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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:58:17 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034178
Secondary Accession Numbers
  • HMDB34178
Metabolite Identification
Common NameGuaiacin
DescriptionGuaiacin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. Guaiacin has been detected, but not quantified in, herbs and spices and ucuhubas (Virola surinamensis). This could make guaiacin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Guaiacin.
Structure
Data?1563862523
Synonyms
ValueSource
(+)-GuaiacinHMDB
4,4'-Dihydroxy-3',5-dimethoxy-2,7'-cyclolignanHMDB
5,6,7,8-tetrahydro-8-(4-Hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-2-naphthalenol, 9ciHMDB
Chemical FormulaC20H24O4
Average Molecular Weight328.4022
Monoisotopic Molecular Weight328.167459256
IUPAC Name8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
Traditional Name8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
CAS Registry Number36531-08-5
SMILES
COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C20H24O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-6,8-12,20-22H,7H2,1-4H3
InChI KeyTZAAYUCUPIYQBR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassAryltetralin lignans
Sub ClassNot Available
Direct ParentAryltetralin lignans
Alternative Parents
Substituents
  • 1-aryltetralin lignan
  • Methoxyphenol
  • Tetralin
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 - 206 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.98 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP4.08ALOGPS
logP4.5ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.85ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.17 m³·mol⁻¹ChemAxon
Polarizability36.38 ųChemAxon
Number of Rings3ChemAxon
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]+179.92631661259
DarkChem[M-H]-177.8131661259
DeepCCS[M+H]+186.54130932474
DeepCCS[M-H]-184.18330932474
DeepCCS[M-2H]-218.38130932474
DeepCCS[M+Na]+193.66830932474
AllCCS[M+H]+179.232859911
AllCCS[M+H-H2O]+176.032859911
AllCCS[M+NH4]+182.232859911
AllCCS[M+Na]+183.132859911
AllCCS[M-H]-186.032859911
AllCCS[M+Na-2H]-185.832859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GuaiacinCOC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C14348.2Standard polar33892256
GuaiacinCOC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C12708.0Standard non polar33892256
GuaiacinCOC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C12711.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guaiacin,1TMS,isomer #1COC1=CC(C2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O2785.6Semi standard non polar33892256
Guaiacin,1TMS,isomer #2COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C)C(OC)=C1)C(C)C(C)C22812.2Semi standard non polar33892256
Guaiacin,2TMS,isomer #1COC1=CC(C2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O[Si](C)(C)C2751.8Semi standard non polar33892256
Guaiacin,1TBDMS,isomer #1COC1=CC(C2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O3065.2Semi standard non polar33892256
Guaiacin,1TBDMS,isomer #2COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)C(C)C(C)C23078.5Semi standard non polar33892256
Guaiacin,2TBDMS,isomer #1COC1=CC(C2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O[Si](C)(C)C(C)(C)C3225.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guaiacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0198000000-4fdda0c8dad227ff180b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaiacin GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-0000900000-fcd558b5a50b01c07ed52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaiacin 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 - Guaiacin 10V, Positive-QTOFsplash10-004i-0019000000-45d47c1564ec1f47ea2d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 20V, Positive-QTOFsplash10-004j-2296000000-51e284b28ea1bf2ab44c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 40V, Positive-QTOFsplash10-03di-4493000000-0c1a94551b40aeb2cef92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 10V, Negative-QTOFsplash10-004i-0009000000-573fa998ce549534ff772015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 20V, Negative-QTOFsplash10-004i-0029000000-95b54e3e9471b86d66552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 40V, Negative-QTOFsplash10-06si-0091000000-56e43fae76d0839fab2d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 10V, Positive-QTOFsplash10-004i-0019000000-b7dca4be8a4ad70859e92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 20V, Positive-QTOFsplash10-004i-0359000000-77f1e52ea8faba6948312021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 40V, Positive-QTOFsplash10-004l-0492000000-d66710f686ad08bb00b92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 10V, Negative-QTOFsplash10-004i-0009000000-fd417bc7f7b273e091542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 20V, Negative-QTOFsplash10-01ta-0079000000-c103e8574373678ee6412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaiacin 40V, Negative-QTOFsplash10-0012-0192000000-7131ed9576e99082bb212021-09-25Wishart 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 IDFDB012470
KNApSAcK IDC00037221
Chemspider ID35013705
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14681584
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1840961
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.. .