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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:39 UTC

HMDB ID

HMDB0000246

Secondary Accession Numbers

HMDB00246

Metabolite Identification

Common Name

Tetrahydrofuran

Description

Tetrahydrofuran (THF) is a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity and a smell similar to diethyl ether. At low concentrations it has a faint, fruity aroma. It is one of the most polar ethers. THF is naturally present in coffee aroma, floured chickpeas, and cooked chicken. It is used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals. Because of its widespread use (industrially) and its presence in many foods, THF is a contaminant of exposure and can appear in human biofluids. THF oxidizes readily, which can lead to instability and result in cytotoxicity. In chemical synthesis applications, THF is often used for hydroborations used to synthesize primary alcohols. THF is frequently used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides). THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF tends to form peroxides on storage in air. (PMID: 16999122 , 12742700 , 14619948 ). THF can be degraded by certain strains of Rhodococcus bacteria (PMID: 19230656 ).

Structure

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

View in JSmol View Stereo Labels

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 )

Ontology

Physiological effect

Health effect

Tetrahydrofuran exposure (HMDB: HMDB0000246)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1911404)

Excreta

Biofluid or Excreta

Feces (PMID: 19167006)

Cellular substructure

Cytoplasm (HMDB: HMDB0000246)

Source

Endogenous

Endogenous (HMDB: HMDB0000246)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Cabbage

Cauliflower (FooDB: FOOD00031)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-108.3 °C	Not Available
Boiling Point	65.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL	Not Available
LogP	0.46	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	69.7 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	111.694	31661259
DarkChem	[M-H]-	105.08	31661259
AllCCS	[M+H]+	113.436	32859911
AllCCS	[M-H]-	120.74	32859911
DeepCCS	[M+H]+	122.749	30932474
DeepCCS	[M-H]-	120.854	30932474
DeepCCS	[M-2H]-	156.249	30932474
DeepCCS	[M+Na]+	130.519	30932474
AllCCS	[M+H]+	113.4	32859911
AllCCS	[M+H-H2O]+	108.1	32859911
AllCCS	[M+NH4]+	118.5	32859911
AllCCS	[M+Na]+	119.9	32859911
AllCCS	[M-H]-	120.7	32859911
AllCCS	[M+Na-2H]-	125.3	32859911
AllCCS	[M+HCOO]-	130.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrofuran	C1CCOC1	851.1	Standard polar	33892256
Tetrahydrofuran	C1CCOC1	589.9	Standard non polar	33892256
Tetrahydrofuran	C1CCOC1	626.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-15e25f01aff47ab7facc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-15e25f01aff47ab7facc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-3a492c8c5b590a04fe86	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0ab9-9000000000-66253634d3f27573c6e6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0abc-9000000000-49362212e0db0e39a608	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00dl-9000000000-f307a5446840a5333e4f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-7M) , Positive-QTOF	splash10-0006-9000000000-15e25f01aff47ab7facc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-6M) , Positive-QTOF	splash10-0006-9000000000-5fecd52ae1047ea6ca80	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-6M) , Positive-QTOF	splash10-0006-9000000000-a72cdfa78bc1624af6ee	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Positive-QTOF	splash10-00di-9000000000-57b4553c011e61c13302	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Positive-QTOF	splash10-00di-9000000000-633756c4cb26edc87875	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Positive-QTOF	splash10-0007-9000000000-f7f21b58e32e3bbdc8e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Negative-QTOF	splash10-00di-9000000000-3191fdff289240be2d93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Negative-QTOF	splash10-00di-9000000000-53ae58b025cd88229a02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Negative-QTOF	splash10-000f-9000000000-e2c11950e59178898ca9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Positive-QTOF	splash10-0006-9000000000-6f602d2adfd99a361876	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Positive-QTOF	splash10-052f-9000000000-db869489a53547fd0e9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Positive-QTOF	splash10-0a4r-9000000000-e32b752db8542e7e4c7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Negative-QTOF	splash10-014i-9000000000-41ba71baeb0e935332bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Negative-QTOF	splash10-014i-9000000000-4ffb3617277fb64e8592	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Negative-QTOF	splash10-0a4i-9000000000-4e009d20cbcc725a95e3	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21494609	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.3 (0.3-25.6) uM	Adult (>18 years old)	Both	Tetrahydrofuran exposure	1911404	details

