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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:40:39 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259193

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Triethylene Glycol

Description

Triethylene glycol, also known as TEG or triglycol, belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3). Based on a literature review a significant number of articles have been published on Triethylene glycol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Triethylene glycol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Triethylene Glycol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Bis(2-hydroxyethoxy)ethane	ChEBI
2,2'-Ethylenedioxybis(ethanol)	ChEBI
2,2'-Ethylenedioxydiethanol	ChEBI
2-[2-(2-HYDROXY-ethoxy)-ethoxy]-ethanol	ChEBI
2-[2-(2-Hydroxyethoxy)ethoxy]ethanol	ChEBI
3,6-Dioxaoctane-1,8-diol	ChEBI
Di-beta-hydroxyethoxyethane	ChEBI
TEG	ChEBI
Triethylenglykol	ChEBI
Triglycol	ChEBI
Di-b-hydroxyethoxyethane	Generator
Di-β-hydroxyethoxyethane	Generator
Triethylene glycol, dipotassium salt	MeSH
Triethylene glycol, disodium salt	MeSH
Triethylene glycol, sodium salt	MeSH

Chemical Formula

C₆H₁₄O₄

Average Molecular Weight

150.173

Monoisotopic Molecular Weight

150.089208936

IUPAC Name

2-[2-(2-hydroxyethoxy)ethoxy]ethan-1-ol

Traditional Name

triethylene glycol

CAS Registry Number

Not Available

SMILES

OCCOCCOCCO

InChI Identifier

InChI=1S/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2

InChI Key

ZIBGPFATKBEMQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Polyethylene glycols

Alternative Parents

Substituents

Polyethylene glycol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:44926 )
diol (CHEBI:44926 )
poly(ethylene glycol) (CHEBI:44926 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-1.3	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	36.64 m³·mol⁻¹	ChemAxon
Polarizability	16.45 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	133.218	30932474
DeepCCS	[M-H]-	130.216	30932474
DeepCCS	[M-2H]-	166.69	30932474
DeepCCS	[M+Na]+	141.736	30932474
AllCCS	[M+H]+	133.2	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	137.4	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TRIETHYLENE GLYCOL	OCCOCCOCCO	2149.0	Standard polar	33892256
TRIETHYLENE GLYCOL	OCCOCCOCCO	1235.0	Standard non polar	33892256
TRIETHYLENE GLYCOL	OCCOCCOCCO	1235.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol EI-B (Non-derivatized)	splash10-0002-9000000000-69330288532aa96f6801	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol EI-B (Non-derivatized)	splash10-0002-9000000000-356b5618f2119c31fc04	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol CI-B (Non-derivatized)	splash10-0udi-2900000000-b7da5de5619a9781baa6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004s-9000000000-b054aaae0b7a7c43b727	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-87679d12d0cd990ab32c	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 10V, Positive-QTOF	splash10-0udi-1900000000-2d8a37f0bc887b2ec948	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 20V, Positive-QTOF	splash10-0udi-6900000000-7758685d6f3361c0fca3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 40V, Positive-QTOF	splash10-0002-9000000000-6a4c2f2ae6ff88af6c64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 10V, Negative-QTOF	splash10-0002-1900000000-f64f327526c3cafc427a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 20V, Negative-QTOF	splash10-0002-5900000000-83aed49357767d31a6a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol 40V, Negative-QTOF	splash10-06r6-9100000000-4199e8993d5c0d09d750	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02327

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13835895

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triethylene_glycol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

44926

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1051221

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Triethylene Glycol (HMDB0259193)

MOL for HMDB0259193 (Triethylene Glycol)

3D MOL for HMDB0259193 (Triethylene Glycol)

3D SDF for HMDB0259193 (Triethylene Glycol)

3D-SDF for HMDB0259193 (Triethylene Glycol)

PDB for HMDB0259193 (Triethylene Glycol)

3D PDB for HMDB0259193 (Triethylene Glycol)

SMILES for HMDB0259193 (Triethylene Glycol)

INCHI for HMDB0259193 (Triethylene Glycol)

Structure for HMDB0259193 (Triethylene Glycol)

3D Structure for HMDB0259193 (Triethylene Glycol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra