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

Record Information

Version

1.0

Creation date

2010-04-08 22:14:47 UTC

Update date

2019-11-26 03:18:27 UTC

Primary ID

FDB020084

Secondary Accession Numbers

FDB030385
FDB013147
FDB000457

Chemical Information

FooDB Name

DL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol

Description

3,4-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 Number

28822-73-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3,4-Dihydroxyphenyl)ethylene glycol	ChEBI
1-(3,4-Dihydroxyphenyl)-1,2-ethanediol	ChEBI
2-Hydroxy-2-(3,4-dihydroxy)phenylethanol	ChEBI
3,4-Dihydroxyphenethyl glycol	ChEBI
3,4-Dihydroxyphenylethyl glycol	ChEBI
beta,3,4-Trihydroxy phenethyl alcohol	ChEBI
DHPG	ChEBI
Dihydroxyphenylethylene glycol	ChEBI
DOPEG	ChEBI
b,3,4-Trihydroxy phenethyl alcohol	Generator
Β,3,4-trihydroxy phenethyl alcohol	Generator
3,4-Dihydroxyphenylethyleneglycol	HMDB
4-(1,2-Dihydroxyethyl)-1,2-benzenediol	HMDB
DL-3,4-Dihydroxyphenylglycol	HMDB
Dihydroxyphenylethylene glycol, (+-)-isomer	HMDB
Dihydroxyphenylethylene glycol, (S)-isomer	HMDB
Dihydroxyphenylglycine	HMDB
3,4-Dihydroxyphenylglycol	db_source
4-(1,2-Dihydroxyethyl)-1,2-benzenediol, 9CI	db_source
β,3,4-trihydroxy phenethyl alcohol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	16.7 g/L	ALOGPS
logP	-0.72	ALOGPS
logP	-0.032	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.8 m³·mol⁻¹	ChemAxon
Polarizability	16.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H10O4

IUPAC name

4-(1,2-dihydroxyethyl)benzene-1,2-diol

InChI Identifier

InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2

InChI Key

MTVWFVDWRVYDOR-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C1=CC(O)=C(O)C=C1

Average Molecular Weight

170.1626

Monoisotopic Molecular Weight

170.057908808

Classification

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:1387 )
tetrol (CHEBI:1387 )
a catechol (CPD-11878 )

Ontology

Physiological effect

Health effect:

Health condition:

Menkes disease

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Cell:

Nerve cell

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 56.47%; H 5.92%; O 37.61%	DFC
Melting Point	130-132 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	-1.01	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, 4 TMS, GC-MS Spectrum	splash10-0a59-0965000000-0c949d05cfff1600a5db	Spectrum
GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrum	splash10-00y3-8900000000-0cb05419b964f5d6016b	Spectrum
GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrum	splash10-0a59-0965000000-0c949d05cfff1600a5db	Spectrum
GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, GC-MS Spectrum	splash10-0a4j-0936000000-6334bc60ea77682060ca	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ly9-2900000000-9512bd346f5c1a6474d1	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-3009500000-7ac807311c5bfb441ee9	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	xi-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00fr-2900000000-fbceba2f96c4ee1154ae	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9300000000-dd28ad7f56904a5c7c7e	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bvi-9200000000-b9f4f1a5509344427d53	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-00y3-8900000000-0cb05419b964f5d6016b	Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-d656bf5821ba57e34cfa	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0uk9-0900000000-d35e76633f689d86ec71	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-98bd90051b89e92f7383	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-785c9bdff21d7558b9b4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-1900000000-953cf944dd232b8d7832	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-7900000000-cb8414fe82a1c814f764	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-a3cd8f79f0fba00900c3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-1900000000-ecff175233ea65fe5f8f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-f8265f1946f33cedd546	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0900000000-e314b75f5fe1649a113b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fl0-0900000000-1e4c5e4e19625ce53572	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-637155f483cd289f34ec	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-73931a09199f234b44b2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0nmr-3900000000-563a89742bb8d15cecc4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9100000000-5934a8f5824689891a5d	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum