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Showing Compound DL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol (FDB020084)

Record Information
Version1.0
Creation date2010-04-08 22:14:47 UTC
Update date2019-11-26 03:18:27 UTC
Primary IDFDB020084
Secondary Accession Numbers
  • FDB030385
  • FDB013147
  • FDB000457
Chemical Information
FooDB NameDL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol
Description3,4-Dihydroxyphenylglycol (DOPEG) is a normal norepinephrine metabolite present in CSF, plasma and urine in humans (PMID 6875564). In healthy individuals there is a tendency for free DOPEG to increase and for conjugated DOPEG to decrease with age; plasmatic DOPEG levels are significantly lower in depressed patients as compared to healthy controls (PMID 6671452). DL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol is found in olive.
CAS Number28822-73-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3,4-Dihydroxyphenyl)ethylene glycolChEBI
1-(3,4-Dihydroxyphenyl)-1,2-ethanediolChEBI
2-Hydroxy-2-(3,4-dihydroxy)phenylethanolChEBI
3,4-Dihydroxyphenethyl glycolChEBI
3,4-Dihydroxyphenylethyl glycolChEBI
beta,3,4-Trihydroxy phenethyl alcoholChEBI
DHPGChEBI
Dihydroxyphenylethylene glycolChEBI
DOPEGChEBI
b,3,4-Trihydroxy phenethyl alcoholGenerator
Β,3,4-trihydroxy phenethyl alcoholGenerator
3,4-DihydroxyphenylethyleneglycolHMDB
4-(1,2-Dihydroxyethyl)-1,2-benzenediolHMDB
DL-3,4-DihydroxyphenylglycolHMDB
Dihydroxyphenylethylene glycol, (+-)-isomerHMDB
Dihydroxyphenylethylene glycol, (S)-isomerHMDB
DihydroxyphenylglycineHMDB
3,4-Dihydroxyphenylglycoldb_source
4-(1,2-Dihydroxyethyl)-1,2-benzenediol, 9CIdb_source
β,3,4-trihydroxy phenethyl alcoholGenerator
Predicted Properties
PropertyValueSource
Water Solubility16.7 g/LALOGPS
logP-0.72ALOGPS
logP-0.032ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.8 m³·mol⁻¹ChemAxon
Polarizability16.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H10O4
IUPAC name4-(1,2-dihydroxyethyl)benzene-1,2-diol
InChI IdentifierInChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
InChI KeyMTVWFVDWRVYDOR-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C1=CC(O)=C(O)C=C1
Average Molecular Weight170.1626
Monoisotopic Molecular Weight170.057908808
Classification
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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 stateSolid
Physical DescriptionNot Available
Mass CompositionC 56.47%; H 5.92%; O 37.61%DFC
Melting Point130-132 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-1.01HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, 4 TMS, GC-MS Spectrumsplash10-0a59-0965000000-0c949d05cfff1600a5dbSpectrum
GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrumsplash10-00y3-8900000000-0cb05419b964f5d6016bSpectrum
GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrumsplash10-0a59-0965000000-0c949d05cfff1600a5dbSpectrum
GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrumsplash10-0a4j-0936000000-6334bc60ea77682060caSpectrum
Predicted GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ly9-2900000000-9512bd346f5c1a6474d1Spectrum
Predicted GC-MSxi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-3009500000-7ac807311c5bfb441ee9Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00fr-2900000000-fbceba2f96c4ee1154aeSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-dd28ad7f56904a5c7c7eSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bvi-9200000000-b9f4f1a5509344427d53Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00y3-8900000000-0cb05419b964f5d6016bSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-d656bf5821ba57e34cfaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-785c9bdff21d7558b9b4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-1900000000-953cf944dd232b8d7832Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg0-7900000000-cb8414fe82a1c814f764Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a3cd8f79f0fba00900c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1900000000-ecff175233ea65fe5f8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-f8265f1946f33cedd546Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID82648
ChEMBL IDNot Available
KEGG Compound IDC05576
Pubchem Compound ID91528
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID661
DrugBank IDNot Available
HMDB IDHMDB00318
CRC / DFC (Dictionary of Food Compounds) IDMKF52-H:MKF52-H
EAFUS IDNot Available
Dr. Duke ID3,4-DIHYDROXYPHENYLGLYCOL
BIGG ID46054
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
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).