Associated Disorders and Diseases

Disease References

Tetrahydrofuran exposure
Ong CN, Chia SE, Phoon WH, Tan KT: Biological monitoring of occupational exposure to tetrahydrofuran. Br J Ind Med. 1991 Sep;48(9):616-21. [PubMed:1911404 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1287631

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

Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. [PubMed:9267307 ]
Sadler BM, Chittick GE, Polk RE, Slain D, Kerkering TM, Studenberg SD, Lou Y, Moore KH, Woolley JL, Stein DS: Metabolic disposition and pharmacokinetics of [14C]-amprenavir, a human immunodeficiency virus type 1 (HIV-1) protease inhibitor, administered as a single oral dose to healthy male subjects. J Clin Pharmacol. 2001 Apr;41(4):386-96. [PubMed:11304895 ]
Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12. [PubMed:12167566 ]
Zhao B, Tham SY, Lu J, Lai MH, Lee LK, Moochhala SM: Simultaneous determination of vitamins C, E and beta-carotene in human plasma by high-performance liquid chromatography with photodiode-array detection. J Pharm Pharm Sci. 2004 Jun 30;7(2):200-4. [PubMed:15367376 ]
Unni LK, Becker RE: Determination of heptylphysostigmine in plasma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1992 Jan 17;573(2):275-81. [PubMed:1601960 ]
Clayton PT, Leonard JV, Lawson AM, Setchell KD, Andersson S, Egestad B, Sjovall J: Familial giant cell hepatitis associated with synthesis of 3 beta, 7 alpha-dihydroxy-and 3 beta,7 alpha, 12 alpha-trihydroxy-5-cholenoic acids. J Clin Invest. 1987 Apr;79(4):1031-8. [PubMed:3470305 ]
Breithaupt H, Wilfling M: Determination of mexiletine in biological fluids by high-performance liquid chromatography. J Chromatogr. 1982 Jun 11;230(1):97-105. [PubMed:7107772 ]
Imbenotte M, Azaroual N, Cartigny B, Vermeersch G, Lhermitte M: Identification and quantitation of xenobiotics by 1H NMR spectroscopy in poisoning cases. Forensic Sci Int. 2003 Apr 23;133(1-2):132-5. [PubMed:12742700 ]
Mahendra S, Alvarez-Cohen L: Kinetics of 1,4-dioxane biodegradation by monooxygenase-expressing bacteria. Environ Sci Technol. 2006 Sep 1;40(17):5435-42. [PubMed:16999122 ]
Authors unspecified: International Conference on Harmonisation; final recommendations on the revision of the permitted daily exposures for two solvents, n-methylpyrrolidone and tetrahydrofuran, according to the maintenance procedures for the guidance Q3C Impurities: Residual Solvents; Availability. Notice. Fed Regist. 2003 Nov 13;68(219):64352-3. [PubMed:14619948 ]
Yao Y, Lv Z, Min H, Lv Z, Jiao H: Isolation, identification and characterization of a novel Rhodococcus sp. strain in biodegradation of tetrahydrofuran and its medium optimization using sequential statistics-based experimental designs. Bioresour Technol. 2009 Jun;100(11):2762-9. doi: 10.1016/j.biortech.2009.01.006. Epub 2009 Feb 18. [PubMed:19230656 ]

Showing metabocard for Tetrahydrofuran (HMDB0000246)

MOL for HMDB0000246 (Tetrahydrofuran)

3D MOL for HMDB0000246 (Tetrahydrofuran)

3D SDF for HMDB0000246 (Tetrahydrofuran)

3D-SDF for HMDB0000246 (Tetrahydrofuran)

PDB for HMDB0000246 (Tetrahydrofuran)

3D PDB for HMDB0000246 (Tetrahydrofuran)

SMILES for HMDB0000246 (Tetrahydrofuran)

INCHI for HMDB0000246 (Tetrahydrofuran)

Structure for HMDB0000246 (Tetrahydrofuran)

3D Structure for HMDB0000246 (Tetrahydrofuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra