Milk Composition Database: Showing metabocard for Tetrahydrofuran (BMDB0000246)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:20 UTC

Update Date

2020-04-22 15:02:35 UTC

MCDB ID

BMDB0000246

Secondary Accession Numbers

BMDB00246

Metabolite Identification

Common Name

Tetrahydrofuran

Description

Tetrahydrofuran, also known as 1,4-epoxybutane or butylene oxide, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydrofuran exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1,4-Epoxybutane	ChEBI
Butane alpha,delta-oxide	ChEBI
Butylene oxide	ChEBI
Furanidine	ChEBI
Tetramethylene oxide	ChEBI
THF	ChEBI
Butane a,delta-oxide	Generator
Butane α,δ-oxide	Generator
Butane a,δ-oxide	HMDB
1,4-Epoxy-butane	HMDB
Butane a,D-oxide	HMDB
Cyclotetramethylene	HMDB
Cyclotetramethylene oxide	HMDB
Diethylene oxide	HMDB
Hydrofuran	HMDB
Oxacyclopentane	HMDB
Oxolane	HMDB
Polytetrahydrofuran	HMDB
Tetrahydrofuraan	HMDB
Tetrahydrofurane	HMDB
Tetrahydrofuranne	HMDB
Tetraidrofurano	HMDB
Tetrahydrofuran	ChEBI

Chemical Formula

C₄H₈O

Average Molecular Weight

72.1057

Monoisotopic Molecular Weight

72.057514878

IUPAC Name

oxolane

Traditional Name

tetrahydrofuran

CAS Registry Number

109-99-9

SMILES

C1CCOC1

InChI Identifier

InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2

InChI Key

WYURNTSHIVDZCO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

saturated organic heteromonocyclic parent (CHEBI:26911 )
cyclic ether (CHEBI:26911 )
oxolanes (CHEBI:26911 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-108.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	0.46	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.35	ALOGPS
logP	0.53	ChemAxon
logS	-0.01	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.55 m³·mol⁻¹	ChemAxon
Polarizability	8.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-15e25f01aff47ab7facc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-15e25f01aff47ab7facc	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-3a492c8c5b590a04fe86	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0ab9-9000000000-66253634d3f27573c6e6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0abc-9000000000-49362212e0db0e39a608	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dl-9000000000-f307a5446840a5333e4f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-15e25f01aff47ab7facc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-57b4553c011e61c13302	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-633756c4cb26edc87875	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-f7f21b58e32e3bbdc8e8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-3191fdff289240be2d93	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-53ae58b025cd88229a02	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-e2c11950e59178898ca9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-6f602d2adfd99a361876	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-db869489a53547fd0e9a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-e32b752db8542e7e4c7e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-41ba71baeb0e935332bf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-4ffb3617277fb64e8592	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-4e009d20cbcc725a95e3	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 27236769	details

External Links

HMDB ID

HMDB0000246

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021917

KNApSAcK ID

C00010358

Chemspider ID

7737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

THF

METLIN ID

Not Available

PubChem Compound

8028

PDB ID

Not Available

ChEBI ID

26911

References

Synthesis Reference

Li, Haixia; Yin, Hengbo; Jiang, Tingshun; Hu, Tongjie; Wu, Jing; Wada, Yuji. Cyclodehydration of 1,4-butanediol to tetrahydrofuran catalyzed by supported silicotungstic acid. Catalysis Communications (2006), 7(10), 778-782.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Showing metabocard for Tetrahydrofuran (BMDB0000246)

Structure for BMDB0000246 (Tetrahydrofuran)