCCS[M+Na]+180.832859911
AllCCS[M-H]-176.732859911
AllCCS[M+Na-2H]-176.932859911
AllCCS[M+HCOO]-177.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediolOC(CC\C=C\C1=CC=CC=C1)CCC1=CC(O)=C(O)C=C14396.7Standard polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediolOC(CC\C=C\C1=CC=CC=C1)CCC1=CC(O)=C(O)C=C12856.9Standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediolOC(CC\C=C\C1=CC=CC=C1)CCC1=CC(O)=C(O)C=C12887.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TMS,isomer #1C[Si](C)(C)OC(CC/C=C/C1=CC=CC=C1)CCC1=CC=C(O)C(O)=C12841.7Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TMS,isomer #2C[Si](C)(C)OC1=CC(CCC(O)CC/C=C/C2=CC=CC=C2)=CC=C1O2840.8Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(CCC(O)CC/C=C/C2=CC=CC=C2)C=C1O2852.6Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C)C=C1O2795.2Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TMS,isomer #2C[Si](C)(C)OC1=CC(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O2779.8Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(CCC(O)CC/C=C/C2=CC=CC=C2)C=C1O[Si](C)(C)C2887.3Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C)C=C1O[Si](C)(C)C2847.0Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CC/C=C/C1=CC=CC=C1)CCC1=CC=C(O)C(O)=C13129.0Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CCC(O)CC/C=C/C2=CC=CC=C2)=CC=C1O3105.1Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(O)CC/C=C/C2=CC=CC=C2)C=C1O3123.1Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1O3291.2Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O3276.3Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(O)CC/C=C/C2=CC=CC=C2)C=C1O[Si](C)(C)C(C)(C)C3344.4Semi standard non polar33892256
4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(CC/C=C/C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3518.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-0900000000-a8b82e4e5be0d1a0bbb62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-5443930000-48269d407f53d52197af2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 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 - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 10V, Positive-QTOFsplash10-001j-0190000000-347df7647b7af978a3f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 20V, Positive-QTOFsplash10-0089-1960000000-dffbbd7c0698a73d64f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 40V, Positive-QTOFsplash10-0ukl-6900000000-b5719d487d1534cd7b6e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 10V, Negative-QTOFsplash10-0002-0090000000-7252f0de668a2d380c3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 20V, Negative-QTOFsplash10-0002-0290000000-8c401993840c10ac8cb32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 40V, Negative-QTOFsplash10-055u-2940000000-59d85696a9c058194f632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 10V, Positive-QTOFsplash10-001i-0290000000-15ddda8d9534a1b76cd82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 20V, Positive-QTOFsplash10-001j-1950000000-c5f3d21fdc656714145b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 40V, Positive-QTOFsplash10-0f76-1900000000-6766eb916b514b547c1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 10V, Negative-QTOFsplash10-004j-0090000000-7955c392e138708206ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 20V, Negative-QTOFsplash10-009b-0970000000-2a869788770013c31cc52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxy-7-phenyl-6-heptenyl)-1,2-benzenediol 40V, Negative-QTOFsplash10-0002-2590000000-26d679a8b65a7300ccce2021-09-22Wishart 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 IDFDB020967
KNApSAcK IDNot Available
Chemspider ID8193153
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10017580
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1889441
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.. .