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

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	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9300000000-dd28ad7f56904a5c7c7e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bvi-9200000000-b9f4f1a5509344427d53	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-00y3-8900000000-0cb05419b964f5d6016b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-d656bf5821ba57e34cfa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0uk9-0900000000-d35e76633f689d86ec71	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-98bd90051b89e92f7383	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-785c9bdff21d7558b9b4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-1900000000-953cf944dd232b8d7832	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-7900000000-cb8414fe82a1c814f764	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-a3cd8f79f0fba00900c3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-1900000000-ecff175233ea65fe5f8f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-f8265f1946f33cedd546	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0900000000-e314b75f5fe1649a113b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fl0-0900000000-1e4c5e4e19625ce53572	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-637155f483cd289f34ec	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-73931a09199f234b44b2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0nmr-3900000000-563a89742bb8d15cecc4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9100000000-5934a8f5824689891a5d	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum