Record Information
Version1.0
Creation date2015-05-07 19:15:24 UTC
Update date2019-11-26 03:21:44 UTC
Primary IDFDB030440
Secondary Accession Numbers
  • FDB022651
Chemical Information
FooDB Name3-methoxy-4-hydroxyphenylglycol
DescriptionVanylglycol, also known as methoxyhydroxyphenylglycol or 4-hydroxy-3-methoxy-B-phenylglycol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanylglycol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vanylglycol can be found in a number of food items such as common bean, arrowroot, tree fern, and garland chrysanthemum, which makes vanylglycol a potential biomarker for the consumption of these food products. Vanylglycol can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. In humans, vanylglycol is involved in a couple of metabolic pathways, which include disulfiram action pathway and tyrosine metabolism. Vanylglycol is also involved in several metabolic disorders, some of which include hawkinsinuria, tyrosinemia type I, tyrosinemia, transient, of the newborn, and dopamine beta-hydroxylase deficiency. Moreover, vanylglycol is found to be associated with hereditary spastic paraplegia, major depressive disorder, olivopontocerebral atrophy, and sepiapterin reductase deficiency.
CAS Number534-82-7
Structure
Thumb
Synonyms
SynonymSource
1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediolHMDB
3-Methoxy-4-hydroxyphenethylene glycolHMDB
3-Methoxy-4-hydroxyphenyl glycolHMDB
4-Hydroxy-3-methoxy-b-phenylglycolHMDB
4-Hydroxy-3-methoxy-beta-phenylglycolHMDB
4-Hydroxy-3-methoxyphenyl glycolHMDB
HMPGHMDB
HydroxymethoxyphenylglycolHMDB
MethoxyhydroxyphenylglycolHMDB
MHPGHMDB
MOPEGHMDB
4 Hydroxy 3 methoxyphenylethyleneglycolHMDB
4 Hydroxy 3 methoxyphenylglycolHMDB
4-Hydroxy-3-methoxyphenylethyleneglycolHMDB
Methoxyhydroxyphenylglycol, (-)-isomerHMDB
4 Hydroxy 3 methoxyphenylethylene glycolHMDB
4-Hydroxy-3-methoxyphenylglycolHMDB
Methoxyhydroxyphenylglycol, (+)-isomerHMDB
4-Hydroxy-3-methoxyphenylethylene glycolHMDB
Methoxyhydroxyphenylglycol, (+-)-isomerHMDB
Predicted Properties
PropertyValueSource
Water Solubility8.99 g/LALOGPS
logP-0.13ALOGPS
logP0.11ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.28 m³·mol⁻¹ChemAxon
Polarizability18.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H12O4
IUPAC name1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol
InChI IdentifierInChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3
InChI KeyFBWPWWWZWKPJFL-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC=C1O)C(O)CO
Average Molecular Weight184.1892
Monoisotopic Molecular Weight184.073558872
Classification
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-85ebe9a57a84ddca41b6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0079-7149000000-54b71f18882477571debJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0uxr-0900000000-fb2c82b5598c8c9bab3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-a449b185542d66dc0be8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-006x-9600000000-316d1194b9b0ed76d178JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f104dd3883189a74b622JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-040295df7423a417edabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f72-3900000000-87310e73492350a05b5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-01cbe4fce361c48afabfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ur-1900000000-b4ac6a118c11eb31a6ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-4a1c057f8cdd445e7125JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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