Tetrahydrofuran
Tetrahydrofuran (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 reslit 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 atoms 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 molecliar mass using gel permeation chromatography. THF tends to form peroxides on storage in air. (wikipedia, PMID: 16999122 , 12742700 , 14619948 ).
Structure for HMDB00246 (Tetrahydrofuran)
C4H8O
72.1057
72.057514878
oxolane
tetrahydrofuran
109-99-9
WYURNTSHIVDZCO-UHFFFAOYSA-N
This compound belongs to the class of chemical entities known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.
Chemical entities
Organic compounds
Organoheterocyclic compounds
Oxolanes
Oxolanes
Aliphatic heteromonocyclic compounds
Detected and Quantified
Not Available
Not Available
Liquid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-66253634d3f27573c6e6View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0abc-9000000000-49362212e0db0e39a608View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-f307a5446840a5333e4fView in MoNA
LC-MS/MS Spectrum – EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-15e25f01aff47ab7faccView in MoNA
LC-MS/MS Spectrum – EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5fecd52ae1047ea6ca80View in MoNA
LC-MS/MS Spectrum – EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-a72cdfa78bc1624af6eeView in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
Not Available
Normal
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 ]
None
Not Available
Not Available
Not Available
Not Available
FDB021917
Not Available
7737
Not Available
F-BETA-D-FRUCTOSYLSUCROSE
Not Available
Tetrahydrofuran
HMDB00246
HMDB00246
Not Available
8028
FU1
26911
- 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 ]
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- 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 ]