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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:27:58 UTC
HMDB IDHMDB0000246
Secondary Accession Numbers
  • HMDB00246
Metabolite Identification
Common NameTetrahydrofuran
DescriptionTetrahydrofuran (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
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-oxideHMDB
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
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-108.3 °CNot Available
Boiling Point65.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP0.46HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+111.69431661259
DarkChem[M-H]-105.0831661259
AllCCS[M+H]+113.43632859911
AllCCS[M-H]-120.7432859911
DeepCCS[M+H]+122.74930932474
DeepCCS[M-H]-120.85430932474
DeepCCS[M-2H]-156.24930932474
DeepCCS[M+Na]+130.51930932474
AllCCS[M+H]+113.432859911
AllCCS[M+H-H2O]+108.132859911
AllCCS[M+NH4]+118.532859911
AllCCS[M+Na]+119.932859911
AllCCS[M-H]-120.732859911
AllCCS[M+Na-2H]-125.332859911
AllCCS[M+HCOO]-130.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TetrahydrofuranC1CCOC1851.1Standard polar33892256
TetrahydrofuranC1CCOC1589.9Standard non polar33892256
TetrahydrofuranC1CCOC1626.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7facc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca802017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-15e25f01aff47ab7facc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-5fecd52ae1047ea6ca802018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydrofuran EI-B (Non-derivatized)splash10-0006-9000000000-a72cdfa78bc1624af6ee2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-3a492c8c5b590a04fe862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0ab9-9000000000-66253634d3f27573c6e62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0abc-9000000000-49362212e0db0e39a6082012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00dl-9000000000-f307a5446840a5333e4f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0006-9000000000-15e25f01aff47ab7facc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-0006-9000000000-5fecd52ae1047ea6ca802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetrahydrofuran EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-0006-9000000000-a72cdfa78bc1624af6ee2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Positive-QTOFsplash10-00di-9000000000-57b4553c011e61c133022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Positive-QTOFsplash10-00di-9000000000-633756c4cb26edc878752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Positive-QTOFsplash10-0007-9000000000-f7f21b58e32e3bbdc8e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Negative-QTOFsplash10-00di-9000000000-3191fdff289240be2d932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Negative-QTOFsplash10-00di-9000000000-53ae58b025cd88229a022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Negative-QTOFsplash10-000f-9000000000-e2c11950e59178898ca92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Positive-QTOFsplash10-0006-9000000000-6f602d2adfd99a3618762021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Positive-QTOFsplash10-052f-9000000000-db869489a53547fd0e9a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Positive-QTOFsplash10-0a4r-9000000000-e32b752db8542e7e4c7e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 10V, Negative-QTOFsplash10-014i-9000000000-41ba71baeb0e935332bf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 20V, Negative-QTOFsplash10-014i-9000000000-4ffb3617277fb64e85922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrofuran 40V, Negative-QTOFsplash10-0a4i-9000000000-4e009d20cbcc725a95e32021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 IDC00010358
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 IDNot Available
Good Scents IDrw1287631
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  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 ]
  11. 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 ]