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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:21:58 UTC
HMDB IDHMDB0000246
Secondary Accession Numbers
  • HMDB00246
Metabolite Identification
Common NameTetrahydrofuran
DescriptionTetrahydrofuran (THF) is a contaminant of exposure and appears in human biofluids. The Food and Drug Administration (FDA) has announced recommendations to revise the permitted daily exposures for THF, and so has the International Conference on Harmonisation. THF oxidizes readily, which can lead to instability and result in cytotoxicity. It is a colourless low-viscosity liquid with a smell similar to diethyl ether and is one of the most polar ethers. Tetrahydrofuran is essentially considered in occupational toxicology, and acute poisoning cases are extremely rare. THF is often used for hydroborations used to synthesize primary alcohols. THF is often 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. (wikipedia, PMID: 16999122 , 12742700 , 14619948 ).
Structure
Data?1582752118
Synonyms
ValueSource
1,4-EpoxybutaneChEBI
Butane alpha,delta-oxideChEBI
Butylene oxideChEBI
FuranidineChEBI
Tetramethylene oxideChEBI
THFChEBI
Butane a,delta-oxideGenerator
Butane α,δ-oxideGenerator
Butane a,δ-oxideGenerator, HMDB
1,4-Epoxy-butaneHMDB
Butane a,D-oxideHMDB
CyclotetramethyleneHMDB
Cyclotetramethylene oxideHMDB
Diethylene oxideHMDB
HydrofuranHMDB
OxacyclopentaneHMDB
OxolaneHMDB
PolytetrahydrofuranHMDB
TetrahydrofuraanHMDB
TetrahydrofuraneHMDB
TetrahydrofuranneHMDB
TetraidrofuranoHMDB
TetrahydrofuranChEBI
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Nameoxolane
Traditional Nametetrahydrofuran
CAS Registry Number109-99-9
SMILES
C1CCOC1
InChI Identifier
InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
InChI KeyWYURNTSHIVDZCO-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility69.7 g/LALOGPS
logP0.35ALOGPS
logP0.53ChemAxon
logS-0.01ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.55 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-3a492c8c5b590a04fe86Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-66253634d3f27573c6e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0abc-9000000000-49362212e0db0e39a608Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-f307a5446840a5333e4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-57b4553c011e61c13302Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-633756c4cb26edc87875Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-f7f21b58e32e3bbdc8e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3191fdff289240be2d93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-53ae58b025cd88229a02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-e2c11950e59178898ca9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.3 (0.3-25.6) uMAdult (>18 years old)Both
Tetrahydrofuran exposure
details
Associated Disorders and Diseases
Disease References
Tetrahydrofuran exposure
  1. 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 IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021917
KNApSAcK IDNot Available
Chemspider ID7737
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTHF
METLIN IDNot Available
PubChem Compound8028
PDB IDNot Available
ChEBI ID26911
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceLi, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]