CHEBI:26911 - oxolane

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ChEBI Name oxolane
ChEBI ID CHEBI:26911
Definition A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.
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Formula C4H8O
Net Charge 0
Average Mass 72.10570
Monoisotopic Mass 72.05751
InChI InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
InChIKey WYURNTSHIVDZCO-UHFFFAOYSA-N
SMILES C1CCOC1
Roles Classification
Chemical Role(s): polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
Application(s): polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
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ChEBI Ontology
Outgoing oxolane (CHEBI:26911) has role polar aprotic solvent (CHEBI:48358)
oxolane (CHEBI:26911) is a cyclic ether (CHEBI:37407)
oxolane (CHEBI:26911) is a oxolanes (CHEBI:26912)
oxolane (CHEBI:26911) is a saturated organic heteromonocyclic parent (CHEBI:36389)
oxolane (CHEBI:26911) is a volatile organic compound (CHEBI:134179)
Incoming oxolan-3-one (CHEBI:166530) has functional parent oxolane (CHEBI:26911)
2-(dichloromethyl)tetrahydrofuran (CHEBI:87308) has parent hydride oxolane (CHEBI:26911)
10-hydroxy-pre-flavunoidine (CHEBI:195495) is a oxolane (CHEBI:26911)
2,6,9-trimethyl-13-oxatetracyclo[6.3.1.16,9.01,5]tridecane (CHEBI:194089) is a oxolane (CHEBI:26911)
flavunoidine(2+) (CHEBI:194091) is a oxolane (CHEBI:26911)
pre-flavunoidine(2+) (CHEBI:194090) is a oxolane (CHEBI:26911)
tanegool (CHEBI:70196) is a oxolane (CHEBI:26911)
IUPAC Name
oxolane
Synonyms Sources
1,4-epoxybutane ChemIDplus
butane α,δ-oxide NIST Chemistry WebBook
butylene oxide UM-BBD
furanidine UM-BBD
tetrahydrofuran IUPAC
tetramethylene oxide NIST Chemistry WebBook
THF ChemIDplus
Manual Xrefs Databases
c0019 UM-BBD
HMDB0000246 HMDB
THF Wikipedia
View more database links
Registry Numbers Types Sources
102391 Reaxys Registry Number Reaxys
109-99-9 CAS Registry Number NIST Chemistry WebBook
109-99-9 CAS Registry Number ChemIDplus
1767 Gmelin Registry Number Gmelin
Citations Types Sources
12571688 PubMed citation Europe PMC
1811956 PubMed citation Europe PMC
1911404 PubMed citation Europe PMC
19716170 PubMed citation Europe PMC
21316415 PubMed citation Europe PMC
21842397 PubMed citation Europe PMC
2675957 PubMed citation Europe PMC
Last Modified
08 July 2022
General Comment
2014-02-19 THF is occasionally found in human urine due to occupational exposure.